Martha’s Vineyard Charter Company
Private Sailing Charters

What makes an amazing island?
The water that surrounds it.
Let’s explore the Vineyard by sailboat, on the water, the way it was explored from the beginning.
Private Sailing Yacht Charters around Martha’s Vineyard await you!

Our Services

Twilight after sunset over the bow of a sailboat during a private charter

Sunset Sails

Get out on the water to enjoy the golden hour of light aboard your private sailboat charter.

Starting at $825

A couple sharing a romantic moment on the bow of a sailboat.

Full Day Sails

Enjoy a full day sailing tour around Martha’s Vineyard taking in the beautiful waters with your own private crew aboard your own yacht.

Starting at $2200

Mainsail of a private yacht half way up the mast as the wind sails the boat through the waters of Martha's Vineyard on a private sailing charter

Half Day Sails

Focus on just the few places you want to see on your shorter private sailing adventure.

Starting at $1100

“It was the best part of the weekend. It was a magical day. Highly, highly recommended!”

– Alexis N. of Brooklyn, NY

“Captains Mason and Lynne took our family on the best boat tour we have ever been on around Vineyard Haven and Oak Bluffs. We have sailed in Hawaii, Laguna Beach and now Martha’s Vineyard and felt the most hospitality with Sailing Our Passion. The boat was comfortable and very clean. From start to finish, the trip was organized, smooth and captured sites that first timers and regulars/locals could appreciate. We even pulled over for a bit to allow my husband and son to jump off the boat and swim – a fun way to end a relaxing sail. Thank you both for such a great memory!”

– Brandon M. of Las Vegas, NV

About Us

What’s better than one captain? Having two!

Our captains have been sailing together for nine years. In fact, their first date was on a sailboat. They have been sailing together ever since.
With a combined 40 years of sailing experience between them, they will offer you unparalleled access and safety on the water. They both are US Coast Guard 100T Masters license holders, certified life guards and passionate about giving you the best time onboard their 42 foot sailboat.
The boat has been from Maine to the Bahamas and from Martha’s Vineyard to Ireland and back. She is more than equipped to offer you a day cruise around Martha’s Vineyard that you will never forget.

Find Out More

QUESTIONS?

Curious about what we can offer your family and friends and how we can make your vacation a memorable one? Please get in touch with us!

Martha’s Vineyard Charter CompanyPrivate Sailing Charters