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The Ultimate Nantucket Vacation Planner: Finding The Best Places To Stay And Things To Do

Updated: Dec 18, 2023

🇺🇸 Download your free Nantucket packing list 🇺🇸

UPDATE: How cool is this, my coverage of Nantucket caught the attention of Buzzfeed and was featured in a recent article about the destination. Check it out!

Greetings to all the lovely people in Nantucket! If you’re visiting the island for the first time like me, you must be excited to discover everything that the area has to offer.

In this post, I have shared my personal experiences at some fantastic places in town to provide you with an idea of what the island has in store for you.

Whether you’re planning a trip to Nantucket or wandering around the downtown streets with my blog in your hand, this travel guide is designed to help you explore the best of the island. So let’s get started!

🚗 Getting around: You can easily get around using ride sharing services like Uber and there are local taxi cabs available, you can easily find them driving around the downtown area.

You can get to the island by ferry or Cape air or speed boat. There are two companies to choose from, Hy-line Cruises and Steamship Authorities.

Together they run 14 departures each direction between mid-May and the start of September. Steamship Authorities is slightly cheaper than Hy-line Cruises but they both range around $40 bucks one way and take about an hour.

☀️ When is the best time to visit: The best time to visit Nantucket is during Summer season and/or early fall. During the fall season you’ll notice the island is free of the pre-Labor Day crowds, and the temperatures are pleasantly mild.

🚑 Insurance: It is always a good idea to protect your investment in travel. Whether you get sick, lose your phone, anything could happen during your vacation and having travel insurance gives you the peace of mind you need to have a safe and successful trip.

Things to do in Nantucket

Visit a museum

The Nantucket Whaling Museum was founded in 1929 and houses artifacts and stories covering four centuries. You can also go here to see a 46-foot sperm whale skeleton.

The MAAH New England’s largest museum dedicated to preserving, conserving and interpreting the contributions of African Americans. You can explore the historic sites in Nantucket locations along with The Museum’s Black Heritage Trails®.

Schedule a photoshoot

the most popular photo spots on the island are Great Light Point, Brant Point Lighthouse, Siasconset Beach, Sankaty Head Lighthouse, Sconsett Bluff Walk, The Nantucket Atheneum (a public library).

Explore the island on bike

Nantucket is a very bike friendly island, with bike trails covering most of the island. You can easily purchase a bike on the island and/or rent one to enjoy during vacation. Guests of the Faraway hotel have access to their branded bikes that you can use to explore at no extra charge.

There are three main bike trails on the island that connect to Surfside to Siasconset and Madaket on the west side.

Take Note: When biking in downtown you’ll notice there are no marked bike trails. Prepare to keep on the road and follow normal traffic rules.

Take a private cruise

I highly recommend the sunset cruise with Ack Sail, it is such a smooth ride on the water. You can bring your own food, drinks, and snacks aboard to enjoy too! Vin will captain the vessel and he is so personable and really knows his stuff! He is a Coast Guard licensed captain and has been sailing Nantucket Sound for over 40 years.

Click here to book and tell Captain Vin, “Aubrey sent you!”

Go shopping

When visiting Nantucket, don’t anticipate or search for major retailers or brands that you’ve become accustomed to in your city. On the island you won’t find a target or Starbucks, but you will find luxury brands like Polo Ralph Lauren, or Vineyard Vines and Lilly Pulitzer and tons of amazing mom and pop shops for you to support locally.

You can also check out the Hospital Thirft Shop, I heard so much about this shop from the locals that I had to check it out and I am so glad that I did.

The mission of the Hospital Thrift Shop is to provide affordable goods to the community of Nantucket and to raise funds to support the Nantucket Cottage Hospital.

Where to dine

I love the variety of options in Nantucket. You can enjoy a sandwich and fries at the popular dining spot called Stubby’s or get amazing pizza’s downtown or go super high end, there’s truly so many options.

The Faraway hotel has an amazing dining destination called the Sister Ship where you can dine indoors or out, they have a cafe and a bar. Its a casual chic attire and vibe. I ordered their scallops for dinner and chocolate dish for dessert.

Check out their menu here.

When visiting Nantucket you have to check out Siasconset or what the locals call ‘Sconset and go to the Wauwinet hotel to dine at Toppers!

They have amazing water views, awesome ambiance and the food is chef’s kiss!

Highly recommend their roasted chicken dish. Check out their menu here.

The Nantucket Hotel & Resort is a must visit when coming to the Island. The hotel has been around for years and offers great amenities to guests and residents who dine, stay and even workout at the hotel.

Breeze restaurant has awesome drinks and even more delectable dishes. highly recommend their grilled Caesar salad and scallop dishes.

Check out their menu here.

Where to shop

Nantucket is home to tons of great shopping and here you can easily support the local economy as most of the retailers on the island are locally owned or ‘mom and pop’ style places.

You won’t find those ‘big box’ stores here aside from Lilly Pulitzer, Polo Ralph Lauren and Vineyard Vines.

I found this super cut bag at a local shop downtown on the Island called “It’s a Shore Thing”. They have cute gift sets, collector items, clothing and accessories.

I love my new tote bag.

I was able to get myself and family items to remember the island buy and spent less than $250 for everything.

Where to stay

I personally can’t recommend The Faraway hotel enough!

The staff is impeccable, the rooms are divine, and if you’re traveling solo to the island or visiting for the first time the hotel is perfectly positioned in Nantucket’s cobblestoned downtown next to the best dining, shopping and local attractions.

Downtown is super walkable and you’ll appreciate having your hotel close by.

Other hotel options to consider and research reviews for…


If you want to go the short term rental route you can explore options available on sites like Vrbo and Airbnb.

In my opinion hotels on the island offer you the connection with the locals to gain insight and perspective from those here before you vs being a short term rental where its a bit more isolated.

For solo travelers or new visitors to the area I would recommend a hotel stay and for families, Bach parties, big groups, you might find short term rentals on the island to best suit your needs.

Have Your Trip To Nantucket Planned By A Professional!

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