Despite Nantucket being the home port of Moby-Dick’s fabled protagonist, Captain Ahab, and his ship, the Pequod, author Herman Melville didn’t visit the island until after the famed novel was published, taking a steamship to the charming crescent of sand off the coast of Massachusetts in 1852. He ambled around the island, conversed with dignitaries, dined out and took in the sights of the evocative locale. On his last day, he briefly met with George Pollard Jr., forlorn captain of the Essex and inspiration for Melville’s opus. Pollard had watched an 85-foot sperm whale ram the ship’s bow in the middle of the South Pacific, but miraculously lived to tell the tale, shocking the seafaring world.
Throughout the 18th and 19th centuries, Nantucket was the whaling capital of the world—turning it into one of the wealthiest communities in America—a legacy that comes with its share of ghostly and grand narratives. Today, 200 years after the sinking of the Essex, whaling history is expertly preserved in Nantucket’s museums, guesthouses, rose-covered fishing cottages and even underfoot.
Jared Coffin House
A former whaling merchant’s home, the regal red-brick building is where Melville stayed during his visit to Nantucket. The inn’s period antiques are updated with modern flourishes, and four swish new suites—named after historic Nantucket women—were revealed this year.
Operated by the historical association, the museum contains thousands of whaling tools, scrimshaw and paintings from the era, in addition to a complete skeleton of a 47-foot sperm whale. Walking tours are also available, showcasing downtown Nantucket, which has the highest concentration of pre-Civil War homes in the U.S. The cobblestones that line Main Street were once used as ballast in 19th-century whalers.
Sankaty Head Light
Built in 1850, the iconic red- and white-striped tower remains a sentinel atop the Sankaty Bluff at the end of ’Sconset Bluff Walk—considered the most scenic path in Nantucket, lined with lavish summer homes and unobstructed ocean views. The lighthouse grounds are open daily, and on certain days throughout high season, visitors can climb the spiral staircase and walk out to the lighthouse balcony for a panoptic view of the island.
Thomas Macy House
Melville drew source material for Moby-Dick from fellow author Obed Macy’s 1835 book, The History of Nantucket. When he visited in 1852, Melville met Macy’s son, Thomas, for dinner at his house. Open during daylight hours for self-guided tours, the Macy House remains frozen in its Federal-style grandeur, surrounded by equally dignified homes.
Nantucket Boat Basin
During the whaling heyday, more than 15 whalers would anchor in the harbor. This was also the location from which the Essex departed in 1819 on its fateful voyage. Today, the site of the original wharves is a full-service marina and luxe destination for sailors and yacht captains, with 240 boat slips mere steps away from winsome waterfront restaurants, boutiques and art galleries.