Martha's Vineyard Tours and Boat Charters

Drone view of our boat Phoenix under sail with a couple on a Martha's Vineyard wedding photo shoot.

"Life is either a daring adventure or nothing"

Helen Keller coined the phrase and we totally agree. At Sail The Vineyard, we take life on as a daring adventure and embrace all that means. We are a unique all-female crew, led by an adventurous, accomplished female Captain who splits her time between Martha’s Vineyard island (MV) and The Caribbean - or wherever else the wind happens to blow. Captain Wendy Lea is not only a US Coast Guard Master Mariner and Royal Yachting Association Yachtmaster, she is the only Certified Instructor on Martha’s Vineyard island, credentialed by the American Sailing Association. She takes great pride in providing amazing things to do in Martha's Vineyard and in mentoring sailors, particularly other female sailors who want to be part of the industry.

The thrill of sailing aboard our sleek, fast, classic sloop-rigged sailboat is the perfect adventure for your vacation to Martha's Vineyard island. Exploring the beauty & history of the Vineyard by sea is a special experience you won't forget. Sail MV and marvel at the picturesque coastline of lighthouses, historic homes, and beautiful beaches - just a few of the beloved sights of the area. Embrace adventure yourself and feel the thrill of the wind in your hair, find your inner mermaid, and maybe learn the art and science of sailing. Tour Martha's Vineyard with us, by boat, and see what sailing the waters around Cape Cod is really about.

Phoenix gliding under full sail during a Martha’s Vineyard private sailing charter.

"The Sea, once it casts its spell, holds one in its net of wonder forever"

Let us show you the magic of the sea on one of our sailing excursions, whether it's a Martha's Vineyard sunset cruise, an under the sea odyssey curated especially to enhance Martha's Vineyard things to do with kids, or the best wind and wine experience ever aboard our Sips and Sails Brunch cruise. If you're not only under the spell of Martha's Vineyard island but also of all things JAWS related, take a bite out of our "Sharkuterie" during an exciting Jaws 50th anniversary sail. Breathe in the salt air, find your inner mermaid, and tour Martha's Vineyard with us. You'll hear the subtle sounds of the ocean as it swooshes by, feel the wonder of the boat gliding across the water as the wind fills the sails and ahhhhh....the magic of sailing Martha's Vineyard that will stay with you, maybe forever!

Sunset over Martha’s Vineyard viewed from the sailboat Phoenix at the end of a sailing charter

To some, it's just water. For us, it's a place to regain sanity

We all need a little help unplugging and regaining some balance now and then. The constant pull of technology - cell phones, email, social media - often prevent us from living in the moment. You've come to Martha's Vineyard island to relax, reconnect with your friends and loved ones, and share some fun and laughter. Our array of Martha's Vineyard sailing charters is designed to facilitate exactly that. Unplug with us. Unwind for a few hours, an afternoon or a day. Laugh. Breathe. Regain your sanity.