Copy My Trip: A long weekend in Nantucket, Massachusetts

Lonely Planet’s Brekke Fletcher recently traveled to Nantucket, Massachusetts for a long weekend with her niece. Here, she shares some tips and insights for anyone planning a visit to this east coast island escape.

Sun. Surf. Seafood. Seafaring. These were all on the menu for a recent weekend jaunt to Nantucket, an island off the coast of Massachusetts, lauded for its whaling history, architecture, beaches and preppy, summery vibe. What was not on the docket was near-constant drizzle, icy cold wind and chilly temperatures. But things don’t always go the way you hoped they would.

My niece Ashley flew in from California to join me on this wee holiday (nonstop flights from Boston, New York City and Washington, DC, as well as a ferry from Woods Hole, Massachusetts), and we messaged in advance regarding the doom-and-gloom forecast. We agreed not to let the weather dampen our spirits – we would double up on sweaters, cover up with waterproof jackets and enjoy our planned itinerary, just without the sunscreen and swimsuits. 

Read more: Don’t let bad weather ruin your vacation

Our adorable cottage was equipped with a full kitchen, outdoor seating and complimentary bicycles (with helmets) © Brekke Fletcher / Lonely Planet

Where did you stay? What was the vibe?

The airy, nautical design of our weekend home, the newly refurbished Cottages at the Boat Basin, immediately put us in vacation mode. The cottage we stayed in, Pawana, was located nearer the street, so it wasn’t exactly private (close those shades when you’re getting dressed), but the comforts were ample.

The bathroom was gleaming white with a huge shower, a strong heater and L’Occitane bath products. Also the place was appointed with white fluffy towels, robes and slippers, and a seriously comfortable bed. As we were special guests, they pre-stocked our kitchen with morning essentials like eggs, sliced sourdough from Born & Bread Nantucket, granola from Something Natural, along with yogurt, milk and coffee (thank you, Aoife!).

Read more: The best places to go on a summer vacation in the USA 

The Lemon Press is a bustling spot for coffee and breakfast © Brekke Fletcher / Lonely Planet

What was the first thing you did?

Our first morning, we made coffee and had the tiniest bite to eat in our snuggly robes. (We needed to keep it light since we had a big lunch scheduled at TOPPER’S at The Wauwinet, which, like the Cottages, is part of family-owned White Elephant Resorts.) Since the cottages are so centrally located, all of downtown’s landmarks, shops and restaurants are only a short walk away.

We made our way along the brick-lined sidewalks to Lemon Press (where we would have a proper breakfast on Saturday) for cappuccinos. This was a chilly Friday around 11am, and let me tell you, the place was jammed. I couldn’t imagine how insanely crowded it must be on a warm summer day. 

Also worth visiting if you’re wandering around downtown is the Whaling Museum, Hospital Thrift Shop, current vintage, Erica Wilson and the Quidley & Company art gallery.

Delicious oysters and paté at TOPPER’S at the Wauwinet; baccala, boquerones and specialty cocktails at chic Via Mare; donuts for days at darling Downeyflake © Brekke Fletcher / Lonely Planet

Any stand-out dining experiences?

The oysters we had at TOPPER’S during lunch were some of the best I’ve ever tasted, perhaps because they were harvested mere steps from our table. The setting inside is both grand and intimate, while the empty outdoor tables were just calling for the weather to warm up.

Two words together I’d never thought I’d love? Fish and pâté. But I found the smoked bluefish pâté to be a perfectly-balanced taste sensation, served with curry lavash crackers, crudité and pickled onions (can we please put this on everything?).

And of course the culinary team at this perfectly-situated New England beach resort makes an exemplary lobster roll served on a lightly toasted brioche. We couldn’t help but wonder: how exactly did they manage that perfect degree of crispness on the cut side of the roll? We may never know.

We simply adored the cocktails at Via Mare at the Greydon House (located downtown in an old sea captain’s home). They were perfectly-executed, including a superb Barrel Aged Boulevardier and a refreshing Last Night I Dreamt of San Pedro with Aperol, prosecco and ginger. The dining room is elegantly sumptuous, and the menu is eclectic and playful. We favored and savored the cicchetti (snacks), including baccala, boquerones and a zippy hot chicken Milanese.

Do not miss out on breakfast at local favorite The Downyflake, beloved for its fresh doughnuts and no-nonsense diner fare – their corned beef hash deserves its own #cornedbeefhashtag.

Read more: How to experience the best of Boston

Scenes from the Bluff Walk in Sconset on the eastern shore of Nantucket © Brekke Fletcher / Lonely Planet

What was your favorite experience?

The Bluff Walk in Sconset is an absolute must. Located on the east side of the island facing the Atlantic, this popular footpath is a lookie-loo’s paradise, cutting behind some very large, very beautiful shingle style beach houses, some of which date from the 1800s.

Though our Saturday midday walk was pretty solitary, I was told repeatedly how clogged up this narrow trail would get at the height of summer beach rush hour. The advice is to go in the morning or an hour before sunset to avoid the throngs, but no guarantees.

The path is narrow – this is single-file walking. As you walk by massive homes on one side, you’ll pass a series of precarious and steep wooden staircases on the other that lead down to the waterfront. I cannot imagine forgetting your sunscreen and having to go up and down those steps multiple times. I also don’t know how I’d feel about a bunch of strangers tromping past my multi-million dollar view all summer, but I certainly do not need to worry about that.

The path switches back to Baxter Road, and then leads you to a drive dotted with smaller, more intimate historic homes that invite you to imagine nineteenth-century life here on the coast. 

Read more: These are the best beaches in the USA

Cisco Brewers in Nantucket specializes in craft beers and cocktails made with local spirits; Ashley delights in a flight © Brekke Fletcher / Lonely Planet

Did you get your party on at all?

If a daytime party counts, we had the most raucous time at Cisco Brewers. What a blast! It’s like a mini-festival on the weekends, with local food trucks (in one case, a food skiff overflowing with shellfish on ice), three bars, live music, picnic tables, fire pits and corn hole. If I was curious as to where everyone was hanging out on this chilly weekend, I wasn’t anymore. 

The music was right on target for this gal, a mix of classic and rock yacht, greatest hits of the 1970s, 80s and 90s. I think I saw every single person singing along to one song or another. The crowd was a mix of twenty and thirty somethings, locals and regulars and tourists, and the vibe was pure joy.

This place is a very, very good time. And I don’t just mean Cisco’s.

Brekke Fletcher traveled to Nantucket on the invitation of White Elephant Resorts. Lonely Planet does not accept freebies in exchange for positive coverage. 

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