Upcoming Shared Trips
Make new friends | Learn new skills | Join the adventure

Shared Trips

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Intermediate Sail Training | Nov 8-14 | Abaco Islands
$9,950.00
Outremer 45 Demo Sails | Dec 1-3 | Abaco Islands
$1,900.00
Outremer 52 Demo Sails | Dec 4-6 | Abaco Islands
$2,200.00

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What People Are Saying

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

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

Captain Jack was one of the most kind, personable, and professional captains we’ve ever had the pleasure of sailing with. From the moment we stepped aboard, he made us feel completely taken care of — genuinely invested in making our experience perfect. He let us shape our trip, tailoring everything to fit our style and pace rather than following a rigid itinerary. The boat itself was absolutely immaculate, a true reflection of the pride and care he puts into his work. He went above and beyond in every sense, and we would sail with him again in a heartbeat — highest recommendation!​​​​​​​​​​​​​​​​
- Kristin

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! With our expert American Sailing instructors you can earn certifications to charter your own boat. From beginner to advanced weeks, we have you covered.

  • Outremer catamarans are the pinnacle of the performance/cruising catamaran market. Race boat speeds while relaxing in luxury and comfort. Combined with our expert crew, this is the best way to experience sailing for the whole family. Our crewed catamarans have

  • 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!

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.
Beach scene with people gathered under a large blue and yellow Bahamian flag, with a black triangle and yellow stripe, near leafless trees, with clouds in the sky. Some people are standing and talking, others are at a table with decorative lanterns,
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.
Two men wearing hats and sunglasses preparing food on a table outdoors at the beach, with fishing floats hanging from a wooden structure and a blue sky with clouds in the background.
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.
Aerial view of a tropical beach with turquoise water, anchored sailboats, rocky coastline, green vegetation, and distant mountains under a partly cloudy sky.
Tropical beach with white sand, large boulders, turquoise water, green vegetation, and palm trees under a blue sky.
A person snorkeling in clear turquoise water with large rocks and palm trees on a tropical beach under a blue sky.
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.
Two people relaxing on a boat deck over the water; a man with a beard, sunglasses, gray hat, and casual clothing reclines with one knee bent and his head propped on his arm; a woman with sunglasses, large hat, floral top, and patterned skirt leans ba
The Greek flag waving in the wind overlooking the illuminated white buildings of Santorini at dusk.
A woman sitting cross-legged on a sandy beach, wearing a yellow bikini, smiling, with rocks and greenery in the background, near the ocean.