Traveling With Lola

As we sat on the pier near Historic Downtown Nantucket, eating our paper wrapped sandwiches from the nearby Walter’s Deli, I asked my friend Skyler “Do you think the birds know how beautiful this island is?”

Below us in the low-tide harbor, ducks floated around looking for scraps of crackers and crumbs that other visitors were throwing in the water. Seagulls circled nearby, and we watched a large male swoop down, grab a two-hand sized crab from the water, and throw it onto the beach. While dodging the sharp crab claws, he pecked with surprising force, flipping the crab on its back and finally penetrating the hard shell. 

Before he got to snack, his female counterpart, a larger gray seagull, hooted with delight and he gave his fresh catch to her without a fight and flew off to watch her enjoy the meal. How….. romantic? 

Just 48 hours before, we arrived in Nantucket following a chaotic scramble to board the last ferry of the evening, which departed from Hyannis on the shore of Cape Cod. Once onboard for the hour-ish long ferry, our chaos turned to calm and we arrived in Nantucket in the dark. 

The lack of light didn’t prevent us from taking in the scene around us: cobblestone streets, old-timey lamp posts, and lighted boutique store windows with furs, purses, and precious accessories way out of our price range.

Nantucket: A First Look

A 7-minute walk on the cobblestone streets took us to our first hotel, The Greydon House. After dropping our bags in a small but cozy Standard Queen room, we headed out to explore Nantucket in the dark. Almost everything was closed, except for one bar recommended by the attendant at the Greydon House front desk, Brotherhood of Thieves, which served warm and delicious clam chowder, and soothed my stomach and cortisol levels. With hardly anyone around, some streets were so quiet that you could hear a pin drop. 

Our evening stroll gave us a sneak peak into what the morning sunlight would reveal: a picturesque historic downtown, complete with cutesy shopping boutiques (there are NO chain shopping or dining outlets in the 48 square-mile island), and a quiet harbor.

The next day, for lunch we grabbed pumpkin butternut squash soup and mozzarella sticks from the only local grocery store, Stop and Shop, and decided to enjoy lunch with a view at the harbor. Almost as soon as we whipped out our warm goodies, the seagulls sensed the presence of oyster crackers and swooped down within grabbing distance, hoping to bum a bite of gluten. Keeping a watchful eye on the birds with long sharp beaks, we pondered what it would be like to live on Nantucket full time. 

According to the eccentric manager of the Greydon House, there are over 70 billionaires with homes in Nantucket. Further research couldn’t confirm exactly how many uber-wealthy individuals live or visit Nantucket but after 4 nights on the island 30 miles south of Cape Cod, I began to understand why “Billionaires’ Isle” attracts these ultra-high net worth individuals, celebrities, and over ½ a million tourists each year. 

An Origin & History

Nantucket has strict zoning laws that dictate land use, building height, and setbacks to maintain the island’s aesthetic and environmental integrity. The effect is that many parts of the town feel like they are preserved in resin, from the time when the island was officially settled by English colonists in the early 17th century. 

Nantucket quickly became a major hub for the whaling industry, known as the “Whaling Capital of the World,” and by the early 1800s, it had the largest whaling fleet globally, until the decline of the market in the late 19th century due to overfishing, the rise of petroleum, and the American Civil War. 

Shingled, cottage style architecture still remains, and the residences feel charming and nostalgic. The houses and architecture may be old, but somehow the island remains buzzy with modern activities, bites, and people, even during the October offseason.

On Saturday, we rented a pair of classic PT Cruiser Bikes complete with a basket on the front. I couldn’t help but giggle as we rode across the sometimes bumpy and uneven cobblestone downtown streets.

The Brant Hotel

In an effort to scout as many hotels as possible, we moved from the beachy, modern Martin House Inn (also run by the Greydon House team) to The Brant, a contemporary classic and quiet property. An inn dating back to the 1900s, Brant Point Inn became The Brant as hospitality group Salt Hotels took over in early 2024. The hotel that just received a well-deserved Michelin Key, code for “a very special stay” from the Michelin Guide team. 

Upon arrival at The Brant, instead of a traditional check in desk and bell for calling reception, we found Manager Jason Mancuso hanging out behind the bar/coffee area/breakfast nook known as “The Barn,” chatting up a couple from Boston. His excitement was contagious as he greeted us with a warm hug. 

Upon showing us to our room (a fabulous Superior One Bedroom suite), he remembered the last four digits of my phone number to unlock our room’s smart lock (Unreasonable Hospitality anyone?!)

The hotel comprises three buildings, with 18 rooms total, the Barn, an outside lounge and games area being in the middle. (Pssst… they are adding a pool on the property by summer 2025.)

The Barn and lounging area at The Brant. The Brant has an exclusive partnership with Champagne Veuve Cliquot.

Jason, along with the evening manager Alex, and their whole team brought a warm, laid back, but intentional hospitality that made a world of difference in our stay at The Brant. 

And did I mention the location was perfect: A quiet, residential neighborhood just a 10 minute walk from downtown and 10 minute walk from Jetties Beach, a perfect location for viewing Nantucket’s crystal clear sunrises and sunsets. 

Exploring Nantucket

We heard a few things about Siasconset (pronounced Scon-set) and decided to throw our bikes on the free island-wide bus system for a trip to the more residential, southern end of the island, hoping to bike and lunch. What we failed to realize is that NOTHING was open on this part of the island this time of year, (I mean seriously, the nearest gas station is 6 miles away.) While biking around with our stomachs rumbling, we met a local named Dan, who was sitting on a bench overlooking the ocean while his chocolate lab chewed a stick (more lunch than we were getting that day.) 

He told us nothing was open, but we should bike along the coast and head down a private road for a glimpse at the beach. “No one is around right now but this is the time of year us locals love,” he told us.

When first planning this trip I was worried we would run out of things to do during this long weekend. I was anxious our activities list was too short, and wouldn’t be enough to entertain us for a whole weekend. But this couldn’t be further from the truth. 

In Nantucket there is no need to rush, no need to be constantly busy or really any sense of urgency. The biggest attraction of Nantucket is the ambiance. The sweet, private, and quiet ambiance. 

Later that day, we watched the sunset from Jetties Beach. I looked up as dozens of seagulls flew east, away from golden light exploding on the horizon in the distance. I thought to myself, the birds must not know how beautiful Nantucket is, or they would be watching this too.