Elena and Ryan have been cruising Western Europe aboard Kittiwake, a Heavenly Twins 26ft catamaran, for just under a year. They are sailing on a budget from the UK to the Mediterranean going slow, anchoring out most of the time, and making money along the way.
In this post, Elena shares some of the things she and Ryan have learned about the cruising life since they moved onto Kittiwake.
Big thanks to Elena for letting me share this article as part of a glimpse at the real-life ups and downs of the cruising lifestyle. Follow her sailing channel Sailing Kittiwake on YouTube and her Instagram.
When people think of cruising on a sailboat, tropical beaches, amazing snorkeling, and barbecues on the beach come to mind. That’s what we hoped our life would look like before we set off, chasing the sun. We knew there would also be struggles, adjustments, and good and bad times, but we weren’t exactly expecting what was to come.
Here are a few things we’ve learned about the reality of living on a sailboat and cruising since we sailed away.
It’s not all crystal-clear waters and sundowners
Soon after we set sail, we endured a big storm at anchor, had to call a mayday relay for a sinking boat, and nearly collided with a fishing vessel. Not exactly what we hoped the liveaboard life would be like!
We were lucky enough to get out of all these situations unscathed and with more, precious, experience. Maybe we prepared for our voyage better than we thought, or maybe it was luck. We’re simply grateful we’re still sailing. Even though we enjoyed cruising the Atlantic, we cannot wait for a long, hot, slow summer in the Mediterranean.
Working while cruising can be tough
While I’ve been super lucky with finding freelance gigs to keep our cruising kitty topped up, working on the move can be a little difficult sometimes.
You may need to leave to go on a passage in a rush so you can get far south enough before the end of the season when a big project comes up and you can’t really say no, because you need the money. I sometimes had to alter sailing plans to accommodate for new work opportunities.
Ryan, on the other hand, has found that launching a freelance business while on the move is harder than setting it up before leaving. You make fewer connections on the ocean, you have a less reliable Internet connection, and you can’t physically go to industry events to make yourself known. It’s been harder for him to find clients.
While working as well as sailing can be frustrating, we are extremely grateful we are able to do it, because ultimately it’s the only reason why we can afford to be out here, living our dreams.
Life’s pace changes completely
When I look back at my old life, it all feels like a big jumble of days that look the same, except for the weekends and holidays. The cruising life is 100% different. No day is the same – we may be sunbathing on deck during an amazing light wind sail, or provisioning on shore, or free diving by some cliffs, or editing videos, or fishing while working. We have made some incredible memories over the past year and we wouldn’t change one bit of it.
While on a day-to-day basis some things slow down – shopping takes hours and doing laundry takes a whole day – the cruising life goes by pretty fast. You do so much and go through so many different experiences every day, that, when you look back, you realize just how much has happened in the past week, or month.
When you’re at anchor for a while, or wintering somewhere, the pace adjusts back to normal speed, which is very much needed every now and then.
You can’t take sleep for granted
When you live on land if you don’t sleep at night, it can be irritating. On a boat, you just have to put up with lack of sleep every now and then. A storm, a windy night, a choppy anchorage, or a loud passage can make it impossible for you to even go to bed. While it feels tiring and a little frustrating at the time, you can usually catch up on sleep pretty soon and a beautiful anchorage will fix your mood.
To avoid spending lots of sleepless nights, we bought an oversized reliable anchor we really trust and we usually go find the most sheltered anchorage for the wind conditions we’re in.
Personal space is overrated
Don’t get me wrong – we all need our own alone time and to do our own thing every now and then, but you don’t need a 50ft catamaran to get some personal space. You can chill on different parts of the (however small) boat, you can go on a rowing adventure on your own, or you can go off to do different chores on shore.
Ryan and I spend 99% of our time together, but we sometimes consciously take half an hour or so apart, so we can keep being loving and kind to each other, while also having something new to share.
You need to make some compromises
Whatever your monthly budget, you’ll need to make some compromises. For us, it’s mainly cutting back on dinners out, shore exploration and attractions, marinas, using the engine a lot, etc. We compromise on luxuries and never on necessities, such as boat maintenance.

While sometimes it can be tough to control yourself and not eat out, all the sacrifices are worth the cruising kitty spared to live this lifestyle longer.
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Carolyn Shearlock has lived aboard full-time for 17 years, splitting her time between a Tayana 37 monohull and a Gemini 105 catamaran. She’s cruised over 14,000 miles, from Pacific Mexico and Central America to Florida and the Bahamas, gaining firsthand experience with the joys and challenges of life on the water.
Through The Boat Galley, Carolyn has helped thousands of people explore, prepare for, and enjoy life afloat. She shares her expertise as an instructor at Cruisers University, in leading boating publications, and through her bestselling book, The Boat Galley Cookbook. She is passionate about helping others embark on their liveaboard journey—making life on the water simpler, safer, and more enjoyable.
The Boat Galley says
I love your story and the reality of what it’s like. The tradeoffs we have to make and what you love about it. Thanks for writing it <3
Rachael bohannon says
Hello to the author, and fair winds to you both!
paul fox says
I watch their videos, which are interesting and informative. I’ve been surprised at how many younger people in Europe cruise. You don’t see that as much in America.