This was the hottest summer on record, so it makes sense that holidaymakers flocked to breezy destinations to escape the city heat. But while July and August are always the most popular months for going on vacation, heading away in September and October is a great way to sneak in a break without crowds and excessive price tags—while still taking advantage of some final summery weather. From island escapes in the Caribbean to grande dame European hotels, these elegant lodgings will help kick off fall on a relaxing note.
Cap Rocat, Mallorca
For something truly unique, venture to Cap Rocat in Mallorca, which is one of the most spectacular resorts in the Balearic Islands. The place is set in a medieval fortress that has been reimagined with ultra-luxurious architecture and décor, and many of the rooms are appointed with private pools and sun loungers facing panoramic views across the Bay of Palma. The scene is particularly spectacular at the Sea Club restaurant, which has some of the best dining on the island—and a wine list to match.
Le Sirenuse, Positano
The spirit of summer in Italy is brought to life at Le Sirenuse, positioned right in the heart of Positano, A favorite since its opening in 1951, the family-owned boutique hotel offers the perfect vantage point for looking out at the yachts on the Mediterranean and the vibrant vertical village that has become a defining feature of the Amalfi Coast. Enjoy classics like spaghetti alle vongole, branzino, and tiramisu at the famed terrace restaurant, La Sponda, and a relaxed itinerary of lounging by the pool with an Aperol Spritz in hand, or sailing out to Capri on the hotel’s vintage boat. “Le Sirenuse transmits an old-world charm and elegance, making each and every guest feel special,” says owner Antonio Sersale.
Jumby Bay, Antigua
All-inclusive resorts in the Caribbean are easy to find, but those that meet the standard of Jumby Bay are not. The Oetker Collection-owned resort is in a class of its own, thanks to its location on a private island off the coast of Antigua, just a four-hour direct flight from New York. Jumby Bay has all of the hallmarks of an idyllic beach destination: flawless stretches of palm-backed white sand; turquoise blue waters; and modern architecture that complements the natural environment. There is also a long list of on-site activities from which to choose, including watersports, an exceptional spa and wellness center, tennis courts, a kids’ center, bicycles, cooking classes, Pilates classes, and three pools. Best of all, the 300-acre island has only 40 suites and rooms, in addition to a limited number of private residences, so it never feels crowded.
Amanzoe, Porto Heli, Greece
Located in Porto Heli (a short speedboat ride from Hydra and Spetses), Amanzoe is a hilltop sanctuary that resembles a modern-day Acropolis. Like many of Aman’s properties, the resort is set around a UNESCO-protected heritage site and boasts stunning, 360-degree nature views. There is also complete privacy—it’s a place to fully switch off and recharge. The resort is arranged like a traditional Peloponnese village, albeit with Aman’s signature gloss, so expect a chic, minimal design, neutral colors, and locally-influenced décor.
Belmond Hotel Splendido, Portofino
Portofino is having a moment, and there is no better place to soak in the romantic la dolce vita vibe than at Belmond Hotel Splendido. Originally a monastery, the hotel occupies a prime position high above the town, with incredible views of the bay and the piazzetta. Belmond certainly knows how to do Italian glamour well (think the Cipriani in Venice, Grand Hotel Timeo in Sicily, and Hotel Caruso in Ravello), and Splendido provides a similarly authentic, elevated experience. The 70-room hotel is close to Cinque Terre and vineyards where guests can enjoy wine tasting excursions—though, once you’re here, there are very few motivations to leave.
Le Sereno, St. Barths
Saint Barth’s is back in business after the devastation caused by Hurricane Irma in 2017, and many of the properties have been rebuilt with fresh new design and extensions. One of those is celebrity favorite Le Sereno, a boutique resort located in Grand Cul de Sac on the northeastern end of the island. Last December, the resort was reopened with all-new waterfront suites and bungalow rooms surrounding the much-Instagrammed pool, along with a new spa and fitness center, a boutique with elevated menswear from Milan (a nod to its sister property in Lake Como), and a restaurant extension leading onto the beach. The suites at Le Sereno are well appointed (there are even Havianas for guests to use), but the stars of the property are the palatial, 7,000-square-foot villas that are perfect when traveling with a group.
Hotel du Cap-Eden-Roc, Antibes
With swings leading into the ocean and an infinity pool positioned on the Cote d’Azur coastline, Hotel du Cap-Eden-Roc is the perfect place to revel in the dog days of warm weather. There are an ice cream and juice bar and fabulous restaurant that serves fresh, uncomplicated dishes with locally-sourced produce, and until the end of October, the hotel will have several sculptures on display from renowned artist Anthony Cragg, adding yet another reason to visit.
J.K. Place, Capri
Since opening in 2007, J.K. Place has earned a reputation as one of Capri’s most fashionable summer destinations. It feels like the private home of somebody with exceptional taste, with the plush spaces adorned with coffee table books, framed photographs and art, fresh flowers, and colorful accent furniture. There are only 22 rooms, most of which overlook the Bay of Naples and Mount Vesuvius. And while the hotel is close enough to the action in Capri, it has the vibe of a secluded retreat, thanks to a frame of manicured gardens and glistening ocean views.
Villa Dubrovnik, Dubrovnik
Game of Thrones has made Dubrovnik quite the tourist trap, but it takes just a short boat ride from the old town to ditch the crowds and find one of Croatia’s most elegant resorts. The main draw of this modernist Villa Dubrovnik is the whitewashed sundeck that descends into the Adriatic—it’s the prime position to park up for a day of swimming and dining al fresco, with views of the town glittering in the distance. There’s also a fantastic spa and wellness center and an excellent Michelin-starred restaurant, Pjerin, that offers inventive tasting menus and an impressive cellar of Croatian wines.
COMO Parrot Cay, Turks & Caicos
Low-key but high-end is the vibe at this stylish Caribbean retreat which, like Jumby Bay, is located on a private island. In keeping with the COMO brand ethos, COMO Parrot Cay offers an extensive range of wellness activities including yoga, healing sessions, meditation, and Ayurvedic consultations, so if you’re looking to start the season feeling revitalized, this is a good place to consider. Naturally, the dining options are fresh and healthy, incorporating the latest superfoods and elixirs—but unlike many other wellness retreats, you can swap out the green juice for a pina colada, if you wish. The resort offers a mix of rooms and private villas, making it appropriate for couples, families, and groups alike.