The Best of Nantucket: Our Family's Favorite Places on the Island

Lobster Clambake

For generations, our family has had the privilege of calling Nantucket home. Over the years, we've watched visitors become homeowners and summer guests become lifelong island residents. One of the questions we are asked most often at Westbrook Real Estate is:

"What are the best things to do on Nantucket?"

While everyone has their own favorites, we thought we'd share some of the places and experiences that make Nantucket such an extraordinary place to live and visit.

Best Beaches on Nantucket

Cisco Beach

If you love surfing and spectacular sunsets, Cisco Beach is hard to beat. The waves attract surfers of all ages, and the relaxed atmosphere perfectly captures the spirit of Nantucket. After a day at the beach, many people head over to Cisco Brewers for live music and a cold drink.

Surfside Beach

Surfside is one of the island's most popular family beaches. With easy bike access and miles of beautiful shoreline, it's ideal for swimming, beach walks, and summer picnics.

Jetties Beach

Located close to town, Jetties Beach is perfect for families with children. Its calm waters and proximity to restaurants make it one of the easiest beaches to enjoy.

Madaket Beach

Nothing compares to a Madaket sunset. Watching the sun disappear into the Atlantic has become a tradition for generations of island residents.

Best Restaurants on Nantucket

Nantucket's dining scene continues to rival much larger destinations.

The Nautilus

Consistently ranked among the island's finest restaurants, The Nautilus has become famous for its creative seafood dishes and lively atmosphere.

Cru

Located on Straight Wharf overlooking the harbor, Cru offers one of the best waterfront dining experiences on the island. Their lobster rolls have developed a legendary reputation.

Galley Beach

Few restaurants in America offer a setting as beautiful as Galley Beach. Dining with your feet practically in the sand while watching the sunset is an unforgettable Nantucket experience.

Millie's

Located in Madaket, Millie's combines a laid-back atmosphere with outstanding food and has become a favorite gathering place for locals and visitors alike.

Something Natural

Known for its famous Portuguese bread sandwiches, Something Natural is a Nantucket institution and one of our favorite lunch spots.

Best Breakfast Spots

Island Kitchen

A local favorite for years, Island Kitchen serves some of the island's best breakfasts and brunches.

Born & Bread

One of the newer island favorites, Born & Bread has earned rave reviews for its artisan breads and breakfast sandwiches.

The Downyflake

No summer on Nantucket is complete without stopping at The Downyflake for donuts and breakfast.

Best Shopping on Nantucket

Part of Nantucket's charm is its unique collection of locally owned stores.

Some of our favorites include:

• Nantucket Looms

• Murray's Toggery Shop

• Mitchell's Book Corner

• Four Winds

• Old South Wharf boutiques

• Erica Wilson

• Sunken Ship

• The Hub

These shops reflect the island's history and character and are part of what makes strolling downtown such a pleasure.

Best Family Activities

One of the reasons families return year after year is because there is something for everyone.

Some of our favorite activities include:

• Visiting the Whaling Museum.

• Riding bikes to Siasconset.

• Exploring Sankaty Head Lighthouse.

• Walking the Bluff Walk in Sconset.

• Visiting Brant Point Lighthouse.

• Watching sunsets in Madaket.

• Enjoying live music at Cisco Brewers.

• Taking a harbor cruise.

• Fishing and boating.

• Spending the day at the beach.

Why We Love Living on Nantucket

For us, the best part of Nantucket isn't any one restaurant or beach.

It's the lifestyle.

It's seeing familiar faces downtown, watching children grow up with the ocean as their backyard, and preserving traditions that have been passed down for generations.

From Brant Point and Cliff to Siasconset and Madaket, each neighborhood offers its own unique charm, and every season brings new reasons to appreciate life on the island.

Many of our clients first come to Nantucket for a week and end up staying for a lifetime.

Thinking About Calling Nantucket Home?

At Westbrook Real Estate, our family has proudly served Nantucket homeowners and buyers for decades. We believe buying a home here is about much more than real estate—it's about becoming part of a remarkable community and embracing one of the most beautiful lifestyles anywhere in the world.

If you're considering buying or selling property on Nantucket, we'd be honored to share our local knowledge and help you discover the very best of island living.

Westbrook Real Estate

Daryl Westbrook and Robert Westbrook