Nantucket, Massachusetts, USA
Nothing like kicking off the summer at an all-American locale like Nantucket. The Massachusetts island boasts an uncanny amount of hydrangeas, great lobster, and, on Memorial Day weekend, the Figawi, a sailing race from Hyannis to Nantucket that signals the start of the season. While the majority of accommodations around the Marina are all booked up, guests can still snag a room at the harborside White Elephant Hotel. Got a big group? There is still a two-bedroom cottage up for grabs as well. Don’t forget to enjoy a Figawi Wowie, a local concoction of mint-infused blueberry vodka, lemonade, and soda, while catching the race.
Book Now: White Elephant Hotel, starting at $325/night, hotels.com.
Montauk, New York, USA
Desperate to get out to Montauk this summer? Believe it or not, you can still head to the end of the world for Memorial Day weekend. Located on the bay side of Long Island, Haven Montauk offers up harbor views, a pool, and a fire pit, and is dog-friendly. Enjoy the quiet stretch of beach alongside the contemporary motel; then head into town and enjoy the 10th Annual Memorial Day Weekend Show on the Green, featuring work by local artisans, and enjoy Bluepoint oysters at Duryea’s. Plus, last year’s East End sensation, the EMP Summerhouse, pops up again for a second season in East Hampton, just a short ride away.
Book Now: Haven Montauk, expedia.com.
CHRIS SANDERS CHRIS-SANDERS.COM
New York, New York, USA
Let’s all be honest, the weather is so hit-or-miss on Memorial Day weekend, maybe you don’t want to be on an East Coast beach after all. A quick trip to New York City is always a good idea—or if you are lucky enough to call the city home, indulge in a staycation. Recently opened Hotel 50 Bowery still has availability. The boutique hotel boasts a chic rooftop, and a cool location—smack in the middle of Chinatown.
Book Now: Hotel 50 Bowery, starting at $362/night, mrandmrssmith.com.