• Main Street - Start your journey on the main street of this bustling harbor town, where independent bookstores, art galleries, and the historic Capawock Theater contribute to the village’s genuine, year-round charm. Unlike other island towns, Vineyard Haven remained a dry town until 2019, highlighting its practical maritime heritage.
• Martha’s Vineyard Camp Meeting Association - Stroll through the Martha’s Vineyard Camp Meeting Association grounds to admire over 300 vibrantly painted Victorian cottages arranged in concentric circles around the Tabernacle. Constructed in the 1860s and 1870s as summer revival tents transformed into permanent structures, these quaint, ornate houses represent one of America’s most extraordinary architectural collections.
• Flying Horses Carousel - Experience the oldest operating platform carousel in America, built in 1876 and recognized as a National Historic Landmark. Situated in Oak Bluffs near the harbor, the hand-carved wooden horses feature real horsehair manes and glass eyes. Riders aim to catch the brass ring for a complimentary ride — a tradition that has endured for nearly 150 years.
• East Chop Lighthouse - Travel to the bluffs of East Chop in Oak Bluffs to view this cast-iron lighthouse constructed in 1878. Positioned high on Telegraph Hill, it provides breathtaking views of Vineyard Sound, Nantucket Sound, and Cape Cod in the distance. The surrounding area, with its grand Victorian summer homes, reflects the island’s Gilded Age legacy.
• Edgartown - Discover the island’s most sophisticated town, where wealth from the 19th-century whaling industry built the impressive white Federal and Greek Revival homes along Water Street and North Water Street. The harbor is filled with sailboats, and the Edgartown lighthouse stands at the end of a sandy path.
• Edgartown Lighthouse - Stroll along the harbor beach to this iconic white lighthouse that has guided ships into Edgartown Harbor since 1828. The current structure, dating back to 1939, was relocated to its present site in 2007. Ascend to the top for sweeping views of the harbor, Chappaquiddick Island, and the outer beach.
• Chappaquiddick Island - Take the small On Time ferry across the narrow channel to Chappaquiddick, a tranquil island off the main island. Explore Mytoi, a peaceful Japanese-style garden maintained by the Trustees of Reservations, nestled in a pine and oak forest with a koi pond and arched bridge. The island also offers access to untouched barrier beaches.
• Katama Beach (South Beach) - Head south from Edgartown to this three-mile stretch of Atlantic-facing barrier beach, the island’s most popular surf spot. The waves here are stronger than those at the calmer north-shore beaches, making it a favorite for bodyboarders. The left side faces the sheltered Katama Bay, providing calm waters for families.
• West Tisbury Farmer’s Market - Visit the rural heart of the island at West Tisbury, where the renowned Wednesday and Saturday farmers market attracts visitors to the historic Grange Hall. Across the street, the Field Gallery’s whimsical white dancing sculptures by Thomas Maley have become one of the island’s most cherished and photographed attractions.
• Menemsha - Explore this quaint fishing village in Chilmark that seems untouched by time, with weathered shingle shacks, lobster traps stacked on the docks, and fishing boats bobbing in the protected harbor. Menemsha is renowned for its stunning sunsets and fresh seafood — enjoy a lobster roll from Larsen’s Fish Market while watching the sun set over Vineyard Sound.

• Self-guided walking tour, fully on the app — explore at your own pace
• Digital Map & Offline Content: no cell service needed
• Instant access: your tour activation code is ready on your ticket, below the barcode.
• Enjoy audio guide access for more than 40 sites across Martha’s Vineyard
• NO live guide or rental equipment provided — please bring your own smartphone and headphones

• Private transportation
• Admission fees, live guide, headphones, transport, parking, food/drinks, internet access and rentals

Welcome to Martha’s Vineyard, the renowned island off Cape Cod that has enchanted visitors for generations with its picturesque beaches and strong independent spirit. This self-guided tour will take you through the island’s six distinct towns, each with its own unique character. Start in the lively Vineyard Haven, where ferries have been bringing travelers since the whaling days, then explore Oak Bluffs with its whimsical Victorian gingerbread cottages painted in a rainbow of colors. Drive to the sophisticated Edgartown, where sea captains’ homes line streets that have remained unchanged since the 1800s. Head west to see the striking clay cliffs of Aquinnah, sacred to the Wampanoag people who have inhabited this island for over ten thousand years. Discover serene fishing villages, untouched wildlife sanctuaries, and the rolling farmland that lends the Vineyard its idyllic countryside charm. From presidents and literary icons to fishermen and farmers, this island draws those who appreciate beauty, solitude, and community.

For a full refund, cancel at least 24 hours before the scheduled departure time.