The island of Nantucket, located 30 miles south of Cape Cod, MA, also known as “the Little Grey Lady of the Sea,” is the oldest and most famous whaling town in the USA. Today it is a magnet for tourists, thanks to its stunning historic buildings, blooming gardens, endless beaches, and unmatched coastal charm and splendor.

Nantucket Vacation Travel Guide

Here are some tips for those planning to visit this New England nautical paradise.

1. Book a local house

Awesome Nantucket Vacation

Just recently, a property in Nantucket was sold for a record-breaking price, and news of a tiny 360 sq. foot cottage offered for a whopping 2.06 million dollars made the news.

The good news is that you don’t have to be a billionaire to enjoy residing in one of the charming cottages, grand mansions, or other houses on the island.

All kinds of properties and residences are offered as short-term rentals throughout the year. You can book a luxurious waterfront mansion for a high-end vacation or wedding or rent a small cottage to spend an unforgettable family vacation in an authentic Nantucket home.

2. Pack comfortable shoes

Nantucket is a popular spot for celebrities, politicians, influencers, and preppies, so it is definitely an upscale vacation destination.

However, when packing for your holiday, remember that the tiny island is perfect for exploring on foot or by cycling, so make sure to bring along some comfortable flats and walking or hiking shoes.

Nantucket is only 14 miles long and about 3.5 miles wide, and it has an extensive network of multi-purpose lanes suitable for bikes, walking, or jogging.

Plus, more than 50% of the island’s territory is conserved, and any building and development are prohibited, so there are some stunning wildlife reservations and other natural resources which you can explore while spending time in Nantucket.

There are easy hiking and walking trails suitable for leisurely walks with the family and dogs, picnics, and bird watching.

If you are determined to bring stilettos, save them for fashionable nightclubs and fine-dining restaurants. For the rest of your stay, relying on more comfortable shoes suitable for the cobblestone streets and walking and biking paths and trails is better.

3. Plan your dining in advance

Nantucket has become a popular culinary destination, with some of New England’s best fine-dining and casual chic restaurants and diners.

Some of the foods to eat while on the island include fresh oysters, scallops, lobster rolls, and clams.

You can enjoy them or other gourmet meals in an elevated style in elegant settings in some of the high-end fine-dining restaurants, such as Galley Beach, CRU, Topper’s, The Chanticleer, and others.

But keep in mind that at the peak of the summer season, finding a table is almost impossible. So, make sure to plan ahead and make reservations for your chosen restaurant at least two weeks in advance.

There are, of course, eateries and places where you don’t need to book ahead.

Cisco Brewers is the heart of the island and is a place that you can visit at any time to enjoy the local brews, wines, spirits, and craft cocktails while listening to live music, eating delicious food, and mingling with the locals.

Vacation on Nantucket

4. Spend a day at sea

Nantucket is a nautical town that has relied and still relies on boats for transport, fishing, and everyday needs.

One of the best ways to explore this picturesque island is by sea.

Luckily, there are many sailing cruises and excursions, and tours you can enjoy there.

Some are short but memorable harbor tours, where you can watch the sunset,

the stunning ocean and waterfront view, and luxurious mega yachts while enjoying a cocktail or fresh oysters.

There are ice cream tours, critter tours for the kids, and sunset or cocktail tours for the grown-ups.

There are more extended excursions around the island and in the open Atlantic, where you can spot some whales, enjoy some fishing, or listen to the fascinating whaling and nautical history of Nantucket.

5. Don’t miss the must-see landmarks

Nantucket is the US town with the highest concentration of impeccably preserved pre-Civil War buildings, streets, lighthouses, and other structures.

The restored and preserved captain mansions, cottages, and other buildings on the cobblestone streets will make you feel like you have traveled back in time to the glorious whaling years of the island.

When you are visiting Nantucket, make sure to visit the must-see historical landmarks there.

The Oldest House – Jethro Coffin House

This house was built in 1686 by one of the most affluent people of Nantucket, Jethro Coffin, for his wife, Mary Gardner.

Today it is a National Historic Landmark and is the oldest surviving house on the island. It operates as a museum. The Oldest House has a fabulous Kitchen Garden in its backyard, with more than 1,700 organically grown herbs and plants from around the world.

Brant Point Lighthouse

This is the first building that greets the passengers arriving in Nantucket by ferry or boat. Located at the entrance of the Nantucket Harbor, Brant Point Lighthouse is the second oldest working lighthouse in the USA. It was first built in 1746 and since then has been rebuilt ten times. Today’s tower is from 1901, and it still beams light to navigate the mariners entering the harbor or passing by the island.

The Whaling Museum

Weekend in Nantucket

Located in the historic downtown, this is one of the top-rated sites to see in Nantucket. Once known as “the whaling capital of the world,” the island’s history, culture, architecture, and lifestyle were strongly influenced and still are by the whaling industry.

The whaling museum is situated in what used to be a whale oil candle-making factory.

It contains thousands of exhibits, including a real skeleton of a giant sperm whale, a Fresnel lens from the lighthouse, many artifacts from the whaling years, pictures and paintings, and more.

You can learn more about the captain and whaling ship that inspired the writing of the American classic “Moby Dick.”

Old Mill

Built back in 1746, this is the oldest functioning windmill in the USA. If the weather allows it, you can even watch how corn is milled with the help of the ocean breeze.

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