Exciting Liveaboard Destinations
Trade Your Cold Weather Blues for a Better Kind of Winter Blues!
So often, our guests tell us it's their dream to spend a week living aboard, sailing during the day, lounging by the sea and enjoying a tropical cocktail. We may be a little biased, but we can't think of a better way to spend some vacation days! We can help you check off your bucket list and not only sail anywhere in the world, we can act as your travel agent and help you arrange every detail of your dream vacation. Warm days, cool nights and cold cocktails...what could be more perfect?
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!
Captain Wendy can provide multi-day live aboard sailing vacations for 2-10 guests.
Prices starting at $3300 per person
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.
People all over the world love our captain! See what people are saying
New Themed Public Sails
Stellar sailing. Unrivaled live entertainment. Brunch. It’s easy – like a Sunday morning.
Swoon to the talented tunes of the island's own guitar artist Rich Giaimo while you sample sweet and savory brunch hors d'oeuvres along with a liquid treat.
Sundays starting June 15.