6 Days. 7 Nights. A Dozen Islands. A Gang of Pirates. Countless memories. And one question: 

Are you in?


On a tiny caribbean island at 3am, with a dash of rum and a two-story campfire, Unsettled was born. Thirty friends had gathered from a dozen countries for a self-supported sailing trip that would become the foundation for a remarkable set of shared experiences. 

Now, it's time to go back to our roots. We're taking a break from work to be our own skippers, sailors, cooks, bar tenders, pirates, and pranksters. Welcome to some of the best that Unsettled has to offer. Welcome to Unsettled Sailing Expeditions. 


The Experience

In a typical day, expect to:

  • sail for 4-6 hours each day
  • form a floating raft party in the afternoon with the other boats in our fleet
  • visit 500 year old seaports and explore uninhabited islands 
  • swim in crystal clear water, snorkel reefs, and sunbathe on beaches in a national park
  • have dingy races, costume parties, and goof off as much as you want 
  • cook family style dinners on your boat's BBQ with your crew, under the stars and under anchor
  • host a party, poetry night, or invite other boats over for a game
  • sleep under the stars or in your cabin and wake up to do it all over again

Ask anyone who joined us in the past few years, and they'll tell you this is not a trip to miss.

What’s Included?

  • 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 are also our friends and community members, who guide you through this week
  • Docking and mooring fees, permits, route planning, and a lot of logistics to make this happen

*Provisions and alcohol are not included. 

The Dates

Future dates TBD, but likely November - December 2017.