PARIS AND NORMANDY
Paris has a lot to brag about—The Eiffel Tower, the Mona Lisa—everything from the effortless je ne sais quois sense of style to the impossible flakiness of their croissants. Paris can also point to its reputation for being a haven for the artists among us. At Le Royal Monceau, take advantage of their in-house art concierge. The sleek hotel not only has its very own gallery, but the building itself, redone by the skilled hands of Philippe Starck is a work of art all of its own. Just a two-hour drive from the City of Light, La Ferme Saint Simeon sits atop the heights of Honfleur on the Normandy coast. The 17th century inn, surrounded by verdant gardens and commanding a panoramic view of the Seine Estuary, was the favored meeting place for the Impressionist masters. When you check in, make a point to look out over the river—the lights you see glimmering on the Seine are the very lights that inspired Monet, Corot, Courbet...the list goes on.
SPAIN AND MOROCCO
Despite being on different continents (to be fair, they’re only nine miles apart at the Strait of Gibraltar), Spain and Morocco are a perfect pairing. Start in Madrid—the flight is shorter and the culture shock gentler—and check into the Hotel Ritz. Decked out in regal threads (literally: the hotel still sources its fabrics from the Royal Tapestry Factory) it’s right next to the Prado and surrounded by bustling tapas bars. An hour’s flight away, Marrakesh is a brilliantly, charmingly chaotic, particularly in the souks and the buzzing main square, Jemaa el-Fna. Overlooking the swirl of activity is La Mamounia Hotel, whose Moorish-inspired majesty—ornate tiling, gilt-lined pools, acres of gardens—rivals that of the Ritz.
SAME BUT DIFFERENT: Both countries are culturally rich—food, the arts, literature—and it’s easy to see the influence they’ve had on one another over the centuries. Take, for instance, the Moorish-style architecture of Madrid’s Plaza Mayor and Las Ventas bullring, or the broad boulevards and cafés of Marrakesh’s Guéliz area.
THE MALDIVES AND DUBAI
Is your dream vacation to experience luxury in the middle of nowhere? Why not pair a stay on a remote private island with a stop in the middle of the silent desert? Naladhu Maldives is like that island paradise screensaver come to life: a tiny island with clusters of swaying palms and just 20 thatch-roofed, butler-serviced, personal pool–equipped villas. All this seclusion is just a 30-minute speedboat ride from the international airport. Break up the long flight home with an extended layover in Dubai, so you can drive out into the Arabian Desert. Flung far into the dunes, Al Maha offers falconry, 4x4 rides and horseback riding, but you’re hardly roughing it. The suite-like tents come complete with pillow menus and plunge pools.
SAME BUT DIFFERENT: These places are both “once in a lifetime” destinations—out of the way and over the top—that go together like yin and yang. Before you go, download a stargazing app: With the utter lack of light pollution in both spots, the constellations seem close enough to touch.
LONDON: TOWN AND COUNTRY
The royal family has done it this way for centuries: do your city business in London, then retreat to the countryside for more pastoral pursuits. Buckingham Palace and Windsor Castle aren’t in the business of accepting hotel guests, but we know places that are nearly as splendid. The Rosewood London updates the quintessentially English hotel experience—valets wearing tweed, an afternoon tea with cakes inspired by contemporary artists, rooms with a posh residential vibe. After faffing about, head an hour outside the city to Cliveden House, a grand manor on an even grander 376-acre estate. Stroll the gardens, take a vintage launch onto the Thames, shoot clays (sorry, no fox hunting), and pretend you’ve slipped back to a realm where Mr. Darcy is still wooing lovely ladies at over-the-top balls.
SAME BUT DIFFERENT: Combining a stay in the bustling, wrong-side-of-the-road-driving city with an impossibly grand stop in Berkshire will tick all of your Anglophile boxes. Assume a noble title and kindly pass the Devonshire clotted cream.
BUENOS AIRES AND MENDOZA
Tango, steak, wine. No place is more blessed with this holy trinity than Buenos Aires, the vibrant capital of Argentina. You’ll see its European flair in the Parisian-style boulevards and the Old World Alvear Palace Hotel, in the ritzy Recoleta neighborhood. In the Puerto Madero area, the Faena Hotel Buenos Aires epitomizes the city’s entrepreneurial, artistic side. Both are bursting with life and flavor. After tango-ing the night away, head to Mendoza, where nearly 70% of Argentina's vineyards are located. Snugly positioned between some of the area’s top makers of malbec and torrontés, you’ll find Cava Wine Lodge. The 18 Spanish Colonial–style rooms with sun-drenched patios and stone staircases overlook the property’s own 60 acres of curling vines.