The Ultimate Itinerary for a Weekend in Nantucket

It’s time for a vacation, and you’ve set your sights on the Grey Lady—now it’s time to start planning. From ferry tickets to fine dining, we have the ultimate Nantucket itinerary to ensure your best island trip yet. What are you waiting for? Set sail today!

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Three Days in Nantucket: What You Need to See and Do

Your swimsuit is tucked into your suitcase neatly, your bucket hat is waiting, and the ferry is boarding—it’s time to trek 30 miles into the deep blue Atlantic, to the untouched magic of Nantucket. While the island is a mere 15 miles long, it is brimming with five-star restaurants, stunning scenery, and some of the best shopping on the East Coast, so where do you start? We’ve made it easy to make the most of your trip with our three-day Nantucket itinerary.

Day 1:

  • Arrive at Anchor Inn

You’ve awed at the vast Atlantic while aboard the Steamship. Now you’re making the turn around Brant Point and into the harbor to begin your journey.

Once you’ve received your bags, you’ll have the option of hailing a cab or making the short walk quarter-mile walk past the sea-worn cottages to your Nantucket home-away-from-home at Anchor Inn. Book your stay in the second-floor Alice Knowles room and settle in with views of Downtown Nantucket and cozy furnishings.

  • Shop the City Streets

Whether you’re looking to shop ‘til you drop or find something special to commemorate your trip, Nantucket offers some of the best retail therapy in the country. Visit Nantucket Looms on Main for delicately crafted linens, apparel, and home decor. Swing into Mitchell’s Book Corner for the perfect beach read. Blend in like a local with a pair of Nantucket Reds from Murray’s Toggery Shop. There’s a little something for everyone waiting on the cobblestone.

  • Dinner at Oran Mor

After a day of traveling and exploring Downtown Nantucket, you’ll be ready to indulge in some of the best food the island has to offer. Oran Mor is the perfect spot in between Main and Centre for a decadent meal and a fantastic wine selection.

You can’t go wrong with any of their five-star entrees, but we recommend saving room for your sweet tooth. Sipping on a Bailey’s-doused cappuccino and biting into their creamy chocolate torte is the perfect way to end your first day in Nantucket.

Day 2:

  • Breakfast at Anchor Inn

Wake up to a warm breakfast at Anchor Inn. Enjoy housemade pastries, yogurt, granola, and freshly brewed coffee each morning of your stay. Take a breakfast tray back to your room or bask in the sun in our airy garden patio.

  • See the Island on Two Wheels

You’ll want to start your day early today—there is so much larking around each twist and turn the island brings. Head down to Young’s Bike Shop to snag the only mode of transportation you need on the island.

The shop will provide you with a detailed map of the island and expert instructions on where to go. All of the island’s lighthouses make for an exciting day’s adventure, but we love the Polpis Road route straight to Sankaty. The ride is light and breezy, and the views from the top of Baxter Road are unparalleled.

From there, pedal south to the tiny village of Siasconset and grab a bite to eat at Claudette’s Sandwich Shop. Keep it simple with roast turkey on whole wheat or dive into the “best meatloaf on the island” with their meatloaf sandwich. It’s the perfect cottage escape with the friendliest of faces.

  • Dinner at Ventuno’s

Ventuno is a local staple. The chic Italian eatery serves up housemade pasta, fresh Nantucket Bay scallops, intricate small bites. Grab a glass of Sauvignon Blanc, a seat at the bay windows, and settle in for the perfect Nantucket night.

Day 3:

  • Brunch at Downyflake

has been serving Nantucket breakfast and lunch for over 80 years. The family-operated business knows a thing or two about serving up freshly baked donuts and Green Mountain Coffee. Swing by early to beat the crowds and leave just enough time for one more island adventure.

  • Visit Nantucket’s Whaling Museum

Make the most of your last day on the island with a visit back in time at the Nantucket Whaling Museum. From the 46-foot sperm whale skeleton to the fascinating scrimshaw gallery, the museum echoes with Nantucket tradition. And its central location steps from the Steamship terminal (and just down the street from Hy-Line’s) make it the perfect stop before heading back to the mainland.

And that’s that! Time sure flies when you’re basking in the Atlantic sun. We can’t wait to welcome you back to our tiny piece of New England paradise!

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