History meets luxury on this iconic New England island, but choose your season wisely.
Savannah/Hilton Head International Airport (SAV) to Nantucket Memorial Airport (ACK)
Duration: Varies by airline
Airlines: JetBlue, Delta
Hilton Head residents have a special affinity for Nantucket. Whether it’s the similar shapes of our islands, the red-and-white striped lighthouses or the complementary climates, many of us are attracted to this northern getaway, 30 miles off the southern coast of Cape Cod. But here’s one big difference: Nantucket has no traffic lights (although there is one functioning roundabout).
Other similarities? Both islands are noted for pristine beaches, bike paths, nature, annual festivals, fine cuisine (with great seafood) and plenty of local culture. But about 850 miles away as the crow flies (and more than 1,000 miles if you’re driving), the weather is that much cooler, especially on summer evenings.
The key to visiting Nantucket, especially in summer, is planning. It’s popular and pricey, and like Hilton Head, the population expands exponentially in season — from 15,000 to over 80,000.
There are only two ways to get there, by sea and by air. Flying is faster, with connections via Charlotte, Boston, or Providence on Cape Air. Ferries sail regularly from both Hyannis and Harwich on Cape Cod, as well as from New Bedford on the Massachusetts mainland. There also are ferries between Nantucket and its “neighbor,” Martha’s Vineyard.
No matter how you arrive, you may not need — or want — a car. There are taxis and shuttle buses, but certain parts of the island only can be reached with your own transportation. If you want to rent, check out Turo.com; if you want to bring a car over on the ferry, book extra early. Bikes are a popular way to get around and are for rent all over, but cobblestone streets in the town of Nantucket and uneven bike paths can prove daunting. When deciding where to stay — in town or out — ask about how to get around and how easy it is to get to nearby beaches.
One of the world’s major whaling ports from the late 17th until the mid-19th centuries, Nantucket gained fame as a summer resort for New England’s well-to-do in the early 1900s. Now a popular (and expensive) getaway/second-home for people from around the world, the island is noted for its many festivals and special events: Daffodils (late April), Food & Wine (May), Film (June), Comedy (July), Harvest (formerly the Cranberry Festival, in October) and the Christmas Stroll (first weekend in December).
Three island lighthouses come with historic significance. The 60-foot, which was first built of wood in 1784, was destroyed by fire in 1816, rebuilt in stone two years later, destroyed in 1984 and reconstructed in 1986. It’s located in the Coskata-Coatue Wildlife Refuge at the tip of seven-mile-long Great Point Beach, an undeveloped barrier beach off the island’s eastern side. A special parking permit is required and obtained in advance, but it’s well worth it for naturalists, bird enthusiasts and anyone who wants to experience a variety of environments including ocean, maritime oak forests, and rolling red cedar savannah.
Brant Point is the oldest lighthouse on the island, dating from 1746, making it the second oldest in the U.S. It’s also only 26 feet tall, making it the shortest in New England, and is located at the entrance to the town of Nantucket where the ferries come in. The town has great shopping, dining and people-watching along the cobblestone roads and by the bustling marina, where besides the ferries are docked everything from little sailboats to giant luxury yachts.
The third lighthouse is the 60-foot-tall Sankaty, which was built in 1850 and overlooks the ultra-exclusive Sankaty Head Golf Club on the island’s east side. It’s at the end of the very special Bluff Walk, which begins in the charming village of Siasconset (also called “Sconset”), which is rich with restaurants and markets. The Bluff Walk is a two-mile public trail along a cliff above the ocean and through the backyards of some of Nantucket’s most beautiful residential neighborhoods. On one side are sky, the ocean and the beach; on the other are stunning backyards filled with beautiful gardens. And wherever you go, notice the shingled architecture that is protected by the Nantucket Historic District Commission.
There are several public golf courses on Nantucket as well as fishing charters and boat cruises — the cocktail cruise is a favorite — that give a very different perspective of the island, such as the multimillion-dollar “cottages” along Old North Wharf. Originally fishing shanties and workshops from the island’s whaling heyday, the roughly 25 cottages here—most with their own boat slips—are now trophy properties, sought after by sailing enthusiasts and wealthy homeowners who want private access to the water adjacent to Nantucket’s bustling downtown.
While most people who rent vacation homes pick up groceries at one of two Stop & Shops, check out Bartlett Farms, which offers fresh, local produce and an amazing order-at-the-counter lunch.
Planning also is required for restaurant reservations, especially on weekends. The most popular places—such as Cru and Loa Burger—book up very quickly. Here are a few other notables:
Galley Beach offers a unique dining experience under a tent on the ocean. Expect breezes, beautiful sunsets and great food.
Cisco Brewery offers a lively social scene with music, craft beers and food trucks, featuring lobster rolls, pizza, and just about anything else. Popular with locals, there are always loads of people enjoying the very festive atmosphere.
Ventuno is a popular Italian restaurant with indoor and outdoor seating. For more casual Italian, try Pi Pizzeria, which even has a white clam pie. For even more casual, the food truck at Surfside Beach on the island’s south shore is known for its delicious crabby patty, while the iconic Chicken Box, aka The Box, is your quintessential beach dive bar with live music.
Also be sure to stop by the original Nantucket’s Meat & Fish Market on Old South Road for fresh sandwiches, soups, meat and seafood. The iconic market opened its third location at Tanger Outlet II in Bluffton in 2021 and has developed a strong local following.
A last word of advice: wait until summer is over and the families have left. September is less crowded, the weather is still good, and it’s much easier to get around town, find lodging and make dinner reservations.