Nantucket Travel Guide
Nantucket, MA - the ideal New England Summer getaway
Our trip to Nantucket, MA
There’s something undeniably magical about Nantucket in May. The quiet coast before the summer crowds, the scent of salt air mingling with blooming hydrangeas, and the feeling that time slows just enough to let you savor every aesthetic corner detail. For my birthday this year, we escaped to this picture-perfect island, and it was everything I hoped for and more: classic New England summer beauty, incredible food, and timeless coastal charm around every corner. In this travel guide of Nantucket island, I’m sharing all the places we loved - from where we stayed and dined to the best ways to explore the island’s hidden gems. Whether you’re planning your first trip or returning to your favorite summer spot, I hope this guide brings a bit of Nantucket’s magic your way.
WHAT TO DO ON NANTUCKET ISLAND
Sconset Bluff Walk & bike to Sankaty Head lighthouse (my favorite)
Sailing Excursion on The Endeavor - a Nantucket tradition for 40+ years
Catch some live music & hang one afternoon at Cisco Brewery
Explore all 3 historic lighthouses on the island: Brant Pointe, Sankaty Head, & Great Point
Walk down the iconic cobblestone Easy St.
Stroll down Straight Wharf + Boat Basin for some shopping, a light bite, & hop on/off the ferry
Take the Ferry to Martha’s Vineyard or Cape Cod for a day
Bartlett’s Farm - grab lunch & stroll the gardens & farmer’s market
Shopping + walking around in town & take in the historic cobblestone streets
Pack a basket, and have a picnic on Steps Beach then grab drinks at Galley Beach after
Take a walk in Monomoy + watch the sailboats
Enjoy a glass of rose on the White Elephant Hotel lawn & watch the boats come into the harbor
Rent a Bronco for a day to drive around the island + see all the beaches
Go biking around the various bike trails and neighborhoods to see the homes + beaches (you can rent bikes or your hotel may have complimentary ones = they are included with your stay at The White Elephant!)
Stroll around The Whaling Museum & learn some of the history of Nantucket
Have a beach day! My favorites were Steps Beach, Sconset Beach, and Madaket Beach
Beaches of Nantucket: Jetties, Steps Beach, Brant Point, Sconset, Madaket, Miacomet, Surfside, Ladies Beach, Coatue
Gaze at the classic beautiful hydrangeas that bloom in late June + early July in the Old North Wharf, Sconset Historic District, Sconset Bluff Walk, Lincoln Ave near steps beach, throughout Town, & the Cliff Neighborhood
WHERE TO STAY: The White Elephant!
One of the first historic hotels on Nantucket, our stay at the White Elephant Nantucket was truly unforgettable. From the moment we arrived, every single staff member made us feel genuinely welcomed and like part of the family. They even had a birthday cake waiting for me in our room at check-in and later in the week surprised us with champagne and chocolate-covered strawberries. Our room, complete with a cozy fireplace and private balcony, was beautifully designed with coastal charm and timeless elegance, reflecting everything you’d hope for in a Nantucket stay. The hotel’s prime location right on the harbor & close to town made it extra special - we loved watching the boats glide in while sipping rosé from a patio lounger on the perfectly manicured lawn. Every detail, from the warm hospitality to the stunning views, made it feel like a dream.
Other notable hotels & resorts to stay on Nantucket Island:
The Nantucket Hotel - in the heart of town
Faraway - boutique hotel in town
Greydon House - in the heart of town
The Wauwinet - a Relais Chateaux luxury resort in the island (sister property to White Elephant)
What to Wear on Nantucket
When packing for Nantucket from May to September, think effortless coastal New England summer style: classic, polished, and breezy. The island style is definitely more relaxed and casual, but refined. Days are often sunny with cooler mornings and evenings, so layering is key. Whether you're exploring cobblestone streets, dining by the harbor, or lounging on the lawn, here's a list of what to wear to feel stylish and comfortable on the island. Shop all my outfits from the trip here on my LTK!
Lightweight sweaters and a lightweight cashmere wrap for layering
White jeans and tailored shorts for a crisp, coastal look
Breezy linen dresses and button-downs
Classic striped tops and nautical-inspired pieces
Comfortable sandals, espadrilles, or white sneakers for walking (remember: cobblestone streets!)
A sunhat and sunglasses for daytime exploring
A light jacket or denim jacket for cool evenings
A chic swimsuit and cover-up for beach or pool days
Woven crossbody purse + my L.L. Bean Boat & Tote was perfect for daytime exploring & bike rides
Polished but casual outfits perfect for dinner out or a harbor cruise
WHERE TO DINE ON NANTUCKET
Nantucket’s dining scene is a culinary delight all year long, but especially between Memorial Day and Labor Day, booking ahead is essential. During the shoulder season in mid-May or September, you’ll still want a reservation for dinner at the island’s top spots as they fill up quickly, but you’ll enjoy a bit more flexibility. Come summer, expect every favorite from beachfront seafood shacks to upscale bistros to be fully booked, so secure your table early and savor every bite!
Morning buns at The Hub and Wicked Island are amazing!
COFFEE + BRUNCH
Handlebar Cafe
The Hub
Black Eyed Susan’s
Lemon Press
Wicked Island Bakery - their morning buns will change your life
The iconic Cru-cumber martini at Cru Oyster Bar is a MUST! Accompanied by their fresh oyster selections of the day.
LUNCH
Provisions - best sandwiches to grab + take with you on a bike ride
Stubby’s - their cookies are amazing + huge
Brant Pointe Grille
Millie’s (also great for dinner + sunset watching after a beach day at Madaket)
Sandbar at Jettie’s - perfect hang during or after a beach day
Straight Wharf
DINNER
CRU Oyster Bar - Best atmosphere by far on the edge of the wharf watching boats + yachts come in. Best lobster roll on the island. Get the Cru-cumber martini. Extensive wine list too
The Nautilus - yummiest + most unique dining experience we had (tough reservation to get - can also snag a spot at the bar if you’re lucky)
Brant Pointe Grill - in the White Elephant. Relaxed vibe + kid friendly, Great view of the Harbor
Topper’s at The Wauwinet - amazing sunset view, adults only, extensive wine list, enjoy the lawn + boardwalk & loungers before dinner
Bar Yoshi - best sushi and espresso martinis
The Chanticleer - beautiful garden + patio area
The Proprietor’s Table
Ventuno’s Restaurant - the best italian
LIGHT BITES
Galley Beach - beautiful sunset view right on the beach + creative drinks
Lola 41 - sushi + drinks
Slip 14 - drinks
DESSERT + POST-DINNER DRINKS:
Juice Bar - delish homemade ice cream
Faraway - vibey interior design in the back bar/restaurant
Lola 41 - fun atmosphere, music, and unique cocktail concoctions
Sister ship
Slip 14
The Chicken Box
Brotherhood of Thieves - cool stone/old-world pub vibe
Gaslight
The Gazebo
WHERE TO SHOP ON NANTUCKET
Murray’s Toggery Shop (classic Nantucket Reds merch)
Ralph Lauren
For Now
Erica Wilson
Alice Walk
Hospital Thrift
Bon Ton
Mitchell’s Book Corner
The Hub (cute, unique souvenirs)
Annie and the Tees
The Jeweller’s Gallery
Hill House
Four Winds Gifts
SO many beautiful unique shops all around town to find & explore while strolling the cobblestone streets!
Helpful Tips When Planning a Trip to the Island:
WHEN TO VISIT
The best time to visit Nantucket depends on what kind of experience you’re after. The high season, from Memorial Day to Labor Day, offers the warmest weather, buzzing energy, and a full calendar of events—but it also comes with larger crowds and premium pricing. For a more relaxed escape, consider traveling during the shoulder season: the week or two before Memorial Day or just after Labor Day (we visited May 12-18). You’ll still enjoy beautiful weather and open shops and restaurants, but with fewer crowds and more availability (and often better rates) at hotels.
Additionally, the whole island is season-driven, so I would not recommend visiting before mid-May because many of the spots you’ll want to visit will likely be closed and the weather may not be as favorable. We hit it just right with each day thankfully being sunny and 65-70 (island perfection!)
When we visited, it was the week of the Nantucket Food & Wine Festival, which was so unique and fun with all the events and tastings happening all throughout the island. Each year, the festival is typically in mid-May.
GETTING TO THE ISLAND + GETTING AROUND:
We flew from Nashville to Boston,, then took a quick 45 min plane ride into Nantucket via Cape Air
The Ferry: From Boston airport, Hyannis is about a 1-1.5 hour drive. The port in Hyannis is where you can hop on the 1-hr ride Seastreak Ferry or Hy-Line Ferry to get to Martha’s Vineyard & Nantucket.
The island of Nantucket is only 13 miles long and 3.5 miles wide, so biking and walking is most popular and a fun way to see it all.
The Wave is the free public bus/shuttle that has routes & stops all around the island - which is clutch if you’re mid-bike-ride and you’ve run out of steam (happened to us lol) because the bus also has a rack for you to put your bikes.
Hotel Shuttles: the White Elephant has a convenient car that takes guests anywhere in town, 1-2 mile radius around the hotel, and over to The Wauwinet Resort (the White Elephant’s sister property).
Uber & Lyft are available too for convenience if needed.
“It’s not goodbye, it’s see you later!”
Nantucket was the most charming and memorable way to celebrate my birthday, and we will definitely be back again! I truly can’t recommend it enough for a spring or summer getaway with the perfect amount of relaxation and exploring. From the harbor views to the incredible food and classic New England summer style, every detail felt like a breath of fresh air. A huge thank you to Travel Advisor and my now sweet friend McKinley Hatcher of MH Luxury Travel (@MHluxurytravel), who helped coordinate everything flawlessly, she made the entire trip seamless and stress-free - reach out to her for booking your next trip!