Bike the Island: Bike paths run throughout most of the 14 miles that span Nantucket. It’s the perfect way to see a lot of the island. If you weren’t able to bring your Lilly Cruiser with you, we recommend Young’s Bicycle Shop & Nantucket Bike Shop in the main part of town. Pedal in print!
Siasconset Bluff Walk: Stroll down our favorite walking path and take in the stunning mansions on one side and the ocean on the other… perfection. See the rose-covered cottages that ‘Sconset is known for and visit the adorable town & market. Make sure to stop at ‘Sconset café for lunch—delicious food.
The Beach: Nantucket has some of the most beautiful beaches in the world. Get the full scoop here. Our favorites are Miacomet & Nobadeer (aka the party beach), Brant Point to watch the incoming boats & Madaket Beach for the best sunsets on the island. Make sure to hang out with all of the surfers at Cisco Beach’s long sand bar too.
Cisco Brewery: The perfect after beach hangout spot. Enjoy live music & a Whale’s Tale Pale Ale or their killer blueberry mojito (FYI it’s home of Triple 8 Distillery too) at this local brewery/ large picnic venue. Major plus, they often have scheduled activities for kids to enjoy while parents sit back & relax.
Bartlett’s Farm: A little farther past the brewery, you’ll find this hidden gem. This isn’t your typical grocery store—think the Whole Foods of Nantucket but better. Almost all of their products are grown right on the farm. Plus, for unbelievably delicious, fresh fish to cook, visit East Coast Seafood (167) nearby on Hummock Pond Road.
Shop: The best shopping is in the heart of town on Main Street and the wharf. Make sure to visit our friends at In the Pink for your Lilly fix. #BuyMeLilly
Juice Guys: Thirsty from all of your shopping? Walk down Straight Wharf and visit the creators of Nantucket Nectar.
Chicken Box: THE bar in Nantucket. A mile away from the main part of town but everyone ends up here. Jam out to the live music and cheers to the night. “Lazy Monday” night here is a MUST. Pre-Chicken Box, get drinks at The Gazebo (literally a giant gazebo with a bar in the middle) which is located in between The Tavern and Straight Wharf in Harbor Square.
Galley Beach: HEAVEN. Presidents & celebrities have dined here and it’s no question why… enjoy a gourmet meal right on the beach (we’re talking feet in sand). Not wanting to splurge on a meal? Watch the sunset from their Beach Bar. Sit by the fire pits, order a Bellini, put your feet in the sand, and take it all in. SO. WORTH. IT.
Cru: Enjoy seafood from the rich waters surrounding the island on Nantucket’s waterfront – great spot for lunch, dinner and happy hour. As far as the menu… we recommend, well, everything.
Black-Eyed Susan’s: Our favorite breakfast spot right in town. It’s very cozy so gets busy fast, but it’s well worth the wait.
Millie’s: Head right off of Madaket Beach and onto Millie’s deck for happy hour. This casual spot is perfect to relax with a plate of fish tacos and the biggest drinks on the island. Make sure to try the “Madaket Mystery” that is served in a mason jar.
American Seasons: Located in town, this rustic romantic spot serves delicious European Tuscan food. Do not pass on dessert… our lives were changed after ordering the “Flying Elvis.” Make sure to check out the owner’s other restaurant- The Proprietors .
The Pearl: The fancier, hip & happening dinner spot in town. Leonardo DiCaprio was spotted there last summer…. need we say more?
Aunt Leah’s Fudge: Sweet tooth? Head to the Straight Warf and you can find the 8th wonder of the world. And no, I’m not talking about the yachts in the marina. It’s better. Aunt Leah’s Fudge has the most delicious, melt in your mouth fudge that you will ever taste. If you can hold yourself back from nibbling on the plane or ferry ride home, it’s the perfect “little something” to bring back to friends and family.
The Juice Bar: There is one bar on the island that people are willing to wait in a line out the door—and that’s the Juice Bar. The one thing is—it’s not juice. It’s the BEST ice cream, which you can get on their homemade waffle cones baked right in the store.
Roberts Collection: Right in the heart of Nantucket, the Roberts Collection has a collection of inns that will make you feel right at home. Their diverse offering of rooms and suites make it a perfect choice for couples, families and groups of any size. The newly constructed Gate House is our favorite… you can enjoy a coffee from The Bean or people watch at Centre Street Bistro without even leaving the property.
Cliffside Beach Club: Close to town, this is the most resort-like property on the Island. Rare on Nantucket, guests can enjoy their own private beach here.
White Elephant: This historic waterfront hotel consists of guest room, suites & garden cottages with amazing views of the harbor. Bonus: It is home of Brant Point Grill, which has the BEST Sunday brunch on the island aka the Billionaire’s Benedict.
The Summer House Cottages in Siasconset: ‘Sconset is a 15 minute drive from Main Street but has a small town of its own. Stay in quaint rose-covered cottages that have a pool of their own. Visit the property’s Beachside Bistro for dinner and/or drinks overlooking the Atlantic Ocean.
Packing your bags for a vacay to ACK? We’ve got you covered. Our Best of Summer Looks include everything you need from the beach to the chicest hot spots on the island. Headed there for the 4th of July? You’re sure to be the brightest in our Fourth of July Styles. Stay warm at night or on an evening sail in our Nantucket Pullover Sweater- easy, cozy & fashionable.