The Flying Horses Carousel is a totally unique landmark. It's the oldest operating platform carousel in the country, having been built in 1876. In the early days, the horses on this ride sported real horse hair! The carousel is still in operation today, though it has been updated for comfort and safety. The tour is over 13.5 miles long, with more than 38 audio stories, and takes about 2-3 hours to complete. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want.

The Cottage Museum is a one-of-a-kind museum and gift shop offering more information about the origins of the Gingerbread Houses and the people who built them. Here, you'll also find all kinds of souvenirs. Whether you're in the market for sterling silver charms, toys, calendars, or postcards, this combination museum and gift shop has you covered.

Inkwell Beach, situated on the eastern side of Oak Bluffs, is a small and pretty beach with a bit of an unsavory past. In the early to mid 1900s, Martha's Vineyard beaches were fully segregated. As a result, beaches like this one were underfunded and generally left in disrepair by local authorities. Today, however, all of that has changed.

As you pass the Caroline Tuthill Wildlife Preserve, you'll want to keep your eyes peeled for any of the more than 300 species of bird which can be found on the Vineyard. This preserve is also home to tons of local flora, including bountiful wildfowers of all sorts. Beyond it, you'll also head about the whaling industry and how it once defined the island.

Chappaquiddick Island, just off the coast of Edgartown's downtown, gets its name from the Wampanoag tribe. In their language, Chappaquiddick means "separated island." And yes, that does mean that its name is technically "Separated Island Island"!

Finally, you'll arrive at South Beach. This long strip of sand is basically two beaches in one, with the placid Katama Bay on one side and the dramatic Atlantic Ocean surf on the other. Whether you want to lounge on the sand, catch some surf, or just break out the binoculars and search for shore birds, this is the beach for you. Your tour concludes here, though there are more optional stops around the island if you want to keep the adventure going.

Passing through Edgartown's Historic District is a truly lovely experience. Wonderfully preserved houses from the 1800s flank the street, while cute shops and restaurants wait on every corner. As you drive, you'll also get a glimpse into how the town got its start, its name, and the role that whaling played in the development of it all.

On Lighthouse Beach, you'll enjoy a pristine sandy beach, gentle surf, and a picture-perfect New England lighthouse. It's a great spot to pause, picnic, and snap that perfect photo from your trip. While you're here, you'll also get a bit of background on that lighthouse.