Tour Itinerary

Choose between a 2- or 4-hour of the beautiful island of Martha’s Vineyard. You will experience the six very unique towns and all the carefully preserved space between:

In Oak Bluffs, we’ll walk among the story-book gingerbread cottages and see the oldest carousel in America, where if you grab the brass ring, you get a free ride! We’ll stroll along the lively little harbor or meander through Ocean Park.

Vineyard Haven is a quaint New England shopping village where you can go for a sunset sail on a large schooner. Wander up and down Main Street, which is filled with cute shops and restaurants.

West Tisbury is home to the oldest store on-island; Alley’s General Store, which first opened in 1858. We’ll pick up some fresh fruit in the farm stand out back to snack on as we peruse the art at the Field Gallery across the road.

Edgartown is surreal, with a harbor and waterfront edged by stately white Greek Revival houses built by whaling captains. The Old Whaling Church stands tall thanks to six massive columns, and along with the Edgartown Harbor Lighthouse and the historic Harborview Hotel, Edgartown really belongs in a museum!

Onwards to Menemsha, we drive past rolling hills that run to the sea, dotted with sheep and horses and framed by the miles of British-style stone walls. A stop at Chilmark Chocolates is a must, but don’t spoil your appetite until we have our seafood picnic on the docks. We’ll provide you with a complimentary bottle of wine that works well with a hot lobster roll, fresh fish, or the best oysters ever! We also offer a sunset tour, where we wine and dine while watching the sunset into the ocean, followed by boat horns and the applause of the appreciative on-lookers.

In Aquinnah, the end of the island, witness our magnificent colorful clay cliffs. Look down on the spectacular beaches and scour the horizon for the Elizabeth Islands off in the distance. Visit the unique shops owned by the Wampanoag tribe to purchase a piece of wampum jewelry. If you’re feeling energetic climb to the top of the Gayhead lighthouse, which we moved a couple of years ago so it wouldn’t fall into the sea!

Touring this special place is made even better with convenient pick-up service from wherever you stay and new and air-conditioned vans.

Don’t hesitate to call us anytime at (617) 359-9298 for answers to questions or to book a tour. Join us on a tour that will make your visit to our island memorable, and see much more than we can put into words here!