7 Amazing Tips for Your First Holiday to Nantucket 

lighthouse during sunset nantucket island

Are you going on vacation to the dreamy island of Nantucket for the first time?

The small and postcard-like island, located 30 miles south of mainland Massachusetts in the United States of America, is a leading tourist and vacation destination for people of all ages, interests, and lifestyles because it has something for every taste.

Even if you are already familiar with the main historical sites, the lighthouses, the beaches, and the charming rose-covered cottages, you may still find these seven tips for making the most of your first holiday in Nantucket useful.

7 Amazing Tips for Your First Holiday to Nantucket 

Choose to Stay in a Local House

One of the best ways to experience the authentic and one-of-a-kind Nantucket vibe is to stay at one of the many local residences which are available for short-term rent.

Just imagine spending your holiday in one of those marvelously restored historic homes built by the first settlers and inhabited by the crews and captains who inspired the great American novel “Moby-Dick.”

Or, spending a luxurious retreat at a stately waterfront mansion with its pool, perfectly designed garden, and multiple high-end amenities.

You can book a magical secluded beach house in a remote neighborhood or a loft near the fashionable restaurants and boutiques Downtown.

This will make your stay on the island even more memorable and save you money, especially if you share the accommodation with friends.

Choose to stay in a local house in nantucket

Make Time to Visit Historical Sites

Nantucket has a remarkable history and is one of the best-preserved historic towns and counties in the country.

The Native American Wampanoag tribe originally inhabited it, and the first settlers arrived in the 1640s. A century later, the island became a leading whaling hub.

Thanks to the never-ending efforts of the local authorities and preservation organizations, there are over 700 fastidiously preserved and restored houses and buildings from those glorious years.

The historic Downtown still has the same cobblestone streets and gas-lighted lanterns as it did centuries ago.

There you can explore the grand captain’s mansions and buildings from those years and get a true feeling of what life was like when the local people earned their living by bringing precious whale oil back from faraway lands.

The Whaling Museum is one of the top-rated sites to visit to learn more about the incredible history of the New England island.

You can also visit the three lighthouses, which are among the oldest still-functioning ones in the US as well as the oldest working windmill in the country.

Make your Restaurant Reservations in Advance 

Nantucket has become an essential culinary center and is home to some of the best fine dining and seafood restaurants in the country.

If you plan on visiting one of the most famous high-end eateries, booking a table well ahead of time is strongly recommended, especially if you are going during the peak of the summer season.

Some of the best upscale restaurants on the island include Galley Beach, Cru, SeaGrille, Straight Wharf, Topper’s, and Chanticleer.

There are other more casual eateries where you can still eat fabulous dishes made of the island’s freshest fish, seafood, and local organic produce.

Don’t miss the chance to try the famous local fresh oysters, Maine lobster rolls, clams, scallops, and other seafood delicacies while you are staying in Nantucket.

And, of course, enjoy the local craft brews, cocktails, and some of the best wines and spirits from around the world when vacationing there.

oysters on a plate
Photo by Viviana Rishe on Unsplash

Rent Bikes to Explore the Island

Bringing your car to Nantucket can be expensive, complicated, and not feasible.

Since the island is so small, has few hills, and has such a well-developed bike path infrastructure, you can get around easily by cycling instead.

You can bring your own bike or rent one as soon as you land on the island.

In many cases, the rental homes also come with complimentary bicycles for the guests.

Even if you are not much of a cycler, you can enjoy some leisurely rides along the seaside or throughout the many natural reservations, and when you get tired, you can hop on a bus and stash the bicycle on its bike rack.

Go on Some Iconic Walks

Nantucket is home to some of the country’s most picturesque walking paths and trails.

Since half of the land of the island is conserved, there are many trails that are perfect for bird watching, seal spotting, and for nature lovers and adventurers.

Most of the walking trails are short and easy, but they are all beautiful and unique.

You can explore the various local nature and wildlife refuges and conserved territories by walking the Tupancy Links, Miacomet, Sanford Farm, or Coskata-Coatue trails.

The Sconset Bluff Walk is a must for all visitors of Nantucket. It is only a mile long but is among the most Instagram-worthy and romantic walkways in the USA.

The path passes through the delightful village of Siasconset, famous for its charming coastal shingle-style cottages, covered with crawling red and pink roses and surrounded by the most beautiful gardens.

The path passes by the scenic cliffs on the east shore, leading to the Siasconset beach and the historic Sankaty Head Lighthouse.

Enjoy the Less Crowded Beaches

The island has more than 25 beaches spread across 80 miles, so you can literally go to a new beach every day during your holiday there.

The number of people on the island can grow up to five times during the peak of the summer season. So, many of the more popular beaches, mainly those on the north shore and closest to Town, tend to be overcrowded then.

The south beaches, such as Surfside, Nobadeer, and Cisco, are also fuller than others due to their popularity among surfers and youngsters.

If you prefer a quieter and more relaxed atmosphere, you can choose one of the less popular and more remote beaches instead.

Some of the best, less crowded options include the Coskata-Coatue, Madaket, Tom Nevers, and Steps Beach.

beach surrounded by water on both sides
Photo by Andrew Wolff on Unsplash

Join the Sunset Cruise

One of the best ways to explore the beauty of the island is by boat. The Sunset Cruise on the Endeavor sailboat is one of the most romantic tours offered in Nantucket.

It will take you around the Harbor, where you can admire the view of the yachts, boats, the Brant Point Lighthouse, and the island.

Watch the sunset over the Nantucket Sound while you are enjoying your favorite beverage and listening to fascinating stories told by its experienced Captain Jim.

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