Survival Guide to Sailing with Strangers


If you've ever wondered what life on board a sailboat is really like, this loosely named survival guide to sailing with strangers is for you. I've lived aboard a sailboat twice now, once when sailing the Greek islands for three weeks and another while sailing around Turkey for a month, both as a liveaboard English tutor for a sailing family I had never met before. These tips also apply to anyone curious about chartering a crewed boat, joining experienced sailors as a guest, or traveling with an organized sailing tour. 

So, how did I happen upon a tutoring job on a sailboat you ask?

I found the gig online through workaway, a site that pairs hardworking travelers with hosts willing to open their homes. Most workaway experiences expect 4-5 hours of help per day in exchange for a place to stay and sometimes meals.

My workaway experience was exceptional and definitely above average. In exchange for English tutoring and helping with basic chores like dishwashing and tidying, I had an life-changing and meaningful experience on a sailboat. I had my own private cabin and bathroom on board and the cost of all of my meals were covered. Lucky me!

The sailing life isn't for everyone though. Sailing with strangers is probably for even fewer people. The survival guide to sailing with strangers below will give you a glimpse of what it's really like to live on a sailboat for a few weeks in case you're curious about the boat life yourself.

Packing Tips for Sailing with Strangers

Packing for sailing is a delicate balance in weighing what you need with what you have space for. Pack carefully. Every inch of baggage is precious and you don't want to find yourself miles from land without something you truly need.

I combined both of my sailing adventures with long-term travel while living as a digital nomad and adventure traveling around Europe, so I never had a true sailing packing list. Maybe someday, I'll armchair travel by creating the ultimate sailing packing list. 

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Pack lightweight layers

Lightweight layers and breathable basics like this linen cover up are perfect for sailing in hotter climates. They air-dry quickly, protect your skin from the sun, and are versatile enough for both marina cafes and remote bays. 

Bring more swimsuits than you think

I'd recommend three bathing suits minimum. To a minimalist packer like me, that feels excessive but is completely justified. 

My host family never stayed in their wet swimsuits after swimming. It was dry suits only onboard. Be prepared in case the same rules apply on your boat.

Bring dozens of (digital) books

In today's world, we crave being able to disconnect and slow our pace of life. Disconnecting completely while sailing is wonderful, but you still need to exercise your mind and fill your days with something.

The Kindle Paperwhite is really suited to sailing. It's waterproof and saves precious space in your luggage that traditional books simply don't. I personally read a lot of books set in Greece and books about sailing while sailing myself. 

External batteries are your friends

The boat I was on was well equipped for modern life. While it didn't have wifi onboard, it did have ample solar power to recharge my electronics overnight. Power and connectivity aren't give-ins when sailing though. Bring an external battery along for peace of mind and a backup personal power source. 

Tips for Sailing with Strangers

Discuss your role in high stress situations

This is the closest we'll come to being a true survival guide today.

I don't have a lot of sailing experience so I was up front with my host family about my lack of sailing knowledge. Before we even left the port, I knew what sailing-related tasks I could help with, how to do them, and where it was best for me to be while we were moving.

When my host family was sailing the boat and in especially tense moments, they would often speak in Turkish as it was their native language. Because we had discussed these things beforehand, I didn't feel awkward when I had to get out of the way or do something quickly.

If you're on an organized sailing tour or a crewed boat, there will be an official safety briefing where you'll learn this info. As a guest, you may need to ask up front. 

Discuss daily routines

While some days may be different than others while sailing, it's always nice to have an idea of what to expect so that you can blend easily into the rhythms of daily life on board a sailboat. I quickly learned that my host family liked to sleep in more than I did, so I was sure to be especially quiet in the mornings. I eventually adjusted to their night owl tendencies and later meal times.

If you're on an organized tour, you'll probably be told the daily schedule in advance. 

Don't be a picky eater

Provisioning, or the process of stocking the boat with food and necessities, is an important part of sailing.

If you're on an organized tour, you'll probably contribute to a collection of shared food. If you're a guest, the last thing you want to do is be a burden on your hosts. Cooking on board a sailboat can be a creative challenge and food is a limited resource while sailing, even if you're catching fish off the bow.

Thankfully, this wasn't a huge challenge for me as I generally enjoyed the Turkish food that they prepared. Even if something wasn't normally my taste, I made it work. I learned to love tolerate mushrooms, dates, and coffee without sugar like never before!  I also became a daily tea drinker.

Be sure to share any dietary restrictions before sailing. The tutor before me had to cut her time short because her strict vegan diet didn't mesh well with the family's meal plan.

Don't expect frequent showers or laundry

This was probably my least favorite part of sailing life. We would only rinse our hair with fresh water at the end of the day, take freshwater showers when at ports roughly every 4-5 days, and do laundry every 2 weeks or so. I've never used less water when brushing my teeth either.

Thankfully, we were swimming in some of the cleanest water I've ever seen, but my hair was a tangled saltwater mess! This detangler was a life changer on my second sailing adventure. Adjusting to the easy, breezy ways of sailing life was an adjustment, and a water conservation wake up call. 

Ditch your expectations

Life on a sailboat is incredible. It's also incredibly unpredictable. Our day changed depending on the wind, how many other boats were around, and what my host family felt like doing that day. I had to learn to go with the flow, literally this time.

I didn't have a say in what islands we would be visiting or how long we would stay in each bay. I didn't even know which port I would be meeting my hosts in to start with until a week beforehand! I spent two weeks in Greece on islands that I hadn't heard of before and I'm so grateful for it.

What you gain in unique experience, you pay for in relinquishing control. It's entirely worth it.

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