We realize that everyone doesn't travel with their own party! In fact, we think solo travel is pretty cool, too. We've added new sailing tours, including some pretty cool themed events, to accommodate our solo and small group travelers. Scroll down to check out the newest additions to our sailing event calendar.
We love a good themed sail! Wear your best themed attire if you like, or come as you "arrrrrr" and leave the antics to us!
"Kids See Magic Because They Look For It"
Looking for Martha's Vineyard things to do on with kids? Curated just for Captains-in-training, this public kids sail will have everyone enjoying our "big blue world."
With our crew "decked out" in our finest ocean attire and our speakers humming the perfect "Happy Little Working Songs", we'll invite you and your kiddos to "Be Our Guest" on this Martha's Vineyard boat tour. We'll serve Under The Sea "ocean water" drinks and themed snacks while we invite the kids to share some sailing love with our onboard cockpit mascots. Enjoy specially selected props for the perfect photo that just begs to make the annual holiday card!
After the sail, the kids will get to search thru the Captain's Treasure Chest for a special treasure to take home. Share a Martha's Vineyard tour on our sailboat and see why Martha’s Vineyard with kids means “we've got no troubles, only bubbles, under - and on - the sea!”
Available on Monday and Thursday mornings
1.5 Hour Sail
Public, 6 guests max
Adults: $185 per person; Kids 12 & under: $150
Click the "Book Now" link below and select "Kids Sail" to choose your date.
Sips & Sails: A Jazzy Brunch Cruise
We'll make sailing with us on Martha's Vineyard Island a "Sunday Kind of Love." This simple, relaxing sail, designed for our adult guests only, with be a highlight of your trip.
Tour Martha’s Vineyard waters, specifically the area around Vineyard Haven, by boat; sample elegant appetizers; and sip mimosas while soothing jazz sets the mood. Bring your besties or your own Sunday love and enjoy the chill vibes of sailing Martha’s Vineyard on this easy sail.
If you choose only one thing to do on Martha’s Vineyard, this is the one. Calming ocean sounds; a cool breeze; some of The Vineyard's most iconic landmarks. What could make it better? Maybe visiting us again for a Martha’s Vineyard sunset cruise!
Available Sunday mornings
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.
Jaws 50th Anniversary Sail: 1975-2025
JAWS and Martha's Vineyard island (aka Amity Island for you movie buffs) have been stirring up action on the water for decades and to celebrate the JAWS 50th anniversary, we're donning our most kitsch JAWS gear for some laughs, some movie history and some factoids.
When you sail Martha's Vineyard on this tour with us, it’s more than just a sail, it’s a “Tour Martha’s Vineyard” experience in which we will we share some inside scoop about things to do in Martha’s Vineyard, like how to master jumping from the infamous JAWS bridge of Martha’s Vineyard, and show you some iconic JAWS Martha’s Vineyard filming locations. Wear your favorite shark shirt and join us for a cool "Shark Infested Waters" beverage and a "Shark-uterie" board. We'll send you on your way with a shark koozie, and a reminder that even we "need a bigger boat!"
Available on Wednesdays and Saturdays afternoons
2 Hour Sail
Public, 6 guests max
$190 per person
Click the "Book Now" link below and select "JAWS Sail" to choose your date.
Experience a relaxing evening as you drift away from the docks for one of the best Martha's Vineyard sunset sails. Take in the scenery as you sip a liquid treat and watch one of Mother Nature's most glorious scenes as she paints the sky with vibrant colors. Spend a romantic evening watching the sun slowly disappear as your expert crew regales you with fun facts and history and our boat makes its way smoothly across the harbor, taking full advantage of the changing natural light reflecting off the sea. For more information, visit our page dedicated to this special time of day!
Call us: 508.493.8767
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Stellar sailing. Unrivaled live entertainment. Brunch. It’s easy – like a Sunday morning.
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.
Sundays starting June 15.