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While the Liberty Hotel may have deep roots in Boston lore, it’s not for the reasons you think. For more than 100 years the hotel existed as the Charles Street Jail, an in-city penitentiary that housed (in)famous inmates like James Michael Curley, Malcolm X, and Sacco and Vanzetti. Its inspired transformation came in 2007, but the owners maintained some of the jail’s vestiges, from the exercise yard to several jail cells, while turning the building into a 298-room luxury hotel. Richly appointed rooms offer sweeping views of the city skyline and the Charles River.

The hotel houses five distinct restaurant and bar venues, all of which attract large swaths of locals, especially on the weekends. Located at the foot of Beacon Hill, the hotel is steps away from the boutique and antique stores along Charles Street and also sits next to the picturesque Charles River Esplanade.

A stroll of St. Kitt’s capital, whether started at Port Zante Marina or the centrally located Independence Square, is an entertaining way to learn more about the island’s past. While the French named Basseterre (it means “low land”), the British are responsible for the town’s most recognizable landmark—the green, cast-iron Berkeley Memorial Clock in the center of the Circus, where several streets intersect. Make sure to visit the area, as well as Independence Square, St. George’s Anglican Church, and the Old Treasury Building, which now serves as the National Museum of St. Kitts. Along your walk, you’ll also find duty-free shops and local boutiques, plus a lively produce market by the waterfront if you come on the weekend.

Boat-building as an industry has existed on Bequia as far back as the 1800s. At one point, the island was even known as the “boat-building capital of the West Indies,” having produced the largest wooden vessel in the region. While construction has slowed over time, it still occurs—albeit on a much smaller scale—at places like Sargeant Brothers Model Boat Shop, just up the road from the ferry landing in Port Elizabeth, where Benson Phillips and other craftsmen make and sell their models. Handcrafted using hand planes, chisels, and carving knives, their boats are incredibly detailed and realistic. Choose from whale boats, sailboats, power boats, and wooden schooners, or commission Phillips to build a custom model of your own yacht. The simplest models take about a week to make, but there are always a few boats available for immediate sale, ranging in price from around $250 all the way up to $7,000.

Even during Antigua Sailing Week, when English Harbour is chock-a-block with yachts from all over the world, the 28-room Inn at English Harbour remains serenely detached from the chaos. The inn is five minutes by water taxi from the center of things at historic Nelson’s Dockyard, but its tucked-away location on a white-sand beach backed by 19 leafy acres (and a no-kids-under-10 policy) ensures tranquility. Four snug rooms, with marble floors and queen beds, occupy two beachside cabanas, while 25 more generously proportioned suites, all with dark mahogany floors, four-poster king-size canopy beds, and verandas or balconies, are in three wooden buildings sitting farther back among the tropical greenery. Although the Terrace Restaurant and Stone Bar are in the property’s original stone house, the rooms, despite their colonial look, are relatively modern, which means there is a flat-screen TV, an iPod docking station, and Internet access.

Just minutes from some of the world’s best surf breaks, the Four Seasons has its own surf school offering lessons for all ability levels, from novices to big-wave riders. Surfari Splurge and book a boat trip aboard the Four Seasons’ Explorer, a three-deck catamaran that can get you to some of the area’s most remote atolls. See the Best Every August the resort hosts a week-long international surfing competition that draws both locals and elite athletes such as Tom Curren. You can buy day passes to watch the action. Sleep Therapy Wellness treatments linked to the lunar cycle are scheduled from 10 p.m. to 1 a.m. at the resort’s spa, which sits on its own island.

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.)

One of Dalmatia’s most underrated cities, Šibenik is finally being recognized as an exciting coastal destination. Its medieval heart is a stone maze of steep alleyways dotted with charming squares and hidden cul-de-sacs, not to mention a pretty harbor and a seafront promenade lined with cafés. Crowning it all is the Cathedral of St. James, an architectural masterpiece incorporating style elements of both the Gothic and the Renaissance. The cathedral is said to be the world’s largest church built entirely of stone—most of which was quarried in the nearby Adriatic islands. Of particular note in this UNESCO World Heritage site: the frieze of 71 heads on the cathedral’s outer wall, which depicts 15th-century citizens of Šibenik with many different moods and personalities.

High-elevation baking might not always (ahem) rise to the occasion...but at Clafoutis, the French family that owns and cooks at this bakery/restaurant has acclimated perfectly to the Sangre de Cristo Mountains. While it might be hard to tear yourself away from red-and-geeen-chile-on-everything while in New Mexico, if you do want to take a break from capsaicin for your morning eats, this is the place. Just to the northwest of the city’s historic core, Clafoutis is one of Santa Fe‘s morning institutions. You can get things to go, but if you wait for a table, you’ll be served café au lait in a bowl along with “Bonne Maman” jams to transform perfectly-textured baguettes into “tartines.” “Bonjour” greets you as you walk in the door, and your eyes will feast on the piles of pâtisseries beckoning from the counter. My wife and I had one of the best chausson-aux-pommes--in or out of France--that we’ve ever tasted. And, in a nod to local tastes, they even offered green chile to go with les oeufs... Be forewarned, though--parking is extremely limited, and weekend mornings are formidably popular. Un peu de patience: so worth the wait!

My deep love for macarons is no surprise to anyone that knows me, so it’s no wonder that after trying perhaps the finest ever in Paris, I’d look for a temporary fix in Los Angeles. This quest led to the discovery of Bottega Louie, one of my favorite restaurants in LA now. Nestled on the chaotic corner of Grand Avenue and 7th Street in downtown Los Angeles, Bottega Louie really knows how to enchant, intrigue, and satisfy the palate. Serving mostly Italian fare, it’s one of the best brunch places in L.A. (try the lemon ricotta pancakes) and certainly the best macaron bakery in the area. My absolute favorite is the salted caramel. Nothing beats people-watching on a breezy weekend afternoon with a platter of macarons and champagne!

If you’re craving for Italian food in Manila, and love those little quaint places, you should visit this place. It’s not in your usual tourist areas, it’s located in Cubao Expo in Cubao, Quezon City, about 20 km from Makati. The Cubao area is more known to the locals as it houses a large wet market, as well as to the sports and live concert enthusiasts who attend events at the popular Araneta Coliseum. In the past, kids loved this area too as there used to be a large indoor carnival. Recently, the commercial area has been rehabilitated, and now also includes a large upscale mall and hypermarket. The owner of Bellini’s is an Italian married to a Filipina and both of them are heavily involved in their restaurant business since 1999. Their food is great as they are all freshly made and uses quality ingredients. Try the beef carpaccio, the pizza is excellent too and I also love their pasta. I also love the decor, they put together some Italian icons on the walls and ceilings and even has a mini Tower of Pisa inside the restaurant :-) After your meal, you can also explore Cubao Expo, which includes small stores selling arts and other quirky stuff. It also has a weekend flea market. If you prefer more upscale shopping, you can go the nearby Gateway Mall.

When he sold his jewelry company in 2007, Canadian expat John Hardy and his wife reinvested much of the money into the Green School, an innovative K-12 school in Sibang Kaja, Bali. The curriculum is very experiential—the international and Balinese students learn everything from aquaculture to Balinese puppetry. Named greenest school of 2012 by the U.S. Green Building Council, the school is worth a visit if only to see the far-out architecture. Many of the complex buildings are constructed entirely of bamboo.

The city’s iconic wood-paneled Tram 28 rambles along a 4.3-mile route from Campo de Ourique to Praça Martim Moniz, navigating tight turns and steep inclines as it passes some of Lisbon’s most endearing attractions. Originally commissioned in the 1930s, these classic Remodelado trams were in fact enlisted for their ability to handle Lisbon’s hilly terrain. They can get painfully crowded—wait times can be outrageous in the high season—so catch an early ride (5:40 a.m. most weekdays, or 6:45 a.m. on Sundays) for unobstructed views of hilltop neighborhoods like Graça and the Alfama.

This iconic landmark in London is popular for a reason...it’s breathtaking! Did you know that Big Ben is the name of the bell inside the tower, not the clock? While you are there, check out the Houses of Parliament (if they are in session). Afterwards, stroll across the lovely bridge and rise the London Eye!

Harbour Island is an out island of the out island Eleuthera in the Bahamas. Home to a scant 1,500 people and more golf carts than cars, Harbour Island is the perfect place to get away from it all. It’s also home to the rich and famous who visit for the same reason the rest of us do, quiet relaxation. As soon as I landed on the island I could feel my stress melt away. It’s hard to get too worried on an island with roosters in the street and golf carts whizzing past. Harbour Island is one of those places that quickly occupies a place in your heart and I know I can’t wait for a return visit.

Less than two hours from Barcelona, in car or via TEISA buses (during the week), La Fageda is a leafy green wonderland after too much time spent in Barcelona’s hectic city center. This beech forest is unique, growing at a much lower altitude than usual for the Iberian Peninsula.In the fall, the vivid red leaves on the trees are especially stunning. No motor vehicles are allowed in the forest itself, but you can hike, bike-ride, or explore the reserve on horseback or even in a horse and buggy for a reasonable fee (reserve ahead). Inside the reserve, visit La Fageda’s dairy farm--you can learn about how the yogurt and ice-cream is made (in Catalan or Spanish), pet the calves, and taste some of La Fageda’s products. Beyond la Fageda, in the larger area of La Garrotxa Volcanic Zone Natural Park, there are volcanoes, Olot and Sant Feliu de Pallerols’ old towns, and a medieval castle to see, as well as numerous routes for hiking, biking and horseback riding.