As much as I am a fan of traveling to new places, there are a few locations that I have come back to year after year and have a permanent place in my travel itinerary, and my heart. Nantucket happens to be one of them. I’ve been coming here for nearly half my life, and it’s one of those places that seems never to change, and feels inherently good and relaxing and simple. I’m deviating from my usual travel guide structure here, and breaking this up by dayparts so you can piece together your perfect itinerary. Note that I’ve normally stayed at rented houses when I visit Nantucket, but if you’re going for a shorter time period, the Sherburne Inn in town is so lovely, and the Carriage House is a cheaper option as well.
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Lemon Press – This tiny all-day cafe recently moved to a new location on Main Street and has a spacious dine-in area. Their cold brew is the best in town, and they offer a range of options from hearty to healthy. My favorite is the breakfast burrito as a bowl, over fresh spinach, in the morning.
Black-Eyed Susan’s – This beloved Nantucket institution has some of the best French Toast I’ve tried to date – it’s made with sourdough bread and topped with orange Jack Daniels butter. They also have a great, simple dinner and you can BYOB at night.
Handlebar Cafe – The tiny coffee shop near The Lobster Trap is a little off the beaten path, but a bit quieter than other Main Street alternatives.
Provisions – One of my all-time favorite Nantucket sandwich shops. Go for breakfast and get “The Original,” which has an herbed frittata and a homemade chipotle jam. Plus “The Other Turkey” is my pick for a beach picnic.
Biking to Madaket – Take a stroll down past Juice Bar, rent a bike at one of the shops near the water, and head out to Madaket Beach. There are bike paths all the way there, and you can stop off at Millie’s when you get out there for a sandwich to have at the beach.
The Lobster Trap – Come here for lunch, sit at the bar, and order what I think is the best lobster roll on the island. The sweet potato fries are pretty good too.
Juice Bar – A true Nantucket institution, this ice cream shop normally has a line down the block, but the homemade, warm waffle cone bowls and cookie dough ice cream are worth the wait.
Cisco Brewery – Looking for a 888 blueberry vodka and lemonade, or a Whale’s Tail Pale Ale? Cisco is your spot. There’s live music, cornhole, and a rotating cast of food trucks as well, making this spot perfect any afternoon of the week.
Sandbar at Jetties Beach – Sit outside at Sandbar with a drink and watch the sunset, or, as we did recently, bring your own picnic and blanket and make your own beach party.
Straight Wharf Fish Store – Tucked away next to Provisions, this little fish market is the perfect place to pick up fresh shrimp and oysters for your night ahead. They also do a mean, creole-style lobster roll.
Bartlett’s Farm – Whether you’re going for the fresh produce, sandwiches for the beach, or the whole lobster dinner, Bartlett’s is an actual working farm with the best local ingredients.
Dune – On a little back patio decked out with twinkle lights, Dune serves up delicious farm to table dishes for dinnertime. A recent favorite was a spicy clam and sausage appetizer that blew the whole table away. Make a reservation.
Nautilus – Asian small plates done incredibly right. You may need to wait in line at lunchtime to get your name in here, but trust me when I say that if there is one dinner on the island that’s worth it, it’s this one. Don’t miss the shishito peppers, beef tataki, tuna lettuce wraps, and corn.
Cru – Skip the overpriced lobster roll here and post up at the bar for a martini and their insanely addictive french fries. I think we came to the back bar here every day during our recently trip, and you had to drag us away.
Afterhouse – My new favorite spot for wine on the island. Walk down a few steps to get to this dark little wine bar and restaurant, which is perfect for a glass of wine post-dinner.