Summer Weekend in Nantucket, MA

The tiny island of Nantucket is the ultimate New England summer weekend destination. Manicured streets and cedar-shingled houses are set against a rugged and remote coastal backdrop. Unspoiled beauty abounds, with long stretches of white sand, blooming hydrangeas, and serene nautical scenes as far as the eye can see. Nicknamed the Grey Lady for the thick fog that often shrouds the island, it’s a mystical place like none other in the world.

Located just 30 miles off of Cape Cod, Massachusetts, Nantucket’s early claim to fame was as the whaling capital of the world in the mid-19th century. Now it’s a coveted seaside escape with world-class dining, shopping, and entertainment that draws well-heeled visitors from far and wide.

Planning an East Coast getaway? Follow along on my summer weekend trip to discover the best things to do in Nantucket. From picture-perfect lighthouses to buttery lobster rolls, here’s how to navigate Nantucket like a pro.

DAY 1: Getting to Nantucket

Although you can access Nantucket via a fast flight from Boston or New York City, we chose to drive to Hyannis, MA to catch the ferry. Our Hy-Line fast ferry would have gotten us there in an hour, but ended up getting cancelled due to weather. Thankfully, they quickly rebooked us with Steamship Authority’s traditional ferry that made the crossing in just over two hours.

Travel tip: Weather can be unpredictable on the island. If you’re wondering what to wear, check out my Summer Packing List for Nantucket.

I didn’t mind being on the water for a little bit longer. We stayed out on the deck the entire journey to enjoy the scenic views. Sailing past the Brant Point Lighthouse just as the sun was setting was the perfect welcome to Nantucket.

Although Steamship Authority can accommodate cars, we opted not to bring one and found that we didn’t need it. I would, however, highly recommend having a bike. The island is just under 50 square miles and is perfect for walking and cycling. You can bring your own bike on the ferry for a small additional fee, or you can rent one on the island from Cook’s Cycles. If you need to go farther, the Wave shuttle buses are convenient and easy to navigate.

Once we docked, we took a short walk from the harbor to the Brass Lantern Inn, where we were staying. We chose this quaint bed and breakfast mainly because we had our dog with us. It offers select, dog friendly rooms for a small additional fee. In addition to its central location and comfortable accommodations, the afternoon tea service and hearty breakfast spread make this a great place to stay in Nantucket.

It was getting late, but we were excited to get a taste of the town. So we walked over to The Juice Bar, a coveted ice scream spot on an island obsessed with frozen treats. There’s almost always a line out front, but it moves fast and is worth the wait.

DAY 2: Biking the Island

We started the next morning on the right foot with breakfast at Black Eyed Susan’s. This no frills, cash only diner is an island favorite. We went early to beat the weekend breakfast crowd and scored a table on their outdoor patio.

Then it was time to work off our pancakes. With a network of dedicated trails, Nantucket is best explored by bike. We followed one of them out of town to Dionis Beach.

Nantucket is known for its pristine beaches and well-protected sand dunes. We were lucky enough to have Dionis completely to ourselves, except for a seal sunbathing on the sand.

For lunch, we biked over to Bartlett’s Farm, the island’s oldest and largest family-owned farm market. We ordered sandwiches from their to-go counter and enjoyed them at a picnic table outside.

Just down the street is Cisco Brewers. It being Saturday afternoon of a holiday weekend, we had to wait in a long line to get in. With live music, food trucks, and a bustling social scene, Cisco is the go-to daytime drinking spot on the island. They claim they are dog and kid friendly, but we found it difficult to navigate the crowds with our pup. But it’s worth checking out, and if you don’t want to bike there, you can catch their free shuttle from downtown.

That evening, we enjoyed dinner on the deck of Queequeg’s. Named after the fictional character in Moby Dick, this unassuming eatery serves up eclectic American food. Afterwards, we sidled up to their Tree Bar, an outdoor patio bar built around, you guessed it, a tree.

DAY 3: Sightseeing in ‘Sconset

The next morning, we grabbed coffee and pastries from Handlebar Cafe, then caught the bus from the stop across the street. It was a super easy and convenient 20-minute ride from downtown to Siasconset (lovingly called “‘Sconset” by locals).

Located on the eastern edge of the island, this upscale enclave is known for its cedar-shingled cottages, shell-lined paths, and fragrant hydrangea blooms. Once we arrived, we grabbed sandwiches from Claudette’s and took them down to ‘Sconset Beach for a picnic.

A must-do when on the island is the ‘Sconset Bluff Walk. This mile-long public walking path offers stunning coastal views as it weaves through the backyards of some of Nantucket’s most impressive private homes. We followed it all the way from its start at 21 Front Street until we reached the iconic red and white Sankaty Head Lighthouse on the eastern edge of the island.

Later that evening, we enjoyed dinner at Ships Inn. Located in the cellar of a historic whaling captain’s mansion, this upscale restaurant is ideal for a romantic night out.

DAY 4: Shopping Downtown

Our final day on the island, we biked over to Tupancy Links. Once a private golf course, the land has been donated and converted into public land. With over 73 acres of green space overlooking Nantucket Harbor, it was a great place to let our dog stretch his legs.

On our way back to town, we stopped at Something Natural, a favorite among locals for lunch. We enjoyed our sandwiches (and the most delicious cookies) at a picnic table on their expansive, park-like lawn.

We then hit Main Street to shop for souvenirs before leaving. Nantucket boasts the most picturesque downtown dripping in New England charm. Cute cafes and chic boutiques line its quaint cobblestone streets. We stopped in Murray’s Toggery Shop, an island institution known for its Nantucket Reds Collection. My favorite was Milly & Grace, an ivy-covered boutique owned by two local sisters who curate a stylish mix of clothing and home goods.

Finally, we headed to Brant Point Light, the closest lighthouse to town. It was the perfect place to watch the sun set before catching the last ferry home.

Explore More: Favorite Lighthouses in New England

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Ready to pack your bags? Discover my Summer Packing List for Nantucket.

If, like us, you want to bring your dog with you, you’ll find that the island is extremely welcoming to four-legged friends. Check out more tips in my Dog-Friendly Guide to Nantucket.

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