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 half hour on the :15 and :45 past the hour . Upon arriving in Oak Bluffs you can enjoy Circuit Avenue, which is the equivalent of a Main Street with shops, ice cream parlors, restaurants, an arcade, and is home to America's oldest working carousel, the "Flying Horses". A short walk from Circuit Ave. is the Martha's Vineyard Camp Meeting Association. Consisting of hundreds of colorful Victorian gingerbread cottages, it's surely something the whole family will enjoy. If you do not wish to see Oak Bluffs now, you can stay on Route #13 and continue on to Edgartown. If you are departing from Oak Bluffs later in the day, you may want to tour it last.
Oak Bluffs Arrival: Take #13 to Edgartown, which departs every half hour on the :00 and :30 past the hour. 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. Edgartown is also home to many great boutiques and fabulous restaurants, as well as a beautiful waterfront and a unique Main Street experience.
From Edgartown to Up-Island: Take Route #6 from Church St. at 12 minutes past the hour to the Grange Hall in West Tisbury. If you would like to go to Aquinnah (Gay Head) for a view of the brightly colored Gay Head Cliffs and the historic Gay Head Lighthouse, stay on the bus. If you wish to go to Menemsha, disembark and walk next door to the West Tisbury Town Hall and catch a Route #4 to Menemsha at 40 minutes past the hour. Route #4 is a scenic drive to the quaint fishing village of Menemsha, which is also home to the Island’s Coast Guard Station.
Aquinnah to Vineyard Haven:
From Aquinnah, take #5 at 10 minutes past the hour to the West Tisbury Town Hall. Stay on this bus and it will become the #3 departing West Tisbury at 36 minutes past the hour for Vineyard Haven.
Menemsha to Vineyard Haven:
From Menemsha, take #4 at one minute past the hour to the West Tisbury Business District. Transfer to #3 at 44 minutes past the hour 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 ports of entry.
If you are departing from a ferry in Oak Bluffs, you will want to take #13 back there. Please be sure to check the schedule for exact times during your travel period.