I have always been intrigued by Nantucket. It has the most expensive hotel prices of anywhere in the United States – a 2022 article showed the cheapest room on the islands going for $525/night in the month of August. And getting there is also difficult: there is a 1–3-hour ferry from Cape Cod for $80 roundtrip but getting to Cape Cod isn´t so easy. There are also flights from New York or Boston, but airfare from most cities in the US connecting through either city is somewhere around $600.
When looking for things to do in my last week in New York City, I discovered that you can fly roundtrip from New York to Nantucket for $120 roundtrip as a day trip. So, I booked an early flight at 7:00 and a return at 17:30 giving me around 8 hours to explore.
A similar deal existed on Martha´s Vineyard but I picked Nantucket because it is further from the mainland and because my cousins live in the town Cape Cod with the ferry. So, I could visit the next time I visit them.
For getting around the island, I arranged a bike rental ahead of time that would deliver the bike to the airport. The bike was $30/day while a car rental was $250.
With everything set, it was time to fly.
June 12, 2023: Nantucket
I woke up at 4:30 am from my midtown Manhattan apartment to head to Penn Station. At 5:07 am, I caught the New Jersey Transit to the Newark Airport, arriving at 6:00. My United Airlines flight departed at 7:20, arriving 43 minutes later at Nantucket´s Memorial Airport (ACK). The airport is made from clapboard wood. Living up to its nickname The Grey Lady, the weather was foggy and in-between t-shirt and sweatshirt weather.
At 8:15, the bike company arrived at the airport with the bike. After a shockingly brief check out process, I headed off!
My first stop was the town of Siasconset, known locally as Sconset, on the east side of the island- a 6-mile bike ride. The tiny town has a couple restaurants and a market. Everything is clapboard. After snacking on a bacon egg and cheese from Claudette´s, I continued north.
One of the main attractions in Sconset is the Bluff Walk, a walking path that cuts through the back yards of all the clap board houses on the coastal bluff. It was created by real estate developer William J Flagg way back in the 1800´s! A sign indicates that it is a walking path and therefore running or cycling is not allowed. Therefore, AI walked my bike along the path. There were a few narrow places where the bike was tough to navigate but I made it through.
At the end of the path, I hopped back on the bike and headed north to reach a Nantucket landmark, the Sankaty Head Lighthouse. The red striped lighthouse was built in 1850, but in 2007 had to be moved 400 feet due to erosion of the cliff.
I then headed north and west along Polpis Road (Nantucket has an exceptional network of bike paths). I crossed a wild cranberry bog and after 10 miles of biking reached the town of Nantucket (known colloquially as “Town”). This is the largest settlement on the island (by far) and is the government center of the combined city/county of Nantucket.
The town is completely made of clapboard buildings and feels exceptionally well-preserved with pre-Civil War buildings. And despite being a weekday, was busy!
Lots of people were walking around, but there was also a lot of car traffic. Despite hearing so much about the bike culture, I did not see any other cyclists. Most of the pedestrians were couples in their late 30´s-early 40´s, older couples in their 60´s-80´s and high school/early college aged girls wearing the New England summer uniform of aqua/pink/navy long sleeved shirt with oversized text of a New England summer destination (like Nantucket or Bar Harbor) and a baseball cap.
Next to the boat dock, the town set up a concierge desk. The town was also policed by an exceptional number of unarmed “public safety officers” who sort of looked like college boys on their summer job. The level of security was not at the level of Algiers, but I probably saw 20-30 – for context the island only has 11,000 residents. I cannot imagine much crime happening here but given the extraordinary amount of wealth on the island and a general wariness of outsiders, it makes sense.
At the boat dock, I noticed the town had set up a concierge desk. This makes sense given that the island is nicknamed “The Resort”.
The main tourist attraction in town is the Whaling Museum, which is set in a historic candle factory.
The name Nantucket comes from the indigenous Wampanoag who historically lived on the island. In their mythology the island was formed by a giant Maushop who lived on Cape Cod. He was tired of sleeping with his moccasins on, so he kicked them off. One became Martha´s Vineyard and the other Nantucket.
In the early 1800´s whaling was the main industry of Nantucket. However, in 1847 a great fire destroyed most of the town moving the industry to New Bedford. The Civil War was the death knell for the industry, as Confederate battleships attacked the whalers. While much smaller than New Bedford´s museum, it was still nice.
The museum also had a special exhibit on the tourism industry, which sprung up after the demise of whaling. Tourists, who mostly came from New England cities, were originally drawn to the cute town and the remoteness of the island. As time went on, they were also drawn to the community, as many people come back every summer for extended amounts of time. In the Northeast, this word “summer” is used as a verb to describe this situation. When walking around, I get the feeling that families create strong bonds here and that the children who grow up summering here all are friends.
The island does have year-round residents. Some of these people are former summer residents who decided to retire here. But others are the workers who keep the island running such as construction workers. While the summer residents are overwhelmingly white American families, the year-round workers come from diverse backgrounds. The museum had display cases thanking the construction companies and telling the stories of some of these workers who came from faraway places such as Romania, Jamaica, Mexico, and the Philippines to Nantucket for work. Interestingly, the diversity of the hospitality workers harkens back to the whaling era which also brought people and ideas from all over the world to Nantucket.
The ticket to the Whaling Museum also included entry to the Hawden House, a mansion owned by one of the whaling barons. On the inside, there were exhibits on the family that lived here. While walking around the house, I overheard a conversation where the young female ticket checker was venting about her career to a young male colleague. She said her dad and grandfather said not to worry about her career and instead spend more time on Nantucket so she can marry rich.
On the upper floor of the mansion, a volunteer explained how to make a lightship basket, a unique style of basket made of rattan that originated in Nantucket. While I did not care at all about the subject matter, I was enthralled by the man´s enthusiasm and stayed there almost 20 minutes.
It was now time for lunch. Based on the recommendations of some local friends, I visited Provisions where I ate a delicious turkey sandwich and washed it down with a Nantucket Nectar (how could I not).
For dessert, I got a $9 scoop of strawberry ice cream from The Juice Bar. I have been told that both places typically have a 45–60-minute wait during the weekends, but since I was here early season on a weekday, I did not wait at all.
I then hopped on my bike and headed southwest to perhaps Nantucket´s most beloved modern institution: Cisco Brewers. This was the only place mentioned as a must-see by all my friends. Located on the site of a winery, Cisco was born in 1992. It is the only brewery on Nantucket and claims to be the only outdoor brewery in the United States. The place is sprawling across multiple buildings- one for production, one for the beer taps and one to purchase cocktails and spirits. But the real action is on the back patio area where there is live music almost every afternoon.
Despite being a Monday, the place was almost full, and I can definitely see it being shoulder to shoulder with people donning their best pastel chic on weekends. I ordered a flight, and it was awesome.
It was now 14:00 and I had 2 hours before I needed to be back at the airport. So, I biked through the suburban areas where it seemed many of the workers lived. Eventually I reached the south coast of the island where I stopped by Surfside Beach. As luck would have it, it started to drizzle.
I decided that this was my sign to head back to the airport. I reached at 15:30, 90 minutes before my flight back to New York. I locked the bike up, called the bike company and walked into the airport. This time, I took JetBlue back to JFK, landing just after 18:00. I did it!
I totally understand the appeal of Nantucket – especially for families. The town is gorgeous, there is so much to do, the infrastructure is fantastic, and the entire island has a strong aesthetic. But the biggest things are the safety and sense of community that living on a remote island brings. Because of this, everybody lets down their guard down; I found the people on Nantucket to be very friendly and far less stuffy than I was expecting. This is in big contrast to Montauk, which is equally as expensive but with a far-worse town and very scene-y.
Due to the sky high prices, I would not recommend paying for a hotel on Nantucket. If you don´t have a friend with a house, I would recommend going as a day trip. Taking the ferry works if you are in Massachusetts, but the flight from New York also was easy. In total, I spent $241 (including the flights). While very expensive for a day trip, it is still less than half the cost of a single night in a hotel.