Emily’s Guide to Nantucket

On a little island 30 miles out to sea, exists my happy place, Nantucket. While I would never turn down the opportunity to spend a leisurely week in Cisco, strolling down dirt roads to the beach and biking to Bartlett’s Farm for dinner ingredients, I wanted to put together the perfect long weekend itinerary for those looking for a quick getaway. Though I stand by the fact that Nantucket is best experienced with no plans at all (okay, except for a few dinner reservations!)

Day One:

Depending on where you’re coming from, you’ll need to travel in either by ferry or plane. I prefer taking the ferry and view it as part of the experience, but I live in Massachusetts and like to overpack.

It also means I can say, “leave your shit at the dock” to everyone I’m traveling with - literally saying do not bring any stress or drama to the island with you.

Once you get to Nantucket, you’ll want to drop off your bags at the hotel. Be prepared to wheel your suitcase across cobblestones, and potentially uphill depending on where you’re staying.

For a long weekend trip, I highly recommend staying at a hotel close to town. Leave the house rentals for stays of a week or longer. Two hotels I’d recommend are the Nantucket Hotel and Resort, and Cliff Lodge Bed and Breakfast.

After you drop off your bags, it’s time to grab lunch and check out what Main Street has to offer.

I know people have different opinions on the best sandwich on the island, but I have to give my vote to Fresh Nantucket (though if I’m in Sconset, Claudette’s all the way - more on that for Day Two). Get the Sweet Boy and thank me later. Be sure to browse the endless shelves of alcohol while you wait, and maybe even pick up a bottle of sparkling wine for later tonight.

Grab your sandwich and head over to the wharf for some people watching while you eat.

Spend a few hours popping in and out of the different boutiques and antique shops, and pick up a book from Mitchell’s Book Corner if you don’t have anything to read for the trip.

If you’re up for it, rent a couple of bikes and make your way towards Cisco Brewery. Most of the time they’ll have live music and food trucks so you can enjoy this spot for another few hours.

Once you’ve wrapped up at Cisco Brewery, head back to your hotel to get ready for dinner. You will most likely need a dinner reservation, especially if you’re traveling in the busy season. Two of my favorites are The Nautilus and The Gaslight. If you like Asian fusion restaurants, these can’t be missed.

After dinner, walk down to the water and take in the view.

Looking for a late night treat? Skip The Juice Bar and instead grab a mudslide from The Gazebo or split a hot pizza from Pizza Gemelle with whoever you’re traveling with.

If you’re not yet ready for bed, sit outside at your hotel with the bottle of wine you picked up earlier.

Day Two:

It hurts my heart to say that my favorite breakfast place, Black-Eyed Susan’s, is closed. I’m still holding out hope that they’ll come back, but in the meantime it’s time to find breakfast elsewhere.

Walk over to Born & Bread for coffee and delicious pastries - you must try the cruffins!

Either sit and enjoy your breakfast in town or take it to go as you head to the bus stop. Nantucket’s public transportation system operates a handful of shuttle buses called The Wave. You’ll want to take one into Sconset.

Once you’re in Sconset, it’s time to find the Sconset Bluff Walk. The walk starts at the end of Front Street and can sometimes be hard to spot. You’ll probably feel like you’re in the wrong spot, but continue on and in a moment you’ll know you found it. On your right, the edge of the bluff overlooking the ocean. On your left, gorgeous cottages and well-manicured backyards. While many of the steps to the beach are private, you’ll find a few that allow the public to explore.

If you have the time, and are wearing the right shoes, I highly recommend continuing the walk on the road all the way out to Sankaty Head Light.

By this point I’m sure you’ve worked up an appetite, and like I mentioned on Day One, if I’m in Sconset I’m getting a turkey sandwich from Claudette’s. It’s so simple, but I dream about this sandwich year-round. Though I can understand if you don’t want another sandwich, and if that’s the case, grab a snack at Sconset Market and jump back on the bus.

Get off Mid-Island and go to Island Kitchen for lunch.

After lunch, you can either take the bus or walk the rest of the way back to your hotel.

Now if this was my perfect Nantucket weekend, I’d probably spend my down time reading Elin Hilderbrand’s latest novel, but you can choose to relax however you’d like between now and dinner.

Before dinner, I like to stop at a different restaurant for a drink and oysters. Even better if you can find a spot outside on a deck or a patio.

Since you had Asian Fusion last night, switch it up with dinner at Ventuno, Cru, Slip 14, or American Seasons.

If you’re looking to go out afterwards, take an Uber to The Chicken Box. No, you won’t find chicken there, but if you’re interested in a late night snack tonight as well, be sure to hit up Stubby’s before you stumble back to your room.

Day Three:

Okay you’re probably tired, but this still counts as a day so make the most of it.

Walk over to Lemon Press and put your name on the waiting list. Whether you’re in the mood for avocado toast or an acai bowl, you can’t go wrong. Don’t forget to get a Grey Lady latte, too!

If you’re up for another bike ride, I like to start in town and swing down past Jetties Beach up to Steps Beach. It’s an easy, picturesque ride, perfect for your last day on island. If you’d prefer to walk, skip Jetties Beach and head to Steps Beach via Cliff Road. You don’t have to go down to the water, but take in the view from the top of the stairs at the very least. It’s one of the best lookout spots, and I’m sure you’ve seen a million Instagram pictures of it by now.

By now it’s almost time to get going, so head back to the hotel and pack up your things. If you have time, do some last minute souvenir shopping in town before heading to the ferry (or just Uber to the airport if you’re flying.) Grab a box of Aunt Leah’s Fudge and a sweatshirt from Annie and the Tees, and make your way to the dock.

While your time on island has ended for now, enjoy the ferry ride back with a bloody mary and a seat on the upper back deck. You’ll get to watch the island fade as you pull away, a magical sight if it’s close to sunset.

I hope you found this post helpful in planning your next trip to the island! And for when you’re craving a little bit of Nantucket nostalgia at home, try stitching a Nantucket Needlepoint Club canvas.

Have ideas for a new canvas inspired by your favorite place on Nantucket? I’d love to hear from you. Feel free to send me an email or leave a comment below.

Emily