A Nantucket Itinerary in 3 Days

A Weekend in Nantucket

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Nantucket, also known as The Gray Lady, is a small but vast island off of Cape Cod filled with white-sand beaches and unpainted, cedar-shingled cottages marked by privet hedges. While many people escape the big cities and vacation here throughout the summer, it is an adorably quaint town to explore over a long weekend. The cobblestone streets are lined with many high-end boutiques, gourmet restaurants, and steepled churches that will provide an inevitably great getaway. 

There are several ways to get to Nantucket. In my opinion, the Hy-Line Ferry is the easiest and most affordable mode of transportation as there are many different ports to travel from. Because of the common fog, flights are often delayed and can be very costly. If you take the ferry, it is highly suggested to leave the car behind, as parking is very difficult and biking and rideshares are easily accessible. However, I would have loved renting a jeep and riding it around town! 

My mom and I decided to take a mother-daughter trip to explore Cape Cod, with Nantucket being where we would spend three days. We stayed at The Ship’s Inn which is a historical inn and restaurant located in the hub of Nantucket. The staff couldn’t have been any friendlier, and we loved our room in the Captain’s Quarters. We were treated to breakfast each morning and dined in the basement restaurant one night, which ended up being one of our favorite meals on the trip. I highly recommend this bed and breakfast for its ambiance, location, and comfortability. If you are looking for a more upscale stay, The White Elephant is a very popular, luxury hotel located very close to downtown.

We spent our first day exploring the downtown area Nantucket, first stop being lunch at The Lobster Trap. Afterward, we spent the afternoon walking along the cobblestoned streets going through each boutique and lightly shopping. To cap off our day, we enjoyed the most beautiful sunset at Galley Beach toasting to a great start to our trip (reservations can be made 7 days prior). Having dinner and drinks in this stunning setting was so picturesque and the best way to enjoy our first evening.

Join me on Instagram:

Outfit Details:

Bohemian Floral Dress, woven flats, headband, earrings, and purse (similar and more affordable bags linked here and here)

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On our second day, we rented bikes and explored the ‘Sconset area (it is about a 40-minute scenic bike ride from downtown Nantucket). Once we made it to 'Sconset, we walked the 'Sconset Bluff Path, which is a lovely trail overlooking the Atlantic ocean on one side and beautiful homes with climbing roses on the other. At the end of the trail, Sankaty Head Lighthouse awaits (and you may be lucky to see some seals!). To reward ourselves for our active morning, we ate a delicious lunch at The Summer House. Another highly recommended restaurant is Claudette's, so be sure to stop by for their well-known sandwiches if you picnic on the beach. On our return biking trip, we stopped by the Windswept Cranberry Bog but was unfortunately closed (something we will just have to do on our next trip back!). After our bike ride, we headed to Juice Bar for homemade ice cream (which is as good as everyone said it would be) and headed back to our hotel to rest and get ready for dinner at The Nautilus. 

On our last day, we did a little more light shopping and exploring. We originally planned on spending the afternoon at Cisco Brewery, but due to COVID-19 and certain regulations, we were unable to attend. However, we have heard such great things about it and will plan on stopping by on the next visit. To cap off our day we did a sailboat cruise through Endeavor Sailing, followed by drinks at Cru and dinner at the fun and lively Club Car.

Sadly all good things must come to an end, and so before heading out the next morning, we grabbed breakfast and coffee at Provisions (the bagels and breakfast sandwich were amazing!) and loaded up on the ferry. Nantucket was such a charming city - from the colorful hydrangeas to the pristine homes - and I am already dreaming of the next trip back to ACK.

Favorite Shops:

• Milly & Grace

• Salt Boutique

• The Skinny Dip

• Blue Beetle

• Cattivo

• Toujours Midi

Places to Eat:

• Breakfast:

  • Black-Eyed Susan’s

  • Lemon Press

• Lunch:

  • The Lobster Trap

  • The Tavern

  • Provisions (great breakfast options as well!)

  • Millie’s

• Dinner:

  • Cru

  • Nautilus

  • Club Car

  • The Ship’s Inn

  • Galley Beach

Things to Do:

• The Whaling Museum

• Rent Bikes

• Cisco Brewery

• Go Sailing

• Enjoy the beach! (Steps Beach, Jettie’s Beach, and Sconset Beach are great options)

Inspired by my trip to Nantucket & the beautiful hydrangeas - I created these custom gift tags that make the perfect birthday gift, hostess gift, you name it! We can have these made to order and delivered within 5 business days. Get your set here >>

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>> Read about one of our other favorite cities here! <<

If you’ve been to Nantucket, what did we miss that you love? I would love to hear what we should do on our next trip back (and hope to go back for an even longer time!).

All the best,

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To see more about what inspires CoCo, check-out her Instagram page at @cocozentner_art!

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