It can be easy to feel overstimulated when you first visit one of Japan’s immense, neon-soaked cities, but Osaka’s manageable scale means travelers can find their footing quickly. Which is handy as there’s so much to do and see, from nonstop shopping to people-watching and barhopping at Amerikamura, the bustling equivalent to Tokyo’s Harajuku. Hotel New Otani Osaka perfectly captures the spirit of this old-meets-new city, facing both skyscrapers and the towering, white-green Osaka Castle, and is especially lovely during cherry blossom season. As an extra bonus, 15 on-site dining outlets, including several lauded Japanese eateries, mean you’re seconds from top-class cuisine.

Spend any time in Rome and you’ll know that Italy just gets it when it comes to delivering wow-factor cities. Ancient and rooted in romance—it was the fabled home of Romeo and Juliet, after all—Verona is a case in point. A center for the arts, each summer it hosts a celebrated opera festival in its first-century amphitheater. And, much like the capital, it’s a strong proponent of la dolce vita, where serving exceptional Italian wines and dishes is a source of pride. Housed in a grand Renaissance villa, Byblos Art Hotel Villa Amistà is a worthy ambassador for the city, deftly blending beautifully curated modern touches with an obvious affection for its remarkable history. And with an unexpectedly bold art collection, a night here also grants you access to works from the likes of Jean-Michel Basquiat, Cindy Sherman, Sol Lewitt and many more. 

With some 700 paradisiacal islands to its name, you could vacation around the Caribbean indefinitely, but connoisseurs know there’s too much diversity across this idyllic region to stick to just one country. Comparatively unknown—and justly nicknamed the "Nature Island"—Dominica is ripe for discovery. Two-thirds covered in rainforest, it’s ribboned with hiking trails that reveal volcanoes and hot springs. And with a stay at the sustainability-minded Rosalie Bay Eco Resort and Spa, set across grounds flush with ginger lily and frangipani, you'll feel at one with nature. Meals feature produce from the resort’s organic garden, a riverfront spa offers rejuvenating treatments, and—perhaps most magical of all—leatherback, green and hawksbill turtles nest and hatch on the bay’s dramatic black-sand beach. 

A substitute for New York City? It might seem like a tall order, but when it comes to capturing the creative spirit of pre-’90s NYC, Detroit delivers. The "comeback city" where both Motown and techno were born still pulsates with music, and the city’s crammed with bona fide cultural heavyweights like the Detroit Institute of Arts, as well as up-and-comers in the Sugar Hill Arts District. The city’s entrepreneurial spirit also gives New York energy when it comes to stays: The Shinola Hotel is one fine example, where Detroit's eponymous label for watches and leather goods has moved into hospitality with a knockout property. With loft-style windows and packed with art, it’s flawlessly curated but feels cozy (plenty of working fireplaces help with that). Stellar dining’s on offer, too: Chef Andrew Carmellini (himself an NYC stalwart) oversees on-site Italian restaurant San Morello.

Paris is often regarded as Europe’s capital of romance, so it does have an edge on Brussels when it comes to branding. But these two continental powerhouses, separated by an 80-minute Eurostar train journey, have plenty in common. Brussels’ gorgeous Gothic squares and art nouveau landmarks are effortlessly explorable thanks to the relatively compact, largely pedestrianized city center. Plus, it’s exceptionally multicultural, so you’ll find every regional cuisine on offer across casual sidewalk cafés and ritzy restaurants. As for where to stay, the new Corinthia Grand Hotel Astoria Brussels sits regally in a belle epoque building and features a swish subterranean Sisley spa. Though rates here aren’t low, it feels like excellent value for a hotel of this quality when compared to the palace-stamped hotels you’ll find in Paris.

Of course, London is unmissable if it’s your first time visiting the U.K., but plenty of Brits will tell you that Liverpool is England’s most gregarious, welcoming city. Its nightlife—colorful, eclectic, super-friendly—is legendary. Famously the birthplace of The Beatles, it's also home to high-profile football clubs, so on matchdays it’s seriously buzzy. An important port city for centuries, Liverpool’s heart is its handsome assembly of statuesque waterfront buildings. Occupying a converted warehouse along nearby redeveloped docks, the Titanic Hotel packs in character and urban allure, nicely complemented by its huge rooms and drinking-and-dining offerings that extend from its lively Rum Bar to a traditional, can’t-get-more-British-than-that afternoon tea.

While perennially popular Tulum is a great introduction to Mexico, savvy travelers are wise to explore more: Just three hours away by car, in a relatively remote area near the border with Belize, beautiful Bacalar offers a more serene setting. Named one of Mexico’s “Pueblos Mágicos,” it straddles an immense emerald lagoon, where guests can kayak through thickets of mangroves or dangle, book in hand, from hammocks. Casa Hormiga, with its cool concrete walls softened by lush greenery, fits Bacalar’s bohemian, effortlessly cool vibe perfectly. Days here are a medley of complimentary yoga sessions, spiritually minded spa treatments and nonchalant lazing at the waterfront beach club, all at remarkably reasonable rates.