Unsettled: Sailing

1 Week Out of the Office, Offline, and Offshore.

Sailing 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 throughout any day.

At Unsettled, 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.

Unlike anything you’ve experienced, an Unsettled sailing retreat is where you practice this to the 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….

Welcome to Unsettled Sailing.

Want to skip the details and apply now? Be our guest…

Upcoming Sailing Destinations…


MAY 14 – 21, 2021


JULY 10 – 17, 2021


OCT 30 – NOV 6, 2021

*Unsettled’s Updated 2021 Travel Policies & Precautions on our Sailing trips

No messing around: Unsettled is committed to returning back to travel, slowly, safely, and confidently.

We believe that when we all do our part, we can do anything together. This is, in fact, the very foundation of what it means to live Unsettled — to co-create a world of possibilities by working with a community of your peers. It’s how we’ve run 100% of all of our experiences to date, and it’s why we feel perfectly suited to return to travel starting today. 

Unsettled’s 2021 Travel Policies are found here and cover our updated policies on payments, transfers, and refunds. Our Travel Precautions can be found here, and these cover the precautions and requirements taken by both Unsettled and participants. Here is how they apply for our upcoming sailing destinations: 

  • Do your part: Get vaccinated. We strongly, strongly encourage all participants to get vaccinated at least two weeks before their trip start date. We will be doing so ourselves! We set our first travel dates of 2021 after assessing the pace of COVID vaccination distribution.


  • Do your part: Upon arriving at our location, all participants will be required to take and pass a COVID-19 test and show results before meeting up with our group. In Baja, tests are administered at the airport, and results are emailed to you with 30-40 minutes. By the time participants begin their experience, we will have confirmation that 100% of participants have tested negative for COVID before coming together as a community. Comprehensive information on getting these required tests in La Paz can be found here. Tahiti’s will be shared as we near our trip.


  • Do your part: All participants are required to mask up and social distance when we are outside of our community. All participants will be required to follow and respect local ordinance on wearing masks, social distancing, allowance of group sizes, etc. with no leeway given when we are in public places. In our departure port of La Paz, masks are currently mandatory and group size is limited to no more than six people in public places. Tahiti’s will be shared as we near our trip.

Unsettled will be doing our part as well.

  • We will share testing sites and update local ordinances.
  • We will stock the boats with provisions (food and drinks) ahead of time so there is no need for large gatherings 
  • Our trips will remain small.
  • Our cancelation and refund policy are more flexible than ever

You can read our latest precautions and efforts here.

When we all do our part, we can do anything together. At Unsettled, this has been a part of our foundational values since day 1, and we call it co-creation. This is what allows us to return to sailing! 

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 or go to shore to check out local scenes
  • 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
  • A shared berth. All participants will either need a COVID vaccine or a negative test administered in our location within 72 hours of departure. Consider bringing a friend or finding one to share a berth with via the Unsettled Global Community.
  • Docking and mooring fees, permits, route planning, water, fuel, and all of the logistics and planning to make this happen

*Provisions and alcohol are not included.


MAY 14 – 21, 2021
Unsettled Alumni: $1500 USD

Guests & New Unsettlers: $1800 USD
La Paz, Mexico


Sailing “the world’s aquarium” with Unsettled…

Baja California is a mountainous spine of land in Mexico separating the Sea of Cortez from the Pacific Ocean. It’s flanked to the west by the cool and rich waters of the Pacific and to the east, the Sea of Cortez (our sailing waters), which are warm nutrient rich waters teeming with fish and sea life like few places on the planet. 

With the well earned nickname, “The Mexican Galapagos” and what Jacques Cousteau called “the world’s aquarium”, it’s best known for its abundant sea life where a mars-like landscape meets deserted beaches and tropical waters.

This sailing trip is unique among even Unsettled’s trips in that it’s set in a complete wilderness area full of wildlife, natural beauty, quiet coves and anchorages, starry nights, and desolate places. This is a sailing trip for those who want an off-the-grid, offline, and offshore retreat surrounded by breathtaking nature.

Location Highlights… 

  • Sail around the famous Sea of Cortez, nicknamed “the world’s aquarium”
  • Explore desert islands, canyons with hanging fig trees, and empty beaches
  • Swim with sea lions and whale sharks in the wild
  • Fish for mahi-mahi and yellowtail and eat your catch right on the boat
  • Explore the coastal towns, islands, and small ports for an unforgettably authentic experience along Mexico’s coast 
  • Eat fresh tacos, while sailing in some of the world’s blue waters, with a cocktail in hand…

Trip Details:

Departure Location: La Paz, Mexico
Dates: May 14 – 21, 2021
Pricing: Unsettled Alumni: $1500 USD | Guests & New Unsettlers: $1800 USD
Arrivals/Departures: You will arrange your own flights to La Paz International Airport in Baja Sur (LAP) so that you arrive by the afternoon of Friday May 14, 2021. You will be able to depart starting at noon on Friday May 21, 2021.


October 30 – November 6
Unsettled Alumni: $2000 USD

Guests & New Unsettlers: $2400 USD

Apply Now

Sailing Tahiti: The Unsettled Adventure of a Lifetime.

MAEVA! Welcome to the week of your dreams: sailing through the Iles sous le vent, or the Leeward Islands.

Tahiti is known as the beating heart of Polynesia, partially because it is home to 75% of the region’s population and from the palpable energy you feel from how the volcanic mountains and tropical valleys meet the crystal clear lagoons of the South Pacific.

Our cruising grounds has some of the most spectacular landscapes in the world, including idyllic Bora Bora, as well as Raiatea, Huahine, Taha’a, and more. We will share drinks at the world famous Bora Bora Yacht Club, fish for Tuna making ocean passages between islands, and dive some of the best reefs in the world. We will be sailing in style, too, with state of the art catamarans as nice as they come.

If you’ve ever dreamed of a trip through the South Pacific, this is your chance.

Location Highlights… 

  • Anchor in Bora Bora’s world famous lagoon and sleep under the same stars that have guided passagemakers for centuries
  • Paddle board across the clearest water you’ve ever seen
  • Fish for Tuna, Mahi-mahi, and Bohar Snapper while sailing in the open waters between islands
  • Hike up some of the famous valleys that make up Polynesia or relax on sugar-white beaches
  • Meet Unsettled alumni from all over the world!

Trip Details:

Departure Location: Raiatea, Tahiti
Dates: October 30 – November 6, 2021 (bring your halloween costumes)
Pricing: Unsettled Alumni: $2000 USD | Guests & New Unsettlers: $2400 USD
Arrivals/Departures: You will arrange your own flights to Raiatea Airport (RFP) via daily flights from Fa’a’ā International Airport. You will need to arrive to our base on Raiatea by the afternoon of October 30. You can depart starting at noon on November 6 from Raiatea Airport (RFP) where you will transfer at Fa’a’ā International Airport.


July 10 – 17, 2021

Unsettled Alumni: $1700 USD
Guests & New Unsettlers: $2000 USD


*2021 Update: We are now accepting pre-booking for July 10-17, 2021!

Sailing The Greek Islands 

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.

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.

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!

Trip Details:

Dates: July 10 – 17, 2021
Departure Location:
Athens, Greece

More info TBA. Pre-Book your spot today!

Ready? Set? SAIL!

Join Unsettled Sailing!


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.