Exumas, Bahamas·January 22 - 29 2022

Unsettled Sailing: Bahamas

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1 week out of the office, offline, and offshore.

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. Unsettled Bahamas departs from the most accessible island of Nassau, where we will gather on land for one night to plan our week of sailing through the islands known as the Exumas for the next 7 days and nights. This is a true gem among our sailing destinations. It may have the clearest water, whitest beaches, and some of the best island-hopping-vibes on the planet.

Retreat Overview


Exumas, Bahamas


1 week


From $2000

Upcoming Trips:

January 22 - 29 2022

Join Unsettled Sailing: Bahamas

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 this retreat with like-minded peers who hold a wealth of experience far deeper than just their careers and join our growing community of Unsettled alumni spread out over 80 countries around the world.

Read what Unsettled alumni are saying about their experience.

This experience is about you. It’s about taking an intentional break from your routine, finding new perspective, building new relationships, growing new ideas, and exploring with intention among an incredible backdrop of people and place. We provide housing, workspace, and an unforgettable experience filled with regular dinner parties, peer-to-peer workshops, happy hours, and excursions.

Unsettled Sailing: Bahamas Highlights



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



The whole week is an adventure thanks to the paddle boarding, snorkeling, spearfishing, sport fishing, and island exploring. Even our die-hard adventurers get enough!



Eating together is always a highlight, whether it's that lobster we just speared or fresh Mahi-mahi. We eat well.



The only screen you'll have to look at this week is the GPS. Kickback, let loose, and unwind.



Life is better on a boat. Pick your favorite playlist, put your toes in the water, and you'll love living on a boat.

A Day In The Life




A Typical Day

  • Sail 4-6 hours each day, learning something new each day
  • Go paddleboarding, snorkeling, spearfishing, or troll fishing 
  • 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, caves, or go to shore to check out local scenes
  • Host a dinghy race, costume party, and just goof off as much as you like

A Typical Evening

  • Go on a sunset sail to test your new skills
  • Host a costume party or 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 onshore and open your wonderment to the starry sky
  • Sleep under the stars and wake up to 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 national parks, secluded moorings, and beautiful seaports

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 happen to be Unsettled founders, staff, alumni and best friends, who guide you through this 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...


Being Unsettled for the last 30 days has felt liberating. It’s about opening up to a whole range of new possibilities, saying yes to new experiences, and not setting expectations that limit your growth.

Rima Bazzi | Entrepreneur & Coach


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 Mohale | 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 Anand | Freelance Journalist & Digital Content Creator

Our Team

Captain Youngblood

Captain Youngblood

When you have a last name like Youngblood, you're destined to be the captain of a pirate ship. Michael started sailing when he was in high school, on a beat-up Catalina 22 he bought with his dad for $1,000. Over the last 20 years, he's sailed thousands of nautical miles across 5 continents/seas and has run every Unsettled sailing trip since 2014.

Captain Kalan

Captain Kalan

Jon Kalan was sailing across the Atlantic Ocean with his dad in elementary school! He's sailing on multiple oceans and lives within a few steps of one. He's an avid spearfisher, and as soon as the sails are down and the boat is anchored, you can find him catching dinner for his crew. 


Read More on Unsettled Sailing: Bahamas


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.

It varies each day. Typially 3-6 hours per day. We sleep at anchor each night and do not sail at night.

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 go shopping as a group and split the bill among the boat.

 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 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.

Most people on an Unsettled retreat are professionals with multidimensional personalities and vast interests. 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 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.

Deposits are fully refundable up to 60 days before the start date of your trip. Your spot is held as soon as you make your payment. Final payments are due no later than 60 days before your retreat's start date. You can transfer your credit to another trip (within 6 months) one time, up until 45 days before your trip start date. 45 days before your trip's start date there are no refunds or transfers. However, if Unsettled postpones the trip, your full payment amount will be credited and available for you to use up to 1 year from your trip start date.

Unsettled Sailing: Bahamas

Bahamas· January 22 - 29 2022· 1 week


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