How to Spend an Off-Season Weekend in Nantucket

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One of our staffers makes the case for a late fall trip.

Welcome to The Weekender, Coveteur's newest series that allows us to hop into tastemakers' overnight bags as they journey on trips around the world. This week, we're joining Coveteur's very own manager of partnerships, Nick Papa, as he spends a weekend in Nantucket, MA. Though the island is often considered a summer destination, he enjoyed seeing the locale in its off-peak season, leaning into the more local, relaxed experience.

How did you decide on this location for your trip?

"As my desires surrounding travel have evolved over the course of the last year or so, I was thinking about locations that have a 'peak season' and what they might be like as their season winds down. In other words, what do the locals do? How does their economy thrive as tourism patterns change? While Nantucket is picturesque in the height of summer, I wanted to experience the island at a slower pace. As I talked to more and more locals who stay on the island year-round, I heard a very similar sentiment: late September through the winter are some of the most exceptional months."

How did you get there?

"We took a quick 50-minute shuttle flight from Westchester County Airport via Tradewind Aviation. Tradewind provides both on-demand private charter flights or scheduled shared charter flights, so if you are going solo you can hop on a shared charter, but if you are traveling with a group you can book a fully private option. I will say, the flight was an absolute breeze and one of the smoothest planes I have flown in—from take-off to landing I barely felt a thing. Within the Northeast, they also have scheduled charters to Newport, Martha's Vineyard, and Stowe, VT along with services throughout the Caribbean."

Where did you stay? What sort of accommodations were you in (hotel, cabin, private home, tent, etc.)?

"Greydon House, which is a 20-room boutique hotel situated in the heart of town. With impeccable interiors by design duo Roman and Williams, the property transports you back in time boasting rich woods, deeply saturated hues, plush textiles, an eccentric art collection, and perfectly moody lighting with quirky lamps thoughtfully placed throughout the meandering halls. As you enter your spacious guestroom, there is a welcomed stark contrast in moodiness transitioning from deep teal to warm white. Each room includes distinctively curated furniture, stylish bed linens by John Robshaw, and hand painted Portuguese tiles in the shower. Nantucket is brimming with charming accommodation options that really lean into the aesthetic of the island, but Greydon House offers something truly unique and unpretentiously luxurious which, as someone who sincerely appreciates design, elevated my stay on the island."

What sort of activities did you do? Was it a weekend of discovery or did you have a specific itinerary?

"While I did have a loose itinerary, it was still a weekend to discover places off the beaten path of a traditional Nantucket trip. Greydon House recently partnered with the only functional medicine wellness center on the island, Lavender Farm Wellness. Lavender Farm now offers curated spa experiences within Greydon House for the winter along with weekend-long wellness retreats for individuals or groups which include everything from massages to functional medicine consultations to nutritional cleanses and meditation practices. Brandon, co-proprietor of Lavender Farm, took us out to Coskata-Coatue Wildlife Refuge for an off-road experience where we drove along the beach as seals waded in the water and waves crashed beneath our truck. After reaching a state of zen while wandering through the reserve by foot, we found a private spot for a 25-minute meditation session. Post-meditation, we enjoyed a beach picnic with prepared salads and sandwiches that we grabbed to-go from The Green Market. The following day, I opted for a massage in the dedicated wellness room at Graydon House which was truly remarkable. Brandon is incredibly intuitive and has a relaxing aurora that you feel as he naturally finds spots of tension throughout your body.

"Outside of my phenomenal experience with the team from Lavender Farm, I spent the rest of my time wandering the winding streets of town and popping in and out of small shops. All in all, I think that when you travel somewhere outside of a destination's peak season, some sort of loosely planned itinerary is key to getting the most out of your vacation."

What were some of your favorite meals and from where did you order them?

"With it being the off-season, many restaurants were closed, but that just makes way for truly special and stand-out culinary options. A short walk from Greydon House, you'll find a space called The Green Market—if you don't want to walk, they've recently begun offering select in-room service at Greydon House for overnight guests. It is a modern take on a general store with highly curated products from small artisans either on Nantucket or in close vicinity. Tessa, the co-founder of the market and a year-round local, developed the concept after feeling overwhelmed with choices in the island's one big-box grocer. She wanted to create a haven where locals and visitors could come and stock up on delicious, health-conscious foods no matter the occasion. On top of the insanely delicious prepared foods, freshly pressed juices, smoothies, and in-house baked goods, you will also find curated vintage home goods, natural skin-care products, and bespoke merch that features their signature halved fruits and veggies printed on various linen pieces. The market is a one-stop-shop on the island that I found myself at more than once…

"If you are looking for a more formal dining option, Ventuno offers traditional Italian dishes like perfectly al dente pasta and freshly caught seafood entrées in a former home-turned-restaurant setting. Greydon House also has an inviting dinner choice, Via Mare, with a cozy fireplace and Italian-inspired small plates. Oh, and you can't go to any town in New England (no matter the season) and not have a lobster roll. I found a mouthwatering, traditional roll at The Lobster Trap's pop up truck at Cisco Brewers."

What was the local scene like? Paint us a picture of the atmosphere.

"Having grown up in New England and after spending many summers as a child on Cape Cod, Nantucket similarly leans heavily into its maritime roots, but has a more refined feeling. As you drive throughout the 14-mile long island, you notice that every structure is uniformly similar and sided in naturally aged cedar-shake shingles. In the off season, the town is mostly filled with locals who live there year-round—artists, restaurateurs, farmers, fisherman etc. They have immense pride in their island and most come from generational families born and raised on Nantucket. All the full-time locals seem to know each other so there is an undeniable sense of community that you notice as you walk into various shops and overhear conversations."

How did you dress for the trip? How did the climate, itinerary, or culture affect your style choices?

"With the temperature cooling off, I opted for thicker layers and casual pieces that didn't feel too fussy: a corduroy overshirt, wool-blend sweaters, easy trousers, and a versatile jacket that provided both style and warmth. Knowing most planned activities were excursion-based, sneakers and activewear were also necessary. I would say that no matter the season, a flat shoe is a must since most streets within town are cobblestones."