How to Learn to Sail

Boat projects abound. Still, it's fun to reflect on how I got to this point. A few people have asked me for advice on learning to sail, since that's probably a pretty important part of this sailing life. Right? 

Optis ready for Junior Week

Optis ready for Junior Week

I learned to sail on a glacier lake in the Northeast Kingdom of Vermont, where the boats we have are old and water-logged and sluggish in the best of winds. My version of sailing, shared by others who also had no real clue about the sport, was one of flogging sails and a whole lot of paddling, spiced by a too-short tiller extension and a centerboard that slipped out if we heeled too far. I learned that sailing was a sport of independence, of frequent mishaps, and maybe, if you were lucky, some moments of sheer bliss. There was also a lot of paddling and swimming.


This is not the ideal way to learn to sail.

Laughter, even in Averill.

Laughter, even in Averill.

My best friend in high school went on to represent the United States on the sailing team in 2 separate Olympic games. From her, I learned the importance of the proper terminology for all parts of the boat, as well as the joys of actually sailing a boat that moved with the power of the wind. When I had the chance to sail with her, on her family’s boat on Lake Ontario, I was treated to a world where the wind was your partner, not something you fought against every second of the time. I learned that sailboats are gorgeous, you can’t tell how much closer you are to the finish line than the other guy until you’re pretty close to it, and big boats shouldn’t involve swimming as a way to get back to shore.


This was a better way to learn to sail.

Random dock photo. Just because.

Random dock photo. Just because.

When I got to college, I decided I’d further my sailing education and joined the sailing club. I went to the University of Virginia, which is situated in land-locked Charlottesville, and we practiced on a man-made lake 30 minutes away from the school. My skipper took pity on me and taught me about hiking out to keep the boat flat, the joys of a well-executed roll tack, and how to rig a 420 while trying to keep your fingers warm. We did, often, sail in cold weather. These college sailing days were filled with laughter and work, endless road trips and late nights of car rides and conversations. Friends introduced me to teaching at Sail Caribbean, a teen sailing camp in the Caribbean where I spent my days teaching teenagers on 50’ sailboats the joys of all aspects of life aboard. Sailing is friendship, cooperation, muscle memory, and travel – and maybe, if you’re lucky, a little money-making on the side.


This was, so far, the best way to learn to sail.


After college graduation, my husband and I bought our own 28’ boat and took off, spending 3 years wandering the Bahamas and the Eastern Caribbean before heading up the East Coast and settling down in Charlottesville. We had to be self-sufficient in ways no 20-year-old thinks about, and every 20 year old ought to experience. From learning the hard way that you better fill your water tanks to the brim before you shove off the docks the first time, to anchoring 5 times for 4 named storms our first year out, to blissful days tacking in and out of anchorages along Venezuela’s bay-studded coast – life was full of adventures both amazing and terrifying. 

Then, when you get older, you can teach your parents.

Then, when you get older, you can teach your parents.

If I had to choose it all over again, I’d pick the last one as my favorite way to learn this sailing thing.


Maybe. Maybe not.


Thing is, all of these had one thing in common. Whether good or bad, all of these involved actually getting on a boat and shoving off from land. I learned something from every single encounter I had with a hull that had a mast stuck in it; actually, I still do. The best way to learn to sail is to get out there and sail, no matter how you get a chance to do it.


If you’ve got access to a cold lake and a heavy old boat, go for it. If you can learn from someone who’s the best of the best, go for it. If you pick up a book, or watch YouTube videos, and then get on a boat and try and try and try again – that’s a perfect way to learn to sail. If you have the opportunity to sail on a large boat in the sun-filled Virgin Islands, or somewhere in the tropics, I can promise you you will learn something.

Start young, if you can!

Start young, if you can!

But what if you’re older, not starting out as a kid or in high school or in college. What then? Is it too late?


There’s a favorite saying that the best time to plant a tree is 20 years ago. The next best time is now. Same holds true with sailing. You might have more patience now, more ability to be deliberate. You might listen better, or research more, or have the funds to pay a decent instructor. Don’t let age deter you from trying something new!


If you’re a parent, lamenting the fact that you are just learning and you want your kid to learn earlier in life than you did, get out on the water. Sure, let them join a junior program or do a sailing-focused camp or send them off to Sail Caribbean or another of the sailing schools designed for teens around the world. Just get them on the water, messing about in boats. Go with them, learn together, and play.


The best way to learn to sail? That’s the way you do it. Stop researching, grab your PFD*, and get out on the water. I bet you won’t regret it.

See you out there.

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Southern Cross to starboard

Cruising is all about moments. There are the really nasty ones, the middle of the night wind shift and consequent move, or the scary almost-wreck-the-dinghy entrance into the anchorage near Dean's Blue Hole in the Bahamas. And there are the other ones, the ones we pull out when we try to describe this life.

As I think of the week we had on Totem, my mind fills with images. Sure, we’ve got a lot of pictures. Pictures of people, of landscapes, of sky and water and sails and ruins. I’ll share a bunch of those at the end of this post.

There are also flashes of our time inked in my head. The camera wasn’t out, or it doesn’t capture the scene, or maybe it was just enough to be in the moment and have it just for me.

Huge waves ahead and behind us as we steadily bashed our way from Linton east to the Guna Yala that first morning on a passage Jamie later told us ranked up there as one of the 10 worst they’ve had in their almost-completed circumnavigation. Totem handled it with aplomb. The crew of Calypso perched in the cockpit, smiled plastered on all of our faces. How many different moments is that?

Seeing the sail of a sailfish appear in front of us, then glide by on the starboard side like a weirdly pointed black plastic bag, on that same passage. Jamie said he’d never seen one.

Catching the glimpse of a pair of dolphins racing towards us then disappearing under the boat.

The Guna village on Isla Machina, with pole-perched solar panels at regular intervals along the narrow pathways that separated the thatch-roofed huts. Side panels of branches tied with twine. One little girl, another little one on her hip who was almost the same size as the one carrying her, peering at us and reappearing at corners. Walking through the huts with cross beams so low even I had to duck a few times. All the hammocks for sleeping, which made my back hurt just seeing them.

Christmas tree worms on the reef, and bright parrotfish pecking at coral.

The dinghy soldiering on under the weight of all 9 of us.

Bee, Mairen, and Siobhan putting away the bedding every morning, whooshing all the air out of the Thermarest* mattresses to turn the main salon back into a living room instead of a dormitory, then reversing the operation at night.

Seeing not one, not two, but three sea turtles on separate sails. Big ones, just hanging on the surface.

Watching the blue-purple sail of a Portuguese Man-O-War jellyfish float by on our last passage, from Portobello to Colon.

Waking up to pinpricks of rain hitting my face, rain that lasted about 5 minutes before scuttling away to reveal a sky bright with an endless carpet of stars.

Sitting in the cockpit in the morning while the coffee grounds settled in my owl mug, looking around at islands and water and sailboats and the sky. It seemed as if I were the only person awake in the world, though I knew that was not the case.

2 dolphins surfacing 10 feet from where I sat in the cockpit at anchor in Portobello.

And waking up at three in the morning and sticking my head out of the hatch, seeing the kite of the Southern Cross to starboard.

Capture your own moments of magic.

See you out there.

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Panama Recap, or - Flexibility is the Watchword!

Tide wash

Tide wash

"Cruising plans are best set in sand - changeable with the tides." "Cruisers and schedules don't mesh." "You can pick the time or the place, but not both."

Very very true. I think we've used these comments on would-be guests a few times, but it's the first time we've really dealt with that aspect of cruising reality from the point of view of the guest.

In an earlier blog, I mentioned that our plans to go through the Panama Canal with the Totems had been stymied by a longer-than-usual processing time between measurement and transit (and a hard-learned lesson about who to buy airplane tickets from!). I thought I'd share what happened!

Instead of this: 

Totem's in the middle here

Totem's in the middle here

We had this:

Anchorage in the Guna Yala (San Blas Islands)

Anchorage in the Guna Yala (San Blas Islands)

Plan A was to go through the canal. No go.

Plan B was to change our plane tickets to be able to go through the canal. No go. (hint - look up prices on sites like Travelocity and Kayak. Actually BOOK the ticket through the airlines. If we had done that, it would have cost us $300 to change our plans. As it was, the full-price-plus-penalty change fee made changing the tickets not possible.)

Plan C was to drive to Carti, a small Guna village on the mainland about 10 miles from the offshore islands. You may know of them as the San Blas - the indigenous peoples there are the Guna Indians, and they prefer the nomenclature of Guna Yala. They actually administer the territory, though it's officially a part of Panama. No go. The Congreso, the Guna leadership, had decreed that all traffic to the area needed to be that destined for Guna resorts. The taxi companies we contacted were reluctant to risk their ability to take anyone, ever, through the border. This change happened literally 3 days before we were to fly out.

Map source:

Map source:

Plan D was to fly out to the islands. No go. Despite the assurances of many people that such flights exist, we were having trouble finding any. And when we did find someone willing to fly us, when we pressed the question of the Congreso regulations, the communication suddenly dried up.

Plan E was for Totem to head to Linton (just east of Portobelo, which you can see on the map), a town outside of Congreso jurisdiction about 45 miles WEST (downwind) of the Guna Yala, where taxis were happy to deliver us. Then we could either continue the jaunt to Colon (further downwind) or decide to bash back upwind to the islands.

The flurry of emails and messages in that last 2 days was astounding. Someone got through to Carti! Oh, no they didn't! They did, but the Congreso at the border was asking to see birth certificates and crew lists. They did, but the guys on the beach at Carti were charging $100 a head for the 5 minute boat ride out to the sailboat. Oh, they actually didn't get through at all. 

By this time, though (and some of these messages/rumors were shared as we were sitting in the airport in DC!), Totem was underway to Linton. Our taxi driver was getting us at the airport in Panama City and delivering us to Linton. We'd decide on the next 10 days over sundowners in Totem's cockpit that very night. Jeremy warned me (as I'd already figured out) that we may well decide NOT to head back upwind - who wants to beat to windward against strong trades if you don't have to?

Safe arrival in Panama City, then Linton. And after unearthing all the US goodies we'd brought to ease the shock of having 4 extra people on a 47 foot boat (maple syrup! Chocolate chips!), the decision was made. Guna Yala, here we come. So Sunday morning, after Behan and I walked to the nearby village of Isla Grande to see what fresh foods we could add to the Totem galley, we picked up the anchor and headed back into the trades, retracing that 45 mile trek they'd done the day before. Jamie says it was one of the 10 worst trips in their almost-finished circumnavigation.

Was it worth it? You tell me.

Boat Project Organization

Winter views

Winter views

It's still winter here in Central Virginia, though the blooming forsythia and the industrious robins helping themselves to bugs or worms or seeds in the backyard are working to convince us otherwise. The calendar and the lengthening days tell us that spring is on its way, and so is sailing season.

Or maybe it's closer to reality to say that "boat work season" is on its way. I'm not sure exactly how much sailing we will get in this summer and fall. Here's hoping we can sneak in a few gorgeous afternoons on the Bay!

Why no sailing? Simple. We have boat projects galore. We've got a few things that have to be done before we can set sail, and the discussion of how to organize said projects is ongoing. There is no right way to organize projects, but I will say that organizing them is really important. Pick a way that works for you and get moving!

One way is by "Things to buy". This is pretty concrete, though the list is deceptively simple. (And lest you think this is all there is, let me assure you it gets added to all the time.) There's no column for the associated projects. The solar panels, for example, involve hiring someone to do stainless work and stanchions and solid lifelines. The windlass doesn't mention the wiring, or the below-decks work, or the battery upgrades.

Screen Shot 2018-03-11 at 12.21.51 PM.png

Another way to organize projects is to think of the things that MUST be done before we leave. There's a bit of this inherent in the "CRITICALITY" column in the "things to buy" spreadsheet, although I'd argue that adding the windlass is way more important than the fish finder*, and personally I'm lobbying hard for the refrigerator to be a pretty high priority (okay, we COULD just use the ARB we have right now as the fridge if we don't have it installed before shoving off . . .). This list is limited to items that are required for safety and comfort: finishing the bed down below, and dealing with reefing gear for the mainsail. Seacocks, especially while the boat is out of the water, are also critical.

We need to get a bunk for us sorted.

We need to get a bunk for us sorted.

This list, though? It keeps being affected by project creep. While we are working on a new bunk for ourselves, we might as well deal with the chart table. And the galley. And the batteries. And cushions. And lighting. And the table will likely need to be modified. And oh, let's finish the hull "ceiling" please, so our home is pretty and cozy.

Project creep. Gotta learn to be diligent in avoiding it, or embrace it. If you've got ideas as to the former, please let me know!

Then there's the "brain dump" version of project lists. Can you tell who makes which list?

Two guesses as to whether this is my list or Jeremy's.

Two guesses as to whether this is my list or Jeremy's.


Sometimes it feels like project lists are a bit like loading a cannon. Put it all in there and light a fuse and hope for the best.

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Reentry - or, the Grief Stages are Real

Drinking a Presidente out of a mola coozie

Drinking a Presidente out of a mola coozie

Reentry after cruising can be really tough, even if the return to a world most people can relate to is a planned one. We did this after our first cruise, when we’d eked out an extra year of our post-college boondoggle of a honeymoon. Three years of cruising the Eastern Caribbean on Calypso, our 28’ Bristol Channel Cutter. I was more than ready to come back to “reality.” I longed for life with a car, with air conditioning, with a freezer.


The pace of life astounded me. How can people move that fast?


There are times when cruising comes to an end and it is planned. Expected. Longed-for, even. And there are times when cruising comes to an end and it’s planned and it’s crushing. (That there are also times when cruising comes to a crushingly unplanned end is a whole other conversation.) While it’s obvious that one is harder than the other, there are some unexpected basics around re-entry that are universal, at least in my experience.


Cruising is tough, there’s no doubt about it. The physical existence. The challenges around simple chores like shopping and laundry and even flushing the toilet. The space and lack of privacy and constant need for vigilance about things like weather and holding and neighbors.

These are all aspects that people “back home” just don’t get. Their understanding of cruising is one from movies and magazines, ones that involve beaches and hammocks or pirates and 50-story waves. No matter how long you’ve been out, their lives have continued in the same routine of soccer practice and traffic jams, waiting for the cable guy and worrying about how effective the tick repellant will be for the dog this year. They may mean well, and welcome you home with open arms, but their main questions will be about storms and pirates and sharks. They might ask how you stayed awake all night every night, or how you managed to feed the family since you were never on land (there is a misconception that going cruising means never setting foot on land, that somehow you just keep sailing the whole time). And then they lose interest.


When we returned from 10 months in the Bahamas, I figured it would be fine. This was, after all, our second re-entry, and this time we’d only been gone for a relatively short period of time. We were coming back to a familiar house, a familiar neighborhood, a familiar school for the kids. Unpack the bags, collect the pets, and life goes on, right?

I’d forgotten how fast life is on land. I’d forgotten how scheduled it was. Our daughter slept in our room for the first month, not because she was nervous or clingy but because for 10 months we’d lived within 30 feet of each other and she liked that. The house felt cavernous and echo-ey and stiflingly small at the same time. We missed the sunset routine of relaxing in the cockpit, searching for the green flash.

The first time I went grocery shopping after our return, something I thought I was excited about – getting everything I want? What? -  I broke down in tears in the tomato aisle. I’d just spent months living in a place where if you saw one kind of tomato in a can, you bought it and celebrated. How on earth can anyone choose between diced and whole and stewed and fire roasted and puree and sauce and paste, let alone all the different brands? Why is this important?

We’d kept a blog while we were gone, and the kids sent regular updates to their classrooms, but there is so much about cruising that is best explained in person. We threw a pizza party and invited whoever wanted to come, bracing for the onslaught of questions.


“What about pirates?”


“Weren’t you scared of hurricanes?”

This is why we went when we did, in the off season.

“Did you just sail around all the time?”

No, we anchored most nights. A night at sea was a rarity, something we did maybe 6 times in the 10 months.

And that was it. Someone else fired off a question about soccer practice, or what teacher they hoped the kids would have next year, or what happened at scouts the week before. Face it. Nobody wanted to hear about our adventure, probably because they had no way to make it real for themselves. While we were searching out laundromats in the Bahamas and building sandcastles, they had been busily living their regular lives back home, shoveling snow and picking paint colors. The shared vocabulary of suburbia didn’t apply anymore, and nobody seemed interested in learning a different language.

The best times were when we were at the yacht club, talking to sailors and friends who could get it at least in some way. They may not have escaped for any longer than a week at a time, but they could envision our lives. They could dream with us.



I spent long hours emailing with friends still out there, desperate to have conversations with people who got it. People who could appreciate the joys of a flush toilet, the terror of life on the highway after life at 5 knots. People whose trials and tribulations (provisioning! Engine troubles! Making the bed on the boat! Laundry!) made sense to me in a tangible, real-life way. Slowly, I reacquainted myself with life on land. That didn’t mean I had to love it, and at first I really didn’t.

We just took 10 days and sailed with our friends on s/v Totem, and I will tell you the re-entry from that 10 days has been every bit as rough as the one from the year-long cruise, minus the conversations about pirates and storms. People can more closely relate to the idea of taking a week off – that’s a vacation length that fits into their world view – but I’m still surprised and a little hurt that so few people have asked about the trip. It feels life-changing. Isn’t that visible from outside?

I felt clumsy driving the car. I looked around our house and wondered why we have so much space. The grocery store felt massive. My daughter sobbed in my arms as she looked at the work she needed to do, the “just get through it” feeling she had on land. As inane as it sounds, coming “back” from cruising is a grief process. And it hurts.

What has helped? Reading posts on Women Who Sail from women who are also grieving. Going through pictures from the week. Talking to friends who are out there, who were once out there. Writing about it. Processing through it while acknowledging that yes, the grief is real and it’s okay to be feeling it.

My daughter said it well when she said, “It’s totally not fair to have something and not have it.” She paused. “But it’s more not fair to not ever have it to begin with.”

Maybe part of my grief this time is that our next cruise is so close I can taste it. That the 10 day interlude was a sharp underlining of how right our decision is. Now I get to live my life on land, trying hard to be present for the process.


See you out there.

A Day in the Life . . . Guest Cruising on Totem


Snapshot of one day on board Totem, a Stevens 47, sailing in the Guna Yala province of Panama (which you may know of as the San Blas Islands) On board for the week are the usual crew of 5 – Jamie and Behan Gifford and kids Niall (18), Mairen (15), and Siobhan (13) plus Mochi the hamster – and visiting cruisers the Waters family – Jeremy and Nica Waters with Julian (18) and Bee (16)

6:30 am. It’s Wednesday, I think. The smell of coffee wakes me, though when I check the clock I decide I don’t need to wake up quite yet and I roll over for another 30 minutes of snoozing.

coffee and sunscreen with a view

coffee and sunscreen with a view

7 am. Coffee in the cockpit is my absolute favorite way to start the day. I see frigate birds whirl overhead, listen to the wind generator spin power, and marvel at the way the clouds move in the sky.

8 am. Behan is making bannock, kind of oatcake muffin scone things that you cook on the stovetop. I’d like to learn the recipe. Mairen tackles the dish mountain from last night while Bee and Siobhan tidy up the main cabin, putting away the extra bedding needed for Bee. 9 people on a boat suited for 5 is a stretch, but so far there have been no complaints. (Read more about living aboard)



            Julian and Niall are still asleep. They’ll likely be there for a while.

            The loose plan for today is to move to another anchorage where we think we can get on a beach and where there are likely to be fewer boats. With this wind, it may well be too rolly for an overnight stay, so it’ll be a lunch stop.

            Here, though, there is decent internet available, and there’s some email and a blog post to take care of. Once that’s done, we’ll get underway. The college application work Niall needed to get out yesterday is done, with the receipt confirmed by the school. Fingers crossed it pays off!

            Jamie changes spark plugs on the dinghy engine, which is not working as smoothly as he’d like.

9:30 am. Hatches closed, anchor is up. It’s a short trek, so we’re charging, running the watermaker, and heating water for showers.

10:30. Anchor down at Gun Cay, a reef just ahead of us and another island where Gilligan might have been shipwrecked off to port. Utopia is 50 yards away. It’s been a 5 mile passage, and it’s Totem’s 555th time anchoring. We’ll celebrate with a swim. The snorkel expedition is a 2-dinghy, 9 people, one. We’re calling it successful, with soft corals, a moray eel, a nurse shark, lobster and crab sightings, and enough fish to keep our interest for a while.


12:30. Corn chowder on the stove, laundry being hung from lifelines. Niall regales us with some highlights from Totem’s almost-complete circumnavigation.

2 pm. I start my workout on the foredeck while the boys go to shore to ask permission to fly the drone. After a sound rebuff, they return to up anchor while I work hard to keep my balance and finish my sweat session.

My gym.

My gym.

3:10 pm. We’re anchored off of Isla Maquina, a Guna village island we’ve been invited by Islaflora, Venanzio’s brother, to visit and tour with him. Venanzio is the master mola maker we bought some wares from the other day. All of us are going in for the tour, though Jamie and Andrew are making noises about wanting to work on Utopia’s watermaker. It just needs to last until Shelter Bay, where the new one is waiting.

4:30 pm. We’re anchored at Gaygar for the night. “Pool is closed,” says Jamie, indicating the silty water, sloped and jungle-y waterfront. Prime crocodile territory. Andrew thinks he saw one on his fish finder, and though we look across the water for logs moving against the wind, we don’t see anything. I’m not sure we’re pleased or not. In any case, there is no swimming tonight!


5:00 pm. The shower parade has begun, as has the conversation about what to have for dinner. Burgers it will be! Behan whips up dough for rolls and we slice onions for the grill, mixing burger meat with seasonings and a few things to stretch the 2 pounds of meat. Leftovers are heated up for nibbles with sundowners in the cockpit – lobster paella and cheese dip. Perfect! Use up leftovers and celebrate another lovely sunset. Wins all around.

5:30 pm. Forward head is clogged again. It takes a little cajoling, a little turning off of water pressure and priming the pump, and it’s clear. Whew.

7:30 pm. Buns are baked, burgers are grilled, and everyone is happily eating. Kids are in fierce competition over bananagrams, so we adults leave them below and eat in the cockpit, discussing the plans for tomorrow and checking weather. The second box of peppermint JoJos is broken into for dessert.

Kids and bananagrams

Kids and bananagrams

9:00. Cruisers midnight. Behan and I leave Jamie and Jeremy pulling out the ipad and the starwalk app to look at the stars, and I fall asleep to the sound of laughter from the main cabin as well as the cockpit.

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How Big a Boat do You Need?


The title of this blog really could be “why don’t you buy a bigger boat?” We’ve been sailing Calypso, our 28’ Bristol Channel Cutter, since we bought her in 1992 (okay, fine, we spent a few months actually getting her ready to go in the water . . .). She’s carried us, when it was just Jeremy and me and our beagle, Toby, from Texas to Florida, down the Eastern Caribbean all the way to Trinidad and west to Bonaire. Back up the East coast of the US to Virginia. She’s carried us, as a family of 4, from Virginia to the Bahamas and Dominican Republic and back again. And we’re getting her ready to take us, just the two of us, no kids or dog, on the next adventure, though where that adventure will be remains up in the air.


Yes, she’s cozy. The current set up down below has the head under our bunk. This was fine when we were in our 20s, but now, ahem, the bladder doesn’t last all night. There’s no way to take a shower down below. I don’t mind jumping over the side for the bulk of my bathing, but these days I’d like to make sure I can get clean even if it’s not the best weather outside or we’re on passage for longer than 4 days. Jeremy, who’s 6’2” tall, can stand up only under the hatches.


So why not buy a bigger boat? One that has, say, a dedicated space for a head and shower down below, with an actual door that closes? One that has, say, standing head room all through for my vertically-endowed husband? Why not spend the money, save the effort of an interior refit, and get something more comfortable?

                                   Under construction. Looking aft from the forward bulkhead.

                                   Under construction. Looking aft from the forward bulkhead.

Believe me, we’ve discussed this one to pieces. We’ve chased boats on Yachtworld, flirted with the idea of weekend trips to see some, and even exchanged emails with a builder. I send Jeremy links to interesting looking boats when they flit like fairies across my screen.


There aren’t a lot of boats that fit our criteria. Boats that look gorgeous (and unique) in our eyes as we dinghy away from them in an anchorage. Boats that sail well. Boats that can carry sufficient supplies for the passagemaking we plan to do. Boats that are simple, robust. Boats that offer substantially more of most of these items than we’ve already got with Calypso, which means we’re looking likely at boats in the 40’ range. Boats that won’t require a mortgage.


Here’s what it comes down to, for us. Comfort is in more than space. Comfort is in knowing the boat. I know where to store things, how to access them. Jeremy installed the engine, installed the watermaker, ran the wiring. I can hoist the main by hand, no need for a winch until that last bit of tightening. We’ve got our anchoring hand signals down, know the routine about how to tack, and can put a full coat of topsides paint on in an hour.


Comfort is in knowing the issues we face. Any boat that would fit our budget, the budget we’ve settled on that will enable us to sail for a long time, will have to be one that’s older. One that requires a lot of work, likely. We know the work Calypso needs. Any new-to-us-boat would come with challenges known and unknown – we might spend a lot of time and money on a different boat and realize that she doesn’t work for other reasons. 

                                               28'. 4 people. 4 jerry jugs. 2 kayaks. 

                                               28'. 4 people. 4 jerry jugs. 2 kayaks. 

We’ve had enough experience with cruising on Calypso to feel reasonably sure of our projected budget, though of course healthcare and health insurance is the hugest unknown factor out there. We are also practical enough to know that at some point, we’ll be no longer able to live on the boat. We want to have a cushion for that eventuality.


This isn’t to say we won’t get out cruising and decide we need a larger boat. We’re keeping that possibility in mind. But maybe, with the changes we’re making to the interior of the boat, we’ll find that cruising in her is as possible now as it’s been since 1992.


When we first bought Calypso, we were (and remain) heavily influenced by Lin and Larry Pardey, whose philosophy is “Go small, go simple, and go now.” Other boats on our short list included boats like the Beneteau 30. A Jeanneau 32. A NorSea 27. Even an F-27 trimaran. They were boats we could afford, not only to buy but to maintain and cruise on. The choice we made has stood the test of time.


I know that a lot of people reading this are thinking we’re nuts. I’m not sure, if I were making the decision as a boatless person right now, I’d choose something quite as cozy as Calypso. But there is deep value in changing the question from “how big a boat should I buy” to “how small a boat can I make work for me?”


Your boat may have a separate head and shower. But when we share an anchorage, we’ll still see the same sunset.


See you out there.

2010-12-15 192000 DSC_0002.JPG

How do You Decide to Go Cruising?


There’s something magical about going cruising the first time. There’s so much loaded into that journey, so many nay-sayers and personal doubts. So many boats sitting on the dock, while owners spend weekend after weekend getting “ready to go” but never actually leaving the dock with the lines kept aboard.

When you head off (and I don’t care if it’s for a week, a month, a year, or “forever”), you’ve joined a special club.

How do you make a decision to go cruising anyway? The decision we made to go the second time, to take the kids and a year and head south, was made, at least on the surface, over the course of one very memorable dinner out.

Sometimes all it takes is a shift in how you ask a question to open it all up.


It was December 28, 2008, our 15th wedding anniversary. For once we got a babysitter to hang with the kids. We opted for eating outside, next to a loud propane heater thing on the patio covered with a plastic-looking canvas tent with plastic-looking “windows” designed to look, from the outside, like some floppy house. It was not the most auspicious beginning to dinner – we’d been counting on being indoors next to the Tulikivi fireplace on this cold December night, complete with freezing rain and a chilly breeze. But reservations are not normally a part of our vocabulary, so when offered the choice of waiting for 2 hours to sit inside or sitting outside, we shrugged back into our coats and went for the outside.

Drinks ordered, we settled back into conversation. When we did get to eat somewhere without the kids, the conversation was usually about the boat or about sailing. Our first wedding anniversary was spent on Bimini, after a really really awful Gulf Stream crossing, and the tradition of talking about “where do you see us in xxx years” and “what was the best part of the last xxx years” started even then.

“Best part, hands down, was going cruising.” That had been the standard answer since 1997.

                                             Sailing the offshore islands of Venezuela

                                             Sailing the offshore islands of Venezuela

“Why was it so good?” I asked. I had my own reasons, of course, and I’d heard Jeremy’s a few times before, but I love seeing him light up when he talks about sailing.

“Freedom. Being in charge of my own choices. Spearfishing. Sailing. Geez, I wish we could go cruising again.”

“Yeah, but that’s not happening again any time soon,” I responded. “We’ve got too much to do here.”

“You’re right.” Jeremy paused. “Let’s put an air conditioner on the boat. It’ll make it more comfortable for weekends aboard. This Chesapeake weather is rough for sleeping when it’s summer.”

We talked about the kind of air conditioner to get, how expensive it would be, what other projects we wanted to do.

I took a sip of wine, then blurted out. “Wait. Why NOT go cruising again? We’ve always talked about wanting to take the kids . . .”

“Why not? Umm, school.” He looked at me like I had 2 heads.

“Homeschool. I'm a teacher, remember?”

                                                                     Boat schooling.

                                                                     Boat schooling.


“We’ll rent it.”

“The boat needs a new engine.”

“Really? Does it?” I was getting into the argument of it. Tell me not to do something, and generally I get fired up about doing it. Contrary nature, I suppose.

“Hmm. Maybe not. And the economy stinks. You’ve already quit your job. I’ll just quit mine.” Jeremy was starting to warm up to this whole idea.

And the conversation continued, getting more and more animated as every objection we could mount became an exercise in figuring out ways around it. We’d stopped asking why we should go – instead we were asking why NOT. It was a challenge. A defiance.

Three little letters.

By the end of that dinner, which had begun in an almost mournful way on an outdoor patio with zero ambience that somehow seemed fitting for a discussion about how everything was better once upon a time, we were casting off our lines in the fall.

Yes, leaving the first time is unbelievable. It shows fortitude and adventure. Showcases a mentality of independence and a little bit of “I don’t really care what you think.” It’s a great dismissive gesture at a society that can’t understand anything different at all. It’s a time of unreal learning, abject fear and terror, and indescribable beauty.

Leaving the second time somehow feels even more momentous. Somehow it means, to me, that we’ve really proved we can do it. Not just once. Bring on the next time.

                                                         Sailing into Warderick Wells 

                                                         Sailing into Warderick Wells 

Provisioning Practice for the Land-Based Planner


When we first decided we were going cruising, I was a newly-minted college grad, playing house with my boyfriend in a 2-bedroom apartment that split the distance between his work and mine. What I knew about cruising was learned from 2 summers of teaching sailing with Sail Caribbean, plying the waters of the BVI and the Leewards on 50’ sailboats with a crew of teenagers. Food was provided, along with lists of what we were supposed to have, what we were supposed to make, and recipes to follow. Those boats had huge freezers and larger refrigerators, and one of the worst jobs was cleaning the charter juice out of the bottom after a 3-week program ended.


Our boat would have a refrigerator the size of a small cooler and no freezer. Nobody was going to magically appear with a few boxes of food on a regular basis, along with a plan of what I was supposed to do with that food. I better learn what to do now, before we left.


It was the early 90s, before the internet made everything accessible at the tap of a few fingers on a keyboard, so my main references were books, mostly purchased from the Blue Water Bookstore. There was the tried and true Joy of Cooking*. A book by Michael Greenwald called “The Cruising Chef”. A couple of pressure cooker and bean cookbooks. And the book that would find a priceless place on my bookshelf, a place it holds firmly today – Lin Pardey’s The Care and Feeding of the Offshore Crew (it’s since been renamed "The Care and Feeding of the Sailing Crew", and that's what the link is for.)

I have a fondness for Lin and Larry Pardey for many reasons, but chief among them has to be that we own a boat designed by the same guy who designed both of theirs. That I’ve since gotten to personally know Lin still feels like a bit of a pinch-me-now situation. When Lin talks about how to organize a galley (which is really like organizing your boat, because the food winds up in lockers all over), it’s like she’s standing in Calypso’s salon, directing me. She’s almost never steered me wrong when it comes to food stuff, although I’m far less of a fan of corned beef than she is.

                                             Lin and me at the Annapolis Boat Show, October 2017

                                             Lin and me at the Annapolis Boat Show, October 2017

She taught me the importance of trying canned goods at home before stocking up. The importance of learning to create meals out of items you’d have left after 2 weeks or longer since you saw a grocery store. And the importance of using leftovers so you don’t waste food.

There may be those reading who are in the planning stages of your cruise. I’ll offer three tips for provisioning practice that you can work on right now, before you move aboard.

1.     Observe the kinds of food you like to eat. Be a student of your preferences as far as food goes. If you like it on land, you’ll LOVE it on board. Understanding what you like to eat is critical to making an accurate list when it comes time for provisioning.


2.     Start thinking about food that lasts a long time, and how to use it. Sure, there are fresh staples like cabbage and onions and garlic, but there’s also some really fabulous stuff in the packaged section you might like to try once to see how you like it. On my list in this category is jackfruit, some of the Thai curry options, and even powdered hummus mix. Will we like it all? Maybe, maybe not; but if we do, we have expanded our options for eating well when we decide to stay an extra few days in that perfect anchorage. I spend an extra few minutes in the sections of the grocery store that are dedicated to my favorite kinds of food (see #1!) and if there is something that catches my eye, I either buy it on that trip or make a note to pick it up next time.

                                                                  long-life cream!

                                                                  long-life cream!

3.     Pick ONE thing to learn how to make from scratch that right now you buy as a matter of course. Maybe it’s queso dip. (no judging – I have teenagers) Maybe it’s fresh bread. Maybe it’s salad dressing or spaghetti sauce or yogurt or hummus. It’s a whole lot easier when you’re cruising to carry ingredients you can use to make a lot of different dishes rather than just buying the specific dish. If you’re so inclined, check out Tasty Thursday, my YouTube playlist, where every Thursday I share a simple recipe or tip designed to make you think, “Hey, I can do that!”. The show’s been running weekly since October of 2012 – there’s a lot there! And if you don’t have a copy of The Boat Galley cookbook yet, what on earth are you waiting for!

                                     homemade pizza

                                     homemade pizza

Provisioning can feel daunting, especially when you see pictures of boats piled high with canned and packaged goods that need to be stored in every conceivable cranny. A little forethought, planning, and understanding can alleviate that feeling. Start practicing now!

                                                           loading up for the Bahamas

                                                           loading up for the Bahamas


Side note: If you’re planning to be at Cruisers University at the Annapolis Spring Boat Show in October of 2018, stop by and say hi to Carolyn and me. She’s teaching a class on hurricane prep, and I’m sharing more provisioning tips plus offering a class on the dreams vs realities of cruising. We’d love to see you.

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When Does Cruising Really Start?

I’ve learned a lot of lessons from cruising, and some I hope I’ve learned. The importance of being present to what’s happening, even while deep in the midst of prepping to leave, is one I’m still working on.

I was 21 when Jeremy said 4 words that would forever change my life.

He waited until the waiter at the pizza place had left the menus, then leaned in.

“I’ve got something to tell you.”

I stared at my hands. At him. At the menu. It’s likely there were tears in my eyes. Was this the break up talk? At College Inn pizza, on a Friday night, surrounded by strangers? My brain raced with the what ifs. Am I the only one whose brain goes immediately to “what did I do wrong” when someone says those words? It feels like being back in the principals office.

The waiter came back. I’m pretty sure I ordered something – that is, after all, what you do when you’re out for dinner. The waiter went away and my fear rushed back in. My mouth went dry and my hands got clammy.

The words came as if from a far distance. “Let’s buy a boat.”

Jeremy, walking down the Lawn on graduation day.

Jeremy, walking down the Lawn on graduation day.

I can still vividly remember the almost levitating feeling of relief. “Is that all?”


“I want to go cruising.”


He’d been sailing and talking about sailing for as long as I’d known him. We met on the sailing team at the University of Virginia (we sailed on a man-made inland lake about 25 miles away), and he’d been teaching sailing on big boats in the Bahamas and the Eastern Caribbean during spring break and summers since his first year at school.


This wasn’t that big of a surprise. How hard could this cruising thing be, anyway? It’s like a fulltime vacation, right?


So we graduated, landed jobs, and moved to Texas (in 1991, there were not many options for a non-US citizen in a really awful job market) with this goal in our heads. The apartment was chosen because it had the all-important second bedroom – not for guests, or for a kid, but for the wooden dinghy he started building even before we unpacked all the boxes. Evenings were spent eating rice and beans (to save money), poring over cruising guides and boat magazines, endlessly discussing the kind of boat we should buy and where we should go. By the following spring we’d found the boat, the 28’ Bristol Channel Cutter we still own, adopted a beagle, and began the cruising prep in earnest. 

Toby the boat beagle

Toby the boat beagle

It was decided. A 2-year cruise was what we could swing, we thought, based on a pulled-from-thin air budget of $1000 a month. Our destination? The Bahamas and the Eastern Caribbean, though the idea of a Caribbean circumnavigation was entertained more than once. Every instant was spent talking about the boat, working on the boat, or discussing the cruise. Was there anything other than the future?


Cruising prep involves a lot of projects, a lot of lists, and a lot of learning. I remember certain moments about those 3 years, but mostly I remember worrying about what was next. A project was finished (putting the head on the boat, building the galley) and immediately the next one started. Enjoy the process? Who has time to do that, when the TO DO list was longer than I am tall. I think I took maybe 3 pictures the whole time, mostly of the mess or of the dog curled up in some corner.


Questions swirled. Would we be able to get the finished dinghy out of the room it was being built in? How would the dog do on the boat? What would life be like in such a small space? How could I cook aboard? Could I get tired of beaches? What actually do you do on a boat all day?


The next three years flew by in a blur of endless boat work and more endless driving (my commute was 70 miles each way, and we carpooled together to save money), and on September 10, 1994, we slipped under the Kemah bridge and into Galveston Bay with enough gear on board to put us down an extra 2 inches on our lines, towing that dinghy (it came out of the room!) and followed by a few friends on their own boats cheering us on as we headed off for our adventure.


I found one of the log books we kept during that first cruise, a map-decorated hardbound journal. Here are some of the entries.


July. We leave in 2 months to go cruising. It’s starting to be real. We’re prepping now – we’ll really be cruising once we leave the dock.

October 10: One month in. We need to find a place to tuck the boat while we head back to Houston for an appointment. When we get back from that, we’ll really be cruising.

November 25: Thanksgiving tied to the dock at Dotty and Waldy’s, finishing up the dinghy seats. They loaned us a car for easy provisioning. Next stop, the Dry Tortugas. When we get there, we’ll really be cruising.

December 25: What a crappy Christmas. It's dumping rain and howling wind. We're all alone in the anchorage, with canned ham, canned peas, and canned potatoes for Christmas dinner. We leave for the Bahamas tomorrow. I can’t wait to really be cruising.

May 1: We leave for Rum Cay tomorrow, then on to the Turks and Caicos. I think this is where we really start cruising, when we leave the Bahamas. I wonder who we’ll see there.


When I re-read logs from the first year, the “we’ll really be cruising when . . .” line is repeated over and over again. It almost makes me sad to go back and read it. Not for the adventures and mishaps that are chronicled, and not even for the sense of nostalgia as I read the words written by 24 year old me. But the constant looking ahead, FOMO even then. That was a lifetime ago. Have I learned anything since then?

How much cruising, how much life, did I miss wondering when it was going to start?


We are less than 2 years out from our next cruise, this time with a timeline of  “as long as it’s fun.” There are lots of projects. Incredible lists that now have titles like “selling the house” and “getting the kids settled in college” and “MUST DO BEFORE WE LEAVE”. The learning feels just as steep, though a few of the worries are just not there any more. There’s no dinghy being built in a spare bedroom, no concerns about “what do you do out there all day?”


I’m trying to be present, to focus on what’s happening now. I know that this part, the prep part, is as valuable and as valid a part of cruising as any of those perfect sunsets or incredible beach walks.


It’s all cruising. No waiting required.



Being Flexible About a Cruising Vacation

At anchor

At anchor

About a year and a half ago, our friends on S/V Totem  (check their website!) came for Thanksgiving. Behan and I had "met" while serving as admins together on the facebook group Women Who Sail, met in real life at the Annapolis Sailboat Show in October of 2016, and when it became clear that they'd still be in the US (and even in the relative geographical area to our landlocked Charlottesville) we invited them for Thanksgiving at our house.

Hanging out with cruisers is a joy. The vocabulary, the shared experiences, even the sense of flexibility in space-sharing and cooking together is something that is hard to translate. Behan and I have the kind of friendship that feels effortless in many ways. It's hard to believe we haven't known each other forever.

Movie time!

Movie time!

During that visit, we casually talked about their plans to go through the Panama Canal and joked about coming down to help them transit.

That joke solidified into something approaching a plan. We've purchased plane tickets, told work (and school) we are taking 10 days off in February to go through the canal with friends, and started assembling the stuff we need. Stuff like masks and snorkels, easy-to-dry towels, and all the goodies they might want us to bring down.

There's an old adage that cruisers and schedules don't mesh well. Trying to get somewhere on a schedule can mean making poor decisions, ignoring weather, or pushing past discomfort in ways that might not be safe. As cruisers (only TEMPORARILY land-bound), we get that, of course - it's far easier for us to be flexible than it is for them. 

This may read as weird, if you're not a cruiser reading this. It's easier for a job-and-school constrained person to be flexible? How? Last I checked my boss was not exactly hot on me saying, "Hey, I'll take vacation next week. Or it might be tomorrow. Or maybe in a couple of weeks. That's cool, right?"

Cruisers moving their boats, though, are moving their homes. A move that on paper is "only" 20 miles away might take a week of waiting for the right wind, current, waves. As a land-based traveler, a change might be  an inconvenience; for a sailor, a change might be disastrous.

Part of the extra challenge with a canal transit for a sailboat is that you're dependent on the canal authorities for everything, from getting measured to getting a transit time and even getting a (required) pilot on board the boat. There is just no way to say, "Hey, let's go through on xxxx date" and have it magically happen. This makes it tough if there is crew flying in, with the need to get airfare at a decent price but not knowing when the transit can happen.

The phone call came in on a January Saturday, about 2 weeks before we were supposed to fly down to help go through.  The word from Totem was that the lag time between measuring and locking in (to start the transit) was running an average of 15 days, not the 7 days that's a traditional average. The weather was crap, making movement difficult and uncomfortable. If Totem was to move as quickly as they comfortably could, they'd get to the marina in Colon to be measured no sooner than the next Thursday, and with the 15 day lag time that put a transit right at the tail end of our existing flight schedule.

So we had a choice. Change flights (which may or may not be possible). Or fly in on our already-booked schedule and figure out getting to the Guna Yala (San Blas islands) where we can play with the Totems on board, in cool islands with amazing culture but miss a transit. 

Bahamas cool islands. Not the Guna Yala.

Bahamas cool islands. Not the Guna Yala.

Both were options. Both required more planning than either of us had anticipated.

But this, when it comes down to it, is sort of a cruising reminder. Best laid plans need to be cast in sand on a tidal beach, with flexibility required for all involved.


Whichever we decided, the crews of Totem and Calypso were together again soon, this time in Panama. Keep reading!

The kids are all taller now. The next picture will be an interesting one!

The kids are all taller now. The next picture will be an interesting one!