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Set at the end of Duval Street, near Sunset Pier and Mallory Square, Pier House takes advantage of its waterfront address with three tiers of balconies and a pocket-sized stretch of private beach. Its location means guests are within walking distance of all of Old Town’s highlights, from the Clinton Square Market to the Harry S. Truman Little White House. Many come to follow in the footsteps of the mayor of Margaritaville himself, Jimmy Buffet, who played his first gig in town in the hotel’s now infamous Chart Room Bar. Order a rum runner, then head to the heated outdoor pool; though it’s on the small side, it has sweet views to Key West Bight. After an adventure-packed day, the rooms and suites offer low-key comfort, decorated with traditional furniture and local art and overlooking the ocean or tropical gardens and koi ponds. Equally serene is the full-service spa, one of the few on Key West.

Just 33 miles northeast of Avignon, the town of Vaison-la-Romaine is home to some of France’s most significant archaeological finds. The Ouvèze River flows through the village, creating two separate banks. On the left, a medieval town features enchanting fountains, houses built into the sides of cliffs, a towering belfry, and the ruins of a 12th-century castle. On the right, the new town surrounds an ancient Roman village, complete with preserved dwellings, a theater from the 1st century C.E., and a Gallo-Roman bridge. Amid the Puymin and La Vilasse archaeological sites, you’ll also find the imposing Our Lady of Nazareth Cathedral (built in the 11th and 12th centuries) and the St. Quenin Chapel (with an apse dating back to the 13th century). A 9-euro (around $10) pass grants 24-hour access to all the sites with guided tours if desired, but you can also just wander the cobblestone streets for free, discovering ancient doorways, striking facades, and hidden statues as you go.

Colombian fashion designer Silvia Tcherassi took the design world by storm when she transformed a 250-year-old mansion in the center of Old Town Cartagena into a contemporary refuge that honors both past and present. Mansion Tcherassi’s seven rooms blend fashion-forward decor (think sparkly gold throw blankets) and original features such as restored stone walls and private balconies, but the vibe is much more understated, with ethereal fabrics, soft colors, and natural wood, in the 42 neutral-hued rooms at sister property Tcherassi Hotel & Spa. You can order fresh-caught seafood and icy raspaos (traditional drinks made with fruit and condensed milk) at the restaurant, while carpaccios, pizzas, and ceviches are on the menu on the rooftop lounge; the Italian restaurant at the mansion extends to a cozy patio facing a plunge pool and vertical garden made with thousands of local plants. After a day spent exploring Old Town’s historic buildings, relax with a Chinese medicine–inspired treatment in the spa, or take a dip in one of the property’s four pools.

If you’re looking for a little adventure, DownTown Racing boasts India’s longest and most sophisticated go-kart track. With bungee jumping, ziplines, ATVs, quad bikes, and paintball, this place is great for groups and adrenaline junkies. The facility also has an arcade and games section for those hunting virtual adventures.

The Corral family’s second and third generations are behind the wheel at Los Olivos, a restaurant set in an old adobe-style building in Old Town Scottsdale. In fact, it’s a family affair from top to bottom – an uncle handcrafted the Spanish chandeliers, cousins greet you at the hostess stand, and an old family friend is the one to thank for those freshly made flour tortillas. For a delicious dose of patriotism, try the Mexican Flag enchiladas. It’s a 3-in-1 dish that comes with a red-sauce beef enchilada and two cheese versions; one topped with sour cream and the other with green chile peppers.

If you research “pretty seaside towns in Greece”, Nafplio often pops up on the search. Located in the eastern Peloponnese, Nafplio boasts narrow, bougainvillea-covered streets, rich-hued neoclassical mansions, wrought-iron balconies and cobblestone and marble streets. It is a popular weekend resort for Athenians due to its waterfront cafes and restaurants, fresh seafood, and pretty boutiques. It is also the perfect base to explore all nearby ancient ruins such as Mycenae, Epidaurus, and Sparta. Sip a cold drink in Syntagma Square, the town center; climb 999 rock steps up the Palamidi Castle for the expansive view; swim in the clear blue waters of the local beaches; and take a sunset stroll along the marina waterfront before dinner.

A day trip to Lake Como from Milan is easy and worthwhile. Although we did not find George Clooney’s villa, we did find the lake-side towns of Menaggio and Verenna to be charming. With no prior planning we took a thirty minute train ride from Milano Centrale to Como San Giovanni and then boarded the public ferry a short walk away from the station. The ferry, preferably sitting on the open deck in the sun, is the best way to see the pretty little towns along the lake. Later we enjoyed a stroll and some lunch in Menaggio and then took another ferry across the lake to Verenna where we caught the train back to Milan.

Prague’s Astronomical Clock is the world’s oldest working one of its kind. Installed in 1410, it is located on the Old Town City Hall in Prague‘s Old Town Square. The medieval clock features an astronomical dial; “The Walk of the Apostles”, an hourly show of moving sculptures; and a monthly calendar dial with the 12 signs of the zodiac. The clock is the center of Prague and the city’s most popular sight. On the top of every hour, huge crowds gather to watch the movement of the Twelve Apostles. Two doors on either side of the clock open and the statues become animated with twelve moving disciples. Animated statues representing greed, vanity and death also add to the performance, which during the Middle Ages was one of the man-made marvels of the world. For centuries it has been displaying the time and date, the position of the sun, the phase of the moon and astronomical cycles. Even in the age of smart phones, that is pretty impressive! It’s easy to spend a whole afternoon, if not a whole day, here. You can visit the Town Hall, climb to the top of the tower for one of the best views in Prague, watch an Astronomical Clock performance, then enjoy a Czech meal in one of the local restaurants.

Telluride’s literary mecca, this beloved store is stacked with more than 10,000 books at any given time. The expertly curated regional books section is a fount of the Wild West’s writing prowess, with illustrative tomes on the town’s lurid backstory (you’ll want to peruse Tomboy Bride: A Woman’s Personal Account of Life in Mining Camps of the West). When your eyelids get heavy, head to the tiny coffee bar—squirreled away at the back of the shop—for a caffeine jolt to bolster an afternoon of reading.

Lose yourself in the fantasy of living life on a small estate in the foothills of Table Mountain at Stellenberg Estate. This private garden is exclusively open to the public one weekend each year (usually the first weekend in November) and is worth the visit if you’re traveling to Cape Town during this time. One of the oldest properties in Cape Town, has been called home by several prominent families over the years. Fortunately, despite changes of ownership, the property managed to escape the ‘Victorianization’ many other homes in the region underwent and retains its classic 18th century Cape Dutch feel. The house is off-limits to visitors and that’s okay because the main appeal are the gardens. The estate is divided into different gardens, each with their own unique characteristics: a white garden, a walled garden, a formal medieval garden, an herb garden, and more. After wandering through each of the areas of the storybook home, there is a small corner of the property where they serve refreshments. Both savory finger sandwiches and sweet cakes are offered, along with coffee and hot or cold tea. There is a small entrance fee, but expect no more than R50-R60 ($6). After all the wonderful inspiration the garden provides, you will be tempted to purchase a plant or two as you walk through their nursery before exiting. The Stellenberg Nursery is open to visitors Monday - Friday, 8:30-16:30.

One of South Africa’s most famous sights, Robben Island is located four miles to the west of Cape Town. Its history as a prison is almost as old as the first Dutch settlement on the cape, dating all the way back to the 17th century. Today, the island is a UNESCO World Heritage site and museum, offering guided tours by former prisoners. After visiting the graveyard and maximum-security facility, guests can finish with a stop at the cell of the island’s most famous prisoner, Nelson Mandela. The half-hour ferry ride to Robben Island includes breathtaking views of Cape Town and Table Mountain. Just note that the ferry only runs three times a day in the low season; in the spring and summer, there’s an additional departure in the late afternoon. Book your tickets far in advance.

Near the northern end of Andros Island, about 15 minutes by air from Nassau, remote Kamalame Cay is worth the effort it takes to get there. The 96-acre private island features 34 rustic-chic rooms and suites, all within steps of a white-sand beach, as well as a central Great House where guests come together to sip wine before dinner and share stories afterward (of course, many opt for a secluded, candlelit meal set up somewhere along the three miles of shoreline). A range of seaside activities keep everyone from the kids to newlyweds to the occasional celebrity happy. There’s a freshwater swimming pool, an over-water spa, world-class fishing off the coast, and entertainment by local “rake-and-scrape” bands. And for those who live in fear of being unplugged, relax. Kamalame Cay offers hotspots around the island for full cell service (if you want it) and Wi-Fi in the reception area.

A visit to John Watling’s Distillery offers both a tour of a historic estate in downtown Nassau and the opportunity to sample locally made John Watling’s rum. The distillery, the only locally owned one on the island, is housed in the Buena Vista Estate, which began construction in 1789. The estate grounds encompass tropical gardens and a 200-year-old water well. Visitors can also take a free tour of the museum and distillery, where you can see the aged white oak barrels filled with rum. Finish the tour with a cocktail from the on-site Red Turtle Tavern, or pick a bottle of John Watling’s rum from the store.

The Twelve Apostles impresses from the moment you turn off the coastal highway between Camps Bay and Llandudno beach and make your way up the winding driveway. Perched at the base of the mountain range for which it takes its name and overlooking the Atlantic Ocean, the views are swoon-worthy. Located about 25-minutes drive from Cape Town’s city center, 12A is adjacent to Table Mountain National Park and is a great escape from the city for a few nights.

Beyond the views, this luxury boutique has a distinct colonial-era vibe complete with period dress for employees, and decor that is old-world posh with a hint of flamboyance. No two rooms are the same, neither in size nor how they’re laid-out, which gives 12A its distinct boutique feel. But all feature plush fabrics in varying hues, many of which match their wallpaper, along with reproduction antiques and lots of mirrors and artwork. It’s definitely creative, although at times a bit over-the top. I loved the marble and glass modern bathroom with a deep soaking tub and bespoke bath products. The bed was also super comfy and the linens quality. Not all rooms have the same views either, so try to book one of the upstairs rooms where you’ll have either a sea or mountain view and a private terrace.

The service is five-star and so is the food. The onsite Azure Restaurant does excellent fresh seafood in romantic environs at dinner and the best buffet spread in town for breakfast, which should be taken on the outdoor patio when the weather is nice. For sunset head to the Leopard Bar, which pairs stunning views of the sun sinking into the Atlantic with an impressive port and cognac selection, along with a full bar. Also onsite are two swimming pools, an award-winning spa -- guests don’t have to book a treatment for complimentary access to the property’s hydrotherapy pool and flotation tank either -- plus a 16-seat movie theater.

Federal Donuts, which sells wacky-flavored handmade doughnuts, coffee, and Korean-style twice-fried chicken, is just one example of how chefs in the City of Brotherly Love are pursuing their culinary obsessions. The original Center City shop has been joined by branches around town (including one at the baseball stadium) as well as a satellite shop in Miami: The owners’ whimsical impulse to pick up a doughnut machine on Craigslist in 2011 now seems less crazy and more like the first steps of delicious empire-building.