Exploring Nantucket: A Travel Guide to Island Vibes

When friends ask what stood out most from our Nantucket trip, I always pause—because it’s hard to put into words. On most trips, I can easily describe the sights, the local events, and how our days and nights unfolded. But with Nantucket it’s different. Its beauty, endless beaches, and amazing food speak for themselves. But the most extraordinary thing about Nantucket is its vibe—something not so easily articulated.

After a few days in Boston, we took a train to Hyannis and a ferry to the island. The Cape Flyer train, running Friday to Sunday from Memorial Day to Labor Day, is easy and comfy. I booked the Steamboat Authority ferry ahead of time. Once off the train, I was surprised by the many ferry lines, which made finding ours difficult. We navigated a bit and boarded just in time.

Nantucket feels like stepping back in time. Cobblestone streets wind past historic whaling-era homes, boutique shops, and cozy cafés. Sailboats fill the harbor, and flower boxes overflow with blooms in every color. It’s charming, walkable, and full of coastal New England character.

There are about 14,000 full-time residents, but in summer, the population can rise to 80,000. We visited in late summer when the crowds were easing.

Nantucket is also expensive—housing costs are over 300% higher than the U.S. average, even more than Martha’s Vineyard. Many wealthy people have summer homes here, while others stay in hotels and inns for vacations. I found a quiet place through airbnb not far from downtown.

The house was surrounded by fragrant hydrangeas which were blooming everywhere throughout the island. Our room was around the back with a private entrance. The a patio faced the large backyard where we sat for our morning coffee. I found outdoor shower both tranquil and exhilarating. We slept with the door open to the screen and woke one morning face to face with a deer. The rental also included the use of a couple of bicycles. These bicycles were a big part of my game plan for exploring the island. Well, what is it they say? The best laid plans…

It had been some time since I had been on a bike. I was a little worried I would be wobbly. But I moved full speed ahead. I selected the smaller, less intimidating one with a cute little basket. I left the taller one with the thinner wheels for the husband.

We headed out on the paved pathway which runs alongside the road at the end of a long driveway. Soon after we started out, I spotted a jogger ahead and decided to check my brakes. And just like that, I was flying headfirst over the top of my bike. Luckily, I fell to the side just in time, landing into the grass and avoiding a head injury. But it definitely took my breath away for a few minutes. I instantly felt as though I had bruised my ribs (which I had). External bruising on the abdomen where it hit the handlebars also appeared shortly after. I felt fortunate that the pain wasn’t worse than it was. I took some ibuprofen, adjusted the plan, and we continued on.

Gone were the bikes and hikes, instead, we hopped on the free shuttle connecting town with the beaches . We caught it just a few feet down the road from our room. Other times we used UBER for a quicker option. We went about enjoying the area but from a little different perspective.

There was no schedule in Nantucket; time didn’t matter. We strolled around the cobblestone streets, exploring shops and restaurants. I found a bookstore and bought a couple of novels signed by local author Elin Hilderbrand. It was her vivid characterization of the island that inspired me to see it in person. I even visited some of the establishments that she used in her books. Nantucket is famous for its delicious cuisine, and my palate was well pleased throughout. The seafood was deliciously fresh. In fact, there was every food type available and we never experience a bad meal there.

Even the lobster roll from a food truck at Cisco Brewers was incredible. A friend had urged me not to miss Cisco while I was in the area. It is the place I kept hearing over and over that I must visit. I am glad we did. It was such a fun, laid back place to have a beer, great food, and listen to the band. They even have their own shuttle from town. 

We visited two of the island’s many beaches. With over 80 miles of coastline, there are a lot of bays to choose from. Each has its unique attributes. Some are known for calmer waters and others for larger waves.

We spent a sunny afternoon at picturesque Steps Beach on the Sound. Time stands still here, staring out at the Atlantic Ocean and Nantucket Sound. This beach is great for swimming, sunbathing, and beachcombing. On another morning, we visited Madaket Beach on the South Shore. This one is more of a surfer’s beach where the waters are less calm. We stayed a short time watching the surfers before walking to the famed Millie’s Market, a quaint beach shack just down the road.

With so many public beaches, no one is too overcrowded. Not all of the beaches are public. Some property owners have the use of private beaches, and a couple of hotels also offer private beach access.

I had intended to ride the bikes to beautiful Siasconset. Then, we would take Bluff’s walk to Sankaty lighthouse. One of three on the island. The footpath runs behind some oceanside homes with breathtaking views. But with the prior day’s mishap, I couldn’t take the four mile hike. We instead took the shuttle and walked around the area as much as possible. Siasconset sits on the eastern edge of Nantucket and boasts beautiful vintage homes. Three of the island’s four golf courses can be found here. We had lunch at The Summer House, a popular hotel and restaurant. We dined oceanside then sipped a couple glasses of wine while reveling in the ambiance for a couple of hours. On the ride back, we were able to view the lighthouse from the road. It wasn’t quite the same, but I appreciated that I got to see it, even from afar. 

There are some guided boat tours available that offer a unique perspective of the coastline and its marine life. There is also a whaling museum mid-town, if learning the history of a place is your thing. For us, however, we just took in as much of the atmosphere as possible in our own way. Enjoying leisurely strolls through the streets, savoring the local cuisine, and soaking up the stunning views that surrounded us. This created a sense of connection to the place and its history that guided tours would never fully capture.

For the return home, we caught a flight to Newark which connected to Phoenix. The Nantucket Memorial Airport is small (although not nearly as small as depicted in the 1980’s sitcom Wings). They do have those small planes, often referred to as pond jumpers, that go to Boston, Hyannis, and Martha’s Vineyard. But also jets that fly to the larger cities. 

I would definitely consider returning to Nantucket someday, if the circumstances were right. Maybe do more walking, hiking and even try that bicycle again. But the trip the way it was, was also amazing. I am glad to have been there to see it all and experience the incredible vibe that is Nantucket Island.