A sailboat on the water during sunset with orange and pink skies, a large main sail, and a smaller sail, with two people on board.

Sail the Vineyard Privately

Aboard LUNA

A private 41-foot Jeanneau designed for refined coastal cruising.

Gray crescent moon with a star and two smaller stars on a white background.

Each Charter aboard LUNA is private and tailored to your group. Below are our most popular ways to experience Martha’s Vineyard under sail.

Select Your Sail


Sailboat on a body of water with cloudy sky overhead, two people aboard

Private Coastal Sail

A relaxed half-day sail along the Vineyard coastline, perfect for experiencing the rhythm of the wind and water aboard LUNA.

Up to 6 guests • Approx. 4 hours

Silhouette of a sailboat anchored on calm water at sunset with colorful orange and pink sky.

Golden Hour Sail

Experience the Vineyard’s golden hour from the water as the coastline softens into evening light. A relaxed sunset sail perfect for couples, celebrations, or anyone looking to enjoy a quiet evening on the Sound.

Up to 6 guests • Approx. 2–2.5 hours

Man with sunglasses and curly hair steering a boat, wearing a red Helly Hansen jacket, on a sunny day with boats and buildings in the background.

Custom Private Charter

A full day aboard LUNA allows time to explore beyond the immediate coastline — sailing at an unhurried pace, discovering quiet harbors, and perhaps dropping anchor in a picturesque spot to enjoy a leisurely break before continuing your sail.

Up to 6 guests • Approx. 6–7 hours

Plan Your Sail

Planning your time on the water aboard Sailing Yacht LUNA? Share a few details below and we’ll be in touch shortly to tailor the experience to your group — whether you're planning a relaxed family outing, a sunset cruise, or a special celebration.

Plan Your Sail

Preferred dates are requested only — Captain Jeremy will personally confirm availability shortly after your inquiry.