5 Ideas on What to Do During Your First Nantucket Vacation

words Alexa Wang

Nantucket may be a small island, but it is among the most popular New England coastal preppy vacation spots. 

This island, 30 miles south of Cape Cod, Massachusetts, is known for its stunning beaches and ocean views, its postcard-like cottages, houses and gardens, the vast areas of untouched nature, and some of the best and most exclusive boutiques, galleries, shops, restaurants and venues in the country.

First Nantucket Vacation

It is also a town, county, and island with an amazing whaling history that you can experience first-hand. This is possible thanks to the hundreds of meticulously preserved historic mansions, lighthouses, cottages, cobblestone streets with gas lanterns, and other landmark sites.

So, even though the island is only about 14 miles in length and from three to five miles wide, there is plenty to do and see in Nantucket.

If you are planning your first trip there, the first thing to do is to find the best place to stay. For a more authentic experience and as a more affordable option, you can choose to rent one of the many available short-term rental residences. There are houses, cottages, lofts, and mansions offered around the island.

You should also book your ferry or plane tickets because the only way to get to Nantucket is by sea or air.

After you are all set up, here are some ideas for the things to add to your itinerary for your first trip to Nantucket.

Explore at least one walking trail

As mentioned earlier, the island of Nantucket is pretty tiny. Plus, it is complicated and expensive to bring your car there or to drive there.

This is why the local authorities and people encourage visitors to get around by bike and on foot. Thanks to the network of multipurpose paths, you can reach from one point to another by cycling or walking easily.

If you would like to explore the stunning local flora and fauna, you will be happy to know that there are many walking trails in the preserved lands of Nantucket.

The local conservation organizations, as well as the authorities, are dedicated to preserving the nature and wildlife of the island. Thus almost 50% of the entire land of Nantucket is protected.

The walking trails are all relatively short and easy to cover. Some of the most popular ones for nature lovers and birdwatchers you can try out include the Miacomet Trail, Tupancy Links Trail, Sandford Farm, Stump Pond Loop, and Ram, Pasture, and Woods.

If you are looking for a romantic walking trail or for one where you can take some incredible vacation photos, then you should walk the one-mile Sconset Bluff Walk. 

It passes through those famous rose-covered old gray-shingled cottages, which you have probably seen in photos from the island.

Enjoy a boating excursion

Nantucket is an island, so the locals have always relied on boats, ships, and ferries for their food, business, and whereabouts.

It comes as no surprise that one of the best ways to explore and admire the beauties of this island is from the sea.

There are many sailing tours and cruises being offered from the Harbor, which you can choose from.

You can enjoy a romantic sunset cruise, a cocktail cruise, and even an oyster cruise. There are tours such as critters and ice cream cruises for the little ones as well.

If you are feeling adventurous, you can go on a longer excursion or tour in the open ocean to enjoy fishing or whale spotting.

Spend time at Cisco Brewers

Even if you are not much of a drinker, Cisco Brewers is the go-to spot to experience the real Nantucket party scene and mingle with the vacationers and the locals during your stay.

This is no ordinary brewery. On the contrary, Cisco Brewers, which was once referred to as “the happiest place on Earth,” is suitable for youngsters, seniors, families with kids, and even for dogs.

It combines the local craft beer brewery, winery, and distillery, so it is the place where you can try all of the local brews, wines, spirits, and handcrafted cocktails.

There is live music every day in the spacious beer garden. And there are various food trucks where you can buy simple snacks and gourmet meals such as fresh oysters, the famous local lobster rolls, and more.

If you are unsure which drink to try, you can join one of the various wine, beer, and spirit-tasting tours offered by the friendly owners and staff of the brewery.

Learn about the history

Nantucket was once declared “the whaling hub of the world.” Thanks to its brave local whaling captains and crews, it used to be one of the country’s most affluent towns and counties.

The local authorities and other organizations are committed to preserving as much of this history as possible. As a result, there are more than 700 preserved historic houses and buildings on the island. Plus, you can walk the actual cobblestone streets with gas lanterns which the people used to walk back centuries ago.

If you want to know more about the island’s incredible history and the whaling ships and stories which inspired Herman Melville to write Moby-Dick, you shouldn’t miss visiting the Whaling Museum.

Some of the other historic buildings and venues you may want to explore are the three historic lighthouses, the Oldest House, the Old Mill (which is the oldest working windmill in the USA), and the Old Gaol, which is the old prison of Nantucket. 

Don’t forget to visit the Shipwreck and Lifesaving Museum to learn more about the 750 and more shipwrecks that occurred on and near the island shores through the centuries.

Go to the beach

The beaches of Nantucket are among the leading reasons why tens of thousands of vacationers and other visitors come to the island every year.

The island is relatively tiny, but it has a beautiful coastline of over 80 miles of beaches and picturesque buffs.

There are over 25 beaches to choose from, each of which is open to the public and free to enjoy.

You can select the more popular beaches suitable for children that are on the north coast and near town.

Or, if you prefer, head to the more remote ones, which are more private and less crowded.

Some beaches are perfect for swimming, others for surfing, kayaking, or fishing. There are beaches that are among the top Insta-worthy locations. Others are an excellent choice for a quieter and more relaxing experience.


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