How do I see the Island in one day?
The best way to tour the Island in one day is outlined below. Please be sure to set aside at least 8 hours in order to see everything without rushing. The following itinerary takes you from your arrival port of either Oak Bluffs/Vineyard Haven to elegant Edgartown, then rural Up-Island (West Tisbury, Chilmark, Aquinnah, and Menemsha), and back down to Vineyard Haven/Oak Bluffs, the two largest ports on the Island.
Vineyard Haven Arrival: Take Route #13 to Oak Bluffs, which departs every 30 or 60 minutes depending on the time of year. Upon arriving in Oak Bluffs you can disembark and enjoy Circuit Avenue and Gingerbread Cottages or continue on to Edgartown on the same bus. If you are departing from Oak Bluffs later in the day, you may want to tour it last. Please note that many of the shops will close around 4pm or 5pm.
Oak Bluffs Arrival: Take #13 to Edgartown, which departs every 30 or 60 minutes depending on the time of year. This scenic route will take you past the long stretch of State Beach, along the Eastern shore of the Island, and over the famous “Jaws” Bridge. Edgartown is known for its stately white-painted captain's houses and churches that are reminiscent of the great whaling era. The popular area of South Beach is also in Edgartown and is accessible by Route #8 from Church St., though it will be quiet during the off-season. Edgartown is also home to many great boutiques and fabulous restaurants, as well as a beautiful waterfront. Please note that in the off-season, many of the shops and restaurants are closed, and the shops that are open will close around 4pm or 5pm.
From Edgartown to Up-Island: Take Route #6 from Church St. (departure times vary, please check the schedule) to Alley’s Store in West Tisbury. Next door to Alley’s Store is the West Tisbury Town Hall where you can catch a Route #5 to Aquinnah (Gay Head) for a view of the brightly colored Gay Head Cliffs and the historic Gay Head Lighthouse. Also from the West Tisbury Town Hall you can catch a Route #4 to Menemsha which will take you on a scenic drive to the quaint fishing village of Menemsha. Menemsha is also home to the Island’s Coast Guard Station.
Menemsha to Vineyard Haven:
From Menemsha, take #4 (times vary, please check schedule) to the West Tisbury Business District. Transfer to #3 and take a ride down State and Old County Roads to Vineyard Haven. While in Vineyard Haven check out Main Street’s shops and sites – don’t forget to visit the harbor, one of the Vineyard’s main entry ports. Please note that most of the shops will close around 4pm or 5pm.
If you are departing from a ferry in Oak Bluffs, you will want to take #13 back there.
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