Exciting Liveaboard Destinations
Trade Your Cold Weather Blues for a Better Kind of Winter Blues!
Set sail for extraordinary destinations and experience the world the way it was meant to be explored — by sea.
So many of our guests tell us they dream of spending a week living aboard: sailing to beautiful harbors by day, swimming in secluded coves, relaxing under the sun with a tropical cocktail in hand, and falling asleep to the gentle motion of the water beneath the stars. We may be a little biased, but we truly can’t imagine a more unforgettable way to spend your vacation.
Whether you envision the Caribbean or the South Pacific, hidden island anchorages or bustling beach bars, nearby or faraway sailing destinations still waiting on your bucket list, your favorite Captain can help bring the journey to life. We can assist with planning every detail of your experience — from itinerary design to provisioning, excursions, dining, and unforgettable moments along the way.
Warm days, cool nights, salty air, glowing sunsets, and cold cocktails shared at anchor… this is more than a vacation — it’s a life at sea.
One of the most unforgettable parts of life aboard is the feeling of complete freedom. There is something magical about sipping coffee on deck at sunrise, sailing toward the next island with warm trade winds filling the sails, and ending the evening beneath a sky full of stars with nowhere else you need to be.
Our multi-day liveaboard sailing vacations are offered between November and April. Learn more about our destination sails below or just contact us to reserve your destination sail.
Picture yourself here, aboard your own liveaboard sailing vacation.
Sailing Vacations and Learning to Sail
Sailing Vacations
Learn to Sail in Tropical Places
Learn to Sail in Tropical Places
Dreaming of getting away from it all, sailing from one island to another, and waking in a new cove each morning? Captain Wendy's expertise in monohull and catamaran sailing offers you an opportunity to spend your vacation time living aboard a sailboat without the worry of how to sail it. In addition to being dual-licensed with both the US Coast Guard and Royal Yachting Association, Captain Wendy has 25 years of travel planning expertise and a wealth of knowledge about many island destinations, Captain Wendy can offer you a vacation you'll remember for years to come.
Some of Captain Wendy's favorite destinations include the British Virgin Islands (BVIs), the Grenadines, St. Martin, The Society Islands of Tahiti, Moorea & Bora Bora, and The Whitsunday Islands of Australia. Have another destination in mind? Let us know and we'll set it up for you!
In addition, if you prefer to completely relax, Captain Wendy has a network of sailing chefs who can prepare your onboard meals and drinks for you!
Multi-day live aboard sailing vacations for 2-10 guests.
Contact us for more information.
Learn to Sail in Tropical Places
Learn to Sail in Tropical Places
Learn to Sail in Tropical Places
Learn to sail in some of the world's best sailing destinations!
Captain Wendy is the only American Sailing Association Certified Instructor on Martha's Vineyard. She is certified and qualified to teach basic sailing as well as coastal cruising, bareboat chartering and catamaran sailing. Her calm demeanor and patience make learning easy and fun. She can offer you and your friends sailing instruction during any of our sailing charters or during a sailing charter vacation to any destination of your choice
Read more about Captain Wendy's experience and credentials on our About Us page.
Contact us for more information about learning to sail.
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