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Top 10 Things to do in Nantucket


Nantucket Activities

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Nantucket vacation

Nantucket is a charming little island 30 miles out to sea off the coast of Cape Cod, Massachusetts. It is most popular between Memorial Day and Labor Day, with the peak season being July and August. If your travel plans can extend into September, we highly recommend visiting after the summer rush when the crowds clear out. The restaurants are still open and there are plenty of Nantucket vacation rentals to be found through Fisher Real Estate. Here’s our version of the perfect day trip and the top 10 things to do in Nantucket.

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Top 10 Things to Do in Nantucket


Grab an early breakfast at Black-Eyed Susan’s…the menu never changes and it doesn’t need to because it’s a Nantucket staple! We suggest you get there early as the line can get long on weekend mornings. Don’t skip their famous Pennsylvania Dutch Cakes with Jarlsberg cheese. Black-Eyed Susan’s is also a hot spot open for dinner with three seating’s available. Cash only.


Enjoy a walk, run or bike ride through one of Nantucket’s vast conservation areas. Nearly half of Nantucket is forever-protected open space. The Nantucket Land Bank is the first conservation program of its kind in the United States. Stop by their office at 22 Broad Street and grab a map of all their walking and hiking trails to kick off your adventure! The cranberry bogs are frequently open to the public and are as pretty as they sound. They are working farms so check to make sure if any areas are off-limits. Fisher Tip: you can bring your four-legged friends too. Read this great blog from Marleah on her favorite Nantucket dog walking trails!

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Get to the beach early and snag one of the island’s fantastic surf instructors to take you out! In the high season, you will find surf schools at Nobadeer & Cisco Beaches. There are other adventurous salty activities to try, from Stand Up Paddle Boarding (SUP) to kiteboarding and wakeboarding to kayaking. Sales & Rental Agent Danno Lynch gave us the 411 on learning how to surf on Nantucket.


The Whaling Museum pays homage to the history of Nantucket when it was the ‘Whaling Capital of the World’ in the 17 and 1800’s. Restored in 2005, the Nantucket Whaling Museum features an exhibition space, a fully accessible rooftop observation deck overlooking Nantucket harbor, a kid-friendly discovery room, a 46-foot sperm whale skeleton and a restored 1847 candle factory. The museum is run by the Nantucket Historical Association, who also maintain over 20 historical sites around the island.

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Downtown Nantucket has great shopping and chances are you will not go home empty handed. Find your very own pair of Nantucket Reds at Murray’s Toggery Shop. Don’t get on your boat or plane without bringing a Nantucket t-shirt home! For the high-end shopper, there are amazing fine art galleries, antique collections, designer boutiques and shops. One treasured local item is the Nantucket Lightship Baskets, which you can only find on our island. During your shopping stroll, grab a tea or coffee from a local hotspot like Handlebar Café or Corner Table and spend some time enjoying the historic, local sights in town. There are benches along every cobblestone street where you can sit and just watch Nantucket go by! Sometimes it feels like we are living in a movie set, every corner looks like a painting!


Nantucket only measures 15 miles long by 3 miles wide, making it an ideal place to rent a bike and tour the island on our wide-open bike paths. You can spend half a day cruising from Downtown (north end) out to either ’Sconset (east end), Madaket (west end), or Cisco/Surfside/Nobadeer (south end). If you prefer to hire a guide and explain history while taking you to the top spots, look no further than our friends at Nantucket Bike Tours.

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We may not officially have “happy hour”, but that doesn’t mean you can’t create your own! In between your day time adventures and evening plans, a delicious seaside cocktail and quick bite is always a wise idea. We suggest a harborside glass of rose and some fresh oysters at Cru. Or try a tropical cocktail at the local-favorite Slip14, or a glass of champagne with your toes in the sand at Galley Beach. In addition to Downtown spots, there’s also the world-famous Cisco Brewers. “The Brewery” is close to the beach and has a free shuttle service from downtown. At Cisco you will find a rustic brewery with live music, tastings, tours, food trucks and 4 bars serving craft beer, wine & craft cocktails.


Ready for dinner? There is nothing like enjoying a New England lobster dinner during the summer months. One of our favorite Nantucket secrets is just a few blocks from the heart of town. Good old Sayle’s Seafood offers complete lobster dinners to-go with all the necessary sides. Bring your feast, beach chair and Nantucket sweatshirt to Step’s Beach for a memorable sunset experience. Sayle’s also has a fantastic selection of fish in their retail market to bring home to your Nantucket vacation rental! If you are looking for something a little more refined, then head over to Straight Wharf Restaurant. Their famous SWR Clam Bake includes over a pound and a half of lobster, taken out of the shell, butter poached and gracefully plated with littleneck clams, spicy chorizo, melted leeks & sweet corn puree. Heaven on a fork and no bib necessary!

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Because you’ve left room for dessert, you MUST experience the homemade ice cream at The Juice Bar. They have an abundance of flavors, including house-made sorbet and vegan selections. The line may look a little long but trust us, it’s worth the wait! For the details on ALL of Nantucket’s ice cream shops read our blog, “The Scoop on Nantucket Ice Cream.” Now that you have explored, adventured and eaten, it’s time to unwind! Grab someone special and take an evening stroll along the docks off Straight & Old South Wharf. There are beautiful boats of all shapes & sizes that are fantastic to “ooh” and “ahh” at. You’ll find yourself quickly dreaming about what your days would be like if you were island hopping in such luxury!


Finally… it’s no secret that here at Fisher Real Estate, we love to fish! We highly recommend making fishing one of your things to do in Nantucket. Whether you hire a charter like Bill Fisher a boat, or head out on the beach with your own rod, you are in for a great experience and hopefully tight lines! Look for our very own, Cam Gammill’s, Fishing Report for the latest news on fishing Nantucket.

We hope something on this list peaks your interest when visiting our magical island. On Nantucket, we truly have something for everyone! For more recommendations on things to do in Nantucket, Massachusetts, follow Fisher Real Estate on Instagram.