Our Visit to “the Grey Lady”: A Guide to Nantucket

I’ve always felt like there were a handful of places around the world I saw in movies or tv shows as a kid that I just would never get to see in real life — as if they were as mystical as Neverland or wherever the ThunderCats are from. The Great Wall of China, Mt. Everest, “White Castle”? I know they’re all real, but there’s some sort of mental block that made me feel like I’d never get to see them in person. Thankfully, that mental block has started to shrink as we’ve gotten older and our world has gotten bigger, and we recently got to cross another destination off that list of “wait, we can actually go there?” places.

We spent part of last week in Nantucket, Massachusetts, and I have to say it felt as dreamy as it did homey. What appeared to be a made-up place out of a Elin Hilderbrand novel instantly felt as familiar as a sweater you’d reach for on a cozy Saturday morning in October. From the New England aesthetic, to the cobblestone streets and faint sounds of the ferry’s horn as it pulls out of the harbor, to the people who welcomed us at the Veranda House, we felt extremely comfortable the moment we arrived.

We chose to stay at the Nantucket Resort Collection, which is a resort made up of three properties: Veranda House, Regatta Inn, and Chapman House. It’s not only a five minute walk to almost anything in downtown you want to do, but it’s also one of the coziest collections of inns we’ve ever seen. We specifically picked the Veranda House, which is appropriately named for the balconies connected to almost every room in the resort, and that was a major gamechanger — I say that because it seems rare to be able to balance the feeling of a “getaway” with that of “bed and breakfast”, but having a place away from everything else seemed to accomplish that.

As far as the inn itself, we woke up each morning, patted the house dog Stella on the head, enjoyed coffee and scones (complimentary continental breakfast was served each morning) on the balcony, and then walked into town before eventually returning to sink into what was one of the comfiest beds known to man. (Seriously, we were exhausted when we got into our room on day one, and had our version of the Joey-Ross nap in Friends. Incredible.)

Like I said, Nantucket was always the stuff of legend to us before last week, so we weren’t entirely sure where to even begin in terms of what to do and, more importantly, what to eat. Regardless, thanks to recommendations from the Veranda House staff, conversations we had with other guests who frequented the area, and some spontaneous web searches, we more than enjoyed ourselves.

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In the event that Nantucket is some sort of “Narnia” for you like it was for us, or if maybe you’re not that weird and just haven’t made time to go, we hope the schedule below can add some ideas for how to spend your time with “The Little Grey Lady of the Sea”.

Day One:

Walked through town and went shopping.
Lunch – “Or, The Whale”.
Coffee – “The Hub”.
Check into room at the “Veranda House”.
Dinner – “Dune”.
Dessert – “The Juice Bar” (Ice Cream Shop).

Day Two:

Coffee – “Veranda House”.
Breakfast – “The Corner Table Café”.
Explore the town – Museums, shopping, bars, restaurants, biking, and historic sights everywhere you look.
Beach Day – “Steps Beach”.
Lunch – Grab “Something Natural” on the way to the beach.
**Recommend biking if you can. It’s walkable, but could be tiring.
Dinner – “Oran Mor”.
Dessert – S’mores by the fire at “Veranda House”.

Day Three:

Breakfast – “Black-Eyed Susans”.
**French Toast + Huevos Rancheros.
Shopping – Great mix of local shops and retailers you’ve always known.
Coffee – “Handlebar”.
Afternoon – Visit “Cisco Brewery” (not just for beer lovers – they have food trucks, wine, margs and other cocktails).
Pre-dinner Drinks – “Gazebo”.
Dinner – “Cru”.
Sunset – “Brant Point Beach”.

Day Four:

Breakfast – “Veranda House”.
Coffee – “Handlebar” (again, because it was delicious).
Lunch – Born & Bread: Mercantile and Bakery
**Sandwiches were so good.
Head to airport (only about a 15 minute drive, and so quick through security)!

*For those with dogs, we brought Banks with us on this trip and took him almost everywhere with us during the day. The Veranda House is a dog friendly inn, and most places around town (including the beaches and restaurants with outdoor seating) were welcoming to our little fluff ball.