5 Things to Do in Nantucket

Located on the Island’s Northeast point, The Wauwinet has a refined yet relaxed vibe, with a lush, lounge chair-dotted lawn that reminds me of The Great Gatsby. Have lunch or dinner at the Inn’s award-winning restaurant Toppers, and be sure to reserve a complimentary, one-hour ride there via water taxi. When choosing your mealtime, consider these scenarios: tucking into the freshest plate of oysters (seriously – they're harvested 300 yards from the property) on the restaurant’s deck overlooking Nantucket bay for lunch, or savoring a glass of bubbles on the boat – the evening cruise offers cocktail service – before dinner in the elegant dining room. Either way, you win.

Examine the 46-foot skeleton of a sperm whale and a 19th-century lens once used in the Sankaty Head lighthouse, both displayed among decorative scrimshaw and other nautical artifacts. After filling up on Nantucket history, follow the heady smell of homemade waffle cones across the street to The Juice Bar and get a double scoop of the Island's best ice cream. Flavors like chocolate Oreo, peppermint stick and crantucket are worth braving the long line. Emmy Rossum agrees.

Rent a bike downtown at Young’s or Cook’s and choose your adventure. With 32 miles of scenic bike paths covering the Island, head for the rose-covered cottages of Sconset, the secluded beaches of Dionis or my favorite 6-mile cruise to Madaket. On the way out of town, stop by Something Natural on Cliff Road and grab a sandwich – made on freshly baked bread (get the herb!) – and a chocolate chip cookie to go. You’ll pass ponds, untouched conservation land and the Madaket Mall (the "take it or leave it" treasure trove found at the Island’s trash dump). Once you get to the end, stay for a picnic and a dip before pedaling back. Pro tip: Madaket beach is also Nantucket’s prime place to see a spectacular sunset.

Cisco Brewers was founded 20 years ago and remains the Island’s first and only craft brewery. Located alongside the Nantucket Winery and Triple Eight Distillery, you can tour all three at 1pm or 4pm daily in the summer months. Before sampling brews like Whale’s Tale Pale Ale and Sankaty Light Lager, in addition to wine and spirits, visit Bartlett’s Farm a half mile down the road and fill up on freshly made salads, soups and desserts at one of the picnic tables overlooking the fields.

If you aren’t planning on ferrying over your four-wheel drive, rent a jeep for the day and head for the Coskata-Coatue Wildlife Refuge. Most rentals come with Nantucket Town and Great Point beach permits, but stop at the Wauwinet Gatehouse on the way in to let some air out of your tires for easy beach driving. En route to the northernmost tip of the Island, where you’ll find the picturesque Great Point Lighthouse, navigate the thin strip of sand slowly to take in the natural beauty and island wildlife, and keep your eyes peeled for seals.