Afternoon & Evening Sails on Martha's Vineyard

Explore the Harbors & Coastlines of Martha's Vineyard Island

Departures in the afternoon and evening  from our marina on Historic Edgartown Harbor
Departure times may vary, please call for information


***It is not necessary to make an advance sailing reservation until one week before you would like to sail, unless you are a party of 10 or more.

Mad Max cruising around Historic Edgartown Harbor

Mad Max cruising around Historic Edgartown Harbor



AFTERNOON SAIL:   (w/cash discount)

Adults                   $85.                    $75.

Children              $75.                    $65.

EVENING SAIL :         (w/ cash discount)

 Adults/Ch.        $95.                     $85.

$10.00 off per person with cash payment!


  • Cancellations made within 72 hours of sail will be charged a 100% cancellation fee.

  • No-Shows will be charged a 100% cancellation fee.

  • Length of sail is approximately 2 hours, we sail rain or shine and everyone has a great time regardless of the weather

 Your Mad Max Adventure sets sail from our new marina dock on beautiful Edgartown Harbor.

Historically, Edgartown (then known as Great Harbor) was a primary port for the whaling industry during the 1800s. From our decks, there are spectacular views of the whaling captains’ houses and classic yachts that line the waterfront. This is a town that was meant to be explored from the water!

Our sail begins as we pass the Edgartown Lighthouse, through the Outer Harbor, and into the tranquil blue waters of Nantucket Sound where motor yachts, sailboats, and fishing vessels are seen traveling between Cape Cod, Martha's Vineyard, and Nantucket. Here the wind direction will determine our course!

One route may take us along the sandy shores of Chappaquiddick Island towards Cape Pogue Lighthouse; another past the colorful town of Oak Bluffs with its quaint gingerbread cottages, ferry port and jetty-bound harbor. Our Evening Sail times our re-entry into Edgartown harbor as day turns into night behind Edgartown Lighthouse. Between the light and the view, it is gorgeous opportunity for a photo you will always treasure!

Guests aboard the Mad Max can enjoy the sun, wind, and water while riding on the spacious decks or relax in the comfort of our shaded cabin. Mad Max is fully equipped with tables and seats, restrooms, and all required U.S.C.G. safety equipment. Our knowledgeable Captains and Crew are dedicated to your safety and comfort, and our 20 plus years in the business insures it.

Guests are welcome to bring along snacks & refreshments (BYOB).

For more information, please refer to our FAQ's

Went out with a crew of work friends and locals, on a bright windy day, and had an awesome sail. We were on board with another group who were fun company. We stocked up brought some beverages and snacks, which added to the relaxing trip. They have a cool netted area on the front of the boat where you can lay out and just hover over the water, very peaceful. The boat is maintained very well, and you can tell the crew takes pride in their ship. The sail is as fun as you can make it. Will definitely do again before the end of season :)