Plan My Trip: A Long Weekend in Nantucket, Massachusetts

Brekke Fletcher from Dinogo Planet recently took a long weekend trip to Nantucket, Massachusetts with her niece. Here, she shares helpful tips and insights for those considering a visit to this charming East Coast island.

Sunshine. Surfing. Seafood. Sailing. These were all part of a recent weekend getaway to Nantucket, an island off the coast of Massachusetts known for its whaling heritage, stunning architecture, beautiful beaches, and preppy summer atmosphere. However, we didn't expect the almost continuous drizzle, biting winds, and cool temperatures. Plans don't always unfold as you envision.

My niece Ashley flew in from California to join me on this short holiday (with nonstop flights from Boston, New York City, and Washington, DC, as well as a ferry from Woods Hole, Massachusetts). We exchanged messages about the gloomy forecast in advance. We decided not to let the weather affect our mood – we would layer up with sweaters, don waterproof jackets, and stick to our itinerary, just without sunscreen and swimsuits.

Read more: Don’t let inclement weather spoil your vacation

What was your accommodation like? How did it feel?

The bright, nautical-inspired decor of our weekend retreat, the recently renovated Cottages at the Boat Basin, instantly set us in vacation mode. The cottage we stayed in, Pawana, was situated closer to the street, so it lacked a bit of privacy (remember to close the shades while changing), but it offered plenty of comfort.

The bathroom was pristine white, featuring a large shower, a powerful heater, and L'Occitane bath products. Additionally, the cottage was stocked with fluffy white towels, plush robes, and slippers, along with an incredibly comfy bed. As special guests, our kitchen was pre-stocked with breakfast essentials like eggs, sliced sourdough from Born & Bread Nantucket, granola from Something Natural, plus yogurt, milk, and coffee (thank you, Aoife!).

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What was your first activity?

On our first morning, we brewed some coffee and enjoyed a light snack while cozied up in our soft robes. (We kept it simple because we had a hearty lunch planned at TOPPER'S at The Wauwinet, which, like the cottages, is part of the family-owned White Elephant Resorts.) Thanks to the cottages' central location, all of downtown’s attractions, shops, and eateries are just a short stroll away.

We strolled along the brick-paved sidewalks to Lemon Press (where we planned to enjoy a full breakfast on Saturday) for some cappuccinos. It was a chilly Friday around 11am, and the café was packed. I can only imagine how crazily busy it must be on a warm summer day.

If you’re exploring downtown, don’t miss the Whaling Museum, Hospital Thrift Shop, current vintage, Erica Wilson, and the Quidley & Company art gallery.

Any memorable dining moments?

The oysters we enjoyed at TOPPER'S for lunch were among the finest I've ever tasted, likely because they were harvested just steps away from our table. The interior ambiance is both grand and cozy, while the vacant outdoor tables were beckoning for warmer weather.

Two words I never imagined I’d love together? Fish and pâté. However, the smoked bluefish pâté was a delightful taste experience, paired with curry lavash crackers, fresh vegetables, and pickled onions (this should be a topping for everything!).

Naturally, the culinary team at this ideally-located New England beach resort serves an exceptional lobster roll on lightly toasted brioche. We couldn’t help but ponder: how do they achieve that perfect crispness on the cut side of the roll? It remains a mystery.

We absolutely loved the cocktails at Via Mare within the Greydon House (situated downtown in a historic sea captain’s residence). Each drink was expertly crafted, including a fantastic Barrel Aged Boulevardier and a refreshing Last Night I Dreamt of San Pedro with Aperol, prosecco, and ginger. The dining room exudes elegant charm, and the menu is both diverse and fun. We particularly enjoyed the cicchetti (small plates), featuring baccala, boquerones, and a spicy hot chicken Milanese.

Don’t skip breakfast at the local favorite The Downyflake, renowned for its fresh doughnuts and straightforward diner fare – their corned beef hash deserves its own #cornedbeefhashtag.

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What was your standout experience?

The Bluff Walk in Sconset is an absolute highlight. Situated on the eastern side of the island overlooking the Atlantic, this beloved pathway offers a glimpse into stunning shingle-style beach houses, many of which date back to the 1800s.

While our Saturday afternoon stroll was quite peaceful, I was repeatedly warned about how congested this narrow path can become during peak summer beach hours. It's best to visit in the morning or just before sunset to escape the crowds, but there's no guarantee you'll have it all to yourself.

The trail is quite narrow, requiring single-file walking. On one side, you'll find grand homes, while on the other, steep wooden staircases lead down to the waterfront. I can't imagine forgetting sunscreen and having to climb those stairs multiple times. Plus, I'd feel strange with strangers passing by my multi-million dollar view all summer, but that’s not my concern right now.

The trail eventually merges back onto Baxter Road, leading you to a street lined with smaller, charming historic homes that evoke the spirit of coastal life in the nineteenth century.

Discover more: The best beaches in the USA

Did you have any fun at all?

If a daytime counts, we had an absolute blast at Cisco Brewers. It felt like a mini-festival on the weekends, featuring local food trucks (including one with a skiff brimming with shellfish on ice), three bars, live music, picnic tables, fire pits, and corn hole. I quickly found out where everyone was congregating on this chilly weekend.

The music was perfectly suited to my taste, blending classic and yacht rock hits from the 70s, 80s, and 90s. I noticed everyone singing along to at least one song. The crowd consisted of locals, regulars, and tourists in their twenties and thirties, and the atmosphere was filled with pure joy.

This spot guarantees a fantastic time. And I’m not just talking about Cisco's.

Brekke Fletcher visited Nantucket at the invitation of White Elephant Resorts. Dinogo Planet does not accept complimentary services in return for favorable coverage.