Sailing in Aquinnah, MA

Sail Narragansett Bay on a private 36-foot sloop with your captain

Private Ladybird sail with crew, music, and room for your own drinks and snacks

Catch the bay breeze past New Bedford's working waterfront

Feel the power of sailing on Martha's Vineyard waters

Sail Narragansett Bay on a private 3.5-hour cruise aboard the 36' sloop Hurrah

Private sailing with room to swim, picnic, and explore Newport’s coast

Sail New Bedford Harbor and Buzzards Bay on a private charter

Sail Vineyard Sound with lighthouse views and secluded swim options

A private harbor sail with landmark views as daylight fades

Sail close to the water on an interactive harbor charter

Relax on deck as the sun sets over the water

Tailor a hands-on sail to the skills you want to sharpen

Sail Martha's Vineyard aboard a historic 1926 schooner

Sail Newport Harbor and Narragansett Bay on a quick, family-friendly morning cruise

Sail Newport’s coast from Fort Adams to Brenton Point

Set sail on a private classic sloop tailored to your group

Private sailing with shaded lounging, hidden-cove swims and Newport coastal views

Share an evening harbor sail as the light shifts over the water

Raise the sails or take the wheel on Martha's Vineyard waters

Private golden-hour sailing with room to relax, dine, and swim

Explore JAWS movie history with shark-themed drinks and trivia

Sail Vineyard Haven Harbor with brunch bites, mimosas, and live jazz