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Vagabonde Adventures gives you the unique opportunity to sail some of the most epic locations with an experienced crew. Whether you’re looking for a holiday with friends and family, sail coaching to level up your skills, or American Sailing certifications, we can tailor the perfect sailing adventure to you.   

One of the purest forms of adventure is traveling by sail. Lifting your anchor and harnessing the wind to navigate to a new bay, a new island or even a new country - that is true freedom and we are inspired by it every day. 

Sail in Paradise

  • Five star reviews.

    I participated in a Greece flotilla week hosted by Vagabonde Adventures. My wife and I had a great time! Our boat came with a captain and chef, both were top notch. The itinerary was excellent, with stops in classic old harbours and also anchorages with plenty of time for swimming and snorkeling in that fantastic clear blue water. I would highly recommend a flotilla organized by this team, a 5-star experience all around! - Joel

  • Five star reviews.

    I did a performance week with Jack and Eta in Greece. They are incredible humans and taught me so much about sailing. The theory was easy to digest and the food was incredible too. So grateful for this experience! Everyone should do a voyage with these legends!! Thanks for having me on board guys. - Sanchia

  • Five star reviews.

    I had the best trip. Jack and Eta were superb organisers, and helped me with my first bareboat experience. I can highly recommend going on one of their trips, and I look forward to my next one. - Oliver

  • Five star reviews.

    Vagabonde Adventures is the best charter company. The experience they provided us in Greece was second to none. Best trip of our lives!! - Nick

  • Five star reviews.

    Love learning to sail and adventuring with Vagabonde Adventures! This was the best experience ever. 200% recommend! - Casey

  • Five star reviews.

    Jack is a fantastic skipper. Had a great experience. Always felt safe. - James

  • Five star reviews.

    Vagabonde Adventures is incredible. We joined the Greece Flotilla in the Saronic Islands and could not have had a better week full of sailing, exploring and meeting cool people from around the world. Whether you’re looking for a unique adventure to experience what living aboard a sailboat is like, or looking to take your seafaring up a notch, look no further. - Sarah

  • Five star reviews.

    Spent a week in Greece with the Vagabonde Adventures with Eta as our captain! She is AMAZING! They did a wonderful job communicating plans and options to the flotilla and taking everyone’s opinions into account. Jack and Eta make a great team, making the whole trip comfortable, relaxing, and so much fun!!! We’ll be joining them on their next flotilla! - Chris

  • Five star reviews.

    I am so grateful to the Vagabonde Adventures team for pulling together the adventure of a lifetime! Everything about this trip was truly incredible, from the location (Greece is just wow!) to the people, the delicious food, the talented and helpful crew who made this so relaxing and fun, and the amazing planning performed by Jack, Eta, and their support team. Thank you, thank you, thank you for the most epic trip. - Stefany

  • Five star reviews.

    I had the best time with Vagabonde Adventures. We spent our time island hopping, swimming, sailing and creating the best memories. I was so fortunate to have Eta as a captain. You'll want to live your life as a sailor after a week with her. Vagabonde Adventures create such a welcoming environment, we were safe the whole time and Eta let us be as hands on as we wanted when it came to hoisting the sails. - Nora

  • Five star reviews.

    We had the BEST time with Vagabonde Adventures! My husband and I did a couple Advanced ASA courses during the week. Jack and Eta were amazing teachers, sailors, cooks, tour guides and everything in between! - Ashley

  • Five star reviews.

    What an epic trip!! The crew is all-time. Jack & Eta are the best team. Both incredible sailors and instructors. I learned a ton throughout the week. Each day had a different adventure from snorkeling, spearfishing, cooking the fresh caught fish over a beach bonfire, just to name a few. We literally did a little bit of everything in just one week. - Billy

  • Five star reviews.

    Vagabonde Adventures is fantastic! Captain Jack and Eta are first rate sailors and hosts! Take a trip of a lifetime or learn the ropes for your bareboat certifications. You won’t be disappointed with Vagabonde Adventures!! - Patrick

We want to share the dream with you.