Escape for the Long Holiday Weekend

by Jessica Howard

Memorial Day might just be the best holiday weekend on the calendar; after all, it ushers in the summer season. Whether you’re keen to hop on a flight to a far-flung destination or prefer a breezy road trip, here are getaway options for every travel taste. Go ahead, add a day or two to the weekend. From picture-perfect preppy beach towns to a mountain-ringed spa retreat, here are the sweetest spots to catch the first rays of summer.

Relaxing and Glamorous

Four Seasons Hotel at The Surf Club

Surfside, Florida

Surfside, Miami’s “uptown beach town,” has remained relatively under-the-radar compared to some of South Florida’s buzzier enclaves—and that’s exactly what makes it so appealing. Back in the ’30s, Hollywood elite like Elizabeth Taylor and Frank Sinatra flocked here for The Surf Club, a membership-only hangout that was recently brought back to life—in hotel form—by the Four Seasons. It’s an ideal Memorial Day weekend escape, whether you’re looking to relax by the pool, indulge in a few fantastic meals or go shopping in nearby Bal Harbour, an area that’s renowned for its luxury retail offerings. With just 77 rooms and a glamorous Art Deco vibe, the resort truly transports you back in time. The property is currently offering a Stay Longer Package (the fourth night is free), which makes booking for the holiday weekend a no-brainer.

Preppy Beach Town

76 Main

Nantucket, Massachusetts

Nothing evokes New England charm more than Nantucket. The Shingle style homes and stretch of natural beaches has one reaching for their lobster shorts and Sperrys come May. The ideal weekend is spent beaching, golfing and perusing the boutiques—all of which can be done with ease on a cruiser bike. Check in at the 76 Main property, which boasts a Vineyard Vines Suite that fulfills all your beach-chic nautical dreams. Pass the rosé.

Caribbean Tradewinds

The Jamaica Inn

Ocho Rios, Jamaica

The best part about a Caribbean weekend: In just a few hours’ time, an airplane can plop you onto the most beautiful beaches in the world. Spend the weekend exploring waterfalls, local markets, and splashing in the sea. The Jamaica Inn, a luxury colonial resort that’s played host to Marilyn Monroe and Katharine Hepburn, is the ideal spot for that old-school luxury scene. Opt for a cottage, where beds are dressed in mosquito netting, and feature a private pool and ocean access. Evenings call for cocktail hour, where tuxedo-clad gentlemen serve up martinis to moneyed families in tony beach attire.

Mais, Oui!

Baumanière Les Baux de Provence

Provence, France

For the real-deal wine weekend, a trip to Provence ticks all the boxes. Skip the tourist-choked region of Marseille and opt to taste from the small group of winemakers in Les Baux-de-Provence village, producing magnificent red, rosé and white wines. The almost-hidden Relais & Châteaux property, Baumanière Les Baux de Provence, is nestled among craggy rocks and lush olive groves. Comprised of five buildings, including an 18-century manor, the estate includes a Michelin-star restaurant, spa, three outdoor pools and a tennis court.

Southern Charm

86 Cannon

Charleston, South Carolina

This Southern city is about as perfectly posh as they come. From the colorful row homes to top-notch food scene, it’s no wonder that so many visitors crush hard on this low-country locale. The 86 Cannon, a luxury boutique property, was constructed in the early Civil War-era, and now serves as a three-story home with five guest rooms designed by Betsy Berry of B. Berry Interiors. Guests can buzz around on the hotel’s bicycles and scoot back in time for the nightly wine and cheese service.‎

Hideaway for the Rich and Famous

The Brazilian Court

Palm Beach, Florida

Home to billionaires and Mar-a-Lago, the retro Florida throwback town is also heavy on the charm factor. Case in point: it’s here that you’ll find the largest croquet complex in the world. This Memorial Day weekend, The Brazilian Court Hotel is playing host to a Lilly Pulitzer Package (through September 30) that includes a studio suite, breakfast, beach picnic, and Lilly-inspired Martone Bicycles. Pack your most colorful shift and off you go.

Amongst the Vineyards

Auberge du Soleil

Napa Valley, California

Napa is a no-brainer for good reason: Michelin-starred restaurants, rolling hills, perfectly warm weather and, of course, the wine. The ideal Memorial Weekend getaway would begin in a cheeky convertible, used to drive from SFO to Napa, and then serve as a fitting accessory for touring the wineries, such as Robert Sinskey and Sciandri Family Vineyards. Post up at the ever-so-enchanting Auberge du Soleil, where each room comes equipped with a soaking tub, fireplace, and private terrace, all set among 33-acres of intoxicating olive groves.

Spa Getaway

Mii Amo

Sedona, Arizona

Sedona, with its crimson buttes set against bright blue skies (a backdrop for the most breathtaking of sunsets), is as magical as it sounds. Visitors flock for the art and hiking, but it’s a spa city at heart, and ideal for a respite-seeking getaway. Hike the Oak Creek Canyon and Chimney Rock, then retreat to Mii Amo, a destination spa comprised of 16 rose-hued casitas. Indulge in Native American-inspired therapies as well as new-agey but luxurious treatments like a rain dance, Pinon body scrub, and energy clearing. If they’re booked, try its sister hotel, Enchantment Resort. But fret not, the neighboring properties share a spa.

Sand and Surf

The Royal Hawaiian

Waikiki, Hawaii

A Hawaiian getaway is a surprisingly zippy trip from the West Coast—and worth every minute in the air. Waikiki, long known for its surfer-chic vibe, is best experienced at The Royal Hawaiian, a historic hotel with a punchy pink façade that’s been nicknamed “The Pink Palace of the Pacific.” The hallways are bedecked with pineapple-print wallpaper and rooms filled with bamboo furnishings; it’s easy to see why an opening episode of Mad Men was filmed here. Tack on the views and envision a serious Mai Tai-sipping session on your lanai.

Ranch Life 

The Resort at Paws Up

Greenough, Montana

“I’m in love with Montana. For other states I have admiration, respect, recognition, even some affection. But with Montana it is love. And it’s difficult to analyze love when you’re in it,” said John Steinbeck. Picture this: a colorful poncho, buttery-soft boots, and a look that’s crowned with the perfect Western hat. It’s the ensemble for your weekend at The Resort at Paws Up in Greenough: a luxury ranch that invented that whole glamping phenomenon.