Sail With Us

"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 and The Caribbean. Our captain is not only a US Coast Guard Master Mariner and Royal Yachting Association Yachtmaster, she is the only Certified instructor on Martha’s Vineyard, credentialed by the American Sailing Association. She takes great pride in mentoring sailors and particularly enjoys mentoring other female sailors.

The thrill of sailing aboard our sleek, fast classic sloop-rigged sailboat is the perfect adventure for your vacation to the Martha's Vineyard. Exploring the beauty & history of the Vineyard by sea is a special experience you won't forget. The picturesque coastline of lighthouses, historic homes, and beautiful beaches are 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.

"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. Breathe in the salt air and find your inner mermaid! Enjoy snacks or a picnic lunch while under way, listen to the ocean as it swooshes by and feel the wonder of the vessel as the wind fills the sails and carries you away.

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

We all need a little help regaining sanity now and then. The constant pull of technology - cell phones, email, social media - often prevent us from living in the moment. Unplug with us. Unwind for a few hours or an afternoon and regain your sanity.