Consider how to get to Martha's Vineyard. You can fly into Martha's Vineyard from almost anywhere, but many people fly into Boston or Providence and rent a car or take a bus to Woods Hole. The bus costs around $32 roundtrip and takes about an hour and one half. US Airways flies into the island airport. Check the regular sites like Expedia, Orbitz, Travelocity, and others to get the best fares.
Take the ferry to the island if you fly into Boston or you are coming from other points by car. You don't need reservations unless you plan to take your car. The Steamship Authority (www.steamshipauthority.com) runs the show for ferry rides to the Vineyard. The cost of the ferry ride is about $13 roundtrip for adults and $7 for children over 5.
Determine how long you plan to spend on the island. If you only plan to day trip, then you need only consider the cost of transportation and possibly lunch and dinner while you are there. That would be the most economical way to do this trip. I have gone many times in my life this way to show people Martha's Vineyard. You get just enough for a taste of its atmosphere, and you don't have to shell out much money.
If you plan to spend more time, you will have to consider hotels or rental properties. There are homes you can rent on a weekly basis, some commercial hotels (none of them are very big), and there are many bed and breakfasts or inns. Doing this will triple your costs of a trip to the Vineyard but it can be lovely.
Pick the area of the Vineyard in which you would like to stay once you have decided the length of your trip. When we went recently, we stayed in a bed and breakfast and had to get two rooms to accommodate our family of 4. The inn was historic and it was called the Edgartown Inn, and it was right smack in the middle of Edgartown. Nathaniel Hawthorne wrote many novels holed up in the Edgartown Inn. It was a pretty place, it was historic, and had very few amenities. Edgartown is filled with tony shops, tony people, and lovely restaurants. It is one of the "in" parts of the island.
You may want something a little more party-oriented and for that you would choose Vineyard Haven. It is a little less tony, a little more rowdy, and a little less expensive. It is also the home of the Black Dog Tavern, one of the most famous places on the island to eat.
If you choose to go to Aquinnah (formerly called Gay Head, but changed for politically correct reasons), then you will be rewarded with fantastic dunes and a more rustic scene with mostly rental homes. It is the home of the Wampanoag Indians, 12th generation Islanders. There are a few hotels there and it is much quieter. When I was a child, you were allowed to roll down the red clay dunes. Now, there is too much erosion but you can still enjoy the beautiful sunsets over the dunes.
Or you might choose Oak Bluffs, where Spike Lee and Vernon Jordan have homes. This area was one of the first places in the region that welcomed African Americans. It is also home to the Gingerbread Houses and the Flying Horses Carousel. You will also find a partying atmosphere here, too, but only in the downtown area. (see step 7 and 8.)
Choose a transportation mode on the island. Driving during the summer on Martha's Vineyard is a nightmare. Many people bring their cars and brave the traffic quagmires. It is certainly more convenient but you can get around quite easily by bicycle or bus. The buses run frequently, will stop and pick up at non-route stops, and have budget all-day fares.
Eat on the island. You can easily shop and picnic almost anywhere on Martha's Vineyard. Fish and seafood are abundant, of course, but you can eat vegetarian and ethnic food, too. Be prepared to eat breakfast, lunch, and dinner (restaurant food) for around $10 and up per person (children, too) plus tax, tip, and beverages. Last year, we averaged $40-50 for four people for each meal and that was budget eating!!
Some of the restaurants we chose were Among the Flowers Café and The Main Street Diner in Edgartown. We did not go to the famed Black Dog Tavern because the wait was too long!!!!
Go to the beach!!! Some beaches are private and can only be accessed if you are renting or if you own a home on that particular beach. However, many beaches are public, don't cost anything, but have very few amenities. Some have lifeguards, restrooms and concessions, but many do not. Bring what you will need for your beach day with you. Don't miss Joseph A. Sylvia State Beach. It is halfway between Oak Bluffs and Edgartown and boasts a wooden drawbridge that everyone jumps off into the calm waters below.
Other beaches I would recommend are: Oak Bluffs Town Beach (within the city limits), Aquinnah Beach (the home of red clay and sometimes nudists even though nudity is against the law) and East Beach (in Chappaquiddick which is minutes by ferry or bridge from downtown Edgartown.)
Make sure you find time to visit the Gingerbread Houses of Oak Bluff's famous "Camp Meeting Grounds." This 34 acre compound of colorful, Gothic-style, and elaborately-trimmed homes were built a hundred or so years ago and have been handed down through the generations. The community still holds group prayers in the middle of the compound and you can visit and be delighted.
Don't miss the Flying Horses Carousel. It is considered to be the oldest working carousel in the country. It was built in 1876 before horses on merry-go-rounds could move. The attraction of this carousel was that if you caught the brass ring along the side of the carousel, you would win a free ride. You can still do it today!
