Nantucket,
Massachusetts:
Before & After.
“I flew into Nantucket from small Massachusetts airfields when I was a college student in Boston. A family friend gave me a key to a large shingled house right in town — use it whenever you want, they said. In winter the streets were empty. The island was just itself. That Nantucket still exists underneath everything that came after. You just have to know where to look.”
In this guide
01 — Then & now
The island before
it became a brand.
Nantucket in the 1970s and early 1980s was a different proposition entirely. Not undiscovered — the island had been a summer destination for generations of New Englanders — but unbranded. The cobblestone streets weren’t a lifestyle statement. The shingled houses were just houses. A college student from Boston could fly in on a cheap prop plane from a small Massachusetts airfield, pick up a key from a family friend, and spend a winter weekend in a large empty house in town with nobody else around.
That was Nantucket before the money arrived in the way it eventually arrived. Before the $40 chowder and the hedge fund summer and the real estate prices that turned every shingled house into a small fortune. Before “Nantucket” became an adjective used to sell things that have nothing to do with the island.
Nantucket — 1970s & 80s
Cheap prop plane flights from small regional airfields. Family friends with keys to houses nobody used in winter. Empty cobblestone streets. The island as a place, not a brand.
Secluded beach houses 20 minutes from town, right on the water. Your family. The Atlantic. Nothing else.
A place people loved quietly, without needing the internet’s permission.
Nantucket — now
JetBlue and Delta direct from New York and DC. $40 lobster rolls. Real estate that sells for eight figures. A “Nantucket aesthetic” that gets licensed to home goods companies.
Summer weeks that book out months in advance. Celebrity sightings in July. A culinary scene that would hold its own in any major city.
And underneath it all — still the same island. The same light. The same moors. The same pull.
“What the money couldn’t change: 46 percent of the island is permanently protected conservation land. The moors still roll to the horizon. The light off the harbor in the late afternoon is the same light it’s always been. Nantucket knows what it is.”
This guide is written from that history — from decades of watching the island evolve without losing what matters about it. We’ll tell you what’s genuinely worth your time, what the crowds miss, and how to find the version of the island that still feels like the one we first loved. The one that was always worth loving.
02 — Getting there
Fly in direct,
or come by sea from the Cape.
One of the things that has genuinely improved since the early days: getting to Nantucket is easier than ever. Direct flights now operate from Washington DC, New York, and Boston. The ferry from Hyannis on Cape Cod runs year-round. You no longer need a connection to a family friend who knows about the cheap prop planes out of a Massachusetts airfield — though that spirit of arrival is still available if you want it.
The island has one airport, Nantucket Memorial (ACK), located three miles from town. It handles everything from Cape Air’s small prop planes to JetBlue’s seasonal jets from New York and DC. The ferry terminal sits in the heart of Hyannis Harbor, a 90-minute drive from Boston.
The bottom line on getting there
Coming from DC or New York: fly direct — JetBlue from DCA or JFK puts you on the island in under two hours total. Coming from Boston: Cape Air prop plane is 30 minutes and genuinely the most memorable arrival. Already on Cape Cod: the Hyannis ferry is the classic route and the crossing itself is part of the experience.
03 — Flying in
The arrival that
sets the whole tone.
Flying into Nantucket has always been a particular kind of experience. The island appears below the wing — moors, ponds, white beaches, the harbor — before you’ve finished the thought of arriving. It’s one of those landings that makes you feel like you’ve actually gone somewhere.
The airport itself is refreshingly small. Three miles from town. No long walks through terminals. No baggage claim theater. You step off the plane and you’re essentially already there.
Who flies where
A note on the small plane experience
Cape Air flies Cessna 402s — nine-passenger prop planes. Luggage is limited (carry-on sized bags, soft-sided). You may be asked your weight for load balancing — this is standard on small aircraft. The 30-minute Boston flight over the Massachusetts coastline on a clear day is one of the better travel experiences in New England. Don’t skip it just because jets are available.
04 — The ferry guide
Hyannis to Nantucket:
one hour, one crossing, no forgetting it.
The ferry from Hyannis is the way most people have always gotten to Nantucket, and it remains the right choice for families, those driving from the mid-Atlantic or South, anyone who wants to bring a car, and travelers for whom the crossing itself is part of the ritual. The drive from Boston to Hyannis takes about 90 minutes. From Providence, about an hour. From New York, count on four to five hours to the ferry terminal.
Two operators run the Hyannis route: the Steamship Authority and Hy-Line Cruises. The Steamship Authority is the only one that carries vehicles. Both run high-speed passenger service that crosses in about an hour.
Should you bring your car?
Probably not. Vehicle ferry rates run around $320 one-way for a standard car — and once you’re on the island, bicycles, mopeds, and taxis handle everything. The town is walkable. The main beaches are reachable by bike. Siasconset (Sconset) is a longer ride but doable. Leave the car in Hyannis and save the money and the logistics headache.
Exception: if you’re staying somewhere genuinely remote and have significant mobility considerations, bringing a car makes sense. Call the Steamship Authority at 508-477-8600 for vehicle reservations — they don’t take them online.
Hyannis parking
Park in the Steamship Authority lots on South Street — arrive early on summer weekend mornings, they fill fast. Alternatively, the Town of Barnstable has additional parking nearby. Budget $20–$30 per day for parking fees. If you’re coming from Boston by commuter rail, the Plymouth & Brockton bus runs directly to the Hyannis ferry terminal — no driving required.
05 — When to go
Summer is famous.
Every other season is better.
We say this having known the island in winter — which is to say, having known it at its most itself. But we’re not purists about it. Every season has a legitimate case. Here’s the honest version.
Summer (July–Aug)
Peak season. The full Nantucket production.
Everything open, everyone there. The harbor is gorgeous and the restaurants are excellent. You’ll share it with a lot of people. Book 4–6 months out for accommodations and popular restaurants. Worth doing once — then consider going in September next time.
Shoulder (June & Sept)
Our recommendation. The insider’s window.
Late June before the July crowds, or September after Labor Day — this is when the island breathes again. All the best restaurants still open. Hotel rates drop. The light in September is extraordinary. The Atlantic is still warm enough to swim.
Daffodil Weekend (late April)
A Nantucket institution worth knowing about.
Three million daffodils bloom simultaneously across the island. Antique car parade, tailgate picnics, the whole town participates. It’s been happening since 1974 and it’s genuinely joyful — and uncrowded compared to summer.
Christmas Stroll (early Dec)
The island’s other great seasonal tradition.
The first weekend of December, the town decorates fully and the whole island comes back to life for a long weekend. Carolers, hot cider, shop windows lit up on cobblestone streets. Hotels book out a year in advance for this one — plan accordingly.
Winter (Jan–Mar)
For those who knew it before.
The island we first loved. A handful of restaurants and inns stay open. The population drops to year-rounders. The moors are empty and wind-swept and extraordinary. The ferry still runs. If you’re looking for the island that existed before the brand — this is still where to find it.
“Go in winter once, at least once, and you’ll understand what the island has always been underneath everything it became.”
06 — Where to stay
In town, out on the moors,
or right on the water.
Nantucket’s lodging scene reflects the island itself — layered, varied, and unafraid of charging for what it is. At the top end, properties like The Wauwinet and White Elephant rival any resort in New England. In town, historic inns on cobblestone streets offer something money can’t manufacture: genuine atmosphere. And for families and groups, a VRBO cottage or beach house remains — as it always has been — the most honest way to experience the island.
The signature properties
Luxury Resort — Remote
The Wauwinet
The only Relais & Châteaux property on the island. Situated on Nantucket’s northeastern shore between the bay and the Atlantic, with private beaches on both sides. The TOPPER’s restaurant is a destination in itself. Not walkable to town — the hotel runs a boat service and a van shuttle, and honestly, you may not want to leave.
Best for: honeymoons, anniversaries, anyone who wants to disappear completely
Waterfront Hotel — In Town
White Elephant
Right on Nantucket Harbor, walking distance from everything in town. Recently renovated, beautifully done, with a full spa and the Brant Point Grill overlooking the water. Suites and cottages available for families. If you want to be in the center of the island’s social life without sacrificing comfort, this is the answer.
Best for: families, couples, anyone who wants location and amenities
Historic Inn — Town Center
Jared Coffin House
A Federal-style brick mansion built in 1845, right in the heart of Nantucket Town. Carved wooden beds, proper antiques, a library, private gardens. Guests return for years — sometimes decades. The staff knows their names. That’s not a cliché on Nantucket; it’s just what this place is.
Best for: history lovers, returning visitors, those who want the real town atmosphere
Boutique Inn — Town
Greydon House
A mid-19th century inn updated with real design sensibility — mid-century furniture, excellent bar, and a restaurant that holds its own against anywhere on the island. Hip without being self-conscious. One of the newer additions to the island’s accommodation landscape that actually earned its place.
Best for: design-minded travelers, younger visitors, cocktail enthusiasts
The case for renting a house
For families and groups — especially those coming for a week — renting a house or cottage is still the most Nantucket thing you can do. My family rented a beach house 20 minutes from town, right on the water, secluded, just us and the Atlantic. That experience doesn’t exist at any hotel price point. It only exists if you rent it.
VRBO has an excellent Nantucket inventory: classic shingled cottages, beach houses in Siasconset, properties near Madaket on the western shore. The per-person cost for a group of six or eight usually undercuts multiple hotel rooms significantly — and you get a kitchen, a porch, and the feeling of actually living on the island rather than visiting it.
Booking reality check
Summer weeks on Nantucket — particularly July 4th, mid-July, and Labor Day weekend — book out 6 to 12 months in advance for both hotels and VRBO properties. If you’re thinking about a summer trip, start looking now. September has dramatically better availability and rates, and the island is arguably at its most beautiful.
07 — Where to eat
A culinary scene that outgrew
the island’s size long ago.
Nantucket’s restaurant scene is, at this point, genuinely world-class — which is both a testament to what the island has become and a slight irony given that the best food experiences here still tend to be the simplest ones. The Downeyflake doughnuts. A lobster roll eaten on a bench near the harbor. A raw bar at dusk with the harbor lights coming on.
That said: the island supports serious cooking, and several of its restaurants would be destination-worthy in any major city. Here’s where to eat, honestly organized.
The Downeyflake
The Nantucket equivalent of Payne’s on Block Island — a beloved, no-pretense breakfast institution that locals and repeat visitors treat as non-negotiable. Famous for doughnuts made fresh every morning. The breakfast plates are equally good. Go early, go hungry, go again.
$
Something Natural
Legendary sandwiches on house-made bread, served from a rambling property on Cliff Road with picnic tables outside. The kind of place that’s been feeding people on this island for decades and doesn’t need to do anything differently. Get there before noon in summer. The sandwiches are enormous and completely worth it.
$
CRU Oyster Bar
Right on the harbor near the ferry docks, with the best lobster roll on the island according to serious people who have eaten many lobster rolls on this island. Outstanding raw bar, enthusiastic staff, water views in every direction. It’s a scene in summer — a scene worth joining. Make a reservation.
$$$
Straight Wharf Restaurant
Waterfront dining with a seasonal tasting menu that changes to reflect what’s being caught and grown nearby. Chef Gabriel Frasca has been doing deconstructed clambakes and razor clam preparations that justify the trip to the dock. Candlelight, craft paper table coverings, and a bar that transforms later in the evening. This is the Nantucket culinary experience at its best.
$$$$
The Chanticleer
In Siasconset, 7 miles from town — which means you need a bike, moped, or taxi to get here, and it’s entirely worth the effort. Contemporary American cuisine in a rose-covered garden setting that in summer is one of the most beautiful dining rooms in New England. The garden in full bloom is genuinely magical. Go for Sunday brunch if you can.
$$$$
TOPPER’s at The Wauwinet
Even if you’re not staying at The Wauwinet, make a reservation for dinner here. Seasonal local ingredients, bay views, the unhurried pace of a remote resort restaurant that knows it has nothing to prove. The 20-passenger boat that runs between The Wauwinet and White Elephant is a genuinely fun way to arrive. Call ahead — non-guests are welcome but reservations are essential.
$$$$
Black-Eyed Susan’s
The beloved breakfast and brunch spot that locals protect fiercely. Creative dishes — lobster eggs Benedict, raspberry and white chocolate pancakes — served in an intimate space with no reservations and a line that forms early. Cash only. Worth every minute of the wait and the lack of a credit card reader.
$$
Cisco Brewers
Not just a brewery — a full compound out in Nantucket’s mid-island that includes Cisco Brewers, Triple Eight Distillery, and Nantucket Vineyard. Live music, food trucks, picnic tables, and the relaxed energy of a place that’s been part of island life since 1995. The afternoon here is one of the better things you can do on a sunny day.
$$
08 — Things to do
Moors, lighthouses, beaches,
and the rare pleasure of being nowhere.
Forty-six percent of Nantucket is permanently protected conservation land. That’s not a statistic — that’s the reason the island feels the way it does. Wherever development has pushed, the moors and beaches and ponds have held. The things worth doing here are mostly outside, mostly unhurried, and mostly free.
Walk the Moors
Nantucket’s interior moors — low-lying heathland covered in heather, bearberry, and wild roses — look like nothing else in America. The Sanford Farm, Ram Pasture, and Woods trail system covers six miles of protected conservation land, ending at the south shore. In autumn the moors turn rust and gold and the light is extraordinary. This is the Nantucket that existed before anyone was selling anything.
Visit Siasconset (Sconset)
Seven miles east of town, the village of Siasconset has been quietly extraordinary since the 18th century. Rose-covered cottages with names instead of numbers. A bluff walk above the Atlantic. The Chanticleer in its garden. The sense that you’ve arrived somewhere that didn’t need the rest of the island to know it was worth being. Bike out, have lunch, walk the bluff, bike back — a perfect Nantucket day.
The Nantucket Whaling Museum
On Broad Street in town, this is genuinely one of the better small museums in New England — not because whaling history is cheerful but because it’s handled with real seriousness and depth. The 46-foot sperm whale skeleton. The scrimshaw collection. The story of an island whose entire economy once hung on a single dangerous industry. Plan two hours and don’t rush it.
Brant Point Light
The second-oldest lighthouse in America, sitting at the entrance to Nantucket Harbor. It’s a short walk from White Elephant and a longer but pleasant bike ride from most of town. Small, red-roofed, surrounded by water on three sides — one of the most photographed spots on the island for good reason. Go at dusk when the harbor traffic is quieting and the light is doing what it does.
Surfside Beach
The south-facing Atlantic beach with the biggest waves and the most consistent surf. A bike ride from town down Surfside Road. More exposed and energetic than the calmer harbor-facing beaches — if you want to actually feel the ocean, come here. There’s a reason it’s popular with surfers and with anyone who finds the calmer beaches a bit too calm.
Walk the cobblestones of Main Street
Nantucket’s Main Street is the cobblestone street that everyone photographs. The trick is to do it early — before 9am in summer, when it belongs to the people who live here rather than the people visiting. The three-block stretch of Federal and Greek Revival architecture, elms overhead, is unchanged in its bones from what it was a hundred and fifty years ago. That doesn’t happen often. Notice it.
09 — Getting around
Bike the island.
Leave the car on the mainland.
Nantucket is 14 miles long and 3.5 miles wide. There are 32 miles of paved bike paths. The island was designed, before bicycles were even invented, to be traversed on foot or by horse — which means the scale is human, and everything works at a pace that a car makes worse rather than better.
Bicycle
The right answer for most people. Rentals are widely available near the ferry terminal and in town. The main bike paths are paved and well-maintained. Siasconset is a 7-mile ride — hilly in places, beautiful the whole way. Young’s Bicycle Shop on Broad Street has been renting bikes since 1931 and is the place to start.
Moped
Available for rental from several shops near the ferry. Covers more ground with less effort — useful if you want to reach the more remote beaches or Siasconset without the full bike commitment. Check current rental requirements; rules have evolved in recent years.
NRTA Shuttle
Nantucket’s public shuttle system runs frequent routes to Siasconset, Surfside, Madaket, and other key destinations for $2 a ride or $10 for a day pass. Seriously underutilized by visitors and genuinely useful. Pick up a route map at the Visitor Services office on Federal Street.
Taxi & rideshare
Island taxis are available and reliable. Uber and Lyft operate with limited availability — don’t count on them as your primary plan. For ferry-to-inn transport with luggage, a taxi is the sensible choice.
10 — Practical tips
What to know
before you go.
Book everything early
Nantucket in peak summer has approximately zero margin for spontaneity. Hotels, VRBO properties, ferry tickets, and restaurant reservations for popular spots should all be locked in months in advance. The island’s desirability has only increased. Plan accordingly.
Fog happens
Nantucket sits in the Atlantic and fog is a fact of island life. If you’re flying in, have a contingency — fog can delay or cancel small plane flights. The ferry is less affected but choppy water crossings can be rough in certain conditions. Build flexibility into your arrival day.
Restaurant reservations
The serious restaurants — TOPPER’s, Straight Wharf, The Chanticleer — book out weeks in advance in summer. Make reservations before you arrive, not after. For walk-in spots like Black-Eyed Susan’s, arrive when they open and be prepared to wait happily.
Dress in layers
The island temperature can be 10–15 degrees cooler than the mainland, especially near the water. Summer evenings often require a jacket. A light layer for the ferry crossing is non-negotiable — the wind across the sound is real even in July.
Cash and connectivity
ATMs exist on the island but are heavily used in summer. Bring cash. Cell service can be spotty away from town — download offline maps before you arrive, and consider the reduced connectivity a feature rather than a bug.
Respect the conservation land
Nearly half the island is protected. Stay on marked trails, follow posted rules in conservation areas, and understand that this land is protected specifically so future visitors — including your children — can experience it the same way you do. The moors and beaches are extraordinary because someone chose to keep them that way.
The best light
Nantucket’s late afternoon and evening light is something photographers and painters have been chasing for centuries. Whatever you’re doing on any given day, be somewhere interesting between 5 and 7pm. The harbor, the moors, the bluff walk at Siasconset — the light will do the rest.
Go in the off-season at least once
Daffodil Weekend in April. The Christmas Stroll in December. A January weekend when the island belongs to the people who love it without needing it to perform. These versions of Nantucket are quieter, more honest, and in some ways more beautiful than the summer version everyone knows. The island’s bones are worth seeing without the crowds.
The island that made itself into a legend — and stayed one.
There’s a version of the Nantucket story that’s about what was lost — the quiet winters, the cheap prop plane flights, the borrowed key to a shingled house in an empty town. That story is real and worth telling.
But there’s another version, which is that Nantucket became famous for exactly the reasons it deserved to. The moors. The harbor light. The cobblestones. The way the island appears below the plane window like something out of a story you were told as a child. None of that was manufactured. The money arrived because the beauty was already there, and the beauty — protected by law and by the stubbornness of an island that knows what it is — is still there.
Go in summer if you need to. Go in September if you can. Go in winter if you want to know what we knew. The island will meet you where you are, at whatever version of itself you’re ready to experience. It always has.