How To: Plan the Ultimate Weekend in Nantucket

For such a small island, there are so many choices. From five-star dining to breathtaking bike routes to the most charming boutiques right off the cobblestone, Nantucket is filled with the best of the best. Make the most of your trip with our exclusive Nantucket itinerary. We’re letting the cat-out-of-the-bag with all of our favorite local spots. Make your trip last a lifetime this year. 

Still want more? Access our exclusive Vacation Guide and expand your Nantucket itinerary. Our on-the-go guide offers hand-picked recommendations on dining, shopping, activities, and more. Best of all? It’s free!

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Everything You Need to Know About Crafting the Perfect Nantucket Itinerary

Plan your best trip to the island yet with our three-day Nantucket itinerary. We have everything you need to know about the best bike routes, bites, and more to ensure an exciting island getaway. Discover it all today!

Day 1: Arriving in Nantucket

  • Settle Into Greydon House

Rooms-Federal Suite - EntranceYou’re rounding the corner of Brant Point Lighthouse with the port in sight. You can smell the fresh seafood and see the sea-washed wooden buildings. You’ve made it to Nantucket. 

You unload and make the short, five-minute walk from the Steamship terminal to the gorgeous steps of Greydon House. You step in, say hello to the friendly staff, watch as your key is carefully removed from the chest of old-timey keys, and follow the helpful staff member as they show you to your home for the weekend. Whether you want to wash up in the hand-painted, Moroccan-tiled shower or take a catnap in your plush queen-size bed, one thing is certain—you’ll want to soak in the beauty of Greydon. 

  • Dinner at Ventuno

Ventuno is a local staple boasting fresh, made-to-order seafood dishes and homemade pasta. They offer an extensive wine list that is sure to make you want to stay awhile. It’s Federal Street location, and large, bay windows make it the perfect spot for people-watching.

  • Dessert and Drinks at Oran Mor

After a day of traveling, you’ll want to find the closest spot for a nightcap. Located just steps from Greydon is the candle-lit Oran Mor. The intimate bistro is nestled into South Beach Street and is marked only by a small, rod-iron sign. Their dessert menu is classic and decadent and pairs perfectly with a Bailey’s cappuccino.

Day 2: The Perfect Nantucket Day

  • Wake Up to Fresh Coffee, Juices, and Pastries at Greydon House

Hit snooze and linger in pure comfort a little longer. When you’re ready, start your day the right way with a fresh breakfast spread. Enjoy fresh fruit, pastries, slowly brewed coffee, and fresh juice choices.

  • Rent Your Wheels

getting around NantucketCars are great, but not really necessary on the island. The best way to see the island is on two wheels. Young’s Bike Shop is a short walk from Greydon House and offers bike rentals, maps, and knowledgable information from the locals who know it best. 

Once you’re set up and ready to go, we recommend heading to Steps Beach for an early beach day. Head down Beach Street and take the cut onto Cobblestone Hill. (the perfect Insta-op) Take a right on Lincoln Avenue and be on the lookout for the hidden Secret Garden-esque entrance. 

From Steps, head back towards town via Lincoln Avenue until you arrive at the Jethro Coffin House, also known as the oldest house in Nantucket. Built in 1686, the home served as a hall-and-parlor dwelling for the Turner family. If you work up an appetite on the way there, make a stop at Something Natural for thick-cut sandwiches and tasty teas.

End your bike tour with a visit to Brant Point Lighthouse. Chances are you spotted it on your way into the harbor, but did you know you can get up close and personal? Head down Beach Street and take a left on Easton and you’ll dead end at the light. 

  • Massage at Sister’s Salon and Spa

After your biking adventure, you’ll be ready for a break at Sister’s Salon and Spa. The Downtown spa offers everything from traditional Swedish massage to reflexology to marine mud wraps and their signature Nantucket Scrub.

  • via mare drinkDinner and Drinks at Via Mare

Come back to Greydon’s own Via Mare. The Bohemian-style dining room effortlessly blends chic and cozy for a dining experience you’ll want to dawdle in. The restaurant serves up a farm-to-fork, revolving menu and the best drink concoctions on the island. Best of all? When you’re ready to roll out, your room is waiting just down the hall!

Day 3: End Your Trip in Style

  • Breakfast at Black-Eyed Susan’s

Don’t leave the island without a stop at Nantucket’s famous breakfast house, Black-Eyed Susan’s. The India Street restaurant serves up traditional breakfast fare from fried eggs to buttermilk pancakes—but in the tastiest way possible. Some of our favorites include the orange, Jack Daniel butter, Sourdough French Toast, housemade corned beef hash, and Pennslyvania Dutch Cakes with Jarlsberg cheese. Get there early as they fill up quickly.

  • Shopping on Main Street

Before heading home, be sure to commemorate your trip with some Nantucket-style shopping. Leave your budget on the cobblestone as you mosey up and down Main Street to some of our favorite Downtown shops. It’s the perfect way to end your visit to the island.   

End Your Nights Nestled in at Greydon House

Rooms-Federal Suite - Sitting AreaIf you’re looking for a Downtown location that is distinctively furnished and quaintly comfortable, Greydon House is the place for you. Book your stay in the Federal Suite and bask in a residential-style entrance, high ceilings, a melt-into queen-size bed, and the finest soaps and lotions. Still need more room? Guests have the option to add up to two adjoining bedrooms expanding over 500 square feet. 

Want to learn more about our cobblestone streets? Discover the best of restaurants, shops, nightlife, and things to do to entertain your trip in our Guide to Downtown Nantucket. We are so excited to welcome you to our little piece of Atlantic paradise!