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Welcome to Martha's Vineyard, the storied island off Cape Cod that has captivated visitors for generations with its windswept beaches and fiercely independent spirit. This self-guided tour takes you across the island's six unique towns, each with its own character. Begin in bustling Vineyard Haven, where ferries have delivered travelers since the whaling era, then explore Oak Bluffs and its fantastical Victorian gingerbread cottages painted in every color. Drive to elegant Edgartown, where sea captains' houses line streets unchanged since the 1800s. Journey west to witness the dramatic clay cliffs of Aquinnah, sacred to the Wampanoag people who have called this island home for over ten thousand years. Discover quiet fishing villages, pristine wildlife sanctuaries, and the rolling farmland that gives the Vineyard its bucolic countryside charm. From presidents and literary legends to fishermen and farmers, this island attracts those who value beauty, solitude, and community.
What's Included
Meeting and pickup
This is a self-guided app-based tour with no in-person guide or fixed meeting point. Your access code is already on your ticket (below the barcode) — enter it in the CloudGuide app to start at the suggested location, or any stop on the route, in the order that suits you best.
Itinerary
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1
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.
1 hour • Admission ticket free -
2
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.
30 minutes • Admission ticket free -
Flying Horses Carousel (Pass by)
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.
Admission ticket free -
3East Chop Lighthouse
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.
1 hour • Admission ticket free -
4Edgartown
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.
1 hour • Admission ticket free -
(Pass by)
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.
Admission ticket free -
5
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.
30 minutes • Admission ticket free -
6
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.
1 hour • Admission ticket free -
7
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.
1 hour • Admission ticket free -
8
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.
1 hour • Admission ticket free
Additional info
- Not recommended for travelers with spinal injuries
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
Tags
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
You can cancel up to 24 hours in advance of the experience for a full refund.
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