Scrub Island, Virgin Islands, British·December 10 - 17 2022

Unsettled Sailing: The British Virgin Islands

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Live Unsettled. Play Unsettled. Sail Unsettled.

In June of 2014, Unsettled was founded on a life-changing, friends-only sailing trip through the British Virgin Islands. We know these waters better than anywhere, and there's a good reason we keep coming back. The wind is consistent. The water is beautiful. The locals are friendly. The drinks are cheap, and the conversations rich. Sailing with Unsettled in the BVI's is not just a time to unwind, though we do plenty of that. It’s about navigating through the unknown to new destinations, and showing up with an adventurous mindset every day. We get on the water to redefine our routine. To challenge our comfort zone, and discover how we can each pursue growth, meaning, and adventure in our professional and personal lives. For 7 days, you will learn how to sail and navigate our boats, cook meals as a family unit, stop at some of the BVI's most famous anchorages, islands, snorkeling spots (and even the weird, local bars famous around the world), and ask the deeper questions on this grand journey into the unknown.... Ready to meet a new crew from around the world, and set sail on the adventure of a lifetime? Get on board quickly - this trip always sells out fast!

Retreat Overview


Scrub Island, Virgin Islands, British


7 nights



Upcoming Trips:

December 10 - 17 2022SOLD OUT

Join Unsettled Sailing: The British Virgin Islands

The Community & Experience

Unsettled is a community for those who refuse to settle in their pursuit of growth, meaning, and adventure. We bring together creatives, entrepreneurs, artists, freelancers, and the intellectually curious who seek to replace routine with adventure. You will share the adventure of a lifetime in the BVI's alongside a curated group of peers who hold a wealth of experience far deeper than just their careers, and join a growing community of Unsettled alumni spread out over 80 countries around the world.

Read what Unsettled alumni are saying about their experience.

Unsettled Sailing: The British Virgin Islands Highlights



The whole week is an adventure: paddle boarding, snorkeling, sailing, water sports, beach games, and plenty of surprises along the way!



A new island every day. That's our motto in the BVIs. We will hit every major (and a few little!) island this week, and then some!



Take the helm! Really, plan on actively sailing the entire week. You’ll be hands on this week, whether it’s your first time or you’re an expert.



We have designated parties on certain nights along the way. That way you know which costumes to bring, and have peace of mind that some nights are relaxed and on others we let loose.

A week in the life




By Day....

  • Sail 4-6 hours each day, learning to navigate, sail, drop anchor, take the helm, and much more.
  • Wake up to slow mornings of snorkeling, paddleboarding, shared breakfasts, beach hangs, and games.
  • Have an easy going lunch under sail or at a beautiful beach pitstop.
  • Anchor in the afternoon to go swim, explore uninhabited islands, go for a hike, or just relax out on the boat with friends.
  • Host a dinghy race, costume party, and just goof off as much as you like

By Night...

  • Go on a sunset sail to test your new navigation skills
  • Host a costume party, themed dinner, poetry night, or inspirational happy hour
  • Cook family-style dinners under the stars on your boat’s BBQ 
  • Build a beach fire on shore and start a dance party
  • Sleep under the stars, wake up, and do it all over again

What's Included

Unsettled provides...

6 days and 7 nights on a modern sailing yacht that'll take you through BVI seaports, national parks, secluded moorings, and famous nightlife

A fully dedicated team of experience leaders and local experts who challenge your perspective and support your exploration, growth, and adventures.

A skipper on each boat, who happens to be one of Unsettled's founders, staff, alumni, or best friend, to guide you through the week.

Docking and mooring fees, permits, route planning, water, fuel, and all of the logistics and planning to make this happen

Paddleboards, snorkels and fins, fishing equipment and instruction, and much more

Shared berths (boat speak for bedroom). Share with a member of the Unsettled Global Community or bring a friend along

Sailing Bahamas

The Unsettled Adventure of a Lifetime.

The Exumas is an island chain made up of 365 cays (islands), one for each day of the year. We spend one week exploring as many of them as we can. We will snorkel a dozen reefs, explore uninhabited beaches, and swim with nurse sharks and even pigs! 

Sailing Bahamas

What Our Community Says...


BVI was inspiring and energizing. We danced a lot. Sailing everyday is good for the mind and playing was great for the body. The Unsettled Team were amazing at inviting people to be fully present and immersed in the experience!

Alexi Coffey | Founder, Luna Labs & Ovary


An Unsettled trip is like venturing into the unknown. You have no idea how the experience or people you’ll meet will be… but that unknown proved to be a very rewarding experience. You’ll leave Unsettled richer. Richer in the memories you create and the connections you make. Worth every minute.

Lesibane | Creative Director at Ogilvy & Mather


I met 29 incredible people from all walks of life, and found a little part of me in all of them. These people were intelligent, witty, bloody smart, beautiful, adventurous, hilarious, and full of joy. 

Shitika | Marketing Lead & Content Producer

Read More on Unsettled Sailing: The British Virgin Islands


Our base in the BVIs is on Scrub Island. We recommend flying directly into Beef Island Airport (EIS), which is a 5-minute taxi and 5-minute ferry ride to our base. It's typically worth the additional costs over flying into the US Virgin Islands (USVI). The more adventurous travelers can fly into the USVI via STT and connect to Scrub Island via taxis and ferries. Our marina is one of the more beautiful ways to start your adventure, and you can take advantage of the pool, spa, and many amenities on site.

It varies each day. The actual sailing time is typically 3-5 hours per day, so come prepared to be involved! We sleep at anchor, on the boats, each night, usually 100 meters from shore. There's plenty of time for swimming, snorkeling, and relaxing on the beach in between sailing.

No! Most participants do not have any sailing experience, and many get to learn on the trip as it is a very hands-on experience!

We recommend arriving vai Beef Island Airport (EIS) and making your way to the marina by 3pm on December 10th. We will share exact arrival instructions once you sign up.

We anchor the boats in the calmest coves we can find. We anchor before sunset so we can relax, debrief, enjoy a happy hour toast, cook, and eat dinner. We plan 2-3 "party nights" where we can let loose and have fun, and on other nights we have family-style meals, star gaze, and sip our favorite drinks in paradise.

Most people on an Unsettled retreat are professionals who are emotionally intelligent, have many hobbies, and are curious and passionate about life. This isn't a post-college party trip. Our average age of participants is mid 30's to mid 40's, but we've hosted folks of all ages. Living Unsettled is truly ageless.

We've hosted CEOs and entrepreneurs, artists and experience designers, and people who are active, even experts, in everything from transcendental meditation to CrossFit, from Bikram yoga to kiteboarding, and from diving to flying. On any given day, however, most of us are content hanging out with each other, exploring new places and trying new things.

Since thinking big about our work and careers is one of the organizing principles of Unsettled, many participants are high achievers who organize major conferences, run businesses, or are even recognized experts in their field. We have a lot of designers, developers, entrepreneurs, and startup enthusiasts on our trips.

All of this being said, it's not required to be working on something or have a "professional CV" in order live Unsettled with us. Many joining us are retired, taking a sabbatical, or deciding what comes next in life and looking for some inspiration.

At Unsettled, we truly focus on building retreats full of dynamic people who have much more to offer to the group than just work experience. These experiences are social by definition, and so one of our main qualifications is to look for people who share some simple principles:

  • Open to spending time with people from different cultures with different value sets
  • Curious about the people and the world around them
  • Considerate of others
  • Basically, as long as you're not an asshole, you'll fit right in.

Please see our latest updates here

You'll be assigned to a boat and captain about a week before your trip. Your captain will reach out before the trip to gather info on what you'd like to cook, prep, and eat for the week. We will order provisions and have them delivered to our boats. Shopping usually comes to around $250 per person for all you can eat and drink on the boat for a week. You also have opportunities to eat at amazing local restaurants. We suggest another $200 if you plan to eat and drink out during the week.

The boundaries between work, life, and travel are becoming blurred, fundamentally changing how we live today. Unsettled brings together groups of travelers and professionals from around the world for uniquely co-created experiences. Each one-week, two-week, or one month retreat is designed to break your routine and inspire a renewed sense of growth, meaning and adventure through transformational travel and peer-to-peer learning.

Whether you're working full time, or going through an intentional career transition, our retreats are designed to help you break out of your routine and explore a new destination with an incredible group of peers.

Unsettled Sailing: The British Virgin Islands

Virgin Islands, British· December 10 - 17 2022· 7 nights


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