Upcoming Shared Trips
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Intermediate Sailing Course in the Bahamas | Nov 8–14
$9,950.00
Sold Out
Outremer 52 Demo Sailing & Training in the Bahamas | Dec 1-3
$2,800.00
Ladies Only Outremer Sailing Training in the Bahamas | Dec 4-6
$2,800.00

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Shared Sailing Trips & Sailing Adventures

Join Vagabonde Adventures for an unforgettable shared sailing trip aboard a performance Outremer catamaran. Our shared sailing holidays bring together like-minded travelers and sailors for a week of sailing, exploring, swimming, learning and adventure.

Whether you're an experienced sailor looking to sharpen your skills, a beginner wanting to learn the ropes, or simply looking for a different kind of holiday, our shared trips are designed to get you properly involved in life on the water.

Sail through the turquoise waters of the Bahamas, explore the islands of Greece and discover what makes performance sailing so addictive. With an experienced captain and American Sailing Association instructor onboard, selected trips combine cruising with hands-on sailing instruction, coaching and certification opportunities.

You don't need to arrive with a group. Book a cabin, join a crew of fellow travelers and spend the week sailing, exploring secluded beaches, snorkeling, enjoying local food and meeting people from around the world.

Your Questions, Answered

  • Yes! We open up new shared weeks once a cabin has been booked, so if the above dates don’t work for you contact us and we can plan a new week.

  • Yes! On week long trips with our expert American Sailing instructors you can earn certifications to charter your own boat. From beginner to advanced weeks, we have you covered.

  • Vagabonde Adventures is built around the sailing itself. We specialize in performance sailing aboard Outremer catamarans, with experienced skippers who encourage guests to get involved, learn, and experience what the boat can actually do. Our trips combine sailing, exploration, coaching and adventure rather than treating the yacht simply as transportation between anchorages.

  • No! Outremer cats are designed for families to sail around the world, so ease of use is extremely important. Sail handling is simple and smooth, and things are designed to work as they should. They can be sailed hard and are a lot of fun, but they can always be cruised easily with a small family.

  • We always endeavour to put together these trips with sailors of similar skill levels. That way you can all advance your skills at similar rates.

  • Eat, sail, swim, repeat! In general we wake up with a morning swim, share breakfast, go through a plan for a day, set sail for a few hours, anchor for lunch, snorkel a coral reef, and then sail to our final destination for the day. Spread throughout the day will be some theory learning, sailing maneuvers and drills. We’ll share dinner onboard or head to a local restaurant or beach bar. Relax with a sundowner and do it all again tomorrow!

  • 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

A white sailing catamaran with four people on board sailing in clear turquoise waters on a partly cloudy day.
A woman snorkeling underwater in a clear blue ocean, wearing snorkeling gear and a red bikini, reaching down towards the sandy ocean floor near a coral formation.
A sea turtle swimming over sandy ocean floor with coral and seaweed.
Woman snorkeling underwater with a yellow mask and fins, swimming over coral and rocks in clear blue water.
Sunset over a marina with boats docked along the pier, colorful houses, a lighthouse, and tropical trees.
A white sailing catamaran anchored in turquoise clear water with two people swimming nearby.
A woman holding a child while walking on the beach at sunset, with calm water and a distant shoreline in the background.
Group of people gathering on a wooden platform near palm trees and a beach, with coastal houses in the background during sunset.
A group of five friends enjoying a boat ride at a marina with sailboats and yachts in the background, smiling and wearing sunglasses on a sunny day.
Aerial view of a coastal island with houses, boats, and clear blue ocean waters
A tropical beach scene with turquoise ocean waves, white sandy beach, and a line of palm trees along the shoreline under a partly cloudy sky.
Aerial view of a beachside neighborhood with houses, palm trees, sandy beach, and ocean under a partly cloudy sky.
A coastal scene with rocky shoreline, waves crashing, sandy beach, and houses among palm trees, with a marina and boats in the background under a cloudy sky.
Aerial view of a tropical beach resort with a sandy beach, turquoise water, palm trees, houses, and a dock with boats.
A waterfront scene at dusk with a wooden pier extending into calm water. There are houses on stilts along the shoreline, surrounded by palm trees and greenery. The sky is pastel-colored with clouds, and a sculpture of a fish is visible in the foregro
Aerial view of a coastal marina with boats docked, a lighthouse, a small island, and buildings surrounded by water at sunset.
Aerial view of a coastal landscape with a boat parked in a shallow, clear turquoise bay, adjacent to a sandy beach and dense green vegetation, with the ocean in the background.
Aerial view of a tropical marina with small boats docked, surrounded by lush green vegetation, sandy beaches, and ocean waves, under a partly cloudy sky.
A sailboat floating on the turquoise ocean with clear water.
A group of five friends on a boat in the water, enjoying a sunny day. They are wearing casual summer clothes, some with hats and sunglasses, and are engaged in conversation and activities on the boat.
Group of people enjoying a sunset on a boat, with water and a distant ship in the background.
Four friends stand on a wooden dock with a sign that reads 'Grabbers' over a beach and water. They are holding drinks and smiling, with one person looking at their phone. The scene takes place during daytime with partly cloudy skies.
Three people on a small motorized boat in a calm body of water during sunset, with a distant island and several sailboats on the horizon.
Three people on a wooden dock at sunset, with a boat nearby. One person is in the boat, and two are on the dock, one helping the other to step down from the dock.
Group of people gathered under a wooden beach shelter, with flags hanging from the roof. One person is seated at a table with a can, and standing nearby are two men holding drinks, engaging in conversation.
People sitting on the beach around a campfire at night.
Group of seven people and a young child on a boat at a marina, with sailboats and yachts in the background, enjoying a boat ride on a sunny day.
A white yacht sailing on calm, clear blue water with a partly cloudy sky and distant shoreline in the background.
Smiling man wearing sunglasses, a striped shirt, and a sunhat grilling fish on a beach outside. Beach with white sand and water in the background, decorated with hanging buoys and a Bahamian flag.
People enjoying a beach day with boats in the water, some standing in shallow water and others sitting on an inflatable boat, wearing swimsuits, hats, and summer clothing.
People relaxing and socializing on a sandy beach with a colorful beach umbrella, some sitting in the water and others standing or walking near a makeshift wooden structure decorated with lanterns, against a backdrop of leafless trees and green bushes
Woman with sunglasses playing guitar under a colorful striped beach umbrella on the sand with people listening nearby
Two men wearing sunglasses on a boat, smiling and giving a thumbs-up, with a body of water and distant land in the background.
An aerial view of a sailboat anchored near a rocky shoreline with clear turquoise water. The boat is tied to a smaller boat on the shore, surrounded by greenery and rocks.
Six white sailboats docked side by side in a small, turquoise bay surrounded by rocky, hilly terrain with sparse greenery and a faded building on the right.
An older man with gray hair sitting on a boat, smiling and relaxing with a beverage in hand.
Two white sailboats with large sails sailing on calm blue sea against distant mountainous islands under clear sky.
People enjoying a sunset in a lake, some on inflatable floats and others with drinks, with mountains and sailboats in the background.
A table filled with various breakfast foods including a large fruit bowl with grapes, oranges, kiwi, and berries, a loaf of bread, a slice of cake with nuts and dried fruit topping, a bowl of yogurt with bananas, strawberries, blueberries, and chia s
Aerial view of a line of seven white sailboats anchored close to a rocky shoreline with clear turquoise water.
A man with a beard, sunglasses, and a beige cap steering a boat at sunset with mountains visible in the background.
A catamaran sailing on the ocean with a colorful sail featuring red, white, and neon green stripes, and a landmass in the distance under a cloudy sky.
A white sailboat with black and gray sails on the open ocean, approaching a distant mountainous coastline.
A shirtless man on a boat during sunset, surrounded by water, with a pile of colorful sails or fabric on the deck.
A white sailing catamaran with black trim on turquoise waters during cloudy weather
A white sailing catamaran with a large purple sail gliding on clear turquoise water under a partly cloudy sky.
A woman sitting cross-legged on a sandy beach, wearing a yellow bikini, smiling, with rocks and greenery in the background, near the ocean.