The Best of Nantucket: A Local Guide to the Island's Most Beloved Places and Experiences

Madaket sunset

Few destinations in America capture the imagination quite like Nantucket. Located 30 miles off the coast of Cape Cod, this historic island is known for its cobblestone streets, stunning beaches, world-class dining, charming cottages, and rich maritime heritage. Whether you're visiting for a weekend, spending the summer, or considering purchasing a home, Nantucket offers a lifestyle unlike anywhere else.

As lifelong island residents and brokers at Westbrook Real Estate, we've had the privilege of helping generations of families discover the magic of Nantucket. When people ask us what makes the island so special, the answer is simple: it's a collection of extraordinary experiences that come together to create an unforgettable place to live.

Here's our guide to the Best of Nantucket.

Best Beach: Surfside Beach

Nantucket is home to some of the most beautiful beaches in New England, but Surfside Beach remains a favorite among locals and visitors alike.

Surfside Beach offers wide stretches of sand, rolling Atlantic waves, and plenty of space for families, surfers, and beachgoers. The beach is easily accessible and provides the perfect setting for a summer day on the island.

For those seeking calmer waters, Children's Beach and Jetties Beach are also excellent options.

Best Sunset: Madaket

No Nantucket experience is complete without watching the sunset from Madaket.

Located on the western end of the island, Madaket delivers breathtaking views as the sun sinks into the Atlantic Ocean. Locals often gather with beach chairs and picnic baskets to enjoy what many consider the best sunset in New England.

It's one of the simple pleasures that keeps people returning to Nantucket year after year.

Best Bike Ride: Polpis Road

With more than 35 miles of bike paths, Nantucket is a cyclist's paradise.

One of our favorite rides follows Polpis Road toward the eastern side of the island. Riders pass cranberry bogs, conservation land, and spectacular views of Nantucket Harbor along the way. It's an excellent way to experience the island's natural beauty while avoiding summer traffic.

Best Historic District: Downtown Nantucket

The heart of the island remains the historic downtown district.

Nantucket Historic District is home to beautifully preserved whaling-era architecture, cobblestone streets, charming boutiques, art galleries, and restaurants. Walking through town feels like stepping back in time while still enjoying modern conveniences.

The downtown area is one of the reasons Nantucket consistently ranks among the most picturesque destinations in the United States.

Best Family Activity: Whaling Museum

For visitors looking to learn about Nantucket's fascinating history, the Whaling Museum is a must-see.

The museum showcases Nantucket's role as the whaling capital of the world during the 18th and 19th centuries and offers exhibits that appeal to both children and adults. The rooftop observation deck provides stunning views of the harbor and downtown area.

Best Place for Fresh Seafood

Nantucket's connection to the ocean means incredible seafood can be found throughout the island.

Among the local favorites are Straight Wharf Restaurant, Cru, and The Nautilus.

From fresh oysters and lobster rolls to locally caught striped bass and scallops, Nantucket offers some of the finest seafood dining in New England.

Best Neighborhoods on Nantucket

One of the things we love most about Nantucket is that every neighborhood has its own unique personality.

Brant Point

Just minutes from downtown and the ferry docks, Brant Point is known for its iconic lighthouse and harbor views.

Siasconset ('Sconset)

Located on the eastern end of the island, Siasconset features charming rose-covered cottages, stunning ocean views, and a peaceful atmosphere.

Cisco

A favorite among surfers and beach lovers, Cisco combines rural charm with easy access to some of Nantucket's best beaches.

Madaket

Known for spectacular sunsets and a laid-back lifestyle, Madaket offers a true escape from the busy world.

Polpis and Wauwinet

These areas provide privacy, conservation land, and some of the island's most beautiful waterfront properties.

Best Summer Events

Nantucket's calendar is filled with exciting annual events that bring residents and visitors together.

Popular favorites include:

• Nantucket Book Festival

• Nantucket Film Festival

• Nantucket Wine & Food Festival

• Daffodil Weekend

• Christmas Stroll

• Race for Open Space

These events help create the strong sense of community that makes Nantucket such a special place to call home.

Why We Love Nantucket Real Estate

At Westbrook Real Estate, we've spent decades helping buyers and sellers navigate the Nantucket real estate market.

What makes Nantucket unique isn't just the homes—it's the lifestyle. Whether you're looking for a historic cottage in town, a waterfront estate in Polpis, or a summer retreat in Cisco, owning property here means becoming part of one of the most desirable communities in the country.

The island's limited inventory, strong demand, and enduring appeal continue to make Nantucket real estate a highly sought-after investment.

Discover the Best of Nantucket

The best of Nantucket isn't found in any single place—it's found in the combination of beaches, history, restaurants, neighborhoods, and community that make island life extraordinary.

As locals who have spent our lives on Nantucket, we're grateful every day to call this remarkable island home.

If you're thinking about buying, selling, or investing in Nantucket real estate, we'd be honored to share our knowledge and help you discover the very best that Nantucket has to offer.

Daryl Westbrook & Robert WestbrookWestbrook Real Estate