How to Make the Best of a 3-Day Trip to Nantucket

Nantucket is a dream vacation spot for surfers, lovers, history enthusiasts, foodies, fishers, and just about anyone. But not everybody has the time and the money to go on a long vacation there.

Thankfully, there is a way to have a great time and see some of the most exceptional sites and venues on this New England Island, even over a weekend or three-day trip.

I recently went on such a trip with several of my old college friends, and I must say – we had an absolute blast and came back wanting to return to this magical island as soon as possible.

When planning a trip like this, I recommend that you first find a suitable short-term rental for your stay, especially if you are going with a group of friends or family members. This way, you will get a more authentic experience, and you can share the costs and save significant amounts of money compared to staying at a hotel.

Then, decide how you are going to get to Nantucket. There are two options – one is via a ferry from Hyannis Port in Cape Cod, and the other is to fly into Nantucket Memorial Airport.

The cheapest option is to take the traditional ferry of the Steamship Authority. The 30-mile ride is about two hours and 15 minutes long, but it is a fun way to start your three-day adventure. There is a faster passenger-only ferry which you can take from the same port. If you are lucky, you can score some pretty affordable airline tickets, especially if visiting Nantucket off-season or traveling mid-week.

Once you have organized your accommodation and made your travel arrangements, you can be ready for your unforgettable three-day trip on this magnetic island.

Day 1

I recommend that you spend the first day exploring historic Nantucket. It is one of the best-preserved historic towns in the USA, with some enchanting views and hidden gems.

The ferry arrives at either Steamboat Wharf or Straight Wharf, each in the heart of the town's historic district.

You can stroll through the cobblestone streets by some of the most beautiful New England-style homes in the country. The downtown is where all of the top restaurants and stores are located as well, but the prices are pretty steep, especially during the peak of the season.

Once you are ready to take a break, I recommend that you visit CRU, where you can enjoy the most famous New England lobster roll while enjoying a stunning waterfront view of the Wharf.

After lunch, don't miss out on the opportunity to see the top-rated attraction in Nantucket, the Whaling Museum. It is set in a historic building that used to be a whale oil candle factory. You can explore the hundreds of exhibits showing the history of whaling which in the 19th century turned the island of Nantucket into the world's whaling capital. Among others, you can see a real 46-foot long skeleton of a sperm whale there.

I recommend the Nautilus for dinner, where you can enjoy some handcrafted cocktails and share small plates with your friends or family. If visiting during the peak of the summer, you may want to make your restaurant reservations in advance.

Day 2

While you can rent a car or take the shuttle bus or cab when in Nantucket, I strongly recommend that you rent a bike instead. A network of bike paths covers the entire island, and there are many bike rentals there. Plus, you can take your own bicycle via the traditional ferry for only $14.

On the second day, you can get on those bikes and explore some of the must-see gems on the island. If you like, you can spend a leisurely second day on one of the more than 25 beaches on the island. There are beaches suitable for any preference. The northern ones are more family-friendly, while the southern beaches are ideal for surfers and adventures.

If you are not too keen on getting your toes wet, you can visit some of the incredible sights, such as Brant Point Lighthouse, where you can take great vacation photos.

On the way back, I strongly recommend that you go to Cisco Brewery. It is next to Nantucket Vineyards and the Triple Eight Distillery. Needless to say, there is a vast array of options for tasting there. The extensive beer garden is a superb way to spend a few hours and more, and there is live music every day. The tasting tours will allow you to taste some fantastic local brews such as Shark tracker and Whale's Tale Pale Ale, some Gale Force Gin, and the local merlots, pinots, or syrah's. You should definitely try the frozen sangria offered throughout the summer season.

In between the beach and the brewery, you can make a short stop at Sandbar at Jetties Beach, where you can enjoy some affordable, delicious fresh oysters, especially during the happy hour from 1 to 3 pm when you can eat oysters for $1.

Day 3

Before leaving Nantucket, make sure you visit the tiny but lovely village of Siasconset, called Sconset, by the locals.

It is located 8 miles from town but is absolutely worth it. There you can take a stroll on one of the most famous walking paths – the Sconset Bluff Walk. You will pass by the iconic weathered gray shingle-style houses and colorful gardens and through the market. The path will take you to the stunning Siasconset Beach and a little further to the easternmost point of the island and the famous Sankaty Head Lighthouse.

Try The Chanticleer, an absolute gem with a magical interior, impressive landscaping, and delicious food, such as tuna tartare, bluefish pate, and oysters if you have time for lunch.

On your way back, you can hop on the shuttle bus along with the bikes and get to your house to get ready to leave this wonderful island.

Once you are back on the plane or ferry, you will find yourself planning your next trip to Nantucket almost immediately!

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