Top Ten Reasons to Set Sail with Unsettled to the British Virgin Islands

By: Michael Youngblood & Jonathan Kalan, Co-Captains, Unsettled.

Ahoy! Are you set to ride the waves and replace routine with adventure? From a seven day work week to embracing the seven seas, we are going back to where Unsettled all began and you’re invited.

Here are our top ten reasons to set sail with us!

1. Learn to Sail, Unsettled Style

We will spend 4-6 hours a day on the emerald waters of the Caribbean Sea. You will learn to take the wheel (technically the helm…you’ll learn all the lingo) from the moment you board your ship (with support from your captain, of course!). For a week, you will learn to hoist up those sails, anchor the ship, and be the skipper of your very own crew. But you do this in the most Unsettled of ways: while or between sailing, you’re filling the day with meaningful conversations, reflections on our work/life balance, and big questions about what we are pursuing and working towards. We also continue our family-style dinners and find some fun ways to host pop-up workshops, whether it’s over a map talking about how we plan and navigate in our lives or on a beach by a campfire.

2. Alumni Reunions

Our sailing retreats largely consist of alumni, friends of alumni, and our most dedicated followers. It’s one big Unsettled family with alumni from all kinds of months, years, and retreats. Not only is it a great way to reunite with your alumni from your retreat, but you will also meet new alumni and learn about their retreats and experiences. Where better to meet Unsettled crewmembers from all around the world than where your very oceans collide? Alumni: send your retreat group a message (you know how) and see who might join us!

3. The Smallest Packing List of All Time

Perfect for you procrastinating packers, you can carry everything you need in your pocket for our weeklong journey. Sunscreen, one or two swimsuits, and a toothbrush and you’re ready to hop on board and sail away for a week. What does this mean for you? It’s amazing how easy we’ve made the logistics to live on a sailboat, getting a taste of the cruising life, for a week. Grab your swimsuit or costume and let’s go!

4. Deserted Beach Brunches

Every day we go to shore to explore an island, national park, beach, a hike, and much more. We might even have brunch beach days when we dinghy to shore with a cooler full of brunch goodies. Will the orange juice and champagne last to day 4 for our “Mimosa Brunch on the Beach”? That is the question and together we will live to learn the answer.

5. Navigate the Open Waters

Every morning as a captain and a crew, we will pull out our chart and compass and talk about where we hope to go that day, what we hope to accomplish (or not accomplish!), and how to get there. That is, we will set a course and work as a team to figure out how we get there. And you may just learn how heading into the unknown in life is much like following your true north on the sea.

6. Unsettled Knows How to Have a Good Time

The British Virgin Islands have seen a lot of good times, especially when the Unsettled crew sails in. Our relaxed and laid back “work hard-play hard” attitude journeys from one island to the next where we will celebrate life and one another.

7. Epic Costume Days

So an Unsettled pirate walks into a bar… Our founders and your captains have been seen captaining ships wearing coconut bras, unicorn tights, and glow-in-the-dark paint. We have also casually walked into island bars with 40 people from 18 countries all clad in neon outfits. What are we wearing this year?

8. Where It All Began

Unsettled was founded on a sailing trip through the British Virgin Islands in June 2014. This year you can experience for yourself the power behind this place and this trip. What could the open waters inspire you to dream up? You might be surprised to learn what a week of unplugged, close connections might bring.

9. Dreaming Under the Stars

Sharing your favorite poem or story with a crew of new friends under the Milky Way? Anything is possible. With clean air, the stars come out in spades. Without a skyscraper in sight, these nights are truly magical.

10. Unplug to Recharge

With the sole mission to sail from island to island and be present, for your crew and for yourself, the setting is ripe for rejuvenation. Recalibrate where you are and where you are heading. Embrace the unknown. Never settle.

Are you ready to get on deck?



Unsettled is a global community for those who live and work differently. 

Growth | Meaning | Adventure

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