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Memorial Day weekend marks a whole new world of travel possibilities, where we can reacquaint ourselves with the relaxed rhythms of summer: sunlit days spent at the beach, dining al fresco, and detaching from the obligations of daily life. And what better way to embrace the new season than by escaping somewhere fun and fabulous, where you can connect to the local culture and cuisine?
Bon vivants might opt for a European escapade and get a glimpse of life on the Mediterranean before the parade of superyachts and tourists arrives later in the year. It’s the perfect time to tour across the Atlantic as, according to Melissa Biggs Bradley, founder of luxury travel company, Indagare, “it isn’t crazy busy and it’s not a holiday weekend for Europeans, so crowds and prices are far less than in July and August.” Venturing further afield is an appealing option, especially if there is potential to add a few days to your trip and perhaps even embark on a week-long getaway.
Those seeking some seaside serenity would be wise to consider the Caribbean, where the weather remains balmy, yet the spring break guests have dispersed. And here in the United States, the quintessential summer playgrounds are reawakening, from the lush vineyards of Napa Valley to the shingled shores of Nantucket, and of course, the Hamptons, where New Yorkers will be flocking each Friday for the season.
It all depends on what your ideal itinerary involves. Ahead, find eight destinations that offer a variety of enticing experiences; places that are low-key but high-end, and boast dreamy hotels to ensure you start your summer on a high note.
Road Tripping in the Hamptons
For New Yorkers, there is no better place to spend Memorial Day weekend than the Hamptons: it’s only a three-hour drive (provided you leave early enough), the beaches are beautiful, and there are various ways to experience it, from the surfer-laden shores of Montauk to the glossy boutiques and bistros of Southampton. And although the seasonal rituals resume each year (coffee at Jack’s in the morning; Duryea’s for rosé and lobster rolls at sunset), the Hamptons is constantly reinventing itself and providing new reasons to —be it an exhibition at the Parrish Art Museum, a concert at The Surf Lodge, a wellness retreat at Shou Sugi Ban House, or simply perusing the shopping mecca of Newton Lane, which has been transformed with the arrival of Chanel, Prada, and Louis Vuitton, alongside perennial summertime favorites, Zimmermann and Reformation (ideal for acquiring breezy linen staples).
Given the towns are all so spread out, having a car is vital—how else could you zip to Amber Waves Farm for fresh berries and on to Sag Harbor for a leisurely lunch at Le Bilboquet? Get an upbeat playlist going and venture out east for a good time that is practically guaranteed.
Stay here: One of the best places to stay in the Hamptons is The Roundtree, located in the heart of Amagansett. It has 13 rooms and a collection of cottages that are ideal for families and people who prefer mature crowds over a scene. Although breakfast is served in the morning, there is no actual restaurant on site, however, it’s a two-minute walk to the village, where there are several good eateries including Il Buco—a chic Italian restaurant with some atmosphere. Another great option is EHP Resort Marina, which, by contrast, is one of the very best destinations for dining, with sunset hotspot, Si Si, and Sunset Harbor. It offers spacious residences with fully equipped kitchens and dining spaces, a pool, and a tennis court.
Explore the French Riviera’s Art Scene
Legendary artists including Picasso and Matisse famously drew inspiration from the French Riviera, citing the inimitable light and the spectacular front-row views of the Mediterranean. But over recent years, the region has undergone a creative renaissance, with notable new galleries, including Fondation Maeght (the site of the Jacquemus spring 2024 show), Fondation CAB, and a wave of talent being driven by Plein Sud—a collective of 71 venues that are amplifying the local art scene. “Collectors are also coming to visit the Fondation Hartung Bergman, the Espace de l Art Concret, and Villa Arson, one of the best art schools in France, to get a first look at up-and-coming artists,” says Sibylle Grandchamp, founding member and the General Coordinator of Plein Sud. “You could spend entire days visiting shows and museums,” she adds.
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But, of course, the painterly wonders are just one of many attractions in the French Riviera. The glittering coast—which spans from Menton to Ramatuelle—has a glamorous heritage that has evolved over the decades, and today, it is a mosaic of enchanting references to bygone eras mixed with contemporary opulence. You could explore the medieval village of Èze in the afternoon and enjoy an aperitivo at Ceto at sunset, located at the peak of The Maybourne Riviera—a modern architectural masterpiece overlooking Monte Carlo. For classic seaside glamour, venture to Grand-Hotel du Cap-Ferrat and book the showstopping Dolce Gabbana cabana, or head to the designer-clad beach clubs on Pampelonne (Loulou, La Réserve à la Plage, Jardin Tropezina, Gigi, and the legendary Club 55 are all worthwhile). There are exceptional Michelin-star restaurants (including Mirazur and La Vague d’Or), superior spas (Dior at Hotel du Cap-Eden-Roc is a notable addition), and cobblestoned villages with quaint boutiques and boulangeries. It is a place to immerse yourself in the finer things in life, surrounded by stunning natural beauty.
Stay here: There are three hotels that meet the highest standards of luxury in the French Riviera (and anywhere, really). They include the Grand-Hotel du Cap-Ferrat, perched on a glittering peninsula between Nice and Monaco; the iconic Hotel du Cap-Eden-Roc in Antibes (the preferred choice for celebrities during the Cannes Film Festival), and The Maybourne Riviera—an ultramodern jewel from the group behind Claridge’s. But if you want to experience classic French Riviera glamour, book one of the suites at Hotel du Cap-Eden-Roc and spend the days lounging by pool, attempting the Instagrammable rings and swings suspended above the Mediterranean. The other Grande Dame is the Grand-Hotel du Cap-Ferrat, which has immaculate new villas and palatial ocean-facing suites, featured in Emily in Paris on her fateful trip to what was said to be Saint-Tropez (actually a two-hour drive away).
Take a Culinary Tour of Capri
“The air in Capri is better than Champagne,” declared Italian artist and resident, Raffaele Castello. He wasn’t wrong—the cascading bougainvillea and lemon trees that adorn the Italian isle are sure to revive the senses. Being so geographically blessed has inspired Capri’s cuisine over the ages, and today, you’ll find traditional dishes like insalata caprese with sun-ripened tomatoes, lobster linguine, and zesty limoncello. So, where should one go to experience it all? According to Italy Segreta’s Marina Cacciapuoti, Il Riccio is one of the best daytime spots. “Not only does it offer excellent food and a dessert room to die for, but it also has a wonderful beach club with direct sea access.” A great alternative to the parasol-studded La Fontelina. Cacciapuoti’s evening favorites? The family-operated trattoria Da Gelsomina, where they produce their own wine on-site; Da Tonino for the delicious eggplant parmigiana; Giorgio al Cucciolo for the priceless sunset views; and Le Grottelle, a recommendation that is echoed by Founder and CEO of Bellini Travel, Emily FitzRoy. “On a warm clear night when the moon is full, this is one of the most romantic places in the world,” FitzRoy explains. “It is built into the rocks (the kitchen and cellar are in a cave) and nestling amidst pine trees not far from the Arco Naturale.”
The Italian travel expert also suggests Torre Saracena. “It is tucked into a little cove with a private beach, and is a superb place to spend the day,” she says. “Sea urchins and tartufi del mare are delivered at regular intervals, but make sure you save room for the grand finale - a splendid soufflé that is as large as a Christmas panettone.” Cacciapuoti explains that May is the perfect time to visit Capri: “There s a great energy from establishments and locals who are excited to start the season, rather than overwhelmed by crowds.” Those crowds can average twenty-thousand day-trippers during the peak of summer, so making the trip early on is a smart move.
Stay here: The most notable place to stay is the oldest and the newest: Hotel La Palma, Capri’s first hotel, which dates back to 1822, was relaunched by the haute hoteliers at Oetker Collection (the group behind Hotel du Cap, Eden Rock, and Jumby Bay) last summer. The 50-room hotel is centrally located by the Piazzetta, with three restaurants and bars on-site and its own private beach club, Da Gioia located at Marina Piccola, where many of Capri’s most renowned summer hangouts can be found.
Sun-Soaked Days in St. Barts
The Caribbean’s most elegant island has been revamped over recent years, with a crop of new restaurants and revered hotels that have unveiled multimillion-dollar makeovers (a necessity in the aftermath of Hurricane Irma). If you’re into the beach club scene, enduring hotspots Shellona and Nikki Beach have some competition, with Cannes stalwart La Guérite setting up shop alongside bohemian newcomer, Gyp Sea, centrally located in Saint-Jean. Over in Gustavia—the main town center—La Petite Plage is the buzziest restaurant to open since Bonito became a celebrity magnet over a decade ago. And last month, the same group launched a chic piano bar, Le Café, for dinner with a side of nightlife. From boutique shopping to coastal hikes, Moke rides, and hopping around stylish beach clubs, there is a lot to do beyond the standard island itinerary spent sunbathing within the confines of your resort. But if a more low-key agenda appeals, it’s also a great place to relax with a book, given the abundance of beachfront hotels that give you no reason to leave. As you might expect from such an affluent destination (that counts the likes of Jeff Bezos among its guests), there are some showstopping hotels that surpass the typical five-star standard, including LVMH’s supremely luxurious Cheval Blanc, Rosewood Le Guanahani with its charming candy-colored villas, and, of course, Oetker Collection’s Eden Rock, which is so iconic, it has a dedicated Assouline book.
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Stay here: Travelling as a group? If you want to do so in the most luxurious fashion, book the sprawling 7,000-square-foot Villa de France at Cheval Blanc on Flamands—widely considered the most beautiful beach on the island. The two-level residence has five bedrooms with glossy marble bathrooms, two infinity pools, a dining room, and its own private spa and wellness center. And if you’re not in the market for something quite so extravagant, Cheval Blanc has a variety of beautifully outfitted rooms, bungalows, and suites throughout the property. It is indeed a bucket-list place that redefines the standards of luxury and is sure to leave you feeling rejuvenated.
Lunch Like the Swans in Palm Beach
The spirit of Slim Aarons and the original jetset lives on in Palm Beach, where cocktail hour can be any hour and Pucci-clad ladies spend balmy days dining on Worth Avenue. Philippe Delgrange, owner of the strip’s most revered restaurant, Le Bilboquet, jokes that these modern-day ‘swans’ are their “gluten-free bread and butter,” dressed to the nines for lunch in the courtyard on any day of the week. It’s standard practice in Palm Beach: leisurely lunches, Chablis-fueled shopping expeditions, tennis, swimming, golf, and on to the next lively locale for drinks and dinner—all activities that make for an excellent holiday destination. Beyond the bustling restaurant scene—with standouts including Café Boulud, La Goulue, Florie’s, Pizza al Fresco, and Swifty’s—it is a naturally beautiful place with a refined ambiance. “I love everything about this special destination—the beaches, the sun, the architecture,” beauty magnate and part-time resident, Aerin Lauder, tells Vogue. “Palm Beach is the perfect mix of old and new. I am inspired by the new generation that is moving to Palm Beach, but there is still a clear sense of heritage and tradition that has never changed.” That heritage can be seen at Whitehall and The Breakers—stately establishments developed during the Gilded Age—and throughout the charming ‘vias,’ filled with Spanish Colonial architecture. But as Delgrange points out, “Palm Beach is more vibrant now than ever,” with modern additions, such as the Royal Poinciana Plaza, and a new wave of affluence—visitors who arrived during Covid and never left. If you’re inclined to order a martini with your Cobb salad at noon, this is the place.
Stay here: The Colony Hotel—lovingly known as the ‘Pink Paradise’—is an iconic establishment that has been the pinnacle of Palm Beach glamour since it opened in 1947. It recently underwent a renovation, and it has been updated with all the requisite contemporary comforts without compromising any of its original charm. There are many highlights, including Swifty’s around the pool (open for breakfast, lunch, and dinner), Tracy Anderson classes on-site, and the new Goop Villa, designed in partnership with New York design firm, Ronan Lev.
Island Time in Antigua
Fly from JFK in the morning and be on the beach by noon, sipping palomas surrounded by palm trees and crystalline waters. That’s the beauty of being so close to the Caribbean if you’re based on the East Coast—it’s easy enough to access for a long weekend of sunshine and rejuvenation, free of too many travel hurdles. As with any destination where itineraries are purposefully designed to be minimal (eat, drink, swim, repeat), your choice of where to stay is key. Jaclyn Sienna India, Founder and CEO of Sienna Charles luxury travel concierge, says that in Antigua, “the only destination our members want is Jumby Bay.” It’s easy to see why—the private island is widely recognized as the finest resort in the Caribbean (up there with Amanyara in Turks Caicos) and is a model of what a truly brilliant all-inclusive resort can be. You won’t encounter any bland buffets or slushy cocktails—the dining scene is distinguished, with three à la carte restaurants offering farm-to-table fare sourced from the island (menus feature lobster, Antiguan conch, and okra from the rustic vegetable gardens). And if you’re in the mood for adventure, you can experience a bevy of watersports—wakeboarding, waterskiing, paddleboarding—and end the day with a sunset cruise. Jumby Bay is a paradise that feels completely removed from the distractions of the real world and is a place where you can truly unwind.
Stay here: The accommodation options on the private 300-acre Jumby Bay island vary enormously: some residences are essentially their own resorts with swim-up bars, private beaches, and multiple rooms—a popular choice for many multigenerational groups. There are also recently renovated villas with outdoor tubs, showers, and pools, and 40 beautifully decorated suites, which are perfect for couples and families.
Wine Tasting in Napa Valley
Visitors have long embraced the signature Cabernets and the laidback country vibe of Napa Valley with equal enthusiasm. With over 400 wineries spread across its bucolic landscapes, farm-to-table restaurants, and elevated boutique hotels, it is a perfect weekend escape, and a popular option for girls’ trips, honeymooners, and, of course, food and wine lovers. “There’s never a bad time to visit but spring is extra special,” explains Linsey Gallagher, president and CEO at Visit Napa Valley. “The new growing season is well underway, and, with the grapevines a verdant and vibrant green, it is storybook beautiful. Plus, it is brimming with live musical performances from world-renowned performers covering all genres of music,” she adds. This Memorial Day weekend, the 11th annual BottleRock Music Festival will take place with headline acts including Ed Sheeran, Stevie Nicks, and Norah Jones. Thomas Keller will also unveil his seasonal pop-up restaurant addendum—a more casual take on Ad Hoc, serving classic American comfort food (a great alternative to his famed restaurant, The French Laundry, where tables can be hard to come by).
Long weekends are always a popular time to visit, so you’ll want to map out your tour in advance and organize your mode of transportation (be it a guide or a private driver). But with such a vast array of options, choosing where to prioritize can feel overwhelming. Our top recommendations? Explore one of the region’s design-driven wineries such as Faust Haus, Ashes and Diamonds, and CADE, along with the more heralded establishments: Quintessa, Clos Pegase, Cardinale, Harlan Estate, and Inglenook—one of the oldest and grandest in the valley. And for a different type of tasting experience, Auberge du Soleil’s director of guest services, Sharon Wyatt, recommends a visit to one of the region’s nearby olive oil producers. “The Mediterranean climate of Napa Valley is not only ideal for wine growing, it’s also perfect for olives, and the start of summer is a wonderful time to take a shaded stroll through the orchards and learn about the region’s other signature crop, and taste how olive oils can enhance flavors,” she says.
Stay here: Auberge du Soleil has long been considered the most luxurious place to stay in Napa Valley, nestled into a 33-acre olive grove on a peaceful hilltop in Rutherford. The 50-room boutique hotel is revered for its Provençal aesthetic and its Michelin-star restaurant, which offers some of the most photogenic views over the valley. A more recent addition to Napa Valley’s luxury hotel scene is the Four Seasons—a group that always captures the essence of a destination, while maintaining their famously high standards. How they’ve done it here? By having their very own winery and tasting room on-site, led by renowned local winemaker, Thomas Rivers Brown. Guests don’t even need to leave the property for their afternoon wine flights—simply wander over from your suite and sample the assortment of complex Cabernets.
Experience New England Charm in Nantucket
Nowhere embodies New England charm quite like Nantucket—an island that is accessible by flight or ferry, thirty miles off the coast of Cape Cod. It’s long been a favorite for preppy East Coasters, and, like other American summer destinations, it comes alive from Memorial Day weekend through to Labor Day, with hydrangea-framed homes that feel straight out of a Nancy Meyers film. Wander around the many public beaches, explore the cafes, boutiques, and antique stores in the main town center, stop for lobster rolls at Millie’s, or try homemade gelato at Juice Bar. Nantucket is a true summer holiday spot, where relaxing with friends and family is the main agenda. But for something a bit livelier, head to Topper’s at The Wauwinet for a lovely al fresco lunch, Galley Beach for a fine dining moment, or LoLa 41 for everything from sushi to burgers with excellent craft cocktails in the evening. The latter is conveniently located close to Nantucket’s most iconic hotel, The White Elephant, which celebrated its 100th anniversary last year with a major renovation. Indagare’s Melissa Biggs Bradley ranks the charming island as a top Memorial Day weekend destination. “Nantucket is a great option for families with kids, couples, or anyone wanting to enjoy the beach before the summer season crowds kick in.” Non-stop flights between New York and Nantucket will resume in May via JetBlue and can often take less time than your daily commute in the city (chartered flights are also available via Tradewind Aviation).
Stay here: The centrally located White Elephant is the most coveted place to stay on the island, with a collection of airy rooms and residences and an excellent restaurant, Brant Point Grill. The property underwent a complete refurbishment last year, and ahead of Memorial Day weekend, it will unveil a full renovation of the Cottages at the Boat Basin overlooking the harbor. If the rooms are booked out, an alternative just down the road is The Brant—a modern 26-room hotel opening next month.