A white sailing yacht floating on clear turquoise waters with three people on deck, near a sandy shoreline with greenery in the background.


Sail. Learn. Explore. Belong.
Vagabonde Adventures is a sailing company built by passionate sailors, for people who want more from their time on the water.

We create crewed sailing holidays, hands-on sail coaching, American Sailing Association certification courses, shared sailing trips and flotillas in some of the world's best sailing destinations. From the Bahamas and Caribbean to Greece and Croatia, our focus is on combining great sailing with exploration, learning and the freedom of life at sea.

We're especially passionate about performance sailing and Outremer catamarans. Our experienced captains and sailing instructors encourage guests to get involved, take the helm, learn new skills and experience what a performance cruising catamaran can really do.

Whether you want to completely switch off for a week, improve your sailing, earn a sailing certification or experience an Outremer before buying one, we create sailing adventures around the way you want to experience the sea.

What we do:

  • Crewed Sailing Holidays

  • Sail Coaching & Performance Sailing

  • ASA Sailing Certification

  • Outremer Specific Training

  • Shared Sailing Trips & Flotillas

What Makes Vagabonde Adventures Different
Vagabonde Adventures is the official Outremer charter and training partner, giving our guests a unique opportunity to experience some of the world's most capable performance cruising catamarans in real sailing conditions.

Our relationship with Outremer goes beyond simply offering their yachts for charter. We sail, train and live aboard these boats, giving guests access to genuine hands on experience with Outremer yachts. Whether you're an experienced sailor, looking to improve your skills, or considering buying an Outremer yourself, our trips are designed to get you properly involved.

When conditions allow, we sail rather than motor. Guests can take the helm, trim sails, practice maneuvers, learn navigation and understand how a performance catamaran behaves under sail. Our dedicated Outremer training experiences go even further, with practical coaching and the opportunity to explore the boat's systems, handling and performance in depth.

Our team brings together professional skippers, sailing instructors, racers, chefs and experienced ocean sailors. You're not simply being taken somewhere beautiful. You're spending time on the water with people who understand the boats, the sailing and the destinations.

The result is a different kind of sailing experience: the opportunity to sail an Outremer properly, learn from experienced sailors and explore under sail, all while enjoying the comfort and adventure of a crewed yacht.

Part adventure, part learning experience and part escape from normal life.

About Vagabonde Adventures

Meet the Crew

A man wearing sunglasses, a wide-brimmed hat, and a light-colored long-sleeve shirt is steering a boat on the ocean. A sailboat is in the background with a person on deck, and the sky is partly cloudy.

  • 2022 American Sailing Outstanding Instructor Award

    Jack first left Australia to cross the Atlantic aboard the original La Vagabonde monohull along with his cousin Riley and Elayna.

    Bitten by the sailing bug, he started out as a charter skipper but soon gravitated towards instructing and found his calling there.

    Now with around 100,000 nautical miles under his belt, Jack is a sailing instructor with both the American Sailing Association to advanced levels, and a Royal Yachting Association Yachtmaster Instructor. Coaching is his passion and he works hard to ensure that people get as much hands-on experience as possible. You can find him happily manning the tiller while at sea or enthusiastically leading a group snorkel adventure.

    Jack loves to sail fast and is always keen to get the best performance from his crew and the yacht.

A woman standing barefoot on a boat, holding a rope, with water and distant hills in the background.

  • Born and raised by the sea, Eta’s first love was the ocean. Hailing from the coastal city of Split in Croatia, Eta has been working as a professional skipper since 2016.

    Never one to shy away from adventure, Eta has just completed a crossing of the Pacific Ocean and has been busy exploring French Polynesia.

    Growing up sailing the Croatian islands aboard her family’s yacht she has a healthy passion for life under the sea. Her dad tells us that even before she could swim she was diving down to look at octopus hiding in the rocks.

    Eta has an enthusiasm for everything that is simply infectious, always cheerful and always involved no matter what we are doing. She epitomizes what the Vagabonde Adventures experience is about.

A woman with curly hair smiling and looking to her right, standing near a body of water with a coastal town and green hillside in the background.

  • From landlocked Montana to the seven seas, Mackenzie has swapped mountain trails for ocean waves and hasn't looked back! Growing up surrounded by Big Sky country gave her a sense of adventure that eventually led her to the water, where she’s spent the last 5 years sailing the globe while whipping up meals that keep crews smiling.

    Before finding her sea legs, Mackenzie managed clients in the tropical paradise of Bali and planned events across Australia's vibrant scene. This jack-of-all-trades background means she brings a little something extra to every boat she steps into.

    Known for easy laughs and a laid-back attitude, Mackenzie creates a relaxed atmosphere whether you’re navigating calm waters or riding out a squall. Come sail with her for good food, good vibes, and adventures worth remembering!

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  • Hugo is your classic French sailor - he’s passionate about life on the water, has a can-do attitude and absolutely LOVES to make yachts go fast. In his early years of sailing he rebuilt a tiny 27ft monohull from the ground up, crossing the Atlantic with no refrigeration and explored the Caribbean North to South for 4 months with no engine. Hugo is a pure sailor.

    With experience instructing, engineering, racing and as a charter skipper he is full of knowledge and the perfect blend of a world class coach and a great host. Having been first mate on the Clipper Round the World, raced the Mini 6.50, OC50 trimarans and Class 40’s he will help you understand everything sail performance. 

    Check his YouTube channel ‘The Sailing Frenchman’, for many great adventures at sea.

A man wearing a hat and sunglasses sitting at the helm of a boat, steering with a binnacle in front of him. He is outdoors on the water with clear skies and a distant person in the background.

  • Kostas is from Thessaloniki in Greece and knows how to sail the Greek islands better than most.

    Not only mastering the Greek waters, Kostas also sails the Bahamas working as a captain and American Sailing instructor.

    Kostas is an incredibly cheerful, helpful guy who always shows his guests a great time onboard.

    Always with a smile, Kostas is a delight to have onboard. If you’re lucky enough to catch him around his twin brother Alex, you’re in for a treat.

A man with a beard smiling on a boat, wearing sunglasses, a white cap, a white long-sleeve shirt, and pink shorts, with water and green hillside in the background.

  • Alex is from Thessaloniki in Greece and knows the Greek islands like the back of his hand.

    Not only mastering the Greek waters, Alex also sails the Bahamas working as a captain and American Sailing instructor.

    Alex is a lovely guy to have onboard and guests love him.

    Alex is always smiling and happy, and if you’re lucky enough to catch him around his twin brother Kosta, you’re in for a treat, they are great together.

A man wearing sunglasses steering a sailboat on the ocean.

  • Born and raised in Zagreb, Tean discovered sailing during his college years while studying kinesiology. After finishing college and few years of P.E. teaching, he decided to pursue his passion and become a full-time skipper, sailing in the Adriatic and well beyond.

    With more then 60 000 nautical miles behind him you can relax knowing you are in capable hands. Tean now works mostly on private charters, where he combines his love for sailing, adventure and teaching. Whether he's trimming sails, anchoring in hidden bays, or leading snorkel trips, he brings energy, curiosity, and a personal touch to every voyage.

    When he's not sailing, you’ll find him hiking, exploring new places with his family, or riding bicycle with his daughters.

A man standing on a boat with the ocean in the background, wearing a white long-sleeve shirt.

  • Pieter, born and raised in the Netherlands, has been sailing his entire life. After a successful career in the early days at Tesla, he decided to turn his lifelong passion for the sea into a profession.

    He has sailed extensively in the North Sea, Mediterranean, and Caribbean, gaining broad experience as both a captain and instructor. Pieter especially enjoys coaching and racing, sharing his knowledge with others and making a boat sail smoothly and fast.

    When not at sea, he can be found kitesurfing, wingfoiling, or exploring on a snorkel safari. Aboard the boat, you can always challenge him to a board game.

    Pieter is an American Sailing instructor and loves to teach folks how to handle both monohulls and catamarans to their full potential.

A man with sunglasses and a mustache sailing on a boat, smiling and holding the steering wheel, with the ocean and sails in the background.

  • Matthew "Bruce" Whitehead has over 15 years in the maritime industry and a lifetime of experience on the water. Growing up in Florida, he spent his youth racing high performance sailboats, teaching and coaching sailing, and went on to campaign for the 2016 Olympics in the Sport of Sailing. Matthew then competed on several professional circuits such as the World Match Race Tour, the Red Bull Youth Americas Cup, and the Extreme Sailing Series.

    Since a serious knee injury in 2018, Matthew shifted his focus from sailboat racing to working as a Yacht Captain. For the past 7 years he has chartered and delivered yachts in various destinations in the Mediterranean, Caribbean, South Pacific, and Indian Oceans. Matthew also coaches the Olympic Development team in the Nacra 15 class and loves sharing his knowledge of the sport.

    Bruce is an American Sailing instructor and you would be lucky to have him showing you the ropes!

A group of five people on a boat, with food on a table, by the water with trees and rocks in the background.

  • Our amazing Flora is from Argentina.

    Her meals are delicious and she is great fun to have around. Flora works as a chef onboard yachts all over the world and dreams of opening a small cafe at home in Buenos Aires.

    Flora cooks colorful, healthy and incredibly tasty dishes. You eat with your eyes first and Flora is a master of presentation.

    Flora has the most lovely character, is super easy to get along with and is always laughing and haopy.

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  • Kylie’s culinary journey began unexpectedly during her college years, when she moved abroad to Spain and enrolled in a local culinary program. Immersed in regional ingredients and Mediterranean food culture, she discovered a passion that would eventually lead her across continents - and ultimately, onto the water.

    After returning to the U.S. and spending several years working in commercial real estate in New York City, she felt drawn toward a more creative and adventurous path. In 2022, she traveled to Croatia to pursue a career in yachting, launching what has now become nearly four years of cooking aboard luxury sailing catamarans throughout both the Mediterranean and the Caribbean.

    Her time in Croatia also reconnected her with her heritage - her grandparents were born there - and inspired her to pursue Croatian citizenship. In 2025, she proudly achieved that dream and was officially sworn in as a Croatian citizen.

    Kylie quickly became known for her professionalism, adaptability, and passion for hospitality. In 2023, she expanded her experience by becoming an instructor for aspiring yacht chefs, helping new chefs enter the industry and refine their onboard culinary skills.

    After two seasons in the Med, she moved to the British Virgin Islands, where she deepened her culinary style and embraced the opportunity to develop new dishes and techniques. Creating memorable, thoughtful experiences for those onboard remains the most rewarding part of her work.

    Kylie’s cooking style is seasonal, globally inspired, and rooted in fresh ingredients and intentional presentation. As a freelance chef and first mate, she brings warmth, creativity, and a strong work ethic to every vessel she steps aboard.

A woman with long dark hair and sunglasses sitting on rocks near the ocean, with a rocky island and blue sky in the background.

  • Hailing from the coastal town of Split, Croatia, Mia has known life on the water from a young age.

    Her Mediterranean inspired meals are delicious, healthy and beautifully presented. She works as a professional chef onboard yachts around the world and our guests love her.

    Mia is great fun to have onboard and you will surely miss her meals long after your summer tan has faded.

A smiling woman with short reddish hair, wearing a white t-shirt and denim overalls, is standing in a kitchen holding a container and a cloth, looking down at it.

  • Daryl is a chef from sunny Cape Town, South Africa. She’s worked all over the world as a private chef but her true love is the ocean and being able to do what she loves so close to it.

    Daryl dreams of opening her own farm-to-table restaurant in Cape Town. She loves cooking healthy, fresh and local dishes to delight and nourish her guests.

    Daryl is very happy and friendly plus she loves to host quiz nights!

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.
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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
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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
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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.
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