What charming bit of New England landscape was bought, in 1659, by a group of Massachusetts Englishmen for 30 pounds and two beaver hats, is shaped like a whale playfully flipping its tail in the air, and is home to fishermen who haul so many succulent lobsters from the sea even the most lobster-obsessed can sate their craving?

The answer: Nantucket Island.

Those in the know have, for years, headed to this island in the Atlantic some 30 miles (48 km) south of Cape Cod, Massachusetts. Though the 10,000 year-round island population swells to 55,000 in high season, Nantucket has remained amazingly unspoiled, with over a third of the island’s moors and marshland protected from development.

The island had a large Wampanoag Indian population until it was sold to nine Englishmen in 1659. In the early 1700s, Quakers moved onto the island to avoid persecution, and whalers soon found it an ideal center for whaling activities; it was a whaling center until the late 1830s. Today’s island residents are delighted to share their island with others and show off its charms.

The Brant Point Lighthouse, on Nantucket Harbor, is America’s second-oldest light station.

Compact in size — 14 miles (23 km) long and 3½ miles (6 km) wide at its broadest point — “the gray lady of the sea,” so named by sailors because of its fog-bound shores, can easily be reached by ferry or airplane. Yet once you’re here, the rest of the world seems far away “in America,” as locals refer to their visits to the mainland.

Memorial Day weekend is the harbinger of Nantucket’s high season, when summer cottage-dwellers and tourists flock here to revel in the island’s history, architecture, one-of-a-kind shops, fine weather and outdoor activities.

Guided walking tours provide an excellent introduction to the town of Nantucket and its busy harbor area, and are a good way to get your bearings. Cobblestone streets shaded by elms are lined with graceful 18th- and 19th-century homes — here a brick mansion, there a lush pocket garden and everywhere boxwood hedges, white picket fences and rampant roses.

Quakers, who first arrived in 1700 to escape persecution on the mainland, and businessmen who profited from the whaling trade — in the 1830s Nantucket was one of the busiest whaling ports in the world — built exquisite houses here that range in style from traditional saltbox and Federal, to Greek Revival and Georgian.

Even after a disastrous fire ravaged the town in 1846, Nantucket still possessed more than 800 pre–Civil War structures. Many homes have a lively historical lineage, which a witty guide will share with you; they’ll likely also share gossip about numerous famed writers who have answered the island’s siren call.

Truman Capote, Christopher Isherwood, Robert Lowell, John Steinbeck, Sinclair Lewis, Henry David Thoreau and Ralph Waldo Emerson all came here. Herman Melville actually based his novel, Moby Dick, on a true story that took place in 1820 when the Nantucket whaling ship Essex was sunk by a whale. Hemingway visited, with his mother, in 1910. Playwrights Eugene O’Neill and Tennessee Williams also stayed on Nantucket, in summer cottages.

Down on Nantucket Harbor, where the passenger and car ferries arrive, the bay is awash in fancy yachts, working fishing craft, speedboats, sailboats, charter fishing boats and cruise boats that take visitors out past the stalwart Brant Point Lighthouse — the second-oldest light station in America — and sprawling cliff-top summer homes.

There’s nothing shabby about Nantucket, which is handsomely maintained and overflowing with flowers — in boxes, planters and pots. Straight, Old South and Commercial wharfs jut out into the harbor, and are lined with cozy rental cottages and a dizzying array of shops selling everything from designer clothes and less-expensive summer wear, to antiques and toys.

There are several restaurants here, too, where you can tuck into lobster dinners while enjoying great views of watercraft en masse, circling seabirds and commercial fishermen bringing in their catch.

Clothing, fashioned in the distinctive tomato-soup shade called “Nantucket Red,” is popular with locals and tourists alike, as are traditional Nantucket lightship baskets. These elegant rattan handbags can run hundreds to thousands of dollars.