Great Itineraries

The outings below cover all the towns on the island, but you don't have to. You might want to spend a short time in Vineyard Haven before getting rural Up-Island or heading for a beach. Or you might prefer to go straight to Edgartown to stroll past the antique white houses, pop into a museum or two, and shop. If you just want to have fun, Oak Bluffs, with its harbor scene and nearby beaches, is the place to go. In essence, pick and choose what you like best from what follows. The Vineyard is small enough that you can pick one town as your base and easily explore other areas.

A Perfect Day Down Island

Start your day in Vineyard Haven. Historic houses line William Street, and you'll find shops and eateries along Main Street. Take a quick jaunt out to West Chop for a great view over Vineyard Sound from the lighthouse; then head back through town toward Oak Bluffs via Beach Road. Spend some time wandering the streets of the Oak Bluffs Campground, where tightly packed pastel-painted Victorian cottages vie with one another for the fanciest gingerbread trim. Then head into the center of Oak Bluffs for a ride on the Flying Horses, the oldest continuously operating carousel in the country.

Instead of going to Oak Bluffs from Vineyard Haven, you could head straight to Edgartown, where you can spend the afternoon browsing the shops and visiting museums. Take the On-Time ferry to Chappaquiddick Island to visit the Mytoi preserve or have a picnic at Three Ponds Preserve. If conservation areas are your thing, the Cape Poge Wildlife Refuge on the island is a must. You'll need a few hours on Chappaquiddick to make the visit worthwhile.

A Perfect Day Up Island

Begin your day with a visit to the West Tisbury farms, some of which have pony rides for kids. A stroll amid Long Point Reservation's 633 acres of open grassland and heath makes for an engaging morning.

Then drive out to Aquinnah Cliffs (formerly Gay Head), one of the most spectacular spots on the island. Go to the lookout at the cliffs for the view, or take the boardwalk to the beach and walk back to see the cliffs and Aquinnah Light from below. Spend some time sunning and swimming at this breathtaking spot. (A note to the modest: the beach attracts nude sunbathers; though it's illegal, officials usually look the other way.)

On your way back from the cliffs, stop in the fishing village of Menemsha. You could also stop at the Winery at Chicama Vineyards in West Tisbury for a tasting. As the day comes to an end, pick up some seafood and take it to Menemsha Beach for a sunset picnic.

A Perfect Rainy Day

After you've assessed that gray skies and steady downpours do not constitute beach weather, start your day curled up with a good book. If you need some good reading material, get up early and visit Edgartown Books in Edgartown or Bunch of Grapes in Vineyard Haven. Book Den East, in a converted barn in Oak Bluffs, is full of rare and fascinating used books. You can also drop by one of the six island libraries.

By late morning, with cabin fever setting in, visit the small handful of island museums. The Martha's Vineyard Historical Society houses exhibits in the Captain Pease House, the Gale Huntington Library of History, and the Foster Gallery -- all in Edgartown. The Vincent House Museum, also in Edgartown, contains displays of early island life. While in Edgartown, have lunch at the cozy Wharf Pub.

After lunch, head to the video arcade in Oak Bluffs and, across the street, the Flying Horses carousel, both for kids and kids-at-heart. The whole family can unwind at the Offshore Ale brewpub, also in Oak Bluffs, where dart enthusiasts can find formidable foes.

By late afternoon and into evening, movies can distract you from the downpour (however, island theaters rarely show matinees earlier than 4 PM). If you're renting a house that has a TV and a VCR or DVD, you're set. There are great video rental shops in the Down-Island towns. If you're Up-Island, try Alley's General Store in West Tisbury and the Harbor Craft Shop in Menemsha. Libraries also have videos for overnight loan, though, depending on the town, you may have to purchase a library card first.

If all else fails, you can always watch the storm through your window and daydream.. of sunny days.