Todd Kingston Plummer’s Little ACK Book

Todd Kingston Plummer's guide to nantucket

Knowingly or not, there’s a high likelihood you’ve read a piece stamped with Todd Kingston Plummer’s byline—whether concerning the connection between Taylor Swift and travel memories, Snow Polo and social calendars, ethical tourism and endangered species, or otherwise. A distinguished American writer (as well as attorney and consultant), Plummer has carved a niche for himself in the world of luxury lifestyle journalism for his insightful coverage of global destinations and travel experiences. (His passport is a testament to that, having traveled to 7 continents and 77 countries on assignment—to date.) Yet, no matter where in the world his stories take him, he remains a true New Englander at heart.

Raised outside of Boston with childhood summers spent visiting Nantucket, Plummer appreciates the island’s evolution and nuances. “For all the ways this island has changed over the years, there’s something so comforting about all the ways it hasn’t,” he says. “There’s something so beautiful about how hard everyone has to work to actually make this island happen: the locals, the small business owners, the seasonal staff, the homeowners, everyone. But they all do it because they believe in this island so much.”

Below, Plummer shares just a few of his favorite island haunts (for which he credits a good portion to his friend Tessa Cressman, owner of the stunning Green Market Farm, for helping him discover), exclusively for Little ACK Book. Otherwise, back on the mainland, you can find him working on his latest passion project: “My polo handicap.”


Hotel: Greydon House (They have the most breathtaking all-white Kristina Wixted window boxes, which I’ve been trying to recreate at my home in Charlestown unsuccessfully for years)

Breakfast Order: BB Egg Sandy, extra sriracha from Born & Bread

Lunch Order: Meatloaf sandwich with the works from Claudette’s

Dinner Order: Tomato salad followed by the burger at Chanticleer

Bar Order: I’ll have whatever Annie’s [ Little ACK Book’s founder ] having at The Boarding House

Café Order: Biggest, blackest cold brew from Handlebar Café

Ice Cream Order: 3 scoops of Green Monster at The Juice Bar

Activity or Attraction for Groups: A morning stroll and gossip sesh at Tupancy Links

Activity or Attraction for Children: Critter Cruise followed by ice cream from Juice Bar

Activity or Attraction for Yourself: A long bike ride on the island’s countless trails–even better, heading out with no plan

Activity or Attraction for Pets: Cisco Beach followed by Cisco Brewers

Beach: Madequecham

Beach Read: Anything Elin Hilderbrand, but now that she’s “retiring” I need a new queen of beach reads!

Person to Know: Captain Mat of the The Blue Peter

Must-Pack Item: My friend May developed this ocean-safe, super clean sunscreen called DUNE that doesn’t leave a white cast on your skin.

Item to Leave at Home: Finery! I’m so bored of the city slickers who get overly dressed up for Nantucket.

Souvenir: A rope bracelet from Sunken Ship

Time of Year: September!

Rainy Day Plan: Books, blankets, an open window

Spot on Island: I want to be where the people aren’t

Morning or Night?: Nights that become mornings

Sun or Fog?: If you don’t appreciate fog, this isn’t the island for you

Land or Sea?: If I wanted just land, I wouldn’t have taken a ferry 30 miles out to sea

Nantucket’s Best-Kept Secret: Like I’m telling you

Anything Else You’d Like to Add: Don’t overplan your trip to Nantucket. Make some dinner reservations, sure, but the best Nantucket experiences are when you sit back and let the day unfold.


Follow Todd: @eatgaylove

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Aerin Lauder’s Little ACK Book

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Jack Carlson’s Little ACK Book