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.
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.
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.
We may have just missed Jazz Fest, but that doesn’t mean you should cross New Orleans off your list. The weather is still favorable during the end of May, and there are still last-minute Memorial Day bookings to be had. In the heart of the Arts District, in a converted 19th-century coffee factory, is the Old No. 77 Hotel & Chandlery, an eco-friendly, pet-friendly, and locals-friendly spot, which is within walking distance of major sites.
Book Now: The Old No. 77 Hotel & Chandlery, from $198, mrandmrssmith.com.
Located on a plateau above the Pink Sands on Harbour Island in the Bahamas, Coral Sands may only be a few hours’ flight from the mainland U.S., but it is easy to fall into the laid-back pace of the island very quickly. Originally opened in 1968 by Hollywood actor Brett “Buzz” King, Coral Sands has played host to both celebrities and designers wanting a laid-back retreat. A recent renovation has seen the boutique resort add new beachfront cottages, and an infinity pool, in addition to a second soaking pool.
Book Now: Coral Sands, starting at $295/night, expedia.com.
Tired of Tulum? Opt for its neighbor, Isla Holbox, an island north of Cancun off the Yucatan Peninsula, which is home to pink flamingos, sea turtles, pristine beaches, and colorful villages filled with thatched-roof homes. Stay at Casa Las Tortugas, a chic little bohemian hotel owned by a European couple (she used to work in fashion; he was a former pro kitesurfer). The hotel features beautiful exposed-beam rooms with balconies looking out onto the ocean, and offers yoga, kiteboarding, whale shark snorkeling, horseback riding, kayaking, and stand-up paddleboarding.
Book Now: Casa Las Tortugas, from $194/night, hotels.com
Checked Mexico City off the list? There is a city three hours northwest of the capital worthy of your attention—San Miguel de Allende. Explore the quaint city by foot and you’ll notice the charming streets are chock-full of colorful pottery, crafts, clothing, and food. The city hasn’t forgotten its cultural traditions, and the city’s center is a UNESCO World Heritage site. Stay at the Belmond Casa de Sierra Nevada, which opened earlier this year in an 18th-century mansion.
Book Now: Belmond Casa de Sierra Nevada, expedia.com.
For those who want to save their beach vacations for their August break, Sonoma is an easy choice for the long weekend. If you’ve visited the region before, or prefer someplace more off-the-beaten-path, opt for the Timber Cove Resort, a '60s-chic-meets-rustic resort on Sonoma’s coast. Overlooking the crashing waves of the Pacific Ocean, the resort offers a host of activities from hiking to yoga, and its restaurant features all organic and local foods. Rent a car and explore nearby wineries and hidden beaches. Whatever you choose to do, be sure to sign up for TabletHotels.com’s Tablet Plus membership and receive a free upgrade on your booking.
Book Now: Timber Cove Resort, from $794, tablethotel.com.
Barcelona seems to be on the tip of everyone’s tongue right now, and for good reason. The historic Barri Gòtic is devastatingly charming, and the city’s 19th-century version of a starchitect, Antoni Gaudí, has left his mark on buildings across the city. The Sagrada Familia is reason enough to visit the Catalonian capital. Stay at the El Palauet Living Barcelona, a boutique hotel offering two-bedroom suites complete with a kitchen and outdoor space. Perfect for a long weekend with friends.
Book Now: El Palauet Living Barcelona, from $866, expedia.com.
Instead of booking a hotel in Capri or Positano, opt for nearby Ravello, famous for its cliff-side gardens. Stay at Palazzo Avino, a 12th-century palace that has been one of Europe’s most well-loved gems since the late 1800s. This will come as no surprise for anyone who has had the pleasure of visiting and witnessed the unbelievable Amalfi Coast views, the beautiful rooms complete with Frette bedding, and the serene spa. An added perk is the nearby Clubhouse by the Sea, from which hotel guests can swim in the sea and sunbathe. Book Now: Palazzo Avino, tablethotels.com.