The Nantucket, Massachusetts Travel Guide | Tuckernuck

The Nantucket, Massachusetts Travel Guide

By Tuckernuck on

Nantucket is an island off of Cape Cod, MA and epitomizes the idyllic summer New England town. While known to many for an amazing restaurant scene, unique boutique shopping and perfect shingled houses surrounded by blooming hydrangeas and manicured hedges, we love the fog-covered "Grey Lady" for her natural beauty and all of the activities she has to offer. Here is our bucket list and guide from 30+ years of summer, fall and holiday seasons on island.

- Maddy & Jocelyn, Co-Founders & Sisters

The Nantucket Bucket List

Where to Eat: Breakfast

The Downyflake

An institution, the Downyflake has a diner vibe and to die for doughnuts. We love the simple plain flavor. 18 Sparks Avenue

Black-Eyed Susan's

A charming cafe in town with great omelettes, pancakes and classic breakfast options.10 India Street

The Green

Chill counter serve in a tiny cottage for juice blends, smoothies & wraps with organic ingredients. 5 West Creek Road

Lemon Press

At Lemon Press you’ll find fresh, organic, and local fare throughout the day. Start your day off right, from energizing coffee drinks to their ever-popular breakfast sandwiches loaded with fresh veggies and eggs. 41 Main Street

Where to Eat: Lunch

Something Natural

A bakery and sandwich shop, this is our favorite place to pick up sandwiches made on the fresh bread baked daily in house. Opt for herb bread! 50 Cliff Road

Claudette's Sandwich Shop

In the town of Sconset, this sandwich shop makes a special sauce we can't resist. Stop for lunch and walk the bluff after biking out via the Polpis bike path. Get the special sauce! 10 Main Street Siasconset, MA

Bartlett's Farm

Close to our favorite beach, Ladies Beach, Bartlett's is our go-to for fresh prepared food like broccoli salad and gourmet groceries. We often pick our own tomatoes and berries at the farm in season as another fun activity. 33 Bartlett Farm Road

The Soda Fountain At Nantucket Pharmacy

Old-school 1929 soda fountain serving sandwiches, basic breakfast eats, frappes & ice cream. Sit at the for a grilled cheese and a black & white or coffee frappe (a frappe is what most people think of as a milkshake). 45 Main Street

Where to Eat: Dinner

Lola 41

A chic hot spot with a global menu featuring sushi, cocktails & gourmet burgers. We recommend the tuna burger and truffle fries if you aren't in to sushi. Contemporary. 15 S. Beach Street


Located in Madaket, Millie's is a great spot to watch the sunset on the second floor while sipping on margaritas and eating fish tacos, steak quesadillas or blackened salmon salad. We go here often, as it's delicious, a laid back spot for families and ideal for spotting Tuckernuck Island. Casual. 326 Madaket Road

Sandbar Jetties Beach

Sandbar at Jetties Beach offers the quintessential beachfront Nantucket experience – with a spacious, open-air restaurant and bar and plentiful seating in the surrounding sand. Enjoy a fresh raw bar, delicious burgers and sandwiches, and seafood. Casual. 4 Bathing Beach Road

American Seasons

Island favorite, chef Neil Ferguson brings 25 years of Paris, London and New York City experience to Nantucket. Focusing on seasonal, local and thoughtfully prepared ingredients, the menu is always changing and incredibly tasty. Enjoy dinner by candlelight in a charming yet rustic, farm decor setting. Upscale. 80 Centre Street

Galley Beach

Quintessential Nantucket, Galley Beach restaurant offers an excpetional american menu surrounded by walls of windows and views of the ocean. Watch the sunset with a cocktail in the sand in their beach bar before dining in the elegant formal dining room. Upscale. 54 Jefferson Avenue

Oran Mor

A Nantucket restaurant on the second floor of a historic, charming house, Oran Mor celebrates the island's finest seasonal dishes, handcrafted cocktails and select wines. Upscale. 2 South Beach Street


Located at the remote and stunning Wauwinet resort, Topperâs is an incredible dining experience for a special occasion. Arrive by boat, boarding at the White Elephant in town for an unforgettable night. Upscale. 120 Wauwinet Road


Originally opened as a small tea house at the turn of the century, The Chanticleer is now one of the premier restaurants on Nantucket. One of the most romantic destinations on the island, you may linger over an intimate lunch in the Rose Garden or come together with family and friends for a convivial dinner in one of our personal dining rooms- al fresco on warm evenings. Upscale. 9 New St, Siasconset, MA

The food in Nantucket really is unbelievable. Menus often feature New England lobster, fish tacos, cod, halibut and fresh salads. The Nantucket Bay scallops are uniquely found in the Nantucket waters, so we highly recommend you order those and anything else local.

Where to Celebrate: Bars

The Club Car & The Summer House

The Chicken Box & Cru

Post-dinner fun can be found at the piano bars at the Club Car in town or Summer House in Sconset. For a more rowdy nightcap, we recommend the famous dance spot the Chicken Box, where you will often find a live band and a long line. For a more elevated experience, Cru offers a gorgeous harbor setting for pre or post-dinner drinks and a walk on the docks.

Where to Shop

Nantucket Looms

Since 1968, Nantucket Looms offers handmade throws, handwoven gifts, artisanal goods, home decor, art and artwork. 51 Main Street

Milly & Grace

A quaint, upscale boutique selling women's clothing from brands like Rebecca Taylor and Joie, Milly & Grace is owned by a sister duo who are absolutely lovely. From cashmere ruanas, to jewelry, home decor & gifts, you'll be sure to find something you love. 2 Washington Street

Murray's Toggery Shop

The most iconic shop on island, Murray's is a family owned clothing store that has been open since 1945. Home of the original Nantucket Reds™and many exclusive designs with Nantucket icons, this is where we recommend you buy something to remember your stay on the Grey Lady. 62 Main Street

The Skinny Dip

The Skinny Dip on Nantucket is a collective concept store housing a well-­curated mix of men’s, women’s and lifestyle brands, with a focus on introducing fresh and new designers from around the country. 23 Old South Wharf

CJ Laing

A curated collection of luxury resort clothing, accessories, and select items from other specialty brands from around the world. 44 Centre Street

Erica Wilson

Her famed needlework and fashion collections for women of all ages make Erica Wilson Nantucket an important destination for islanders and visitors alike. Featuring contemporary apparel brands and unique accessories, her style is laid back chic with an eclectic twist. 25 Main Street

The Atlantic

Located on Federal Street, the Atlantic offers an assortment of art, antiques, accessories, apparel and jewelry. With an attention to artistry and craftsmanship, the owner Colleen is an exceptional curator. 16 Federal Street

Lion's Paw

A home decor shop, this clean, classic and airy shop offers everything from picture frames and table accessories to bedding and furniture. 30 Main Street

The boutiques on Nantucket feature many unique designers and are fabulous for clothing, gifts and home decor shopping. There is also a fantastic artist community on island. Head over to Osana's Auction house or the Nantucket Artist's association for antiques and original artwork.

What to Do

Cisco Brewers & Sankaty Lighthouse

Cisco Brewers is a brewery, distillery, and winery. Our happy place on island, we often wind down after a beach day with a Whale's Tale or Blue Haired Lady cocktail to low key music. Biking the island via the Polpis bike path and exploring the charming town of Sconset is equally as fun for a more active day. Park your bikes by the market, grab a sandwich at Claudette's and walk to Sankaty Lighthouse (1 of 3 lighthouses on island) via the famous Bluff Walk.

Jetties Beach & Shearwater Excursions

The beaches in Nantucket are public, expansive and abundant. It's hard to know where to start. If you are close to town, Jettie's, Steps Beach and Dionis are nice with more gentle surf. If you want to boogie board or try to surf, go to Cisco or Ladies Beach. Fishing with Captain Tom or clamming, whale watching, or a cocktail cruise with Shearwater Excursions are all great options for exploring Nantucket by sea. For kids, the Critter Cruise is a fun morning activity and gets you out on the water!

Where to Stay

White Elephant Nantucket

An island landmark, the iconic White Elephant, has been named among the finest luxury hotels on Nantucket Island for decades. Edging the harbor, White Elephant is steps from Children's Beach, the Brant Point Lighthouse, and Nantucket Town. 50 Easton Street


A blend of charm and sophistication, The Wauwinet is a seaside refuge with breathtaking views, historic architecture, and luxury amenities for the perfect hotel stay on Nantucket Island. As Nantucket's only member of Relais & Châteaux hotels, this historic inn is known worldwide for its outstanding cuisine, and accommodations. 120 Wauwinet Road

Greydon House

Come experience this exquisite new boutique hotel in Nantucket’s downtown historic district with 20 uniquely appointed luxurious rooms and suites and an internationally inspired and very lively restaurant. Greydon House weaves the warmth and comfort of a village inn with the many eclectic and worldly touches for today’s generation of sophisticated travelers. 17 Broad Street

Regatta Inn

A contemporary take on the classic Bed & Breakfast, the Regatta Inn (also sister to the Centerboard Inn across the street) is located on a charming street in town. Recently renovated with elegant decor and modern finishings, this quaint 9 bedroom inn is charming, comfortable and a perfect option for a couple's romantic weekend getaway. 78 Centre Street

#Tuckernucking in Nantucket