The ubiquitous “Nantucket Reds” — distinctive salmon-pink color pants and shorts, produced and distributed by Murray’s Toggery Shop on Main Street – -would be Nantucket’s unofficial uniform if there were one. Sporting these “Guaranteed to Fade” togs or the equally preppy Madras patchwork pants is like a right of passage with the well-heeled preppy set who’ve summered on the island for generations. The more beat up and faded, the greater the status. Preppy attire is optional and so is a car when visiting this little island 30 miles off the coast of Cape Cod.
At the secluded waterfront Wauwinet, an exclusive enclave nestled between the Atlantic Ocean and Nantucket Bay on the northeast corner of the island beside the Coskata-Coatue Wildlife Refuge, the pre-arrival concierge will plan your entire stay in advance so all you need to think about is romance. Take the ferry from Hyannis, and upon arrival, you’ll be whisked off by complimentary shuttle to your luxurious island retreat. A day on Nantucket might include lounging at one of the Wauwinet’s private beaches on the Atlantic Ocean or Nantucket Bay, paddling together on the water in a kayak or exploring the island by bike.
It’s a bit remote, which is what makes the Wauwinet quiet and romantic, but if you feel like shopping or exploring “in town” as locals call it, the hotel will shuttle you there by private jitney or in their boat, the Lady Wauwinet. Early risers should definitely partake in a local tradition — heading to the Downyflake for a box of fresh doughnuts. Wander the historic downtown cobblestone streets with their grey shingled houses and visit the Jared Coffin House, the oldest house on the island. On Main Street, you’ll find the “Three Bricks”, a series of three identical brick Victorian mansions whaling merchant Joseph Starbuck built in 1837 for his sons. Look up to see the “widow’s walks” platforms atop the peaked roofs of many of the 19th-century residences. Folklore has it that these were built as observation decks for wives to watch for incoming whaling ships, hoping their husbands had returned from sea.
From the mid-1700s to the late 1830s, Nantucket was the whaling capital of the world. Pop into the Whaling Museum to learn about some of the local lore that inspired author Herman Melville to write Moby Dick.
To pass their time at sea, some whalers and lightship mariners crafted Nantucket Lightship Baskets, labor-intensive handwoven rattan or cane baskets with wooden bases adorned with scrimshaw pieces. First created over 150 years ago, they are still in production and you can see them at the Nantucket Lightship Basket Museum. You won’t find a more genuine and distinctive local handicraft, but you’ll need deep pockets to purchase one.
Unwind from the shopping spree back at the Wauwinet with a complimentary afternoon glass of port accompanied by cheese. Cap off the day with a sumptuous dinner at Topper’s, the hotel’s restaurant whose seasonal locally sourced cuisine is so local that the Retsyo Oysters on the half shell were cultivated just 300 yards away.