If you think you can visit Nantucket island once and get it out of your system, we are here to tell you that you are wrong. This is our fifth trip and if anything we love it more than we did the first time. The salt air. The hydrangeas. The lobster rolls that make you briefly question every other meal you have ever eaten. This is our five-star guide to six days on the island: where to stay for the best island experience, the restaurants worth the reservation, the beaches worth the drive, the boutiques worth the credit card, and the golden hour moments that make it all completely impossible to leave.
Table of Contents
Why We Keep Coming Back to Visit Nantucket Island
Nantucket is a charming island with a rich and salty past just off the coast of Cape Cod. Once the whaling capital of the world, this small island played a big role in 19th-century maritime history. Today it has traded harpoons for hydrangeas, but you will still find traces of its nautical roots in every cobblestone alley, sea captain’s home and harbor view.
- Town is the historic heart with cobblestone streets, the best boutiques and the top restaurants
- Mid-Island is the the quieter residential stretch with everyday conveniences
- Sconset on the eastern end is its own world entirely: a postcard village of rose-covered cottages
- The North Shore runs from Brant Point along the cliff neighborhoods toward Dionis, with calmer water and some of the prettiest residential streets on the island
- The South Shore faces the Atlantic with bigger waves and wide open beaches like Surfside and Cisco.
- Madaket on the western end is where you go for the best sunset on the island
We have been exploring all of these for five years, and there is always something new to find when you visit Nantucket Island.
How to Visit Nantucket Island
There is more than one way to swap city skylines for salt air. Whether you have a free afternoon or a full travel day to burn, getting from New York to Nantucket is easier than you think and half the fun is choosing your own adventure. Here is how to make your escape.
OPTION 1: FLY DIRECT
- Route: Delta or JetBlue from JFK/LGA → Nantucket (ACK)
- Time: ~1 hour
- Best For: Speed + convenience
- Notes: Seasonal service May–Sept; you can be on cobblestones before lunch
OPTION 2: DRIVE + FERRY
- Route: NYC → Hyannis (~5 hrs) → Steamship Authority Ferry → Nantucket (1–2 hrs)
- Best For: Flexibility + a proper road trip feel
- Notes: Book the car ferry well in advance for summer weekends as it sells out
OPTION 3: FERRY FROM NYC (SEASONAL)
- Route: Seastreak Ferry from Manhattan → Nantucket
- Time: ~6 hours
- Best For: The full slow-travel, ocean-air experience
- Notes: Weekend-only seasonal service; no connections, no cars, no stress
OPTION 4: PRIVATE CHARTER OR HELICOPTER
- Route: NYC → Nantucket via Blade or Tradewind
- Time: ~1 hour door-to-door
- Best For: Maximum luxury, minimum logistics
- Notes: The splurge option but fast, scenic, and worth every penny if the budget allows
When to Visit Nantucket Island
The best time to visit Nantucket island stretches from late spring through early fall, when the island is fully alive with coastal charm, warm weather and everything worth coming for. That said, every season has its own personality. Here is how to choose when to visit Nantucket island.
LATE SPRING (MAY – JUNE)
We visited Nantucket in late June on our last two trips. The climbing roses are at absolute peak, the hydrangeas are out in full force, the restaurants are in full swing, and the island has not yet hit the wall-to-wall July chaos. The light is golden until 8pm and you can still get a reservation without a miracle. If you can only go once, go in late June.
SUMMER (JULY – AUGUST)
Peak season in every sense with the warmest weather, most events, most people and highest prices. The beaches are packed and the restaurants are full, but the energy is undeniable. Book everything well in advance.
EARLY FALL (SEPTEMBER)
Still warm, still beautiful, considerably less crowded. September is a quiet favorite for people who want the full Nantucket experience without the summer chaos. Some seasonal spots begin to wind down but most of the good ones stay open through the month.
LATE FALL & WINTER (OCTOBER – DECEMBER)
A completely different island. Quiet, cozy, and surprisingly magical around Thanksgiving and the famous Christmas Stroll. Most of the summer businesses close up, but if you want Nantucket without the crowds and with a lot of festive charm, this is your window. Just pack accordingly.
Where to Stay When You Visit Nantucket Island
Before you unpack your sun hat and sandals, you will need a fabulous home base. We always recommend staying near town so you can walk or bus to most destinations. Here are three standout hotels that strike the perfect balance between coastal charm and genuine luxury.
- Nantucket Resort Collection — This collection of boutique inns includes Veranda House, Chapman House, Regatta Inn, and Sherburne Inn. This trip we stayed in the Regatta Inn. Each property brings its own personality while delivering the same blend of sophistication and island ease. Nestled steps from downtown, expect curated interiors, plush linens, and serene outdoor spaces where afternoon rosé is not just encouraged, it is practically a house rule. Perfect for design lovers and anyone who wants a little flair with their escape.
- The Nantucket Hotel & Resort — This New England-style resort delivers family-friendly luxury with every extra you could want: heated pool, fitness center, spa, and complimentary beach shuttles. Spacious suites, activities for the kids, and genuinely five-star service make it the go-to for families or anyone who wants to be pampered.
- 76 Main Ink Press Hotel — Housed in a former sea captain’s mansion at the crown of Main Street, this boutique hotel weaves coastal charm with a literary sensibility. Every room nods to Nantucket’s storied print history, and the chic courtyard complete with fire pits and a BYOB mixer bar. This is exactly where you want to be after a long day on the island. A stylish, central pick for couples and creatives.
VISIT NANTUCKET ISLAND – DAY 1: BEACH DAY
AFTERNOON: LUNCH AT SANDBAR & RELAX AT JETTIES BEACH
After dropping your bags at the hotel, toss on your swimsuit and coverup and head straight to Sandbar at Jetties Beach for lunch. Sandbar is a 20 min walk from from town. The vibe is casual, the view is pure postcard and the lobster rolls and crispy fish tacos are the kind of thing you will be thinking about long after the trip ends. Grab a table on the patio, steps from the sand and enjoy a fabulous meal.
After lunch, kick off your sandals and spend the rest of the afternoon at Jetties Beach, one of Nantucket’s most beloved stretches of sand. Jetties has calm, shallow water perfect for kids and enough people-watching to keep you entertained for hours. Pack towels, sunscreen and your most oversized sunglasses.
EVENING: SUNSET DINNER AT STEPS BEACH
Steps Beach is one of Nantucket’s best-kept secrets. It is a small, tucked-away stretch off Cliff Road on the north shore with some of the most beautiful sunset views on the island. Facing west over the harbor and the sound, the light here in late June is warm, golden, and completely magical.
Stop into Murray’s Toggery Shop to pick up a bottle of pink champagne, grab a wood-fired pizza from Pizzeria Gemelle and taxi to Steps Beach. Watch the sunset from the top of the steps or lay out a blanket on the sand. Either way, pop the bottle and watch the light fade over the harbor. It is one of those Nantucket evenings that costs almost nothing and feels like everything.
VISIT NANTUCKET ISLAND – DAY 2: LIGHTHOUSE & WAVES
BREAKFAST & BRANT POINT
Start the morning by fueling up with breakfast at the inn before heading out to Brant Point Lighthouse, one of the most photographed spots on the island. It is the second oldest lighthouse in the United States, after Boston Light. Brant Point sits right at the entrance to Nantucket Harbor and the views of sailboats drifting in and out are pure magic at any hour. Go early, bring your camera and take your time.
AFTERNOON: EXPLORE THE SOUTH SHORE
Grab a taxi and head to the south shore for the afternoon. Start at Cisco Brewers, the legendary Nantucket campus that houses Cisco Brewery, Nantucket Vineyard, and Triple Eight Distillery. There is almost always live music, the drinks are excellent and the crowd is always bustling. If you are visiting in June, do not miss the Farmer’s Day Off drink. This summer cocktail tastes exactly like Nantucket feels with organic vodka, fresh strawberries, soda and lemon. Pair it with lobster rolls from Nantucket Lobster Trap. Then sit back and enjoy a fabulous lunch while the live music plays.
From Cisco, head to Ladies Beach for a swim. Wide, beautiful and a little wilder than the harbor beaches, Ladies Beach is the kind of place that reminds you why you came to a visit Nantucket island in the first place. The waves are real, the sand is soft and the afternoon light is gorgeous. Bring a towel, leave your schedule behind and soak it all in.
EVENING: DINNER AT AMERICAN SEASONS
End the day with a dinner at American Seasons, one of Nantucket’s gems. The menu changes with the seasons and leans into New England ingredients in a way that feels genuinely creative rather than predictable. Start with the NGC 19th, made with their housemate mixers. Order the scallops and halibut. In the summer, book ahead as this one fills up fast.
VISIT NANTUCKET ISLAND – DAY 3: HARBOR VIEWS & BEACH
MORNING: BREAKFAST & NANTUCKET TUG CO
Start the morning with breakfast at the inn before heading down to the harbor for one of the most memorable experiences on the island. Book a charter on the Chugalugatug, a vintage tugboat run by Nantucket Tug Co. Prepare to see the island from a completely different angle. The harbor from the water looks nothing like it from shore. You will glide past sailboats, take in the Brant Point Lighthouse from the water and feel the kind of easy, unhurried joy that Nantucket does better than anywhere else. Bring a sweater, your camera and nothing resembling a schedule.
AFTERNOON: LUNCH AT SLIP 14 & ICE CREAM AT THE JUICE BAR
After the boat, head to Slip 14 for lunch. This spot is right on the harbor and serves fresh seafood and great cocktails. Order the lobster roll and the Aperol Slips. From Slip 14, walk over to The Juice Bar on Centre Street for dessert. This Nantucket institution has been scooping homemade ice cream since 1977 and the waffle cones are completely non-negotiable. The line moves fast and the flavors rotate daily.
LATE AFTERNOON & EVENING: GALLEY BEACH & GREYDON HOUSE
Spend the late afternoon at Galley Beach. The open-air setting right on Cliffside Beach is stunning. Whether you settle in for a drink at the beach bar or linger over a late afternoon snack, this is the kind of place that makes you never want to leave.
End the day with dinner at Greydon House. Set inside a beautifully restored 1850s inn, the atmosphere is sophisticated without being stuffy, and the menu is creative, seasonal and deeply satisfying. The cocktail menu is exceptional, the wine list is serious, and every dish feels considered. Definitely order the chicken parm. Dress up, slow down and let the evening unfold.
VISIT NANTUCKET ISLAND – DAY 4: SCONSET, SANKATY & SIPS
MORNING: THE BLUFF WALK & SANKATY
After breakfast at the inn, hop on the Wave Bus east to Sconset, one of the most beautiful corners of the island. The Sconset Bluff Walk is a clifftop trail that runs along the eastern edge of Nantucket with sweeping Atlantic views that will genuinely stop you in your tracks. The path winds past the backyards of some of the most charming shingled cottages on the island. In late June, the climbing roses are at absolute peak. It looks like a painting. Go early, take your time and bring your camera.
From the Bluff Walk, continue to Sankaty Head Lighthouse, a candy-striped beacon perched at the island’s eastern edge. One of the oldest lighthouses in New England, it sits at the top of a bluff with panoramic views of the Atlantic stretching out in every direction.
AFTERNOON: LUNCH FROM SCONSET MARKET ON SCONSET BEACH
For lunch, stop into Sconset Market, a tiny, beloved village market that has been a Sconset staple for years. Pick up chicken salad wraps, drinks and walk straight to Sconset Beach. Eat your lunch on the beach with the Atlantic in front of you and rose-covered cottages behind. This is one of the simplest and most perfect things you can do on this island.
EVENING: DINNER AT THE PROPRIETORS BAR & TABLE & NIGHTCAP AT CLUB CAR
Head back to town for dinner at The Proprietors Bar and Table. You must order the Hades cocktail. The globally inspired small plates menu means you try everything on the table. We recommend the funnel cake with caviar and the roasted chicken- they are spectacular. Close out the evening with a nightcap at Club Car, a Nantucket institution since 1975. Settle into the piano bar, order a cocktail, and let the evening wind down the way only a Nantucket night can.
VISIT NANTUCKET ISLAND – Day 5: MAIN STREET & MADAKET MAGIC
MORNING: BRUNCH AT BLACK EYED SUSAN’S
Do not leave Nantucket without brunch at Black Eyed Susan’s. This spot has been serving some of the best breakfasts on the island for decades and every single bite earns its reputation. The room is tiny, the energy is warm and the menu is wildly good. The Thai curry scramble is a must-order. It is bold, unexpected, and unlike anything else you will find on this island. The pancakes are equally legendary. Order both and linger over every course. Get there on time. The line forms fast and the room fills faster. It is worth every minute of the wait.
AFTERNOON: SHOP MAIN STREET & LUNCH AT EASY STREET
After brunch, spend the morning exploring the best boutiques on the island. Nantucket’s shopping scene is genuinely one of a kind and these are the stops you do not want to miss:
- Four Winds Gifts on Straight Wharf is the oldest gift shop on the island. It has the cutest sweaters and souvenirs.
- Hill House is a beautifully curated lifestyle boutique with the kind of coastal home goods and fashion that will have you rethinking your entire wardrobe.
- Roller Rabbit is an absolute must. Their Nantucket-print pajamas are the cutest thing on the island and the kind of souvenir you will actually wear.
- It’s For Now on Centre Street never disappoints with their rotating pop-up events and exceptional swim and jewelry selection.
- Erika Wilson has iconic needlepoint designs that make the best gifts.
When hunger strikes, grab lunch at Easy Street and order the southern spread and the fried chicken sandwich. We couldn’t stop eating the spread. The sandwich was crispy, satisfying, and the perfect fuel before heading west.
EVENING: SUNSET AT MADAKET BEACH
Hop on the Wave Bus west to Madaket for a magical sunset. Stop at Millie’s to pick up lobster rolls and then walk over to Madaket Beach. Facing directly west over Nantucket Sound, Madaket delivers the best sunset on the island. Spread out a blanket and enjoy the lobster rolls, while watching the sky turn every shade of gold and pink. Bring a bottle of wine, bring a layer for the wind and stay until the last color leaves the sky.
VISIT NANTUCKET ISLAND – DAY 6: COBBLESTONES & CRU
MORNING: SUNRISE & BREAKFAST
Set your alarm to catch the sunrise at Brant Point Lighthouse. You can watch the harbor wake up in the most beautiful light of the entire trip. The stillness of early morning at Brant Point, with the boats bobbing quietly and the sky turning pink over the water, is one of those Nantucket moments that stays with you long after you are home. Bring your camera, bring coffee and give yourself time to simply stand there and take it all in. After the sunrise, head back for breakfast at the inn.
AFTERNOON: CONSTITUTION HOUSE & CRU
Check out of your hotel and make your way to Old North Wharf, one of the most charming and historically rich corners of Nantucket. Originally built in 1770, the wharf was once the beating heart of the island’s whaling industry. Today its former warehouses and fishing shanties have been converted into picturesque private cottages, each named after a historic whaling vessel. Keep an eye out for the Constitution cottage, named after one of the whaling ships owned by the legendary Coffin brothers. In late June through July, roses, hydrangeas, and trailing flowers are in peak bloom.
From there, wander the cobblestone streets one final time. Pop into any shops you missed, pick up a last-minute gift from Four Winds Gifts on Straight Wharf. Make your way to CRU Oyster Bar for a final lunch. The raw bar is impeccable: oysters, littlenecks, chilled shrimp, the whole spread. The harbor view is exactly what you want on a final Nantucket afternoon. Definitely order the CRUcumber and the warm lobster roll. It has won awards. Then walk back to your hotel and taxi to the airport.
Whether this is your first time or your fifth, use this five star guide to help you visit Nantucket Island. Save this guide, share it with whoever you are planning to drag along, and tell us in the comments — have you been to Nantucket or is it still on your list? If you need a 5-day itinerary, check out last year’s guide.
It’s the ocean…It makes everything better. – The Five Star Weekend, Elin Hilderbrand
