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Sacsayhuaman is an impressive Inca fortress on a steep hill that overlooks all of Cusco. The ruins are humongous, but archeologists believe that the original site was as much as four times larger. What remains today are the impressive outer walls constructed in a zigzag formation across three levels. As with many Inca sites, the walls are made from massive, irregularly-shaped boulders that stick together like a jigsaw puzzle without any additional support. The stones are laid together so tightly that a sheet of paper will not fit into many of the cracks. As the night comes down, this is a perfect location to appreciate the stars.

Quinn’s gastropub specializes in meat, meat, and more meat — everything from crispy pork belly to wild boar sloppy Joes to roasted bone marrow and foie gras frites. Choose an assortment of small plates to share, or get a large plate all to yourself. The two-story restaurant feels casual but intimate, with dark wood furnishings and candles at the tables, and the lighting is romantically low. Service is cordial but leisurely, so peruse their extensive drinks list and settle in with a Trappist beer, a fine whiskey, or a craft cocktail and enjoy the Capitol Hill people-watching through their floor-to-ceiling windows.

Coconut Grove represents old-school Miami. This small pocket of bayfront parks, marinas, shops, and restaurants just south of downtown Miami was one of the city’s first neighborhoods, and people from all over the city are realizing that the Grove is cool again. Recently, independent shops and restaurants have been opening, and young families have started moving in to enjoy the art galleries, green spaces, and pedestrian-friendly streets. Coconut Grove’s waterfront location and historic charm kick off its appeal, but the real winner here is the dining scene. Mouthwatering options include French, Peruvian, Hawaiian, and Mediterranean cuisine, creamy gelato, and more. Come hungry.

The beef goes back centuries, and will never be entirely resolved: what are the true origins of pisco, a grape-based, aguardiente distillate that became a national symbol of Chile…and Peru. To end the conflict, the people behind this bar and restaurant invented a new, independent republic dedicated to Pisco that is known as Chipe Libre. Inside a vast Lastarria mansion, this imaginary state unites lands in southern Peru and northern Chile, in obeisance to a sole monarch, pisco. The bar features a good 100 labels and cocktails like “Pisco’s in the Air,” made with lime juice, raspberry, papaya and basil; plus a full range of what are among Santiago’s best traditional sours. Standout food include the crunchy-seafood saltado (marinated and grilled beef strips), with mango, served on a sizzling grill; the joint’s star sandwich, El Presidente, is a solid slice of roast beef, fried egg, and shoestring potatoes. To avoid any sovereignty disputes, Chipe Libre flies its red-and-black, center-starred flag as the republic’s national colors.

Don’t be discouraged when you see the long line winding through the store, out onto the sidewalk, and back into the building — it moves surprisingly fast, and Piroshky Piroshky is worth it. Plus, the wait will give you time to peruse the glass case and make the agonizing decision: chocolate cream hazelnut roll, cheddar cheese and garlic roll, or their signature fish-shaped smoked salmon pate roll? (It’s a trick question. Get one of everything and share.) There’s no seating, so take your pies to go and eat at the small waterfront park nearby. If the weather’s foul, you can duck back into the indoor market to eat.

Hop on the commuter train at Lido Station (next to the Piramide Metro stop) and make the 25-minute trip to Ostia Antica, Rome’s ancient port town and administrative center. The teeming city of up to 100,000 residents is relatively well preserved and allows visitors a peek into the daily life of ancient Romans. Walk the basalt streets, visit the Forum, descend into Mithraic sanctuaries, and peruse the market stalls, which were in use until around the 5th century C.E.

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.

You’ll never sleep anywhere closer to Machu Picchu than Belmond Sanctuary Lodge—it’s adjacent to the site entrance, and the only hotel on the mountain. In fact, the lodge is built on the former staging area for American explorer Hiram Bingham, who rediscovered the “Lost City of the Incas” in 1911. You’ll pay a pretty penny but consider the price a once-in-a-lifetime splurge. If you arrive the day before your visit to Macchu Picchu on the bus up from Aguas Calientes, you can be at the gates right when they open at 5 a.m. and get a head start on most of the crowds—and the sunrise. And if you’re coming off a days-long hike on the Inca Trail, the spacious showers and plush robes will be the best you’ve ever experienced.

There are only 31 rooms here, some with terraces and mountain views but all with exquisitely comfortable beds and marble bathrooms. The light-filled restaurant—only open to guests—serves both international and Peruvian dishes, and the bar is a great place to enjoy a pisco sour after a day of exploring the ruins. If you really want to stay in style, consider arriving by the elegantly restored Belmond Hiram Bingham train from Cuzco—the hotel offers packages.

You have to climb a few steps to reach this romantic restaurant, but it’s worth the effort, even after Machu Picchu. Beautifully presented dishes range from beef tenderloin to grilled trout with golden aguaymanto berries. The Tree House is one of Aguas Calientes’s best places to try alpaca steak, yet vegetarians find tempting options, too, like ravioli with goat cheese and mushrooms. The tight dining room, nestled in the boughs, is romantic and dreamy. Be sure to make reservations.

The village of Roslindale is filled with unlikely gems. Joanne Rossman Design is at the top of that list. Billed as a Purveyor of the Unnecessary & the Irresistible, it’s a destination filled with treasures you never knew you couldn’t live without. Charming artwork, wonderful cookbooks, scented natural soaps, divine fragrances and a collection of vintage accents for your home, each deserving of their own special place. Make sure not to miss the designers own handmade slippers, scarves and throws. Each is one of a kind, and created from the extensive selection of antique trims, fabrics and buttons that Joanne has culled over the years from all corners of the globe. The neighborhood has a slew of good restaurants, so it’s easy to spend an afternoon perusing the area.

Ollantaytambo’s namesake archaeological site is one of the best examples of Incan architecture in the region. It’s easy to spend a half day exploring the temples and other structures there, especially if you factor in time to hike up beyond the ruins. Meanwhile, the quaint town itself remains much as it was in Incan times, with original houses, streets, and waterways. Some buildings are open to the public, offering a fascinating glimpse into a centuries-old way of life. Most Machu Picchu–bound trains leave from the station here.

Every Saturday from 7 a.m. to 1 p.m., the island’s largest open-air market sprawls across the University of Hawai‘i Maui College campus, creating a lively scene with more than 200 vendors. Many of Maui’s best boutiques sell their wares here, but for much cheaper prices than at their brick-and-mortar locations. Browse for muumuus, wood carvings, and other handmade crafts like bone and shell jewelry, or treat yourself to a shave ice while perusing piles of leis, local fruit, and homemade baked goods. The market is especially strong when it comes to street food—don’t miss the spam kebabs, banana bread, and goji kombucha.

For those who want to do some serious shopping, the St. Rose Shopping Mall in Philipsburg is home to international chains, luxury brands, boutiques, and art galleries. Peruse stores like Cartier, Façonnable, Lalique, and Beach Avenue all in one place. If you’re hungry, the nearby boardwalk is full of restaurants and bars offering views of Great Bay. Tip: Make sure to get a sweet crepe or ice cream from Café Vanille & Chocolate, known for their tasty desserts. Ask your hotel to check if there are any events happening at St. Rose Shopping Mall, too, as the venue hosts concerts, performances, and exhibitions throughout the year.

Among the sleek high-rise buildings of El Golf, right off the Plaza Peru, is Tiramisú (aka Santiago‘s best pizza). If you are yearning for an authentic, Italian pizza with thin crust, buffalo mozzarella, and primo ingredients pull up a chair. Always buzzing with a long wait for tables at lunch and dinner, this family-run establishment starting 12 years ago with only a dozen or so tables--and is now over 132. Besides pizza, the large salads, calzone, and bruschetta are delicious. Isidora Goyenechea 3141, almost corner Augusto Leguía Norte (Metro El Golf) Phone: 56 (2) 2519 4900

As if the picturesque Umbrian hill-top town of Spello wasn’t perfect enough, it’s also home to the fantastic Vinosofia wine bar and shop. This beautifully designed space is as warm and welcoming as it’s owner, American expat, Brenda. Vinosofia boasts a wide variety of local wines and, each month, features a different region in Italy. When I visited, I was able to taste some spectacular Sicilian wines, alongside bottles from neighbouring towns like Montefalco. Although wine is the star of the show, it’s not the only player at Vinosofia. Taste delicious local cheeses, salami and olives from the trees you see around every corner. You can also peruse and purchase a collection of cookbooks, in both English and Italian. Vinosofia might just be the perfect wine bar... further tasting, er testing, is required.