A Nantucket summer kicks off with the Figawi, a sailing regatta with nearly 250 boats that marks the unofficial start of the season on the island. Charming cobblestone streets, shake-shingled homes of seafaring captains, and more than 80 miles of beaches make this the perfect weekend getaway to soak up lazy seaside days.
Hop aboard Steamship Authority’s or Hy-Line Cruises’ high-speed ferry and arrive to the island in just under an hour, or take the Steamship’s more leisurely two-hour-plus traditional ferry cruise. Another great option is Freedom Cruise Line, sailing from Harwich Port’s Saquatucket Harbor. You can also choose a quick, scenic flight via Cape Air/Nantucket Airlines or the Rectrix Shuttle; trivia geeks will love that the small Nantucket airport was the set of the 1990s hit television show Wings.
Once on Nantucket, navigating the island is actually quite easy. You can explore by bike, or rent a car from Nantucket Windmill Auto Rental, which is conveniently located at the airport (they’ll also bring your vehicle to the ferry dock). Or ride the Nantucket Regional Transit Authority, offering several routes around the island.
For lunch, head to Topper’s at The Wauwinet, a legendary bayside restaurant located inside the historic inn, which has been welcoming guests since 1875. Topper’s serves local and seasonal dishes with an emphasis on seafood. Grab a seat on the deck, order some Retsyo oysters (cultivated a few hundred yards away) and enjoy your view of the water. Topper’s is also noted for their 1,450-bottle wine list—oysters and wine are excellent companions. (120 Wauwinet Road, Nantucket)
The Nantucket Whaling Museum started back in the 1840s as candleworks, producing whale tallow candles until the end of the area’s whaling industry in the 1860s. Today, the revamped museum houses the skeleton of a sperm whale, among other artifacts that celebrate the rich cultural heritage of Nantucket’s whaling era. Though he never visited the island, Herman Melville set his famed novel Moby Dick off the shores of Nantucket, so legendary was their whaling industry. (13 Broad St., Nantucket)
Brant Point Lighthouse contains some serious Nantucket history. The first iteration was built in 1746, but burned down; the current lighthouse was built in 1901, automated in 1965 and is still in operation. Stroll around and collect shells while you capture the picturesque bay views of a quintessential Nantucket landmark. (2 Easton St., Nantucket)
The Brant Point Grill at the White Elephant Hotel is a classic island dinner destination. Watch the sunset over the harbor as the sailboats float by, and savor a flavorful steak or seafood dinner. They’re known for their lobster, including a delectable lobster mac and cheese entrée—a house specialty. (50 Easton St., Nantucket)
Rent a bike and pedal the seven-mile stretch (or drive) to the quaint former fishing village of Siasconset, on the opposite side of the island. Stroll through ‘Sconset (as it’s known to locals) and admire the funky cottages and historic houses, some dating back to the 18th and 19th centuries.
Grab breakfast or sandwiches at local favorite Sconset Market to bring to Siasconset Beach. Wash it down with a juice from Nantucket Nectars, the beverage that got its start on the island. (4 Main St., Siasconset)
After the beach, tour Cisco Brewers (which also houses a winery and a distillery). Tours are offered twice daily in season and the admission price includes a tasting glass, which you can use to sample two beers, two wines and two spirits. Cisco also regularly hosts food trucks and live music; it’s a laid-back, friendly place to while away a Nantucket afternoon with a frosty Whale’s Tale Pale Ale or a Grey Lady in hand. (5 Bartlett Farm Road, Nantucket)
Sunset at Madaket Beach is one of the most unforgettable things to do. Stroll the beach and collect shells as the sun dips toward the horizon and colors the sky hues of pink, orange and blue. Bring a bottle of wine and some cheese and bread for the perfect pre-dinner snack.
The Jared Coffin House, a brick mansion built in the 1840s by successful whaling ship owner Jared Coffin, is a Nantucket landmark and historic hotel. It’s also home to Nantucket Prime, the island’s newest steak house, which also has a stellar raw bar. (29 Broad St, Nantucket)
Brunch at Breeze Restaurant at Nantucket Hotel & Resort is a special affair (book ahead online). While you choose between dishes like the lobster Benedict and the bacon waffle, relax on the porch and enjoy live music. (77 Easton St., Nantucket)
On your last afternoon on Nantucket, cruise the downtown cobblestone streets and check out the shops. While there are boutiques aplenty, you won’t want to miss the classic Murray’s Toggery Shop to pick up your crustacean-embroidered Nantucket Reds.
If shopping isn’t your thing, a truly memorable way to end your Nantucket getaway is a hike through the Coskata-Coatue Wildlife Refuge, whose miles of trails traverse the rugged point of the island and attract scores of wildlife, from horseshoe crabs to deer. Visit the historic lighthouse at the end of Great Point, and bring your camera to capture the scenic vistas of forest, rolling dunes and tidal pools. (Wauwinet Road, Nantucket)