Weekending in Nantucket

A charming New England island where past meets present


The White Elephant’s harborside setting in Nantucket / Photograph courtesy of White Elephant Resorts

When I was growing up, my parents frequently watched Wings — that sitcom about two brothers running an airline on Nantucket — and I became enamored of the postcard-perfect enclave, with its cedar-shingled homes and history of transforming from a 19th-century whaling capital into a popular summer retreat. I just ticked it off my bucket list, and with direct seasonal service from Philly via American Airlines (only a 90-minute flight), you can, too.

What to do

Downtown’s cobblestone Main Street and side roads are easy to explore on foot and lined with locally run boutiques and art galleries, among them the Hospital Thrift Shop. (Go early for high-end secondhand goods on the cheap.) A guided walking tour takes you from the Whaling Museum to notable buildings and homes of prominent islanders, including Lydia Folger Fowler, the first American-born woman to earn her medical degree. (The island has a legacy of women in leadership.) Staying at the newly renovated White Elephant? Consider a driving tour with Captain Rob McMullen to see the darling circa-1700s fishing village of ’Sconset, the red-and-white-striped Sankaty Head Lighthouse, and more.

Where to eat


Butter-poached lobster at Topper’s in Nantucket / Photograph by Connie Zhou

Bar Yoshi’s sushi menu is ideal for lunch on the water, while the Tap Room at Jared Coffin House — once the home of a ship owner — is a cozy dinner option. For true luxury, book a sunset dinner at Topper’s at the Wauwinet, a Relais & Châteaux hotel on the northeast end of the island. The caviar service should be paired with a bubbly from the 1,550-bottle wine cellar.

Where to stay

The White Elephant in Nantucket

The White Elephant in Nantucket / Photograph by Connie Zhou

In May, the 100-year-old White Elephant debuted a refresh to its 54 rooms and suites and 11 garden cottages. The latter range from one to three bedrooms and feature cheery designs inspired by native plants like holly. The main hotel’s rooms are outfitted with blue and seafoam hues, nods to the namesake pachyderm, and art such as Clara Hallencreutz’s pastel lobsters. (Most rooms offer direct access to the waterfront lawn for relaxing on Arhaus’s teak lounge chairs.) In the lobby, a painting of a woman in a rowboat encapsulates the island’s tranquility; sample that feeling when you watch the sunrise from nearby Brant Point Lighthouse. Rooms from $375 per night.

The Can’t Miss List


The Straight Wharf at the end of Main Street / Photograph by Clarence Holmes Photography/Alamy Stock Photo

1. Go boating on the Wauwinet Lady. If you’re dining at Topper’s, take the Wauwinet’s eponymous 20-person boat across the bay.

2. Bike to Cisco Brewers. Rent a bike (White Elephant offers them gratis for hotel guests) and pedal out to the über-popular brewery.

3. Try the Lobster Bloody Mary at the White Elephant’s Brant Point Grill. The iceberg-size hunk of lobster lurking beneath the surface makes it worth the $50 price.

4. Shop at Current Vintage. Pick up a poppy piece from a bygone era, then browse the 400-plus bottles of wine.

5. Learn about lightship baskets at Sylvia Antiques & Four Winds Craft Guild. They developed in the 1800s and have a wooden base, rattan staves and cane weavers.

Published as “Jaunt: Weekending in … Nantucket” in the August 2023 issue of Philadelphia magazine.