Cape Escape: Off-Season Nantucket Has Charm & Lowkey Luxury In Spades

At the risk of sounding eccentric, my 14-year old daughter Eva and I share a love for the atmospheric melancholia of autumn: the ever-darkening afternoons, the crunch of leaves under foot, the chance to wrap up in our favourite winter coats. So we are both thrilled by a sudden dramatic downpour as we huddle in the little clapboard ticket office in Hyannis, Cape Cod, waiting to board our one-hour ferry to Nantucket.

By the time we’ve clambered up the gangplank and found two seats in the steamy main cabin alongside an assortment of fellow out-of-season holidaymakers, fishermen and island workers, the rain has been replaced by a heavy fog, so we see nothing of the place until we’re pulling our suitcases over the cobbles towards our hotel.

Originally named Natocke (‘the faraway island’) by its native Wampanoag inhabitants, boomerang-shaped Nantucket, with its mild summers and wet, windy winters, is New England in a bottle: long, wild beaches, pretty lighthouses, historic villages, cranberry bogs and rolling moors. Its sweet spots are April and May, but also October, when lots of shops and restaurants are closed but enough are not and you can almost hear the island exhaling.

We are staying right in Nantucket town, in a pretty whitewashed cottage belonging to the waterfront White Elephant Hotel where we find a roaring fire and copies of Moby Dick by the bed. There are, of course, some spectacular rentals around, like the one Kourtney Kardashian booked for her family holiday or the one they used to film the televised version of local writer Elin Hilderbrand’s novel, The Five Star Weekend, starring Jennifer Garner, Regina Hall and Chloe Sëvigny, which was shot just before we got there. But those don’t come cheap.

Nantucket’s year-round population of about 14,000 – artists, farmers, fishermen, builders, and those working in businesses that maintain all those fancy houses – swells to around 80,000 in the summer. I grew up spending Augusts on Cape Cod so know first-hand the ‘crazy’ of summer and the queues for a coffee.

Heading out for our first early evening stroll, we catch the most amazing pink sunset over the harbour before heading up Main Street, past the world’s prettiest branch of Polo Ralph Lauren in an 1830s brick townhouse and the only major chain (apart from the supermarket Stop & Shop) given permission to open on the island. Many locals see Nantucket as a salt-in-your hair, sand-in-your-sneakers type of place, but given average house prices in 2025 hovered around $4.7m and last year there were about 75 billionaires on-island, Ralph Lauren doesn’t seem that out of place.

Nantucket’s first wealth surge came in the mid-18th century when it became the global centre of the whaling industry, and merchants and ship owners built the island’s first Greek Revival houses. By the late 19th century, tourism had replaced whaling, and artists, actors, and writers began building homes.

One summer in the 1890s, a band of Broadway actors decamped to Siasconset (‘Sconset), a pretty little village on the eastern tip of the island, when their stiflingly hot theatres closed for the summer. Some of them clubbed together and built a ‘hall of amusement’ they called Sconset Casino, with tennis courts, a bowling alley and a theatre where elaborate summer productions are staged to this day. Writer and humourist Robert Benchley began spending family holidays in Sconset in the 1930s; in 1974, his grandson Peter’s novel Jaws was published, inspired by his summers there.

Today, the island’s tourist season kicks off with the Nantucket Daffodil Festival in April, which includes a fancy dress vintage car parade, and ends in December with the Christmas Stroll, when town is transformed into one big Christmas market. In the middle (June) is the Nantucket Film Festival, run by Ben Stiller and friends, which has attracted everyone from Meg Ryan to Woody Allen.

We visit the excellent Whaling Museum and do a downtown walking tour. We also explore the shops. My favourite is Commonwealth, selling secondhand designer clothing (Prada stilettos, Balenciaga bags, Armani jumpers) and really great wine. Nantucket Looms is a wonderful interiors shop, filled with elegant baskets and bowls and shawls, much locally produced, with a working weaving studio upstairs. Then there’s Murray’s Toggery, home of the island’s famous Nantucket Reds – terracotta canvas trousers that fade over time to a fabulous dusty pink.

We transfer ten miles north to White Elephant’s sister hotel, the Wauwinet (wauwinet.com), a beautiful Cape-style inn with a renowned seafood-leaning restaurant, Toppers, local art-and-book-filled drawing rooms, roaring fires, and complimentary daily sherry and cheese at 4pm. It sits on a sliver of land so narrow you can see the sea on either side of you: Nantucket Sound (great for kayaking and fishing) at the foot of the garden and the Atlantic right behind. The Wauwinet also offers free bikes, an hourly shuttle service into town and cruises with knowledgeable local, Captain Rob, in the hotel’s motorboat.

On my last day, I cycle to Bartlett’s Farm, the island’s best produce shop, to sample their tangy cheddar, then to the Cisco Brewery for Whale’s Tale pale ale. Both are open year-round. There’s one place I regrettably don’t make it to: The Chicken Box, a refreshingly raucous sounding dive bar I’m told by absolutely everyone is the out-of-season port in a storm. Next time.

Francecsa’s return flights from London Heathrow to Boston had a carbon footprint of 1,549.6kg of CO2e (ecollectivecarbon.com).

Which New England Tribe Are You?

Nantucket, Massachusetts

WHO GOES: Joe Biden, Ben Stiller, Drew Barrymore, Amy Poehler

VIBE CHECK: Preppy, understated and elegant, Nantucket attracts billionaires and birdwatchers alike. The island’s discrete old money atmosphere has been somewhat diluted by a flashier tribe, gliding in by private jet. Otherwise it’s an eight-seater flight or a one- to two-hour ferry from the Cape, so it takes effort to get here, helping keep it exclusive.

Martha’s Vineyard, Massachusetts

WHO GOES: The Obamas, Spike Lee, Ted Danson and Mary Steenburgen, Larry David, Mia Farrow, Carly Simon

VIBE CHECK: If billionaires go to Nantucket, millionaires go to Martha’s Vineyard. Long a haven for liberal A-listers, writers, activists and academics, Nantucket’s neighbour has always had an exclusive yet inclusive, laid-back atmosphere and is twice as big.

The Hamptons, Long Island, New York

WHO GOES: Beyoncé and Jay-Z, Jerry Seinfeld, Gwyneth Paltrow, Jennifer Lopez, Alec Baldwin, Robert de Niro

VIBE CHECK: Old money summer retreat-turned-new money party place, this eastern tip of Long Island has long been a playground for wealthy New Yorkers. A string of villages, each has a different atmosphere: Southampton (old money), East Hampton (new money), Montauk (surfy).

Newport, Rhode Island

WHO GOES: Jay Leno, Larry Ellison and Jason Schwarzman

VIBE CHECK: The original one- percenter capital and summer playground for the Vanderbilts and Astors, who built their Gilded Age mansions here. It is now a year-round hub for tech and finance titans. Historically a centre for the transatlantic slave trade, it has a unique cultural heritage and is home to the legendary Newport Jazz Festival.