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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.)

Built in 1928 by Asia’s oldest hotel brand, the Peninsula Hong Kong is one of the most historic properties on the Kowloon Peninsula, just across Victoria Harbour from Hong Kong Island. Designed originally as an upscale accommodation for passengers riding the adjacent Kowloon-Canton railway, the Peninsula has been a fixture of Hong Kong society throughout the region’s history. It was a magnet for Hollywood stars and dignitaries, the site of Hong Kong’s surrender to Japanese forces at the start of World War II, and temporary housing for residents following the war.

In 1994, a 30-story tower was added to house 135 additional rooms and suites as well as shops, a spa, a fitness center, twin rooftop helipads, and Felix—the hotel’s 28th-floor fine-dining restaurant, designed by Philippe Starck. The entire property was renovated in 2013 to update rooms with creamy colors, polished wood, and stitched leather and introduce high-tech extras that include a bedside control panel allowing guests to adjust the room’s light, sound, and temperature without getting out from under the covers. Today, the hotel is sleek and modern, but historic relics evoke the glory days that established the Peninsula as the “Grande Dame of the Far East.”

There is something truly distinctive yet quirky about staying in a former fine department store. Situated in a plum spot on West Broad Street, a convenient 30-minute ride from the Richmond airport, is the Quirk hotel, which is part of the Destinations Hotel Group. This is the labor of love of owners Katie and Ted Ukrop, who spent more than 10 years transforming a 100-year-old department store into a 75-room hotel with a rip-roaring rooftop bar scene, arguably the finest in the city. You’ll sleep on cushy beds made with joists salvaged from the former store, and bathe in the Barbie-like aura of the “love and happiness” rooms (incidentally, Sherwin Williams has a paint swatch by that same name). Rooms have lovely details like scallop-patterned nightstands, Tivoli radios, generously sized bay windows, and well-worn floors that look vintage. You can slake your caffeine addiction at the chic coffee bar in the lobby, or do a bit of retail therapy in the “Gallery” boutique off the lobby. It sells branded pink-and-white plaid pajamas and items like custom Na Nin hand-poured double-wick candles, crafted by Richmond resident Kate Jennings. The coffee for sale comes in brightly patterned signature rose tins that won a packaging award. “There’s no decade or theme to this gallery,” one employee assured me, but the vibe is decidedly mod-chic and whimsical, befitting the hotel’s name. The communal-style restaurant, Maple & Pine, is situated right in the middle of the lobby and is truly convivial. The culinary program is headed by chef David Dunlap, who was formerly with the Ashby Inn. Room rates from $225.

A pilgrimage to this enchanting park is a must for any Antoni Gaudí fan. Located atop Carmel Hill to the north of the city, the park was inspired by English landscape gardens, but its fantastical elements make sure you know it was created by Catalonia’s most eccentric architect. Though there are multiple entrances, the most impressive is via a grand staircase guarded by an enormous, mosaic-tiled dragon. It leads to a sprawling plaza with a mosaic-covered cement bench stretching some 328 feet around the perimeter. Park Güell was originally designed as a gated residential development, but it failed; a show home built to lure buyers is now the Gaudí House Museum (not included with park admission). Visitors should reserve an online ticket to avoid lines.

Over the past two centuries, the covered market at Borough, not far from London Bridge, has become one of the country’s most famous foodie spots. From Wednesday to Saturday each week hundreds of traders gather to sell homemade breads, hand-reared pork, artisan chocolate and all manner of ingredients—plus excellent coffee, fresh juices and organic wine. Plentiful samples add to the convivial vibe, and restaurants around the market’s edge provide additional sustenance for longer stops.

More and more cruise ships are arriving to the well-known Greek islands for day exploration. And while that is a boon to the local economies; crowded restaurants and beaches are not what you have come to experience. Some of these popular islands actually have very few year-round residents as the cruise visits are seasonal. So that “real Greek” town that you came to see, really isn’t. The solution? Try one of the lesser-know but equally beautiful Greek Islands like Ios in the Cyclades Islands. Here you’ll find five-star hotels, mom and pop inns, historical monuments, miles of sparkling beaches, dynamite restaurants, vibrant mountain towns, incredibly reasonable shopping, breathtaking vistas, and local wines, but most of all Ios can be your own paradise. The island of Ios is still a place where real people live and work, but there is plenty of support for tourism (sometimes it’s party central at Mylopotas Beach) and you will find true hospitality, safe streets to wander and new activities like the recently opened hiking path system. Imagine walking at your own pace to archeological sites, beaches, churches and mountain villages just like the early inhabitants did for centuries? The Greek Cultural Mountaineering Club of Fyli has long wanted to repair and connect the ancient paths and a few months ago the project was completed with the help of volunteers and the Municipality of Ios. Over thirteen kilometers of paths are open and well-marked by signs connecting other paths and old roads of Ios for you to enjoy. Not a hiker? The shopping is sublime. Not for the collectors of designer handbags but those desiring handmade leather sandals, precious gem jewelry and smart local-style clothing designs. Lounging by the pool is always a favorite. Stay at the elegant Liostasi Suites and you will be pampered like a jet-setter. Wish for a low-key stay? The Pavezzo Hotel and Suites is painted in beautiful colors and embellished by flowers offering family-style rooms, rooms for one or two and vantage points with sea views set on the side of a mountain with cooling breezes and the friendliest owners. If you are a fan of Greek cuisine there are many terrific restaurants, some right on the ocean like Drakos Taverna at the end of Mylopotas Beach. A favorite in Chora, the town above the Ormos harbor which is completely accessible on foot, is Elia. Visit the cathedral and one of old windmills the island is famous for while wandering the maze of winding stone streets that spill down from top of the hill. Or down in Yialos by the harbor pop into one of the very casual tavernas. Be sure to visit the food shop called Mosenta at the port to watch them create, and for a taste of sesame seed and honey cakes. They also package local wild herbs and make a great body cream that is made from their own honey and olive oils. Insider Tips: Go in Fall for peace and quiet and best rates on rooms. There is no airport so take the ferry from Pireaus, Athens or Santorini. Images Kurt Winner Photography

From its perch on Travis Park, just three blocks from the Alamo, The St. Anthony hotel has witnessed a lot of San Antonio history. First opened in 1909, the hotel was technologically-advanced for its day (think private bathrooms and automatic doors and lighting), and soon became known as one of the most luxurious hotels in the country, hosting everyone from the local elite to visiting royalty, presidents, and movie stars. Now on the National Register of Historic Places, the 10-story landmark emerged from a multi-million-dollar renovation in 2015, when it was e-launched as part of the Starwood Luxury Collection. The history is celebrated in details like 12-foot ceilings, antique piano, and gold leaf-topped columns found in the emerald-hued Peacock Alley lobby space, and the marble and bronze figures of the Sculpture Garden, while a contemporary style and jewel toned colors are featured in the 277 guest rooms and suites, many of which have park views. (If you’re interested in learning more about the hotel’s past—and hearing some legendary stories—schedule a tour with a staffer.) The light-fill Loggia restaurant is an elegant spot for breakfast and lunch, while the dramatic Rebelle features Texas farm-fresh produce and coastal seafood in its shareable dinner menus. Drinks and light bites are served at the seasonal Pool Bar, set around the outdoor swimming pool and featuring views of downtown; and at Haunt, a sleek indoor space playfully named for the rumored resident spirts. Once a private club for the city’s movers and shakers, The St. Anthony Club now welcomes all with signature drinks like the Triple S.

Before there were art galleries in Santa Fe, there was La Posada. Built as a private home in the 1880s by wealthy local merchant Abraham Staab for his beloved wife, Julia, the elegant pueblo-meets-Spanish-style complex expanded in the 1930s, when new owners added adobe casitas to the six acres of lush, high-desert gardens—and then invited artists such as Georgia O’Keeffe and Will Shuster to stay and work. When La Posada became a hotel shortly thereafter, the walls were already lined with works by the many artists who continued to pass through. Even now, the lively lounge—a see-and-be-seen spot for artists of all kinds—and the high-ceilinged rooms—with their kiva fireplaces and traditional viga ceilings—are adorned with works by some of the foremost contemporary American artists. All works are available to buy, too, for guests who want to take home a piece of their trip. Or, you can make like most guests, and just keep returning to this refined retreat that has offered respite from the world for more than a century.

Colca Canyon, a three-hour drive north of Arequipa, is one of Peru’s most popular and extraordinary tourist attractions. The chasm is over 13,600 feet deep, making it one of the deepest in the world, and more than twice as deep as the Grand Canyon. From the Cruz del Condor viewpoint, it is possible to get a panoramic view of this special place along with the chance to witness the flight of majestic Andean condors. This is a great place for partaking in adventure sports with a surreal view.

One of the most cost-efficient hotels in Montreal! Hotel ZERO1 is located in the heart of Montreal’s Festival District and minutes from Chinatown, Old Montreal, and the Latin Quarter - in other words, the location is unbeatable. Rooms are modest in size (it is a 3* hotel after all) but the decor is sober, yet stylish and very modern with apparent concrete walls and large windows. Some rooms even have a small kitchenette area. Good to know: the airport shuttle bus stops right across the street.

When it comes to sleeping options in Barbuda, private guesthouses are a popular option. One excellent choice is Barbuda Cottages. On a calm and gorgeous sweep of isolated beach at Coral Group, on the south coast, are four traditional wooden Caribbean cottages built right on the sand, next to one of the best beach bars in Barbuda, Uncle Roddy’s. The water in front of these chic, upscale self-catering cottages is also awesome for swimming as it is very safe and calm and there are rock pools to explore. A good family option, the newly constructed, eco-friendly beach houses are owned and run by Barbudans and offer one or three bedroom options. The cottages are located a 15-minute taxi ride from the village where the ferry pier and airport are – if you’re going to cook for yourself (recommended for most meals) stock up in town before heading to the southwest coast.

This little private church is probably the most photographed stop in Oia. Our rented house was right next to it but lower on the steps so we could see lots of people getting lots of photos. Married couples would take their photos next to it, photographers were offering workshops that included this spot. I woke up at 5.30AM to wonder when nobody else was around. Best time of day to walk around this very busy tourist destination.

You’re planning a visit to Sonoma. Where will you stay? An inn? Typical hotel room? B & B? I have a recent find in Sonoma wine country that you might not have considered: Graton Hotel Resort & Casino. Even if your adrenaline isn’t primarily sparked by gaming, here are some reasons to stay that will open your eyes. And you just might want to play a hand of Black Jack while you are there. First it is right in Sonoma. It’s classy, clean, new and has 200 spacious, bright, stylish hotel rooms and suites. The hotel part of the resort is completely separate from the casino section with valet service and a serene waterfall feature to welcome you. The expansive lobby, beautifully decorated with wood and stone, original artwork and bright custom-loomed carpets, rivals any luxury resort hotel. The materials and color palette were specifically chosen by the Tribal Chairman of the Federated Indians of Graton Rancheria, Mr. Greg Sarris.“ I wanted it to be opulent, but to reflect the colors of wine country.” he says. The property is near the wonderful little Santa Rosa Airport and transport from the property can be arranged, or is an easy cab ride away, or by car from SFO in 40 minutes. The first-class Spa & Salon At Graton would be enough reason for me to stay here. This full service oasis is staffed by caring professionals and caters to both men and women. The Privai Hydra Facial which combines cleansing, exfoliation and hydration is a non-laser skin resurfacing treatment. I can attest to the exceptional results. The salon has a Walkabout Foot Love service that leaves you with soft feet and beautiful toes either with or without polish. Dining options here either come from existing local hot spots or are concepts created exclusively for Graton Resort & Casino. An Italian restaurant, by San Francisco favorite Tony’s of North Beach serves delicious artisan pizza and Italian classics. Boathouse Asian Eatery serves favorites like sushi, sashimi, Steamed Whole Fish, Chinese Duck Noodle Soup, and Beef Chow Fun made with tenderloin steak and wide flat Fun noodles. For a modern take on Asian-fusion the Jalapeno Poppers with spicy crab, cream cheese, sriracha and unagi sauce are divine. The ubiquitous casino steak house has been re-imagined here as the casually elegant 630 Park Steakhouse. Go “all in” and start with the Seafood Jumbo Jackpot a multi-tiered offering of Maine lobster, shrimp, oysters, Dungeness Crab, and crab claws. Double-down with any of their tender, aged steak cuts or the Ahi Tuna Steak, just seared on the outside and sliced for you. Don’t miss the sides like Creamed Corn (this one is special) Classic Tater Tots or creamed Spinach. There is a ballrooom and event center in a separate building with state of the art sound and lighting in a space that can be configured for a small or large event. Come for a show featuring top talent like Patti LaBelle, Art Garfunkel or Kathy Griffin. The pool area is gorgeous, reminiscent of Miami with its sun lounges and private cabanas upholstered in an eye-popping orange. “Cabo lounges” sit right in the pool so all you have to do is lie down, soak up the sun and trail your hands or feet in the water. And yes there is a full-service pool bar which also makes for a romantic spot at night when the glowing fire pits are lit up under the Sonoma stars.

The Viceroy Riviera Maya is a 41- villa resort set on the sugary-white-sand beach along the Riviera Maya. Surrounded by a lush jungle ambiance dotted with dense with ferns, palms and guava trees, it offers a luxurious retreat for guests 16 and older. Guests are treated to an ancient Maya blessing, performed by the onsite shaman - guaranteed to transform worries into a relaxed mindset to mesh with the tranquil resort. The spa employs Maya healing techniques and traditions, while a lagoon pool, fine-dining restaurant, seaside grill, private pier, fitness center and a library lounge are some of the many guest amenities. A menu of artisanal soaps offers a choice of scents. Once the selection is made, the Soap Concierge slices personalized bars from large blocks of soap for their use. Pet packages are available and include a blessing from the shaman, personalized, hand-made portable pet palapas and personalized menus designed by resort chefs.

Built in 1927, the neo-Gothic structure of the Windsor Arms was intended to resemble the buildings of the University of Toronto. (The hotel is near Victoria College at the university.) The entrance feels like stepping into a castle, the Windsor Arms logo perched neatly beside the portico, doorman at the ready. The hotel was purchased by developer George Friedmann in 1995 and resurrected with modern touches for a fresh debut in 1999. The hotel is birthplace to the idea of the now-famous Toronto International Film Festival (TIFF). It continues to attract celebrities who want a boutique feel, and though TIFF has shifted its headquarters south, the Windsor Arms will always be a refuge for those who want Old World charm and exclusive service. The streetside patio is perfect for people watching during the lively month of September. And in the hotel’s hallways, you can “stargaze” at the portraits of celebrities, from Robert Redford to Barbra Streisand.