Set Sail on a Jazzy Cruise with us for the best sailing excursion on Martha's Vineyard

Stellar sailing. Unrivaled live entertainment. Brunch. It’s easy – like a Sunday morning.

This sailing charter invites you to swoon to the talented tunes of the island's own guitar artist Rich Giaimo while you  sample sweet and savory brunch hors d'oeuvres along with a liquid treat.

Looking for more of an evening vibe? Scroll for details about our Sunset Jazz Cruise.

Discover the magic of Martha's Vineyard in a brand new way. The newest and best Martha's Vineyard sailing excursion invites you to experience the island's first and only sail with live music. Step aboard as the sounds of smooth jazz guitar set the mood for a relaxing and fun Sunday morning. Sip a liquid treat and enjoy gliding gently past some of Martha's Vineyard's top attractions like East Chop Lighthouse and Jaws filming locations.

Our expert crew will present you with your own brunch plate of curated hors d'oeuvres while  regaling you with fun facts and history about the harbor and the island as our vessel makes its way smoothly across the harbor.  This Brunch Jazz Sail is an unforgettable way to enjoy smooth tunes set against the backdrop of New England's best sailing harbors.

This adults only shared cruise includes live musical entertainment, individual hors d'oeuvres plates, 2 mimosas per person and your time aboard. 

Sunday mornings 10:00 - 12:00

2 Hour Sail

Public, 6 guests max

$215 per person

Click the "Book Now" link below and select "Sips & Sails" to choose your date.

*Guests must be 21+ years old for this excursion.

If an evening vibe is more your style, join us for stellar sailing, live music and hors d'oeuvres. Step aboard while the sounds of smooth jazz guitar set the stage for Mother Nature's splendid goodnight kiss to the day.  Sip a liquid treat and enjoy gliding gently past some of Martha's Vineyard's top attractions like East Chop Lighthouse and Jaws filming locations.

Our expert crew will present you with your own curated hors d'oeuvres plate while regaling you with fun facts and history about the harbor and the island as our vessel makes its way smoothly across the harbor.  This Sunset Jazz Sail is an unforgettable way to enjoy smooth tunes set against the backdrop of New England's best sailing harbors.

This adults only shared cruise includes live musical entertainment, individual hors d'oeuvres plates, one mimosa per person and your time aboard. 

Thursday evening sunset cruise**

2 Hour Sail

Public, 6 guests max

$215 per person

Click the "Book Now" link below and select "Sips & Sails" to choose your date.

*Guests must be 21+ years old for this excursion.

**Time varies as sunset times change throughout the season