Quite Weekend on Nantucket
That excitement about exploring Cape Cod was high, but our anticipation for Nantucket was off the charts! Ever since we learned about our new location, Amity had her heart set on visiting the island, which made it an easy choice for a little birthday week celebration. Although it was shoulder season, the lack of crowds and the freedom to explore the island at our own pace was amazing—something you can’t do during the busy months. All we had to do was hop on a ferry and dig our feet into the sand!
Mile: 60,721
Quote of the Blog: “A traveler has no fixed plans, and is not intent on arriving.” - Lao Tzu
Song of the Blog: “Nantucket” - The Longest Johns
To reach Nantucket, we drove down to Hyannis, MA, where the ferry terminal is located. We parked our car and walked onto the fast, foot-traffic–only ferry (there’s also a slower, car-friendly option). The modern boat was terrific—though we laughed that we never imagined spending so much time on ferries; this was our sixth route since the adventure began! Our only complaint on this trip was the lack of puzzles on board.
When we pulled into the harbor, Nantucket’s view came sharply into focus. It was a slightly foggy yet sunny day, and the temperatures were on the cooler side. After disembarking, we set out to find our rental inn and drop off our bags. The Periwinkle, a charming colonial-style inn just a five-minute walk from downtown, turned out to be adorable. They did not have any staff on site, and just had some envelopes with keys and information at the door. Pretty simple and efficient if you ask me. We’d read that we could leave our bags in the back until our room was ready, but when we walked in at 10 a.m., our room was already prepared, and we’d even been upgraded. Clearly, shoulder-season perks!
Once settled, we wandered into town for coffee at The Corner Table Café. The coffee was spot-on, and with cups in hand, we strolled over the uneven cobblestone sidewalks—Amity, ever the physical therapist, pondered how many ankle sprains occur here each year! Downtown Nantucket was delightfully quiet, a stark contrast to peak season. In one shop, a local vendor greeted Amity with mock disdain—“Oh, you’re staying at The Periwinkle?”—and revealed that rooms go for over $500 a night at peak rates, which we definitely weren’t paying. We loved the jaded local humor!
Next on our list was the Nantucket Whaling Museum. Arriving right at opening let us explore without crowds. We dove into stories linking the town to Moby Dick and the Essex, admired artifacts from early whalers, and marveled at the original oil press and candle-making area—candle production was one of Nantucket’s biggest exports. We also learned the island’s nickname, the “Grey Lady,” comes from the frequent sea fog—which we experienced fully that weekend. Before leaving, we climbed to the rooftop for panoramic views of the harbor and downtown.
After the museum, we admired the town’s uniform architecture—designed to preserve its historic charm—and noted how meticulously everyone tended their gardens, even though the flowers were not yet in full bloom. We’ll have to return when everything is popping! While getting coffee earlier, we’d decided to rent a car instead of bicycles—an electric microcar was cheaper than two bike rentals, and hilariously fun (with one firm rule from the shop: don’t drive on the sand). Over the next 24 hours, it proved perfect for island exploration.
Our first car adventure took us to Siasconset on the east shore, where we hiked the Bluff Trail past vine-draped seasonal cottages. The path wound between a high bluff and the water, threading through private backyards, which we could only image what it looked like during peak season. Would kind of suck to live in one of these houses. One event had a “gate” protecting it’s property, but no fence to go along with it. We turned back when the sights grew repetitive and the wind chilled us. Next, we headed to Pocomo Head in search of scallop harvesters—too cold that day, but we beach-combed a couple of beautiful scallop shells.
By mid-afternoon, we drove to Cisco Brewery, the island’s only brewery, which looks more like a farmyard—a design choice reflecting local agriculture. With just one food truck open off-season, Amity ordered garlic fries. When they came, they were sprinkled with sesame seeds (a first for us and unfortunate since she’s allergic). We enjoyed a quick beer and live music, then braved the wind-swept beach until our fingers went numb and it was time for dinner.
Most restaurants were closed for the season, but we snagged a reservation at Brotherhood of Thieves, the only downtown spot open. Its sailor-themed décor and standout lobster sushi roll did not disappoint. After dinner, we headed upstairs for a nightcap and discovered the band was the same group we’d heard at Cisco. We chatted with them, admitted our unintentional “tour,” and even got free band shirts. “Shots Down” are now our favorite Nantucket groupies! We ended the night with a walk back to our “junker of an inn,” still laughing at that description—our room was more than comfortable.
The next morning, we grabbed coffee at The Hub of Nantucket (parking there is chaotic—no lines, just a free-for-all) before driving to Madaket Beach on the northwest end. We walked as far as the road allowed, then followed gravel-turned-sand until dunes swallowed the houses in a semi-apocalyptic scene. Along the shoreline, we spotted our first seal of the trip—apparently, a booming seal population has attracted more sharks, though we saw no sign of them, just their food.
Our final excursion was to Eel Point. The paved road ended abruptly, so we walked into the sand—thank goodness for the rental rule against driving there! At the beach, we celebrated with Nantucket Nectar, my childhood favorite, found live scallops, and collected clam shells for Amity’s crafts. Before long, lunch beckoned back in town; en route, we passed a colonial farmhouse built in 1686—I can’t imagine what Whitefish, MT, or Kirksville, MO, looked like back then.
On the way back into town we stopped for a photo-op on Sparks Street! We then returned the car and walked to Stubby’s for sandwiches, marveling at how we’d explored Nantucket without crowds or chaos. As the perfect birthday weekend wound down, we caught the next car ferry back to Hyannis—an hour longer with only tiny portholes, but we didn’t mind, napping most of the way. Back in Hyannis, we retrieved our car and stopped at Trader Joe’s—35 minutes away but worth it for Scandinavian Swimmers and Amity’s favorite gnocchi. Tired from our Nantucket adventure, we’re only one week into thirteen here in Massachusetts, and our list of adventures is still miles long. Time to rest up and get ready to Live Rad all over again!