What are our sailing trips like?

We sail for the adventure. For the sunsets and sunrises. For the costume parties and the family-style dinners. To disconnect, and to connect with travelers from around the world. We sail to be close to nature and to share meaningful moments.

Upcoming Trips:

Greece: August 24 - 31, 2024

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How "hands-on" is the sailing?

As much as you want! We love teaching and giving you the helm. Be ready to steer, raise the sails, learn to tack, drop anchor, and much more! There are no passengers, we're all crew!

"Can we anchor with a sunset view?"

Yes, this happens to be our specialty.

How does food and drinks work on our boats??

So much of this trip is a collaboration, especially for food and drink. You'll host happy hours, hors d'oeuvre, and family-style dinners. We venture to land for vineyards, distilleries, and hole-in-the-wall beach bars. We make lots of coffee in the morning, make quick and easy lunches, and we all pitch in to make family-style dinners under the stars.

Sardinia Sailing Winery with Solo Travelers

What activities do we do during the week?

These are active trips! Within a 3-4 hour span, you might find yourself sailing, snorkeling, kayaking, standup paddleboarding, hiking, and exploring new islands. We sail about 3-4 hours each day, which leaves lots of time to relax, swim, snorkel, and yes, we go to land to explore most days on our trips!

Go Kayaking on our sailing trips in Tahiti

Snorkeling on a sailing trip with Unsettled

Join a sailing trip in Tahiti with Unsettled

Who joins these trips?

We typically have 1 to 2 boats per location, and 7 - 8 participants per boat. Unsettlers come from around the world. Diversity is who we are - participants help us build our inclusive and diverse community. Our average age is 35 to 55 'ish' and most people come on their own. The community comprises of entrepreneurs, solopreneurs, and creative, legal, and nonprofit professionals.

What does day 1 look like?

You've just flown across the world and arrived in paradise. Now what?

On arrival day, expect lots of hugs, an orientation to your trip with your captain, a big shopping trip to load up your boat, your first sunset, and lots of new friends!

Upcoming Sailing Experiences

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Saint Vincent and the Grenadines

6 - 13 April 2025

The Windward Islands

The Idyllic Caribbean Sailing Week

FREE

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Ready to join us?

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What Does Sailing With Unsettled Feel Like?

Sailing with Unsettled is an immersive adventure, where you'll immerse yourself in a community, a beautiful destination, and personal growth.

If you bring the right mindset, it'll be a platform for profound experiences, with just enough structure to guide you.

During an Unsettled Sailing trip, anticipate a week full of sailing (yes, you're actually sailing), swimming, paddleboard... But mostly, expect adventures of the mind; of growth; and wonderment.

While we explore some of the most beautiful waters in the world, these trips aren't sightseeing experiences. Dive into conversations about life, savor family-style meals, and toast to new friendships during happy hours.

This is an opportunity to craft memories, share stories, and create unforgettable experiences with amazing people.

So how do they feel? They're completely unsettling -- and they'll shake up your routine and perspective in life more than you ever imagined.

Next Sailing Departure: Greece: August 24 - 31, 2024.

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