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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

  • Five star reviews.

    Truly one of our best family vacations. My family of 8 sailed through the Abaco Islands. We hired Mackensie as our chef which was one of the highlights as we are all foodies. The meals & drinks she prepared were 10/10, Delicious!!! Eta was our captain & could not have been more accommodating, especially w/ an 18 month old on board. She went above & beyond daily for us & handled any challenges on board as a true pro. We will definitely use Vagabonde Adventures again & would highly recommend them to anyone looking for a great family vacations. - Shannon

  • Five star reviews.

    Jack with Vagabonde Adventures is a fantastic teacher and Captain! My husband and I enjoyed a week in the Abaco Islands from crossing the Whale to Manjack Cay to Hope Town to Little Harbour to receive our ASA 114 Cruising Caterman certification (me) and ASA 106 Advanced Cruising certification for my husband. Jack provided us the best experience in learning to sail a beautiful performance catamaran! Not only was it fun, but it was also educational and a confidence booster for us to sail the Abaco Islands in the VERY near future! Thank you, Jack! We look forward to seeing you in Annapolis! - Michelle

  • Five star reviews.

    Expect a 5-star experience with Vagabonde Adventures! You will not be disappointed. My wife and I enjoyed a fun and relaxing week with Jack and Vagabonde Adventures cruising the Bahamas' Abaco Islands. Jack was very communicative throughout the registration process and leadup to our arrival. Jack is a great teacher and coach. My wife earned her ASA 114 (American Sailing Association Cruising Catamaran Certification) and I earned my ASA 106 (American Sailing Association Advanced Coastal Cruising Certification). The Abacos island chain is a sailing paradise. Jack, an expert guide, knows his way around all of the islands and cays. We loved the island rhythm, soft white sand, secluded waters, and no-frills restaurants and bars. Don't forget to try a Goombay Smash, the Bahamas' most famous drink! - Tom

  • Five star reviews.

    After spending a week with Vagabonde Adventure in Croatia last summer I was pretty sure nothing can beat that experience. Boy, was I wrong! We had a mind blowing week in the Abacos on the Bahamas late January. Alone sailing the Outremer 45 has already made my holiday and snorkeling the coral reefs, seeing sea turtles, sea rays, sharks in the crystal clear waters will make this experience unforgettable. My favorite moment was our dinner barbecue on an empty beach on the island Tilloo. Thank you VA for this great organization, sailing lessons and guidance during our first sail in the Bahamas ❤️ - Zoran

  • Five star reviews.

    This was absolutely one of the best family adventures we’ve ever had. I highly recommend Vagabond Adventures. We took our family, son 17 and daughter 14, to get sailing licenses with them in the Bahamas and it was bucket list dream come true for all of us. The perfect blend of sailing and vacation for the whole family. We had Jack as our Skipper/instructor and his passion for sailing and teach was evident in everything he did.

    If you’re even considering sailing or chartering a boat with them you can’t go wrong. We will for sure be sailing with them again. - Chad

  • Five star reviews.

    Sailing for 7 days in Greece on a catamaran exceeded every expectation I had of a vacation. The views in Greece are simply breathtaking—it’s beauty like nowhere else. One of the highlights was connecting with a group of incredible people from all over the world, each with unique stories that inspired me to embrace more adventure in my own life.

    A huge thank you to @mariellethetraveler for treating us to the most gorgeous and delicious meals and to @vagabondeadventures for guiding us through the best of sailing life. Your passion for sailing is truly contagious.

    From epic hikes and rock jumping to daring tricks off the boat—coming home with a few bruises was totally worth it! The cooking competition (which we won, thanks to @ulbirds23!) and the costume contest (yes, also champs 😂) just added to the nonstop fun. Every moment was a blast. Already dreaming of the next adventure! - Kristin

  • Five star reviews.

    Jack and the Vagabonde Adventures team are amazing! The catamaran sailing trip was amazing, perfectly planned out, they are absolute professionals at what they do. We went to the most beautiful places and always felt safe and taken care off. The highlight of the trip was watching a movie on the sails with the moon and the stars above, incredible! I can’t wait to do a sailing trip with them again soon!! - Simon

  • Five star reviews.

    You will not regret going with these guys! Professional, personable, and most importantly so much fun!! My partner and i have done several trips with Vagabonde Adventures and they have exceeded expectations every time! - Igor

  • Five star reviews.

    Book it already!!! These guys take experiential travel to a fantastic level, it’s so much more than just a sailing holiday. Food, history, nature, culture and community all delivered in perfect amounts. You’ll come away having made some travel pals for life. - Simon

  • Five star reviews.

    We had a blast sailing around Greece with Jack, Eta, and the whole Vagabond Adventure crew. Great days spent sailing, hiking to picturesque cliffs, eating beautiful meals together, and getting to know fellow travelers. Plus movie night on the jib! Would highly recommend! - James

  • Five star reviews.

    My partner and I LOVED sailing around Corfu, Greece with Vagabond Adventures. Eta, our skipper was fantastically adept at navigating us to the most amazing spots, and Mia, our chef, took care of us with delicious food and drinks. Jack is also great at organizing and making sure everyone has a great time. It was especially nice having a cabin and bathroom all to ourselves on our 42 foot catamaran. We couldn’t have imagined a more perfect 7 day holiday! - Rachel

  • Five star reviews.

    Fantastic experience. The crew really made it a great trip! - Jade

  • Five star reviews.

    I just returned from the Greece Flotilla with Vagabonde Adventures, and it was an experience of a lifetime! From the moment we set sail, the crew’s professionalism and passion for sailing made the trip both exhilarating and relaxing. The islands we visited were breathtaking, and every stop was well-thought-out. The combination of adventure and serenity was perfectly balanced. Whether you’re an experienced sailor or a beginner, they cater to all levels. I highly recommend Vagabonde Adventures for anyone looking for an unforgettable sailing vacation! - Antonis

We want to share the dream with you.