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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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.

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.

*As an Amazon Associate I earn from qualifying purchases.