Begin your tour on the main street of this working harbor town, where independent bookshops, art galleries, and the historic Capawock Theater give the village an unpretentious, year-round character. Unlike other island towns, Vineyard Haven was a dry town until 2019, reflecting its practical seafaring roots.

Walk through the Martha's Vineyard Camp Meeting Association grounds to see over 300 brightly painted Victorian cottages arranged in concentric circles around the Tabernacle. Built in the 1860s and 1870s as summer revival tents evolved into permanent structures, these tiny ornate houses are one of the most remarkable architectural collections in America.

Ride the oldest operating platform carousel in America, built in 1876 and designated a National Historic Landmark. Located in Oak Bluffs near the harbor, the hand-carved wooden horses have real horsehair manes and glass eyes. Riders try to grab the brass ring for a free ride — a tradition spanning nearly 150 years.

Drive to the bluffs of East Chop in Oak Bluffs to see this cast-iron lighthouse built in 1878. Perched high on Telegraph Hill, it offers sweeping views of Vineyard Sound, Nantucket Sound, and Cape Cod in the distance. The surrounding neighborhood of grand Victorian summer homes reflects the island's Gilded Age heritage.

Explore the most elegant town on the island, where fortunes made from the 19th-century whaling industry built the stately white Federal and Greek Revival homes lining Water Street and North Water Street. The harbor is filled with sailboats, and the Edgartown lighthouse stands at the end of a sandy walkway.

Walk out along the harbor beach to this iconic white lighthouse that has guided ships into Edgartown Harbor since 1828. The current structure dates to 1939 and was moved to its present location in 2007. Climb to the top for panoramic views of the harbor, Chappaquiddick Island, and the outer beach.

Take the tiny On Time ferry across the narrow channel to Chappaquiddick, a quiet island off the island. Visit Mytoi, a serene Japanese-style garden maintained by the Trustees of Reservations, set in a pine and oak forest with a koi pond and arched bridge. The island also offers access to pristine barrier beaches.

Drive south from Edgartown to this three-mile stretch of Atlantic-facing barrier beach, the island's most popular surf beach. The waves here are stronger than the calmer north-shore beaches, making it a favorite for bodyboarders. The left side faces the protected Katama Bay, offering calm water for families.

Stop in the rural heart of the island at West Tisbury, where the famous Wednesday and Saturday farmers market draws crowds to the historic Grange Hall. Across the road, the Field Gallery's whimsical white dancing sculptures by Thomas Maley have become one of the island's most beloved and photographed sights.

Visit this tiny fishing village in Chilmark that feels frozen in time, with weathered shingle shacks, lobster traps stacked on the docks, and fishing boats bobbing in the protected harbor. Menemsha is famous for its spectacular sunsets and fresh seafood — grab a lobster roll from Larsen's Fish Market and watch the sun sink into Vineyard Sound.