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  • When I first moved to the island, I joined a friend in the Old City for a tour and lesson on the history of Puerto Rico. When passing by this little section of town near Pigeon Park, my friend and native-turned-tour-guide said that this was the smallest house in Old San Juan. Wow, okay, so this little yellow portion is technically a house? I’ve visited this site several more times since then and have never actually seen anyone enter or leave this door. Whether it’s true or not, it makes for a cool story and great photo.
  • 3924 W 72nd Ave, Westminster, CO 80030, USA
    Step back into the 1800s when you tour the Bowles House Museum. Thanks to the Westminster Historical Society, this home, located near a smattering of industrial buildings, was preserved and placed on the National Register of Historic Places. It was once owned by Edward Bruce Bowles, who drove cattle westward in 1863 and eventually became a homesteader. He was known for breeding fine horses. Besides touring the home, the grounds are well kept and beautiful. But it’s only open for tours on Saturday from 10 a.m. to 3 p.m. and by appointment from Dec. 31 through April 20.
  • Cleo Street Beach, California 92651, USA
    Located next to Main Beach, the much-quieter Cleo Street Beach is a favorite of scuba divers, who come here to explore the Foss 125 Barge. The wreck, which sank just offshore in 1958, is submerged in a mere 55 feet of water, making it easily accessible to even the novice diver. Those up for the adventure will find an extremely well-preserved site, wrapped in coral and surrounded by Laguna’s Marine Reserve, which boasts everything from seals and otters to colorful fish and even some larger sea life. If you’re not a diver, Cleo Street Beach is still worth a trip to stroll the sand with a coffee from the nearby Orange Inn in hand. Just be sure to bring your four-legged friend along, as the beach welcomes dogs.
  • 479 King St #200, Charleston, SC 29403, USA
    Once the hip newcomer, this craft cocktail lounge is now a King Street veteran that attracts a more mature crowd than the line-up-outside adjacent clubs catering to the college set. Locals meet here for half-price happy hour (Wednesdays feature bourbon) and before shows at the Charleston Music Hall nearby. The stock of spirits is impressive, as are the intricate ways they’re mixed, like a “Macho Man Dandy Savage,” with house-infused dandelion gin, honey, and yellow Chartreuse. The mixologists here have a history of winning local bartender competitions. Complementing the flavors are the gorgeous environs in an historic building that features exposed beams, leather furniture, and a swanky rooftop garden that’s a welcome respite just off the buzz of King Street below. It all sits atop The Macintosh, chef Jeremiah Bacon’s stunning seasonal fare restaurant that shares a mutual owner.
  • 11 Yulgok-ro 10-gil, Gwonnong-dong, Jongno-gu, Seoul, South Korea
    Amass Hotel may be located in the heart of one of Seoul’s most traditional neighborhoods, but its interiors are modern and industrial. Black-and-white rooms are compact yet comfortable (think heated floors); opt for a quad room for double the space and a private terrace with a covered long table and benches. The rooftop bar offers views of N Seoul Tower and the city’s skyline, and a downstairs café provides a convenient breakfast option, with many others within walking distance. The nearby Bukchon Hanok Village and Insadong-gil street are shopping hubs for souvenirs, folk art, and handicrafts, and the Changdeokgung Palace is across the street (best to buy tickets in the morning and return later for the tours). The hotel offers free bicycle rentals but is also very subway accessible.
  • 113 Macdougal St, New York, NY 10012, USA
    Michelin-starred Minetta Tavern, which opened in 1937, has attracted plenty of literary luminaries over the years, including Ernest Hemingway and e.e. cummings, and continues to attract the famous and not-so-famous with its Paris-bistro-meets-NYC-tavern menu and vibe. There’s roasted bone marrow and trout meunière, and plenty of aperitifs, beers, wines, and cocktails (including one named for a Hemingway novel) to wash down whatever you order. Before or after your stop at this iconic Greenwich Village stop, walk through nearby Washington Square Park (as close to a “campus” as New York University gets) or watch a game of basketball at the famous West 4th Street courts.
  • 1206, 155 Steuart St, San Francisco, CA 94105, USA
    Perched next to San Francisco Bay, Hotel Griffon makes an ideal base for business travelers who work nearby and visitors who want a waterfront location. Free town car service to the Financial District is available every weekday morning, while a fifth-floor boardroom provides a short commute for conference-goers. Leisure travelers can arrange Alcatraz tickets, tours, and sought-after reservations through the concierge.

    The eco-friendly hotel is green down to the smallest details, from recycling unused hygiene products as part of the California Green Lodging Association and Clean the World to recycled notepads. All of the rooms were remodeled in 2012 and get turned down every evening with chocolates. Top-floor suites also have a wet bar so guests can raise a glass to their view of the city or bay and toast their time in San Francisco.
  • 80 Route 214, Phoenicia, New York
    Set in the Catskills, the Graham & Co is a boutique hotel that has reimagined the classic weekend mountain getaway. Located about two-and-a-half hours from New York City, this retreat offers spacious minimalist rooms, some with kitchenettes. Details include Mexican blankets, Tivoli radios, and custom bath amenities that are available for purchase at the front desk. The Graham & Co is designed as a place to sit back and read while putting your feet up next to the fire pit. Plenty of outdoor activities (fishing, hiking, skiing) are nearby, but many guests settle into the property and its Adirondack chairs, hammocks, and picnic area for a welcome escape from the bustle of city life. Explore the town of Phoenicia on a complimentary bike or simply stay put at this unpretentious mountain property.
  • 1201 Boul St-Laurent, Montréal, QC H2X 2S6, Canada
    The name makes it sound like the driest place in Christendom, but the SAT, as it’s known by locals, is at the forefront of coolth. This giant building on Boulevard Saint-Laurent near Rue Sainte-Catherine is dedicated to electronic culture and entertainment, which means it hosts some of the best art events, dance parties and music performances in town. The top level of its four storeys includes the famous Satosphere, a dome structure that allows for mind-blowing, immersive 360-degree visual projections. Events include presentations and master classes in addition to dance nights by the likes of Borgore, Brodinski and MYD. Don’t forget to stop by the in-house restaurant, the FoodLab, which is constantly pushing the gastronomical envelope. Photo: Sébastien Roy
  • De Hidalgo 16, 68247 San Agustín Etla, Oax., Mexico
    If you’re looking for a break from Oaxaca‘s cultural delights and would like some downtime, maybe to enjoy some swimming during your stay, the best place is in San Agustin Etla. It’s about a 20-minute drive from the Oaxaca city center, but it’s well worth making the excursion. This swimming place has five pools, with a couple that are good for kids and one that is heated, as well as a couple of water slides. The setting is beautiful with great views of the surrounding mountains. You can choose a table near the pool of your choice and order drinks and food from passing waiters. During Easter break and on weekends when the weather is hot, Vista Hermosa Balneario can get very crowded. For a quiet and relaxing time, head there during the week.
  • Km. 3, Carr. Internacional, Cerro del Fortín, Faldas del Fortin, 68030 Oaxaca, Oax., Mexico
    Enjoy some of the best views of Oaxaca city while you dine on local specialties such as tlayudas and parrilladas. Come for breakfast, lunch, dinner, or just for drinks. It’s open from 8 a.m. to 2 a.m., and the view is great any time of day. El Mirador is mostly popular among locals and you won’t find many tourists, probably because it can be a bit difficult to find. From the parking lot at the lookout point on the hill, there are steps leading down. You won’t see a sign until you’re near the bottom of the steps, where you’ll find the entrance to the restaurant. I’ve found the food and service to be variable, but the prices are good and the view is exceptional.
  • Jamaica
    You haven’t quite experienced the most authentic Reggae concert in Jamaica until you’ve been to Rebel Salute. While Sumfest gets all the press and is more commercialized, Rebel Salute—held every January—is Jamaica’s largest strictly-Reggae all-night show, headlining every single big Reggae music name you can think of. Now held on the north coast, on the picturesque grounds of Grizzly’s Plantation Cove, this well organized, alcohol-free event welcomes everyone from families to couples. Camp out by bringing your lawn chairs and blankets to indulge in the best of Reggae all night long, under the starry nights of the south. Food and soft drink vendors are present, of course, as are souvenir sellers. Tour operators do arrange group round trips to the event—inquire with Clive’s Transport--and hotels near the venue offer deals.
  • Şahkulu Mah., Kumbaracı Ykş. No:57, 34425 Tünel/Beyoğlu/Beyoğlu/İstanbul, Turkey
    Leb-i derya is one of those fabulous fancy restaurants perched high above the streets of Beyoğlu with amazing views of the Bosporus, Maiden’s Tower, Asia and old Istanbul’s peninsula. You could walk past the building so many times on its dimly lit street without realizing how magnificent the view from the top is. This light and bright sophisticated rooftop restaurant offers traditional Turkish flavors with a modern twist, as well as gourmet-style international favorites. In summer, management opens the doors to an open-air terrace ideal for sunset cocktails. It really is an iconic city rooftop for special occasions—or for saying good-bye to Istanbul on your last night in the city. Enter off the sloping Kumbaracı Yokuşu (street) which runs off Istiklal street near Tünel. Reservations are advised.
  • From the outside, San Giorgio looks like one of Greece’s ubiquitous whitewashed homes. Inside, traditional Greek textiles and locally made furniture adorn the 33 unfussy rooms. Most feature rough-hewn wooden dressers, large circular jute rugs, and beds canopied with mosquito netting. Some have terraces with views of the Aegean Sea. Guests can relax during the day in cocoonlike hanging swings near the pool or take a 10-minute walk to the popular beaches Paradise and Paranga. In the evenings, it’s not uncommon for DJs such as Bob Sinclar or David Guetta to make guest appearances in the hotel’s open-air lounge.
  • Cerro Alegre, Valparaíso, Región de Valparaíso, Chile
    One of the delights of Valparaíso is exploring the colorful hillsides that ramble down towards the sea. Take the century-old funicular elevators Ascensor Concepción (Turri) or El Peral near the main plaza, constructed between 1883 and 1911. Once high into the hills of Cerro Concepción & Alegre, explore the meandering alleyways and cobblestone streets on foot. There are boutiques, cafés, mom-and-pop shops, old school bakeries, bars, restaurants, art galleries, and church bells tolling. It often feels more like a small village than a city. Climb up and down the many staircases often lined with bright graffiti. In the distance, the bay gleams in sunlight and the busy port never tires. At dusk, the lights twinkle like fairylight. Grab a table at a spot like Café Turri for a view of the sunset and a cocktail.