Unsettled: Sailing

30 Friends | 3-5 Sailing Yachts | 1 Incredible Week
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 Unstructured | Unbounded | Unexpected

Experiences that push you to live more.

At Unsettled, we travel to live differently. To redefine our routine. To create a space where we can challenge our comfort zone, and discover how we can each pursue growth, meaning, and adventure in our lives.

And unlike anything you’ve experienced, an Unsettled sailing retreat is where you practice living your fullest. For 7 days, you will learn how to sail and navigate our boats, cook meals as a family unit, and ask the deeper questions on this grand journey into the unknown….

There’s a reason you’ll find our founders on these trips. A reason why these sell out early…

Welcome to Unsettled Sailing.

30 to 50 crew of all ages and from all over the world, 3 to 6 boats, and one hell of an adventure. You will get close with your crew, learn the ropes of sailing, share stories under the stars, cook family style meals, and live every moment to its fullest. 

Want to skip the details and apply? Be our guest

Ready to join us? Upcoming Sailing Destinations…


Upcoming Dates TBA


Upcoming dates TBA

Baja California, Mexico

Upcoming dates TBA

Our Guiding Philosophy


We bring together artists and entrepreneurs, designers and developers, teachers and activists from over 80 countries, but when out on the water, it doesn’t matter much what you do, but who you are. Come sailing with Unsettled to simply be who you are.


In Baja, we sail into a true wilderness area. In the Bahamas, we snorkel the oldest coral reefs in the world. And in the BVI, we eat fresh lobster, dance by a beach fire, and ask introspective questions while crossing the Sir Francis Drake Channel. 


Each boat has a co-created purpose that guides this journey, and your are the chief inspiration officer, the minister of cuisine, or the navigator of the unknown. You spark the conversations, decide when to throw a dance party, and what time happy hour is.

The Unsettled Sailing Experience

In a typical day sailing with the Unsettled community, expect to:

  • Sail 4-6 hours each day, learning something new each day 
  • Have an easy going lunch under sail or at a beautiful beach pitstop
  • Anchor in the afternoon to go swim, to a beach, or just hang out on our boats
  • Explore uninhabited islands
  • Snorkel reefs or go hike on shore 
  • Host a dinghy race, costume party, and just goof off as much as you like
  • Cook family style dinners under the stars on your boat’s BBQ 
  • Host a party, poetry night, or inspirational happy hour
  • Build a beach fire on shore and open your wonderment to the starry sky
  • Sleep under the stars and wake up to do it all over again

What’s Provided

  • 6 days and 7 nights on a modern sailing yacht that’ll take you through national parks, secluded moorings, and beautiful seaports
  • A skipper on each boat, who happen to be Unsettled founders, staff, alumni and best friends, who guide you through this week
  • Docking and mooring fees, permits, route planning, and all of the logistics and planning to make this happen

*Provisions and alcohol are not included.
**$150 discount if you bring a friend (for both you and your friend).


Reschedule Dates Coming Soon
Unsettled Alumni: $1300 USD

Guests & New Unsettlers: $1600 USD

Apply Now

Sailing Greece: The Details!

Beautiful landscapes, secluded islands, Mediterranean cuisine, art, history, philosophy… the Ancient Greeks had it made when they were laying the foundation of Western Civilization a few thousand years ago.

In June 2020, Unsettled is heading back to the Mediterranean to soak up its summer sun, beautiful beaches, vibrant nightlife, and amazing food!  We have over 220 islands to choose from this week, and we are going to get as much of it in as we can.

We will sail Greece’s Cyclades Islands, and visit some of its most beautiful beaches, ancient villages, top party spots, and best dive sites. But with Unsettled, we always take it a step further. Imagine creating our own floating Unsettled society this week by adapting the foundations from Ancient Greece and exploring art, philosophy, food, and a much more mobile life in 2020.

Location Highlights… 

  • Sail among 220 islands in the Cyclades archipelago
  • Explore wild beaches and the relaxed, rural ambiance of European island life
  • Go out in some of Greece’s famous summer hotspots
  • Spend long days swimming in cobalt blue waters, drinking local wine, and eating fresh, local food
  • Discover impressive architecture, colorful buildings rising from the sea, and ancient sites
  • Meet Unsettled alumni from all over the world, as this trip is popular among our alumni!

Departure Location: Athens, Greece
Reschedule Dates Coming Soon
Pricing: Unsettled Alumni: $1300 USD | Guests & New Unsettlers: $1600 USD


We're going somewhere very special...

Details to be announced this coming fall. Stay tuned for one of our wildest and furthest adventures yet…


Are you interested in creating a private, custom sailing retreat with Unsettled? If you have a crew and you want Unsettled to create a one-of-a-kind, transformational experience on the water for your team, family, or friends, email us at sailing@beunsettled.co to learn how we can set one up in dozens of locations around the world for you.

"Inspiring" "Unforgettable"

An inspiring, unforgettable experience. I absolutely loved my time with Unsettled and still keep in touch with the amazing people I met there (with reunions in 6 countries so far!). 

-Colin Decker, Creative Director


It was an extraordinary experience, one that left me feeling affirmed, motivated and inspired. I’ve never experienced group travel in the way that Unsettled does it, and the co-curation of our time together made it so much more than just a trip.

-Shani Jamila, TED Speaker / Artist

"Life changing is an understatement"

-Rani El-Khatib, Managing Director of Dubai-based Creative Agency

"Break up the routine..."

If you’ve been wanting to break up the routine… give this experience a try. It just might prove to you that a totally new way to live is not just possible, but possibly right at your fingertips.

-Selena Welz, Senior Editor


I had some of the most interesting, raw, and enlightening conversations of my life at Unsettled. For those conversations alone, the Unsettled experience has truly enriched my life!

-Jaqui Pawson, Senior Analyst 

Why Unsettled?

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 misfits from over 80 countries who seek to replace routine with adventure in destinations around the world.

Our experiences are not itinerary-driven. Rather, we provide a platform for you explore, connect, and discover a new destination at your own pace. With a calendar full of events to choose from, local experts to connect you to the city, and a curated community to explore with, Unsettled is a shared experience for people who don’t do group travel.

Unsettled is a global community for those who embrace the unknown and value meaningful human connection. Our mission is to inspire a lifelong pursuit of growth, meaning, and adventure through travel and shared experiences.