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Hailed as one of the country’s first true boutique hotels, Hotel San José started its life as a 1930s tourist court and became a 1950s roadside motel before falling into disrepair in a bad part of town. In the mid-1990s, Liz Lambert bought it and transformed it into a minimalist, mid-century–inspired hot spot, the first of her distinctive Bunkhouse hotels, and the South Congress neighborhood changed with it. Although it’s now a must-visit for out-of-town hipsters (and its bar a hangout for trendy locals), the hotel stays true to its roots; a majority of the furniture was made by local artisans from reclaimed wood and Texas leather, the three most affordable rooms have a shared bath, and Lambert’s experience renovating the hotel and contributing to the neighborhood’s gentrification prompted her to make the documentary The Last Days of the San Jose.

Nowadays, SoCo is Austin’s hottest neighborhood, and Hotel San José is in the heart of the action, hosting local and touring bands in its courtyard and parking lot, and offering some of the city’s best coffee at Jo’s, its affiliated café. Plan to spend at least one evening making new friends over Shiner Bocks at the long tables in the courtyard lounge.

The bustling corner of Walnut and 17^th streets is anchored by the Latham, a stone-and-brick tower built in 1907 as luxury apartments for moneyed Philadelphians. While other Center City historic structures met their demise in the late 1960s, a group of investors doubled down on the stately building, transforming it into Philadelphia’s premier business hotel in 1970. The prestigious address completed a top-to-bottom renovation in 2011, bringing the Latham firmly into the 21st century while preserving period artifacts and style.

True to its apartment roots, arriving at the hotel is more like entering a tony doorman building, and the Latham’s residential roots bestow spacious guestrooms with tall ceilings, bay windows, and big bathrooms. Gold and gray hues are complemented by pops of blue, while big bathrooms keep it simple with a tub/shower combination.

There are now 35 locations of Eataly, the massive Italian food hall, around the world, with 18 of them in Italy itself. The New York City one at Fifth Avenue and 23rd Street, which opened in 2010, was the first in the United States (it’s been joined by others in Boston, Chicago, and Los Angeles, as well as by a second outpost in Manhattan, near the World Trade Center site at 101 Liberty Street). For connoisseurs of all things Italian, this is a must-visit—or, more accurately, a must-shop and must-eat stop. Covering more than 50,000 square feet, Eataly NYC Flatiron includes five different restaurants (plus occasional pop-ups) offering opportunities to graze on antipasti, fish, pizza, and other dishes. A popular rooftop beer hall is open all year round (thanks to space heaters and a retractable roof). While you will want to eat your gelato on the spot, there are also a number of stores where you can buy gifts from biscotti to olive oils to take home a little bit of Italy via New York.

Located in the wine-growing region of Oberbergen, this long-running restaurant earned a Michelin star way back in 1969—and has held firmly to it ever since. Owner Fritz Keller’s family has been producing and importing wines since the 19th century, and Schwarzer Adler is very much an oenophile’s spot, with a list that spans around 2,500 labels (including bottles from the Keller estate as well as other European wines, with a focus on Burgundy and Bordeaux). The Francophile menu—designed by long-standing chef Anibal Strubinger (who continues to support the team alongside new head chef Christian Baur)—perfectly complements the wines, with dishes like liver pâté, lobster, and poulet Bresse with black truffles. Adding to the food’s classic feel, the dining rooms are old-fashioned and intimate, with wood-paneled walls and vintage tiled stoves. Service is friendly and efficient, and there’s a small terrace for dining outdoors in nice weather.

It was raining when we arrived in Donostia-San Sebastian, but the skies cleared on our second day, and we rode the funicular railway up Mount Igueldo to take in the view back on the city, La Concha Bay, and the empty beach. The “low” travel season had just begun, and the strange little children’s amusement park on the mountaintop had shuttered up for the fall and winter, adding just the right disorienting touch of weird desolation to the Basque country panorama.

A belle epoque grande dame presiding over San Sebastián’s iconic La Concha Beach, the Hotel de Londres y de Inglaterra has been a palace, casino, hospital, and of course hotel since its construction in 1865. Before and after World War I, it was the kind of place where well-to-do Europeans went on seaside holidays for months at a time, enjoying direct beach access, the city’s renowned seafood, and the hotel’s elegant design. Nowadays, the society consists of a somewhat less star-studded lineup—once Toulouse-Lautrec, Archduchess Elizabeth of Austria, and Mata Hari were all guests—but the unobstructed Bahía de la Concha views, lovely rooms (all with private balconies), and pride of place at the heart of the city remain. The window-lined brasserie takes its cue from classic French bistros—it’s not hard to imagine that the well-dressed gentlemen at the next table are French aristocrats-in-exile—and its tables along the beachfront promenade are the perfect place to while away a few hours over pintxos, txakoli (a sparkling white wine from Basque Country), and people watching. If you were to spend a few months in a seaside town, this would be the way to do it.

The W Santiago is where the cool kids stay. Which other hotel would dare to have a sign reading “WHATEVER” at the entrance? Since opening in 2009, the hotel has earned a strong following, both from locals and visitors. Dimly lit with a color scheme of purples, greens, and black, the rooms are modern, with full-length windows overlooking the city. Located in Santiago’s financial district, officially known as El Golf, the W is part of a large skyscraper (hotel reception is on the fourth floor) filled with restaurants and shops. The 196 rooms reach to the 21st floor, and the W has arguably the best roof terrace in town (Hotel Noi Vitacura being a close contender). The roof terrace has an infinity pool, knockout city views, and a heli-pad for those who want to whiz off to wine country or hit the ski slopes in speedy style.

This small, family-run wine shop in the Oltrarno district has been a gathering place for Florentines since 1947. Now run by the founder’s grandson and his family, it remains a place where neighborhood denizens come to buy wine to take home or to have a chat over a glass. Inside the shop, floor-to-ceiling shelves display bottles from a variety of Italian regions and vintages, with options in every price range. Glasses of red or white wine, dispensed from taps, can be enjoyed at the narrow bar. Or linger a little longer: Ask for a seat at one of the sidewalk tables, then order a glass of Chianti and a snack of chicken liver pâté (made from Nonna’s recipe) served on grilled Tuscan bread.

An institution throughout Mexico since the 1970s, this lively bar is especially popular with tourists. A non-stop party atmosphere includes waiters who spontaneously start singing or acting out in comical skits and instant conga lines. Menu items range from American to tacos and other Mexican fare. Drink offerings include basics such as beer, tequila and wine but can become “interesting” with the likes of the “Poison Kiss,” a potent blend of vodka, gin, brandy, red wine and amaretto mixed with orange and lemon juices.

At this luxury property perched over Matauri Bay near the top of the North Island, the colonial-style buildings are dwarfed by the endless wavy greens of a championship, par-72 golf course that ends at the Pacific. The ocean views and holes positioned adjacent to plunging precipices make Kauri Cliffs one of the most famous golf resorts in the world. The hilltop infinity pool is another crowd-pleaser, especially when it reflects the pinks and purples of the sunset. Featuring a beach-meets-country vibe, lodge interiors are outfitted with New Zealand artwork and furnishings imported from Europe and Australia. Outdoors, patches of totara trees dot the 6,000-acre property—one section houses the tranquil spa. Walking paths lead to a waterfall, three secret beaches, and picnic sites that offer sweeping views of Cape Brett and the Cavalli Islands.

You probably didn’t think of traveling to Peru for world-class French cuisine, yet here it is. The minute you walk in, you leave the Andes behind in favor of a European vibe, reflected in music, decor, and, of course, what’s on the table. Everything on the menu is French, including the expansive choice of wines. The five- or seven-course tasting menus are the perfect way to sample as many flavors as possible, but if ordering à la carte, save room for sumptuous desserts and a delicious coffee, picking your personal ideal from a wide range of blends.

A whole lot of history converges at the Fairmont San Francisco—as do all of the city’s cable car lines, which offer easy transportation to the Financial District, Union Square, and Fisherman’s Wharf. The hotel was built in 1906 but damaged in the Great Earthquake and subsequent fires before it even opened, so celebrated architect Julia Morgan was brought in to repair the building. Once it debuted, the hotel quickly became a city favorite, hosting more than its share of historic events, including the series of meetings in 1945 that resulted in the formation of the United Nations. The hotel’s storied bar, The Venetian Room, also featured big names, from Ella Fitzgerald and Nat ‘King’ Cole to Tony Bennett, who first performed I Left My Heart in San Francisco here in 1961 (Bennett still frequents the hotel).

Today, the Tonga Room & Hurricane Bar is a draw for tourists and locals seeking a kitschy, iconic San Francisco experience, with live music, Polynesian food, and Mai Tais severed against a backdrop of occasional staged thunderstorms. Other dining options include Laurel Court for all-day coastal California fare and the famous Afternoon Tea, a local tradition since 1907. The opulent design of the hotel extends from its lobby—with marble floors and sumptuous fabrics—to the 606 luxurious rooms, each outfitted with comfortable furnishings and modern technologies. Of the 62 suites, 10 also include balconies with city and bay views.

The main branch of the New York Public Library is one of the country’s grandest Beaux Arts buildings, a temple to learning on Fifth Avenue between 40th and 42nd streets. At the end of the 19th century, John Bigelow, who oversaw the Tilden Trust, decided that as New York was becoming a global financial capital, it required a grand public library. When the Astor and Lenox libraries faced financial difficulties, he convinced them to merge and, with the Tilden Trust, underwrite the library that now stands next to Bryant Park. The firm of Carrère and Hastings was entrusted with the design, and construction began in 1902 on the building that would be the largest marble structure built up to that time in the United States. The elegant main reading room with its soaring carved-wood ceilings is the highlight of its interiors. The library hosts temporary exhibitions related to literary and cultural topics that draw on its extensive collection of books and other printed materials. The two beloved lions in Tennessee marble—Patience and Fortitude—have stood at the entrance to the library since it opened in 1911 and were created by sculptor Edward Clark Potter.

Catch a taxi at the Old Town’s main bus station and head to Korčula’s first organic wine producer for a taste of the island’s traditional wines. A century after the indigenous grape variety grk disappeared from Korčula, vintner Frano Milina replanted it and started making what is now his signature Bire Grk white. Today, he offers daily tastings at the winery between 10 a.m. and midnight.

Work your way from Excelsior’s top floors (slinky Chloé dresses, Balmain leather jackets) to the main floor (watches, speakers, a sea of colorful iPad cases), then down to the subterranean floors for the impressive wine shop and restaurants.