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American sommelier Brian Patterson, his wife, Jenn, and their massive Leonberger-Retriever mix, Bear (the Beartender!) are the consummate hosts at Lisbon’s newest, most interesting, and surely smallest wine bar. Located on pretty Praça das Flores in Principe Real, Patterson curates his all-natural wine list with a laser focus on small producers from around Portugal. He sources his finds on reconnaissance drinking missions around the country, including some of Portugal’s more underdog wine regions. His updated-daily chalkboard menu includes a half dozen or so offerings by the glass (€3.50-7) along with two batch cocktails, as well as intriguing bar snacks to accompany (his hummus is destination-worthy in and of itself). The bar doubles as a bottle shop; rightfully so, there is only room at the bar for about 11 provided everyone is sucking in their wine guts. File under: Wine Revelation.

When Nashville natives Ann and Jack Waddey decided to open a hotel within walking distance of downtown, they went all out to make guests feel at home. In lieu of a traditional reception area, visitors check in using their mobile device at the virtual front desk, and though daily housekeeping services are available, staff goes off duty at night. The property’s 24 residence-style suites feature bedrooms with separate living areas, each decorated with dramatic tropical wallpaper offset by white furniture, as well as full kitchens with stainless-steel appliances and penny-tile backsplashes; naturally, they’re stocked with hyperlocal goods like Bongo Java coffee, or whatever you wish should you opt in to the hotel’s grocery program. Rounding out the list of homey amenities are C.O. Bigelow products and velvety robes in the bathrooms, plus dry cleaning services and free parking.

This luxury hotel melds historic charm with 21st-century designer sass. Located deep in the middle of Barcelona’s bustle, it occupies a 1920s building that’s been lovingly reworked by architect Oriol Tintoré. Original features, most notably the winding neoclassical stairway, are immediately apparent in the stately lobby entrance, and these heritage touches continue into the hotel’s public spaces and many of the rooms. Not that the rooms are traditional; on the contrary, they’re very slick, decked out with modern conveniences such as media hubs, complimentary minibars (restocked daily), and rain showers. The rooms, arranged so they face outward, are generously flooded with daylight, which highlights the restrained color palettes and elegant wooden floors. Shared facilities at the hotel include a roof terrace with infinity pool, a Mediterranean bistro-style restaurant, and a comprehensive spa and wellness center.

The hippest kid on the block has risen from the most unlikely of origins: the Fenway Motor Hotel, a run-down mid-century relic that once housed all manner of misbehaving musicians. Today the hotel feels more like an of-the-moment Los Angeles enclave, with mid-century furnishings, floor-to-ceiling Mondrian stained-glass windows, and upscale bathrooms. Local music and pop-culture memorabilia decorate the rooms and foyers, from framed Boston Phoenix covers (the city’s now-defunct alt-weekly) to vintage speakers and ‘70s-era phones.

In keeping with the rock-and-roll theme, both the lobby and the outdoor pool area regularly host live music. Lansdowne Street, home to legendary clubs like House of Blues, is just steps away, and of course no visit to Boston is complete without a stop at next-door Fenway Park (tours of the ballpark are available daily and year-round).

A delightful peach-colored villa set directly on Treasure Beach, this Jamaican-owned guesthouse is a gem, and feels more like a vacation home than a hotel. There are six spacious guest rooms and two larger suites, each with their own patios or balcony with a glorious sea view. The interior is intricately decorated with carefully chosen African-themed paintings and sculptures, and the owner—who returned after many years in the US—takes pride in providing true Jamaican hospitality. There’s a bar and no restaurant on site, but that doesn’t prevent the large kitchen and staff cook from taking your daily orders for breakfast and dinner, dishing out excellent local specialties that are served poolside with the sea in front of you. It’s one of my favorite places to stay and get away from it all.

Thai cuisine, with its balance of three to four fundamental taste senses, may be complex but that doesn’t make it difficult to pick up the basics. Bangkok has a plethora of cooking schools, some of which are attached to renowned Thai restaurants such as Bo.lan and Blue Elephant. Blue Elephant is one of the most respected venues in the city and its tuition reflects its exalted status. Two courses are offered daily, with the morning session featuring a visit to a local market and the afternoon session including a detailed introduction to Thai ingredients. A homier option is Amita Thai Cooking Class. Classes are held in an antique canalside home and include an explanatory visit to the resident herb garden.

You’d be hard-pressed to find a better view of Hamilton Harbour than the one at Newstead Belmont Hills, where the 60 one-, two-, and three-bedroom suites satisfy the Airbnb set with in-room kitchens, Jacuzzi tubs, and sleeper sofas. Though there’s no on-site beach, the resort’s shuttle can transport you to the nearest shoreline (about 10 minutes away), and a private water taxi is on hand to ferry guests to the restaurants and shops of Hamilton. Care to stay put? One visitor per room is gifted a complimentary round of golf on the property’s championship 18-hole course with your stay, the harbor-front infinity pool and club becomes one of Bermuda’s top happy-hour scenes come sunset, and Beau Rivage, the island’s only French restaurant, is renowned for its Gallic specialties such as Provençal shrimp risotto and foie gras–stuffed beef Wellington.

With no sign above its unassuming storefront, Tartine is most easily recognized by the line that snakes out its door and down Guerrero Street. People patiently wait for flaky pains au chocolat (the best outside Paris, in my opinion), decadent banana cream tarts, and hot-pressed sandwiches stuffed with fillings like smoked sheep cheese and quince jam. The bakery’s James Beard Award–winning pastry chefs also turn out loaves of stone hearth–baked bread, available every day after 4:30 p.m. Nurse a coffee and nibble on a croissant at the communal table, or take picnic provisions to nearby Dolores Park.

Every day at noon at the Plaza de Armas (also called Plaza Mayor), trumpets blare, drums pound, and cymbals crash as the guard changes outside the presidential palace. Enjoy the Spanish fanfare like a local: from a plaza bench with an ice cream cone. The Plaza is also the site of festivals, concerts, and the much-loved annual National Pisco Day when the fountain spouts free high-proof grape brandy for all.

Nothing defines Boston quite as much as the town’s devotion to sports (10 championships since the turn of the century doesn’t hurt), and with all due respect to the five-time-Super-Bowl-champion Patriots, it’s Fenway Park, not Gillette Stadium, that’s the temple of sports fandom. Opened in 1912, the quirky green bandbox between Lansdowne Street and Yawkey Way is almost as famous for its obstructed-view seats as it is for its fabled Green Monster wall in left field, but that’s a price Sox fans gladly pay in exchange for maintaining Fenway’s historic layout. It’s both intimate and loud on game day even in years when the Sox aren’t contenders (tickets are often hard to come by, so plan ahead); the old ballpark also is open for one-hour, behind-the-scenes tours that take you inside and atop the Green Monster. You’ll be able to stroll around the field (the warning track, not the grass), and visit the press box, the Pesky Pole, and (on days with no games) the dugouts and bull pens.

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

Singapore may not have bicycle lanes on its roads, but the country does have a wonderful and growing network of bike-friendly asphalt paths along its many canals and rivers that are sometimes joined up with pathways in parks and along old rail corridors (in Singapore, they’re called park connectors). An easy 3-mile round-trip stretch to sample runs along the Singapore River. Join the riverside pathway just off Zion Road near the Great World City shopping mall—you can rent your chariot nearby from Bike Connect, at 23 Hoot Kiam Road—or grab a two-wheeler from the now ubiquitous bike-share steeds parked everywhere. Pedal all the way to the old shophouses of Boat Quay where the river empties into Marina Bay and then the South China Sea at the heart of Singapore’s colonial core. From there, get a glimpse of the grand Fullerton Hotel (once the national post office), the Asian Civilisations Museum (originally intended to be the city’s courthouse), and several historic bridges.

The end to a perfect day in Bozeman is waiting for you somewhere on the doorstep of the beautiful Lehrkind Mansion Bed & Breakfast, quite possibly the most picturesque building in all of Montana. The Victorian marvel is a perfect base for a few days of exploring Bozeman, with a great library filled with inspiring tomes and photography books that will stir your Montana wanderlust further. Each of the mansion’s nine rooms has its own unique character, though The Muir Room is where you want to stay if you’re a writer looking for a spark.

A popular and new cultural attraction in Montego Bay, the Rastafari Indigenous Village offers a fun and insightful day of Rastafari history, music and food to anyone interested in immersing and learning about this unique group. The day begins with a hike to the village, reached by spelunking across a river, and a medicinal plant tour. It continues with various activities, including culinary demonstrations of Rasta “Ital” or organic, vegetarian dishes, drumming circles and stories on the evolution and struggles of Rastafari culture in Jamaica. It’s an easy reach—about 20 minutes from Montego Bay—and a good pick for those short on time.

Central Plaza is a lovely place to spend the day and watch the community wind down in the evening. During the day, the plaza is full of music and children playing, and the surrounding streets are full of restaurants, shops, and art galleries. As the sun sets, the plaza gets quieter; the town’s lights turn on, and the children leave, one-by-one, to go home for the night. Stay late and enjoy the peace and quiet of the sleepy plaza, or head down one of the side streets and partake of the local nightlife!