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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.)

This hotel is on our list of The 10 Best Hotels in Canada.

Fogo Island Inn sits at the very edge of the north Atlantic on isolated Fogo Island in Newfoundland. Designed by internationally renowned architect Todd Saunders, the inn’s arresting modern appearance is suggests an iceberg from a distance, with its raised section representing the island’s traditional stilted fishing platforms. But when visitors get close, they see the wooden boards layered together, and it’s clear that everything is handmade. The by-hand ethos covers all the furniture and furnishings, created by local artisans who’ve worked with artists in residence to create contemporary versions of traditional objects.

Staying at the inn is admittedly expensive, but this is essentially a living art piece that supports the local community and aims to honor the island’s past while carrying it to the future. It feels like a grand home with attentive staff. A private 42-seat cinema, partnered with the National Film Board, carries a movie library for guests to enjoy at any time; there’s also an art gallery, a well-stocked library, and a supply of Gore-Tex hiking boots and other outdoor equipment to borrow. The inn shows off the dazzling landscape, and it’s easy to spend all day at the windows watching the sea while whales breech, icebergs float past, or storms dash on the rocks.

A chic deli to be sure, Belmondo serves American-style sandwiches like Reubens, tuna melts, grilled cheeses, etc.—about which its young, fashionable adherents rave—but the menu holds some surprises as well, like a barbecued brisket or a chicken curry on peasant bread. The salad selection is varied and creative, in everything from an old-fashioned Cobb to exquisite local beets with goat cheese and avocado. Breakfast (weekends only before 1:45 p.m.) is also about greatest hits; think eggs Benedict and French toast or one of the very few bagels with gravlax you’ll ever see south of the Rio Grande. The place, in Roma Norte, is famed for celebrity sightings and generally crowded, yet the vibe is low-key, cool, and friendly.

While in Cape Town, be sure to take the red bus route and head to Camps Bay Beach. Camps Bay is a beautiful spot to enjoy dinner and watch the sunset for a perfect way to end the day. Many restaurants have outdoor seating facing the beach so you can enjoy a bottle of delicious South African wine while admiring the last rays of sun in the afternoon. Camps Bay has really cool rock formations and the views of the Twelve Apostles mountain chain.

Debre Birhan Selassie is a small church located in the heart of Gondar, Ethiopia. The original church was was built by Emperor Eyasu II, grandson of the great Emperor Fasilides, in the 17th century. The present day church was rebuilt in the 1880s following damage by marauding Sudanese Dervishes. I found the exterior of the church to be rather unassuming but once inside, I understood why this little church is one of Ethiopia’s top tourist attractions. Every inch of wall and ceiling space is covered with painted images. The beamed, painted ceiling will immediately grab your attention. Look up and you’ll see the faces of 123 winged cherubs representing the omnipresence of God and the walls depict biblical scenes and saints. On one end of the chapel, two curtain covered doors lead to Holy of Holies where the church’s copy of the Ark of the Convenant is housed. Above the two doors are icons of the Holy Trinity (the Father, Son and Holy Spirit as represented by three identical men with halos) and the Crucifixion. There’s a lot of significance to the murals and this is the one place where having someone explain them to you makes sense. The priests do offer tours – just be sure to leave a small contribution behind when you leave.

Driving up Independence Pass is a beautiful way to spend the afternoon and along the way to the top of this 12,096’ pass you can stop at highlights. For the thrill seekers, near the Grottos there is a series of waterfalls that flow into a crystal clear pool of mountain river water called the Devil’s Punch Bowl. People jump from 20 foot cliffs into borderline hypothermic cold water that takes your breath away when you hit it. Make sure you jump out far enough so you don’t hit the jutting rock bed on the way down. Some might think it is crazy but it is the ultimate adrenaline rush.

One of the most fun places I dined at in Italy was Il Latini, in Florence. It’s in a large, maze-like building with aged prosciutto hanging from the ceilings, and art collaged upon the walls. Seating is at communal tables, and at times it felt like we were all at a wedding. In our case, my boyfriend and I sat with another couple from Australia, who were beginning their tour of Italy, but it’s easy to meet locals at this spot, too. The waiters and the owner are very persuasive when it comes to traditional Florentine food. I requested half of a Florentine steak, but I am sure I was given a full one—one of the largest I have ever seen served. It was cooked rare, and was extremely tender and flavorful. However, I am not much of a carnivore, and as such, my favorite part of the dinner was the fresh sage ravioli. After our meal, the waiter kept bringing shots and wine, which appeared to be on the house. There are no exact prices, and the waiter determines your meal’s cost.

Shopping is not only for humans in Aspen. Your dog should be spoiled with gifts too, especially if you left them at home for the trip. There is no better place for that than C.P. Paws. Look for their sandwich board sign on Hyman Avenue walking mall and walk down the alley. If your dog is with you they will generally sniff it out and lead the way. This is not your ordinary pet shop. Sure inside they have the toys, treats, coats, dog beds, leashes and collars but they have so much more. Get a hand painted dog bowl with your dog’s name or maybe you need a coffee mug with the breed of dog you have to let everyone know you love your pup. Everything is of a high quality and very stylish. Steve, the owner, and his faithful companion, Baxter, are there most days and will gladly help find the right accessories for your loved one. I bought a harness for my very lovable “Marley and Me” yellow lab that was pulling me everywhere and he helped me fit it to her and he even special ordered the perfect color. Your dog might forgive you for leaving them if you bring them back something good.

To get from point A to B on the river delta, you’ll need to board a water taxi. These polished wood boats cruise the canals day and night, dropping passengers off and picking them up at rental houses, cabin complexes and restaurants along the way. The ride, of course, is part of the fun. Board one at the harbor - and make sure you know where it’s going before you sit down, or it might be awhile before you find yourself back in civilization.

This leather workshop is hidden away in a former Franciscan monastery next to Santa Croce. The Scuola del Cuoio was originally founded to provide skills and work for some of the city’s orphans after World War II; masters and apprentices still produce wallets, purses, journals, and jackets. Take a quick tour of the beautiful cloisters, frescoed corridors, and workspace, or sign up for a full workshop and try your hand at making something of your own. Everything is crafted on-site using traditional methods. Be sure to get your purchases personalized with a gold-stamped monogram.

O’Donoghue’s Bar, which dates back to the eighteenth century, is arguably the most famous pub in Dublin for traditional Irish music. The bar is lively, rammed with a mainly—but by no means exclusively—local crowd, and has a great, welcoming atmosphere. There is a huge beer garden, and on busy nights there will be someone serving the tables outside. The main draw, of course, is the live traditional music, which kicks off mid-evening seven days a week. Unlike many other venues that boast live trad and there is no sense that the music at O’Donoghue’s is a performance put on for the tourists. In fact it’s quite the opposite: you get the feeling the musicians are playing solely for themselves, and don’t care whether you listen or not. Which is lucky, really—the night we were there the bar was so crowded, and the conversation so raucous, that you had to get really close to hear the music. If you’re a fan of, or curious about, traditional Irish music, O’Donoghue’s is definitely a place to check out. And make sure to keep your eyes open as well as your ears: such local musical luminaries as the Dubliners and Christy Moore have been known to swing by in the past!

Jimmy’s Corner is long and narrow, as if some great prophet looked at a hallway and said, I see a dimly lit saloon here, complete with an extended bar and walls plastered with photos of boxers. Opened in 1971 by erstwhile pugilist James Lee Glenn, Jimmy’s sits midblock on West 44th Street, between Sixth Avenue and Broadway, in Midtown Manhattan. Which is what makes this no-frills bar unique. It’s a classic American dive, and the only one around, a relic from when the Times Square area was more depravity than Disney. Bartenders, who can spot a near-empty glass with the eyes of a hawk, are friendly but gruff. Case in point: As a 50-something woman with spiky bleached blonde hair mixed me another whiskey soda, I nodded to the boxer-bedecked wall behind the bar and said to my friend, “They don’t really like boxing much here, do they?” The bartender looked down the bar, pointed her finger at me, and bellowed with a thick Russian accent, “He make feeble attempt at joke!” She might have been right. If you go to this watering hole, make sure you’re thirsty (drinks are cheap) and your jokes are not so feeble. This appeared in the August/September 2013 issue. Image courtesy of Shanna Ravindra

Why I was so surprised to find a food truck in the village of Volcano outside of Volcano National Park, I’m not sure. All I know is that it was one of the many culinary surprises on the Big Island. This truck was packed with all kinds of wonderful things, and almost all of it was healthy too. If you can find it, and I have no way of telling you where they will be parked, ask for the special drink they mix up daily, I think it has ginger it in, but they’ll know what you mean. The company is called Higher Taste Vegetarian Cafe, and this truck was parked outside of the Rainforest Gallery at Niaulani near Volcano Village. That’s the best I can do, but then again, finding the truck is half the fun!

São Paulo has a thriving culture scene that can be seen in its museums, craft fairs, graffitti, and artsy shops. If you spend a Sunday there, be sure to head over to São Paulo’s main avenue, Avenida Paulista, for a three-part cultural experience. First, the Museu de Arte de São Paulo (São Paulo Museum of Art, or MASP) is well worth a visit. It houses Latin America’s finest collection of Western art, including pieces by Picasso, Rembrandt, Monet, and other European masters. The museum also houses excellent temporary exhibits. If you’re hungry, you can eat at the museum’s cafeteria or wait and get snacks at the nearby crafts market. As you leave, spend some time perusing the huge antiques market that takes place every Sunday under the museum. Then cross the street and wander the “feira,” or crafts market, for typical Brazilian crafts (some of which are quite expensive) and good street food. Finish up with a stroll in the adjacent Parque Trianon, where musicians often play on Sundays. MASP is open 10-6. Admission is about $8 and $3.50 for students. Parking is available in lots and garages on side streets, and the metro station is Trianon.

From the dusty street, the Hotel El Convento in León, Nicaragua, beckons with its stately façade and red Spanish-tiled roof. Step inside and you instantly feel at home amidst ornate period furnishings that are surely a far cry from the building’s humble beginnings as the 1639 San Francisco Convent. The elegant Restaurante El Victoriano offers an indoor-outdoor retreat centered on the hotel’s manicured, tropical courtyard—an example of the colonial hacienda style found throughout León. The restaurant is a meeting place for people from all walks of life—aged former Sandinistas who now hold positions of leadership, locals splurging on a fine meal, or foreign students from one of the city’s many Spanish language schools seeking tranquility and an excellent cup of coffee.