Unlike the Hamptons or Aspen—where the beautiful people compete to see who can look more beautiful—the island of Martha’s Vineyard is where the rich and the famous like to let their hair down. Titans of Wall Street walk around Edgartown  with sand in their rolled-up Dockers, while Hollywood actresses don sandals and leave (most of) their makeup at home.
The island really was covered with wild grape vines when explorer Benjamin Gosnold first happened upon it in 1602 and named it for either his daughter or mother-in-law (you be the judge). Many years later, the scenic island 25 miles off the Upper Cape  developed a reputation as a retreat for writers and artists. Celebrities followed, and residents got used to seeing the likes of Billy Joel and Michael J. Fox at the corner market.
All that ratcheted up a notch in the 1990s, when president Bill Clinton made the Vineyard his “summer White House,” and an A-list of Hollywood liberals such as Sharon Stone and Sean Penn descended on the beaches. While the celebrity wattage has dimmed since then, the island still exists somewhere between the planes of it-island and laid-back retreat. The landscape of the Vineyard is the star attraction, with endless beach roads and peaceful salt-water ponds, often lit by the stunning golden light that drew the artists here in the first place.
Ferries leave for the Vineyard from a variety of locations. From Woods Hole to Vineyard Haven  or Oak Bluffs , take the Steamship Authority (508/477-8600, www.steamshipauthority.com , year-round). From Falmouth  to Edgartown , take Falmouth Ferry Service (508/548-9400, www.falmouthferry.com , late May–early Sept.). From Hyannis  to Oak Bluffs, take Hy-Line Cruises (800/492-8082, www.hy-linecruises.com , late May–mid-Oct.). Hy-Line also runs boats from Nantucket  to Oak Bluffs (late June–early Sept.).
From New Bedford  to Vineyard Haven, take Martha’s Vineyard Express Ferry (866/683-3779, www.mvexpressferry.com ). During the summer, several flights a day are offered by Cape Air (508/771-6944, www.flycapeair.com ) from Boston , New Bedford, Hyannis, and Nantucket.
Unless you are going to be spending a lot of time up-island, a car is by no means essential. The Martha’s Vineyard Regional Transit Authority (508/693-9440, www.vineyardtransit.com ) runs buses between all of the towns. If you must have your own wheels, AAA Island Auto Rentals (196 Main St., Edgartown, Five Corners, Vineyard Haven; 800/627-6333, www.aaaislandautorentals.com ) offers free pick-up in Edgartown , Oak Bluffs , and Vineyard Haven .
A less expensive—and more fun—option is to rent a moped from one of several dealers around the island. Try Adventure Rentals (19 Beach Rd., Vineyard Haven, 508/693-1959, www.islandadventuresmv.com ) or Ride-On Mopeds and Bikes (9 Oak Bluffs Ave., Oak Bluffs, 508/693-2076, www.mvmoped.com ).