Life doesn’t get much more idyllic—or frankly, more preppy—than it is in the cobblestoned main streets, salt-box homes, and creaking docks of Nantucket, renowned for its past life as the whaling capital of the world. It was that status—enjoyed from about 1800 to 1840—that brought great wealth to the community, which is to this day studded with the immense captain’s homes of yore. That wealth is still readily apparent today in the form of new gargantuan mansions (sometimes complete with a helipad or two in the backyard), and boutique shopping that puts the “up” in upscale.
Not for nothing was Herman Melville’s Moby-Dick set partially on Nantucket: This little spit of land was a major international player—in fact, the source of the world’s whale oil—for nearly the first half of the 19th century. Nantucket was settled in 1658 by a small band of Massachusetts colonists who had their fill of the Puritans’ intolerance and were looking for a solid place to raise some sheep.
When the first sperm whale washed up on the beach in 1712, however, it sparked a gold rush of whaling vessels that increased Nantucket’s reputation and its coffers as they sailed around the world. By 1850, however, the whaling era was over; whales had been overhunted, and new forms of fuel were replacing whale oil. Nantucket’s economy took a dive, and it wasn’t until the island discovered and slowly capitalized on the appeal of its historic charm as a resort that the money started flowing back in.
As recently as two decades ago, the island was still a sleepy summer haven for bluebloods, full of family cottages, fusty country shops, and few tourist attractions. But the world has since discovered its charm, and Nantucket Town is now packed with luxury inns, high-end restaurants and stores, and bed-and-breakfasts that are as pretty as they are pricey. Its waters still teem with boats, to be sure, but nowadays they’re more apt to be cruise ship–sized yachts than humble little schooners.
Outside of the main town sit two outlying communities known as Siasconset (or simply “’Sconset,” if you summer or live here) and Surfside. Both are blink-and-you-miss-it small, with just one or two eateries and stores to mark them as quasi-towns. The rest of the island, meanwhile, is dotted with homes both new and historic (more than 800 houses here were built before or during the Civil War) around its beaches and large swaths of untouched land. Much of it, thanks in no small part to the ongoing efforts of the island’s conservationists, is as similar to what it was in the island’s yesteryear as Nantucket Town itself is now different.
Ferries leave for Nantucket Town from Hyannis  on both the Steamship Authority (508/477-8600, www.steamshipauthority.com ) and the Steamship Authority Fast Ferry. Also leaving from Hyannis: Hy-Line Cruises High Speed Ferry (508/778-2600, www.hy-linecruises.com ). You can also get to Nantucket from Oak Bluffs  on Martha’s Vineyard  (late June–early Sept.).
Several of the usual national agencies rent vehicles from Nantucket Airport, but unless you’re visiting in winter, a car isn’t really necessary, given the close proximity of everything in town and the excellent bike paths running over the island. The Nantucket Regional Transit Authority (508/228-7025, www.shuttlenantucket.com ) does continuous loops between Straight Wharf in Nantucket Town and Madaket, Surfside, Siasconset, and the airport.