🍂 A Fall Getaway to Nantucket: According to a Sommelier

There’s a certain magic to Nantucket in the fall. And if you’re a “‘ber” girl like me, you live for that soft exhale the island takes once summer ends and your shorts make way for cozy sweaters and earth tones. When the air turns salty and crisp, the hydrangeas fade to mauve, and the crowds thin just enough to make space for a proper glass of wine you know you’ve landed in autumnal heaven. The kind of moment that makes me crave a crisp-yet-decadent Chablis, sipped slowly while you blend in among locals who know they’ve got the island back to themselves.

I was just there for a long weekend, and it was one of those rare trips that hit every note: cozy, delicious, a little indulgent, and full of tiny discoveries I’m still thinking about. If you’ve never been, Nantucket (especially this time of year) is everything you expect and need it to be. But what surprised me most, though, was the wine. Every list I encountered was thoughtful and dynamic; a mix of classic heavy hitters and under-the-radar gems, each perfectly aligned with the food and the vibe of the place. And while you can, of course, expect a touch of island markup (this is a destination where the average home price is, well, not modest), I never found it offensive. If anything, it made me want to order another bottle just to see what else they were hiding.

From the best martini on the island to a cooking class that had me rethinking my relationship with poached eggs, here’s everything I loved about a fall weekend in Nantucket.

Where to Stay

We stayed at The Faraway, which feels like staying in your impossibly chic friend’s summer home. The one who somehow mixes rattan, velvet, and vintage art without trying too hard. It’s giving major Anthropologie-meets-coastal-cool energy vibes. For true home-away-from-home vibes, book The Federal Suite. It’s a three-bedroom house with every comfort you could possibly want: a fully stocked kitchen (yes, including sphere ice molds in the freezer), a cozy living room, and a bright little salon area that basically begs for cocktail hour. There’s also a private patio for lazy mornings or nightcaps under the string lights and because it’s part of the hotel, you still get all the perks like daily housekeeping and that rare kind of hospitality that feels personal.

Day 1:

Morning:
Around the corner you’ll find Born and Bread; a bakery that during season will have a line around the block, but this time of year feels much more civilized. Their coffee game is strong so caffeinate to your specifications, cue your favorite spotify playlist, and take a slow stroll through town. It’s the kind of morning that makes you want to cancel all your plans and wonder why you don’t actually live here.

Midday:
If you can, book a cooking class at The Corner Table, easily one of my favorite things we did. The class is taught by an actual chef, Jason Smith, who somehow makes risotto, stock, and egg poaching feel both approachable and elegant. We made a creamy mushroom risotto, perfectly seasoned and cooked so the starches reach that oozy but not goopy consistency I’ve never quite been able to master. Then we topped it with a poached egg which, thanks to Jason’s clear, calm direction, I now feel genuinely confident making at home. 

It’s intimate, hands-on, and surprisingly educational - the kind of experience where you leave both well-fed and a little more skilled than when you arrived.

After class, spend the afternoon shopping in town. Nantucket is delightfully chain-free (save for Ralph Lauren), which means you can actually find things that feel special. A few highlights:

  • Current Vintage — part wine shop, part consignment boutique affiliated with Oran Mor. I found a gorgeous MOTHER coat there and could have easily walked out with a bottle or two of Burgundy to go with it. It’s a dangerous combo, in the best way.

  • The Hospital Thrift Shop — a local legend, and honestly one of the most fun treasure hunts on the island. Go with an open mind and you might walk out with something fabulous for $8.

Evening:
Start the night at The Pearl with their Ohhh Mami Martini. Opt for the caviar-stuffed olives if you’re feeling cheeky, and a half-dozen oysters if you’re feeling civilized.

Then, head to Oran Mor, which came highly recommended by every local I talked to … and for good reason. Their pasta (especially the truffle one) is rich, decadent, and exactly what a chilly Nantucket night calls for. Don’t miss the oysters Bourguignon either. I’m a bit of an oyster purist myself, but I was fully on board with the absolutely unacceptable amount of butter, garlic, and herbs it was doused in.

Day 2

Morning:
Coffee on The Faraway’s outdoor patio is a must. t’s peaceful, slightly nautical, and feels like you’re on your own private veranda. If you want to change it up, the Faraway’s coffee program is fantastic so you can grab it there, or opt for a return trip to Born and Bread. This time though, you’re grabbing a BB Egg Sandy breakfast sandwich (trust me) and then walking it off with a stroll to Brant Point Lighthouse. The walk along the beach is crisp, breezy, and perfectly quiet this time of year.

Afternoon:
Lunch at Cru is non-negotiable. It’s right on the water, has the best selection of Nantucket oysters which I have to say are probably my favorites right now. They’re plump, saline, and taste like the Atlantic itself. While Champagne is the classic move, I actually love pairing them with chilled sake. It’s a little unexpected, a little sommelier-nerdy, and absolutely perfect. That said, Cru’s wine list is excellent, so you really can’t go wrong.

Afterward, wander through town and take in the fall colors on the cobblestones at golden-hour before dinner. No soundtrack needed.

Evening:
Dinner at either Proprietors Table or The Nautilus. Proprietors is globally inspired with an adventurous, spice-driven menu and plenty of wines to match (orange wines, Jura, chillable reds, aka my love language). The Nautilus is more lively and cocktail-forward, great for small plates and people-watching but a fantastic way to try LOTS of things since it’s smaller, more tapas-style fare. Either way you can’t go wrong

Day 3 — One Last Bite

Before heading out, stop by Provisions and grab a Turkey Terrific sandwich to go. It’s practically an island institution: cranberry sauce, stuffing, turkey, mayo -  basically Thanksgiving in a sandwich, and exactly what you’ll want on the ferry.

Sommelier’s Tips for First-Timers

  • Skip the car. The island is walkable and the shuttles are easy 

  • Book ferries and accommodations early, even off-season. Nantucket’s version of “quiet” still fills up.

  • Layer up. Fall weather shifts quickly, and there’s no such thing as too many sweaters. 

  • Stop by Epernay Wine & Spirits. Owner Jenny Benzie is a sommelier and has a knack for small-production finds - perfect for a cozy night in watching Practical Magic.

  • Pack a beach picnic. Grab oysters from Sayle’s, a chilled bottle of Muscadet, and pretend summer never ended.

other Wines That Will Make the Trip Even Better

  • Chablis or Albariño: crisp and perfect with oysters, duh.

  • Pinot Noir or Cru Beaujolais: light enough for seafood, cozy enough for fall. ‘Tis the season

  • Champagne: Always