SAIL IN PARADISE

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

The Perfect Sailing Adventure
Vagabonde Adventures sails in some of the most beautiful waters on Earth.
Check out our different options for your adventure below:

The Holiday
Are you looking for an idyllic holiday where you can kick back, forget about work and enjoy waking up in paradise every day?
Experience secluded anchorages, beach bonfires with family and friends, snorkel crystal clear waters and get a taste of life at sea. Our expert crew will look after you from start to finish. 

Learn the Ropes
This is a tailor-made, hands-on sail coaching adventure that lets you truly experience the sailing lifestyle for yourself. Our experienced crew will help coach you in whatever aspect of life at sea you desire. Perfect if you want to brush up on your skills, or you just want to see if sailing is something you enjoy.
Get involved, hoist the sails and learn to sail the boat to its optimum performance. This week long journey will build your confidence and leave you excited for your next adventure.

Get Certified
Get certified through the American Sailing Association with this week long live-aboard sailing course. With courses from Beginner to Advanced, you can get certified to charter your own boat.
This trip is about building your experience, skills and confidence in a friendly, supportive atmosphere. Enabling you to plan your own adventures safely and letting you enjoy the sense of independence and freedom that sailing brings.

Join a flotilla

Flotillas are the most social way to sail. You will make new friends from all around the world, all bonding over this shared experience.


We organize multiple boats to sail together from destination to destination, rafting the boats together in the evening. We share big group dinners, take tours together and enjoy fun evenings spent together as a group.


Joining a flotilla can also be the most economical way to go sailing. It can be hard to organise a big group of friends to charter a full boat. Why not just grab your best friend and go for it - book a cabin, join a shared boat, and get out there to explore the world.

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!

Man with long hair and beard smiling while sailing on a boat in the ocean, with a shoreline and buildings in the background under cloudy sky.

  • 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.

A young woman with light brown hair sitting at a restaurant table, smiling and wearing a dark blue polo shirt with a small logo on the chest. There is a bottle of rosé wine and a glass of rosé wine on the table in front of her.

  • 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!

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