Athens, Greece·August 24 - 31 2024

Unsettled Sailing: Greece

Join Now

Embrace the Unsettled Life in Greece!

Set sail on an unforgettable adventure with Unsettled: Greece, departing just outside of Athens. From August 24th to 31st, 2024, we invite you to embark on a 7-day and 7-night sailing adventure through the Greek Islands, home to sailors, adventurers, and life explorers for centuries. Picture this: A week of pure bliss along Greece's mesmerizing coast, where sun-drenched islands beckon with their timeless charm, vibrant culture, and crystal-clear waters. Now throw in a couple of dozen Unsettlers from around the world, hosting pot-luck dinners on our yachts and throwing toga parties into the night. Only to wake up, paddleboard, sail, swim, and explore new islands. Time is of the essence, prices increase: On June 1st, prices increase by $100 USD.

Retreat Overview


Athens, Greece


7 nights


From $2450

Upcoming Trips:

August 24 - 31 2024

Join Unsettled Sailing: Greece

The Unsettled Experience

From time to time, you'll hear us say, "The Unsettled Experience”. Here's what we mean by that:

Unsettled does more than guide people down a trail in the wilderness. 

Before you ever hop on a plane, we meet online (in the interactive Unsettled style) and walk through an adventure-inspired workshop. 

While you're on your trip, we have a series of dinners and discussions designed to guide you on a unique journey. The goal is to get you to step outside of your routine, expand your perspective, and articulate what calls you, inspires, and engages you in this world. 

Many alumni say continuing the purpose-driven journey through our workshops and community engagement is the best part. As an Unsettled alumni, you can join our quarterly meetups and workshops online with our community from around the world.

Unsettled Sailing: Greece Highlights



The food and wine are plentiful and delicious. We stock our boats with Greek specialties, including traditional sweets and fresh, locally-sourced food.



The whole week is an adventure: paddle boarding, snorkeling, sailing, water sports, beach games, and much more.



Life is better on a boat. Pick your favorite playlist, put your toes in the water. You're going to love living on a boat.



The evenings on an Unsettled sailing trip are magical. Some nights we enjoy the cool breeze and relax on the boat. Others we go to shore for a local Greek restaurant. And some nights there are no plans and we just let it all unfold in the flow of night.



As if Unsettled sailing trips weren't mythical in their own rights, imagine this unfolding in the Greek Islands. We stop at our favorite historical site in the isles, throw toga parties, and relax like Greek gods.

A week in the life




A Typical Day

  • Sail 4-6 hours each day, learning to navigate, sail, drop anchor, and much more!
  • Wake up to snorkeling, paddleboarding, sunbathing, and beach games.
  • Enjoy an easy-going lunch under sail or at a local restaurant on an island.
  • Anchor in the afternoon for a swim, visit a local beach, or hang out among the boats
  • Explore local islands, beaches, vineyards, and nightlife
  • Host a potluck dinner on boats, throw a costume party, or make a cocktail happy hour

A Typical Evening

  • Go on a sunset sail to test your new skills
  • Cook family-style dinners under the stars on your boat’s grill 
  • Take an evening walk through a Greek town and stop for some local wines
  • 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 Croatian seaports, national parks, secluded moorings, and famous night life

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 is a local guide, teacher, instructor, and your best mate

Docking and mooring fees, permits, route planning, water, fuel, and all of the logistics and planning to make this happen

Shared berths (boat speak for bedroom). Share with a member of the Unsettled Global Community or bring a friend along

6 breakfasts and 6 lunches on the boat

A paddleboard or kayak on each boat, snorkels and fins, and stops at all the fun places along the way!

*Not included: Your flights, travel insurance (required) meals on shore, alcohol, and dinners (they are split among crew; see FAQs)


We recommend arriving/departing in Athens, Greece. Our base is located about 30 minutes from the Athens International Airport. 

Aim to arrive at the Athens airport no later than 2 pm on Saturday, August 24th.

You can depart anytime on Saturday, August 31st, but we suggest scheduling flights for 11 am or later. 

It varies each day. We spend about 3 to 5 hours sailing per day. 

That amount of time allows everyone to be hands-on and learn, and it gives us just enough time to move from one place to another. Our goal is to see several islands this week. We want to visit the beaches, historical ports, and remote coves! 

We sleep at anchor, on the boats, each night, usually 100 - 200 meters from shore.

Nope. 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. From there, every night is different - some nights we go out in the towns for a drink and others we enjoy the stars and moon from the boats. 

Most people on an Unsettled retreat are mid-career professionals with 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.

Please see our latest updates here

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. 

Unsettled loads the boat with breakfast, lunch, and snacks. 

As a crew, you will plan and organize dinners. Themes and all. Usually, two crew members from the same boat pair up and plan one dinner. You'll go to the store, shop for what you need, and split the costs evenly among the crew. Plan to pitch in around $75 for dinners. 

You also have opportunities to eat at amazing local restaurants. We suggest another $200 if you plan to eat and drink out during the week.

Alcohol is not included. It's organized and costs are split among the crew.

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.

Unsettled Sailing: Greece

Greece· August 24 - 31 2024· 7 nights


Get Unsettled. Straight To Your Inbox.

Drop us your email and we'll keep you posted with news, fresh stories, exclusive trip updates, and special offers. Don't worry. We hate spam as much as the next person, and respect your privacy.

Unsettled’s Updated Travel Policies & Precautions