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  • Norzagaray 204, San Juan, 00901, Puerto Rico
    Old San Juan is known for its atmospheric and historic hotels, but none quite match the Gallery Inn for personality and creativity. Composed of six intertwined town houses, this endlessly fascinating hotel beckons guests to wander through its nine interior gardens and patios, and seven parlors and porticos. Dating to the mid-1700s, the oldest building, La Cueva Del Indio, is located above Old San Juan’s north walls, meaning the views out to sea are the same ones that captivated the conquistadors.

    Owner Jan D’Esopo, is a well-known sculptor and her works dot the hotel’s meandering interior, which has enough comforts and homey character to avoid feeling like a museum. Equally unique are the 25 rooms, decorated with everything from silk screens and watercolors to sculptures and paintings. Some even feature elegant, four-poster beds and balconies with views of the ocean. Just don’t expect to watch TV—one, there are no TVs, and two, the views out over the old fortress walls are better than anything on Netflix.
  • Badweg 10, 8001 Zürich, Switzerland
    This is river swimming at its most civilized. Zurich’s oldest badi, the men-only Männerbad Schanzengraben, is tucked away near the stock exchange and surrounded by the ivy-draped old city wall (you’ll miss it if you don’t look for it). Come evening, the badi transforms into the popular Rimini Bar, where both men and women mingle on floor cushions and rugs lining the pool’s edge.
  • Badweg 10, 8001 Zürich, Switzerland
    A midsummer night’s fantasy—Zurich-style. Tucked away near the stock exchange, the city’s oldest badi, the men-only Männerbad Schanzengraben, transforms into the popular Rimini Bar come evening. The scene is surreal: a mixed crowd mingling along the edges of the pool, a shooting fountain, technicolor lights—all surrounded by the ivy-covered old city wall. On Monday evenings, local fashion designers add to the mix by showcasing their creations.
  • Santa Korda Kalea, 4, 20003 Donostia, Gipuzkoa, Spain
    At La Cuchara de San Telmo, on the corner of the plaza Valle Lersundi in San Sebastian, the specialties were hot pintxos, quickly prepared to order--from the menu or the specials board, or by pointing to what your neighbor was eating. This was one of best scallops I have ever tasted. But then, so was the second one we had when we returned after another hour or so of pintxo bar hopping in the Parte Vieja (Old Town).
  • 1 Collins Diboll Cir, New Orleans, LA 70124, USA
    This is the oldest and grandest art institute in a city that’s long captivated artists. The Neoclassical building sits amid the greenery of massive City Park (conveniently at the end of the Canal Streetcar Line). It’s an especially good destination for admirers of Edgar Degas, who spent an extended vacation in New Orleans visiting relatives in 1872; a number of his works are displayed here. Just outside the museum is the beautifully landscaped and well-curated five-acre Sydney and Walda Besthoff Sculpture Garden, which perfectly melds the old and new. Some 60 sculptures are arrayed amid reflecting lagoons and 200-year-old live oaks.
  • 1206 19th Street
    Sonny’s has been open since 1944, making it the second oldest continuously operating eatery on Galveston Island. Hit it on a Friday gumbo night if you can, which comes in your choice of shrimp, crawfish, or both. Sonny’s may seem like a hole-in-the-wall, but don’t let that scare you off. It’s just old school and really friendly seafood place. Photo via galveston.com
  • Playa Maderas Maderas, Nicaragua
    We had an unforgettable experience staying at Buena Vista Surf Club, while visiting San Juan del Sur. The eco-lodge is set into a hill overlooking the jungle and Playa Maderas with a giant sundeck where guests could enjoy the view. It was a great place to catch some rays and watch the dragonflies dance during the day. Guests can schedule sunset yoga classes on the deck for the ultimate zen experience.
  • 55 Rue Saint-Jacques, Montréal, QC H2Y 1K9, Canada
    To me, no other place in Montréal represents the city better than Place d’Armes. After all, it is the second oldest public site in the city, and its center is home to a statue of Paul de Chomedey, the founder of Montréal. And the varied architectural styles surround the square in a way that clearly demonstrates just how old and historic Montréal is. A blend of Gothic Revival, classic Art Deco, and ultra-modern sleek skyscrapers illustrates the major periods of Montréal’s development. It’s definitely a great place to start or end an Old Montreal exploratory tour, or to stop and people watch!
  • 1950 W San Xavier Rd, Tucson, AZ 85746, USA
    Just to the southwest of Tucson, on the San Xavier Reservation, sits the late XVIII-century Mission San Xavier del Bac, one of the finest examples of Spanish colonial architecture in the U.S. The combination of late Baroque and Moorish-inspired design is a beacon any time of the year, but on this winter day, the flooded fields worked some magic—panoramas of reflected landscapes are almost nonexistent in southern Arizona! The ‘white dove of the desert’ is the oldest intact European structure in Arizona, and it still serves as a parish church for the Tohono O’odham people.
  • Whether you wander by boat, bike, or tuk tuk (or, highly recommended, a combo of all three), Bangkok spills over with places both new and very old to explore. Along the way, modern-day wonders rub shoulders with traditional Thai culture. Hop from the floating market to a day cruise on the Chao Phraya River to a cocktail at one of the city’s innovative bars. Make meals of tastes from street food vendors and mix in some table service at some of the city’s most renowned restaurants. Overwhelmed by all the options? Stop for a Thai massage. Need souvenirs? The weekend market awaits.
  • Whether you’re looking for an ultramodern take on Tokyo, like the one you’ll find in Shibuya, or something like Nakameguro, where you’ll find trendy restaurants and shops, as well as residential streets, Tokyo has neighborhoods that will give you a distinctive taste of Japan. Find old temples and cutting edge art galleries, neighborhoods where sassy teenagers pose in outlandish outfits and shopping streets that boggle the mind (and fill up the suitcase). Welcome to Tokyo, land of the past, present, and future.
  • Step back in time to Prague’s Bohemian past—the Old Town Square, St. Vitus Cathedral, Prague Castle, the romantic Charles Bridge—before visiting the somber memorial to its Communist rule. Today Prague basks in modern optimism, evidenced by such landmarks as Frank Gehry’s Dancing House Hotel and DOX Centre for Contemporary Art.
  • Housed in everything from a 17th-century palazzo to an ancient fortress to a 350-year-old farmhouse, Malta’s best hotels blend history with modern luxury. Whether you want a spacious room with views of the Grand Harbour, a great location within walking distance of major sites, or a rooftop pool to relax by after exploring the capital city, you’ll find it all, along with loads of traditional charm, in this fascinating island nation.
  • Mount Ulia, 20013, Gipuzkoa, Spain
    Most visitors never cross the river from the Old Part, and the vast majority overlook what has to be one of the most beautiful hikes from here to California. At the edge of Gros, a trail heads up some stairs (at the end of Calle San Francisco) and continues for hours, all the way to the neighboring village of Pasaia. It’s a family-friendly trail in terms of difficulty, and the views are breathtaking. A must-hike.
  • 158, Calle Flamboyan, Vieques, 00765, Puerto Rico
    Designed by Fuster + Architects, an award winning firm located in San Juan, Puerto Rico, El Blok takes its visual cues from the surrounding light, land and sea. In addition to being a playful structure, it is highly functional and built to withstand storms and hurricanes (a big plus anywhere in the caribbean!). It is located at the beach, at the start of Esperanza’s sleepy malecon, with its low-key seaside huddle of restaurants, bars, and stores, most of them back open after hurricane Maria’s devastating sweep of the island.

    I loved my room, one of the spacious corner suites. The way the space captured the light was uncanny, every time I got back to my room, a new play of light beams and shadows was waiting for me. The restaurant downstairs serves up amazing food, hands down the best I had on island. Executive Chef, Carlos Perez. brings to the table a delicious, fresh take on Puerto Rican cuisine, centered around their bayahonda mesquite fired grill and Rotisol rotisserie. Just don’t expect much of a breakfast at the hotel. I took a short walk each morning to some cafés nearby, to grab a coffee and omelet. El Blok’s rooftop bar was ‘the’ place to hang in the evenings with locals and travelers alike, while listening to amazing music. When we were there, the duo Más Que Dos was playing and it made for an all around perfect sunset.

    El Blok currently has 22 rooms and is adding another 11, slated to open in summer 2019. We were warned about construction noise between 8am and 2pm, but I can honestly say it didn’t interfere at all with my stay. It’s of course when you’re supposed to be out and about anyways, exploring the island!

    Rates start at $140 per night plus tax.

    A heartfelt thank you to Discover Puerto Rico (@DiscoverPuertoRico) for 3 days in beautiful Vieques and a fun stop-over in San Juan, Puerto Rico.