Once you've reached Edgartown, a car isn't necessary. It's actually a hindrance, as parking can be very tight in summer. The Martha's Vineyard Transit Authority operates a fleet of buses that can get you almost anywhere you want to go. The town runs a well-stocked visitor center on Church Street.
The best way to get around Chappaquiddick Island is by bike; bring one over on the ferry and ride the few miles to Cape Pogue Wildlife Refuge. Sign up for a tour with the Trustees of Reservations for an in-depth look at the island's wonders.
Unspoiled by the "progress" of the past few decades, the working port of Menemsha is a jumble of weathered fishing shacks, fishing and pleasure boats, drying nets, and lobster pots. The village is popular with cyclists who like to stop for ice cream or chowder.
Vineyard Haven sees ferry traffic year-round, so this port town is always active. If you're traveling without a car, you can get around by taxi or the white buses run by Martha's Vineyard Transit Authority. Bike, scooter, and car rentals are also possibilities. Much of the downtown area is easily explored on foot, and a good number of the lodgings are within reach. Vineyard Haven is 3.5 mi west of Oak Bluffs.
The Nantucket Historical Association's 90-minute Historic Nantucket Walking Tours, offered twice daily in season ($10), provide an overview of the island's history and encompass such sites as Petticoat Row, upper Main Street, and the wharves, churches, and library. The self-guided Black Heritage Trail tour covers nine sites in and around town, including the African Meeting House, the Whaling Museum, and the Atheneum. The trail guide is free from the Friends of the African Meeting House on Nantucket, which also leads a "Walk the Black Heritage Trail" tour by appointment in season.
West Tisbury retains its rural appeal and maintains its agricultural tradition at several active horse and produce farms. The town center looks very much like a small New England village, complete with a white-steepled church.
Menemsha, is often busy with folks eager to see the sunset. You can take a Martha's Vineyard Transit Authority bus here; there's frequent service in summer, and more-limited service the rest of the year.
If you're exploring the area by bike, you can get between Menemsha and the Aquinnah Cliffs via the Menemsha Bike Ferry. It's a quick trip across the water ($8 round-trip), but it saves a lot of riding on the busy State Road.
Circuit Avenue is the bustling center of the Oak Bluffs action, with most of the town's shops, bars, and restaurants. Colorful gingerbread-trimmed guesthouses and food and souvenir joints enliven Oak Bluffs Harbor, once the setting for several grand hotels (the 1879 Wesley Hotel on Lake Avenue is the last remaining one). This small town is more high-spirited than haute, more fun than refined. Look for the yellow tourist information booth at the bottom of Circuit Avenue. It's open from June through mid-October and is staffed with helpful folks from the area.
First a fishing outpost and then an artist's colony (Broadway actors favored it in the late 19th century), Siasconset—or 'Sconset, in the local vernacular—is a charming cluster of rose-covered cottages linked by driveways of crushed clamshells; at the edges of town, the former fishing shacks give way to magnificent sea-view mansions. The small town center consists of a market, post office, café, lunchroom, and a combination liquor store–lending library.
The Martha's Vineyard Transit Authority buses makes stops at West Tisbury, 8 mi west of Edgartown and 6½ mi south of Vineyard Haven.
Aquinnah, called Gay Head until the town voted to change its name in 1997, is an official Native American township. The Wampanoag tribe is the guardian of the 420 acres that constitute the Aquinnah Native American Reservation. Aquinnah (pronounced a-kwih-nah) is Wampanoag for "land under the hill." You can get a good view of Menemsha and Nashaquitsa ponds, the woods, and the ocean beyond from Quitsa Pond Lookout on State Road. The town is best known for the red-hued Aquinnah Cliffs.
Oak Bluff is the terminal for seasonal ferries. If you have a car, it's best to find a space and leave it while you walk, bike, or take the white buses operated by Martha's Vineyard Transit Authority.
Chilmark is a rural village where ocean-view roads, rustic woodlands, and sparse crowds have drawn chic summer visitors and resulted in stratospheric real-estate prices. Laced with rough roads and winding stone fences that once separated fields and pastures, Chilmark reminds people of what the Vineyard was like in an earlier time, before the developers came.
Perhaps best known for its association with the Kennedy clan, the Hyannis area was also a vacation site for President Ulysses S. Grant in 1874 and later for President Grover Cleveland. A bustling year-round hub of activity, Hyannis has the Cape's largest concentration of businesses, shops, malls, hotels and motels, restaurants, and entertainment venues.
This is the end of the world, or so it seems when you're standing on the edge of the cliff looking out over the ocean. Aquinnah, 6½ miles west of Menemsha and 10 miles southwest of West Tisbury, gets lots of traffic, for good reason. You can drive here (and pray for a parking space) or ride the Martha's Vineyard Transit Authority buses, which have frequent service in summer.
Once a well-to-do whaling center, Edgartown remains the Vineyard's toniest town and has preserved parts of its elegant past. Sea captains' houses from the 18th and 19th centuries, with well-manicured gardens and lawns, line the streets.
A sparsely populated area with many nature preserves, where you can fish, Chappaquiddick Island, 1 mile southeast of Edgartown, makes for a pleasant day trip or bike ride on a sunny day. The "island" is actually connected to the Vineyard by a long sand spit that begins in South Beach in Katama. It's a spectacular 2¾-mile walk, or you can take the ferry, which departs about every five minutes. On the island's Mytoi preserve, a boardwalk runs through part of the grounds, where you're apt to see box turtles and hear the sounds of songbirds. Elsewhere you can fish, sunbathe, or even dip into the surf—use caution, as the currents are strong.
Chilmark, 5½ miles southwest of West Tisbury and 6 miles west of Aquinnah, is served by the big buses of the Martha's Vineyard Transit Authority. The fare is $1 per town, including the town of departure.
Most people call this town Vineyard Haven because of the name of the port where ferries arrive, but its official name is Tisbury. Not as high-toned as Edgartown or as honky-tonk as Oak Bluffs, Vineyard Haven blends the past and the present with a touch of the bohemian. Visitors step off the ferry right into the bustle of the harbor, a block from the shops and restaurants of Main Street.
At the height of its prosperity in the early 19th century, the little town of Nantucket was the foremost whaling port in the world. Shipowners and sea captains built elegant mansions, which today remain remarkably unchanged, thanks to a very strict building code initiated in the 1950s. The entire town of Nantucket is now an official National Historic District encompassing more than 800 pre-1840 structures within 1 square mile.