Travel: Plan Your Nantucket Trip Now

History and culture complement this scenic coastal destination.
White Elephant Resort Seen From Nantucket Harbor Credit White Elephant Resorts

White Elephant Resort has a front-row seat to Nantucket Harbor’s summer boating season. (COURTESY WHITE ELEPHANT RESORTS)

Daybreak arrives early on a crescent of sand 26 miles off the coast of Cape Cod, Massachusetts. The fog lifts, revealing a boat-filled harbor. Birdsong and sunlight fill the sky, setting the stage for the spectacle that is summer on Nantucket.

A foghorn announces the arrival of the M/V Iyanough ferry. It carries day trippers and locals who will walk the same cobblestones tread by Melville, Emerson and Thoreau. Some line the sidewalk outside Black-Eyed Susan’s, awaiting buttermilk pancakes. Most don’t mind the wait. It’s worth it just to be on Nantucket, a place that’s ephemeral and enduring. And you don’t have to be a novelist or philosopher to figure that out.

Nantucket was, and still is, a place of contrasts. It’s remote yet worldly, thanks to whalers who sailed the globe, bringing wealth and fame back home. It’s historic, yet forward-thinking and fashionable. It’s thrashed by waves and graced with gardens so luxuriant, a single bloom makes a bouquet. The weather, too, is fickle. One day, the “gray lady” hides behind fog. The next, she basks in brilliant sunshine, tempting plein air artists to capture her quicksilver beauty.  Long before the early 1700s to late 1850s, when Nantucket was the whaling capital of the world, the Wampanoag people called it “the faraway place.” Perched on the edge of the Continental Shelf, it seems remote. However, within a half day of traveling from Orlando, you can arrive in a climatically and culturally different destination. You recognize this when you land at Nantucket Memorial Airport, with its cedar-shingled terminal topped by a weathervane.

Jared Coffin House Credit White Elephant Resorts

The Jared Coffin House stands in the Nantucket Historic (NANCY MORELAND)

Legendary Lodging

History isn’t confined to textbooks on Nantucket. You feel it in the bumpy cobblestones laid in 1837, see it in every 18th century gray-shingled saltbox that a modern family calls home, and hear it in the accents of ninth-generation Nantucketers.

Set the stage for your exploration by staying at the Jared Coffin House. A hotel since 1850, it once hosted Herman Melville, who immortalized the island in Moby-Dick, his novel about the great white whale. The renovated inn provides complimentary conveniences: robes, slippers, beach towels, chairs, bicycles and umbrellas. Downstairs, the Nantucket Tap Room serves upscale and classic comfort fare.

Many of Nantucket’s notable sights are minutes from the inn’s stately steps. To understand the island’s past and present, spend a few hours at the Whaling Museum. Don’t miss the Roofwalk, with its view of the harbor and Brant Point Light Station.

Follow this by walking along Orange Street, where 134 sea captains once lived. Further uphill on Main Street, houses known as “The Two Greeks” and “The Three Bricks” were built by whaling merchants. For a glimpse of 19th century opulence, tour the Hadwen House at 96 Main St. The Quaker Meeting House and Research Library at 7 Fair St. reveals the island’s simpler side. Before heading back to the waterfront, make a detour down India Street to admire the Atheneum, where Frederick Douglass spoke against slavery to an audience of abolitionists. For a deeper dive into local lore, book a Nantucket Historical Association walking tour.

To fuel your excursions, stop by Provisions at Harbor Square for a Nantucket Nectars juice and Turkey Terrific, a treat one local calls “Thanksgiving on a sandwich.” Claim a bench on the wharf and savor your mighty meal to a soundtrack of happy chatter coming from the sidewalk cafés.

Main Street Nantucket Town Credit White Elephant Resorts

Nantucket’s walkable downtown features boutiques, galleries and restaurants. (NANCY MORELAND)

By Land or By Sea

Nantucket is best explored on foot or bicycle. Borrow a bike from your innkeeper, and you can explore a 35-mile path winding past moors, woods and windswept beaches. The former fishing village of Siasconset (known locally as Sconset) is a worthy destination. Its narrow lanes and endearing cottages feel more British than American. Enjoy lunch at Claudette’s, then bike 1.4 miles north to Sankaty Head Lighthouse. On the island’s western side, Madaket is the go-to spot for stunning sunsets, cocktails and dinner at Millie’s. Tip: You’ll cover more ground by riding THE WAVE bus. Each bus accommodates two bikes.

Nothing connects you with Nantucket like sailing, so schedule a sunset cruise on the Endeavor. Or save the salt spray for another day and enjoy the view from Brant Point Grill. At day’s end, boats and houses along the harbor blaze orange in the sunset. Take a mental snapshot while enjoying Great Point oysters, pulled-from-the-water fresh with no briny bite.

White Elephant Residences 2 Credit White Elephant Resorts

Lush gardens surround the White Elephant’s residences (NANCY MORELAND)

Seasonal Highlights

Few places shine like Nantucket from mid-June through Labor Day. Vining roses cover cottages and beach dunes. Atlantic breezes blow so fresh and cool, they once inspired poet and essayist Ralph Waldo Emerson to write, “The air of Nantucket comes into your face and eyes as if it was glad to see you.”

Focus solely on summer though, and you miss Nantucket’s other charms. The islanders understand this and carpe diem regardless of weather. The first weekend of December, downtown resembles a Dickens novel. Carolers in period costume stroll the streets, which are illuminated by gaslight and lined with Christmas trees. The last weekend of April, the Daffodil Festival welcomes warmer weather, and cherry blossoms burst into bloom in mid-May. Springtime is less crowded than summer, with lower rates and shorter restaurant waits. The same holds true for late September, October and November.

Sunsets, seafood and the seasons are fleeting pleasures, but Nantucket is a different story. One visit and it’s anchored in your memory, calling you back to a magical crescent of sand surrounded by sea.

Great Point Oysters Credit Nancy Moreland

Fresh, local Great Point oysters (NANCY MORELAND)

By the Way…


Located in the heart of Nantucket Town, the Jared Coffin House rates start at $185/night. Its sister property, the White Elephant, offers rooms, suites, cottages, residences, a pool, spa and the Brant Point Grill. A short walk to Children’s Beach, the family friendly resort provides guests loaner bikes and Radio Flyer wagons. Rates start at $325/night.   


If élan could be purchased, you’d find it in downtown’s stylishly curated shops. Check out Murray’s Toggery Shop for iconic “Nantucket Reds” apparel. For exquisite handwoven blankets and home goods, visit Nantucket Looms. Bibliophiles enjoy the “independent and out to sea” character of Nantucket Bookworks and Mitchell’s Book Corner.


If visiting outside of May to October, check museum, tour and restaurant hours; some will close or limit hours during the off-season. Fog can delay flights and ferries at any time of year, and it’s wise to wear layers. Windbreakers, hats and sweaters are handy, even in summer.


Fly to Charlotte, Boston, Newark or New York City, followed by a quick connecting flight to Nantucket Memorial Airport.

Categories: Travel