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What do you get when you mix a little Don Draper, a bit of Andy Warhol, a smidge of The Jetsons, and a touch of PeeWee’s Playhouse? The vision of two local architects, the cheerful Vintage Design Hotel Sax is a paean to post-war optimism in the Malá Strana neighborhood, where each of the 23 affordable accommodations are individually decorated with restored vintage furniture and artwork, colorful geometric wallpapers, and retro pieces. Rooms aren’t particularly spacious but are comfortable nonetheless and include amenities like smart TVs, free WiFi, and air conditioning. There isn’t an on-site restaurant, but the lobby bar sells salads and sandwiches throughout the day, and a space off the lobby stocks free coffee and tea, as well as wines and soft drinks for purchase. The complimentary breakfast, however, is served buffet style (you can pay to order à la carte items) and can be enjoyed from the hotel’s fourth-floor terrace overlooking Prague Castle and the Petřín Lookout Tower.

You won’t find a better pool than the one that awaits at this 357-room family-friendly resort situated on the powdery sands of Palm Beach. With cascading waterfalls, a swim-up bar and grill, two outdoor Jacuzzis, and a two-story waterslide, the 8,000-square-foot stunner is every kid’s dream. If more adult-centric diversions are on your wish list, the concierge can arrange catamaran-sailing excursions, deep-sea fishing trips, and snorkeling and scuba-diving expeditions off nearby shores, as well as spa treatments that utilize local ingredients like red mud, seaweed, and aloe vera. The resort’s 10 dining options provide plenty of atmosphere for winding down after a jam-packed day: sample seafood specialties like scallops a la plancha in a setting inspired by the island’s plantation ruins, or watch the sun set over the water, rum punch in hand, from your perfect perch at the pier bar.

In a pastel villa that presides over pine-covered slopes and the deep blue waters of the Ligurian Sea, Belmond Hotel Splendido was a 16th-century monastery before it became a cliff-side luxury hotel at the turn of the 20th century. Today, it is one of Portofino’s most iconic resorts, with 70 sunlit rooms (think herringbone hardwood floors, marble baths, and wrought iron terraces) that have hosted the Duke of Windsor, Ava Gardner, and Catherine Deneuve. You’ll get the VIP treatment while sipping champagne on a sunset cruise aboard the hotel’s Chris-Craft Corsair 36, dining on seabream ceviche at La Terrazza, or indulging in a chamomile footbath at the spa. A shuttle can run you down to intimate sister property Splendido Mare, which overlooks the central Piazzetta and is a dressed-up version of a fishing village pied-à-terre, with 16 whitewashed rooms and its own buzzy restaurant.

Tucked away on the less-trafficked slopes of Mount Portofino, above the picturesque waterfront town of Camogli and scenic Riviera di Levante, Villa Rosmarino is that Italian friend’s vacation house you’ve been dreaming of. Owners Mario Pietraccetta and Fulvio Zendrini left Milanese corporate life to transform this dilapidated turn-of-the-century palazzo into a midcentury-style oasis with touches of Italian modernism, then moved in permanently, inviting others to experience their personal brand of la dolce vita. The library is outfitted with stylish armchairs, warm wood ceiling beams, and a collection of art and travel books that spans the walls, and the living room’s well-stocked honesty bar is the backdrop for friendly nightcaps. Rooms aren’t numbered, and the sprawling gardens are easy to get lost in. Mario and Fulvio are likely to chat guests up while lounging by the pool or sipping espresso on the balcony, offering their insider knowledge about the area and arranging one-of-a-kind excursions, from visits to secluded beach clubs to rides in their wooden motorboat.

Head to the edgy Santa Fe Railyard District—just a 20-minute walk from the plaza—to browse the various contemporary galleries that have taken up residence there. Stroll through the small parks, enjoy a meal at offbeat Southwestern eateries like La Choza and Tune-Up Café, and of course, visit the bountiful farmers’ market to check out the local produce and, in season, the famous Hatch green chile peppers.

Though toma means “take it” in Spanish, this intimate cafe offers far more than takeaway service. Toma’s staff are able to interact with customers while showing off their impressive coffee knowledge (as well as English language prowess). Homemade pastries, cookies, and cakes are available, with some gluten-free options. The current consensus around town is that Toma Café has the best staff, bean sourcing, and know-how on pulling a proper shot. Best coffee in a city of coffee drinkers is a mighty statement, but I’ll stand behind it.

Wine aficionados set their sights on the Guanajuato Wine Route, now perhaps second only in Mexico to the trails in Baja California’s long-established Valle de Guadalupe. While wineries have existed in this region for several decades, San Miguel only recently received official designation as a wine route, thanks to wineries like Vega Manchón (owner Ricardo hails from Mexico City); Bodega Dos Búhos, where art by Peter Leventhal mesmerizes visitors almost as much as the wine; or Vinícola Toyán. Newcomer labels like Santísima Trinidad have joined the old-timers in hosting vendimia events every weekend in August, with Santísima adding extra attractions like polo games and olive-oil demonstrations. No going Sideways for oenophiles here; they will head home with a new wine destination secret—and a bottle or two.

From the first “woof” of welcome from the resident Canine Ambassador, guests feel a part of this storied hotel’s century-plus history. Located in the Back Bay, not far from Beacon Hill, Newberry Street, and the Freedom Trail, the landmarked Fairmont Copley Plaza houses 383 comfortable guest rooms, each featuring modern-elegant decor as well as signature pillow top mattresses, 46-inch TVs, and coffee makers. Snag a room on the Fairmont Gold concierge floor for extras like private check-in, complimentary Wi-Fi, and use of a snack-stocked lounge.

Sweeping views of the city can be enjoyed from the 3,000-square-foot rooftop gym (which is lined with floor-to-ceiling windows) and the sophisticated event spaces (which, decorated with chandeliers and ornate furnishings, are a top pick of Boston brides). The hotel’s convenient location makes it easy to sample the city’s great eats, but you’ll do well if you stay in, too, thanks to the handcrafted cocktails and farm-to-table dishes served at the on-site OAK Long Bar + Kitchen.

Located in the charming neighborhood of Colonia Lafayette, Hotel Demetria is among Guadalajara’s trendiest boutique hotels. In addition to stylish rooms, a rooftop pool, and a popular restaurant, the hotel features a contemporary art gallery and bookstore on its mezzanine level. Even more impressive, however, is the fact that the steel-and-glass structure is sandwiched between two pieces of architectural history—Casa Franco and Casa Quiñones, designed by Mexican modernist masters Luis Barragán and Pedro Castellanos, respectively.

Located in the middle of New York harbor, less than half a mile from Manhattan (and even closer to Brooklyn), 172-acre Governors Island feels like a world unto itself, far from the bustling city. It has played a key role in the defense of New York at various points and two fortifications here, Fort Jay and Castle Williams, reflect that history. From 1966 to 1996, the island was a Coast Guard station; since it closed, the city, state, and federal governments have discussed various plans for the island’s development. In the meantime, it is open to the public for six months each year, from May 1 to October 31, when it is possible to wander among the Coast Guard barracks, visit the commander’s house, and bike around the mostly car-free island. Ferries depart from both Manhattan and Brooklyn starting at 10 a.m. and running until 6:15 p.m. on weekdays and 7 p.m. on Saturday and Sunday. During many weekends in the summer, art fairs, food festivals, and other events help draw visitors to the island, but even if you go on a day without anything special scheduled, a journey here provides a refreshingly different perspective on New York.

The Old Town’s main street, Stradun, also known as Placa, can’t be missed—it’s the biggest and widest of all the thoroughfares, and you will probably walk it several times during your stay here. It’s especially nice in the late afternoon, when the angle of the sun makes the pavement shine and the swallows soar overhead. Continue down to the old port and along the waterfront to the far end. Porporela Pier, built courtesy of the Austrian administration’s rule in Dubrovnik during the 19th century, is today somewhat of a lovers’ rendezvous. After your stroll, the benches along the pier provide a simple relaxing moment to take in the views of Lokrum island and Cavtat in the distance.

The location for the most charming scenes in the movie Amélie, this once-forgotten neighborhood is now a destination for the young and fun-loving. As soon as the weather turns warm, picnickers line the paths along this 19th-century waterway, watching bridges rise and turn to allow barges to pass. Shopping, food, drink, and diversions also abound here: Artazart (83 Quai de Valmy) is recognized as one of the best design bookstores in Europe, while Le Comptoir Général, just across the bridge, offers live music and cheap drinks. Chez Prune has one of the city’s most popular terraces for enjoying a glass of something refreshing and a chance to watch Paris go by.

Everyone who visits Santa Fe walks along the famed Canyon Road. Originating as an old footpath that once accessed water, it now primarily showcases an expansive range of shops and galleries with Native American art and landscape paintings. A stroll is not complete without a stop at one of the award-winning restaurants, a la Geronimo and the Compound.

The 20 de Noviembre market has a variety of food stalls where you can sample many Oaxacan specialties, but carnivores flock to the one corridor that’s known as “El Pasillo de las Carnes Asadas” (the grilled meats aisle). Follow your nose to find it: smoke and the smell of meat grilling are thick in the air. You can select the raw meat that looks best to you and have it grilled to your specifications as you watch on. Find a spot at one of the long tables with benches and order salsa and guacamole to accompany your feast. Buy some tortillas from one of the passing vendors, and enjoy!

Nearly 1,000 years after the once-powerful central Mexican city of Cacaxtla was abandoned, would-be looters of the hilltop palace ruins came across fantastically well-preserved and still colorful murals painted in a somewhat puzzling Mayan style. Excavation continues today under an enormous protective shed roof. The Mural del Templo Rojo, pictured, adjoins a stairway leading to the Governor’s Room. The huge nearby Mural de la Batalla, dating from 700 CE or earlier, is a grisly blood-and-guts depiction of a fierce battle between “jaguar” and “bird” warriors. The relatively un-touristed site is a short drive from Tlaxcala, slighting longer from Puebla. You come away from a slow stroll through the labyrinthine ruins with the feeling that centuries of mysterious history have seeped into your heart and bones.