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Hidden away just to the left of Starbucks is a corridor that leads you to a medieval courtyard. Numerous artists, craftsmen, and civil servants have lived here since medieval times, and the residences are still in use today. So much of life in medieval times took place in courtyards like this one, away from the prying eyes of the street. Stepping into Platzl Gassen feels a little bit like slipping back in time a few hundred years. Of particular interest are the houses at Platzl 2 and 3 with their “Ohrwascheln"—asymmetrical roofs.

A delightful peach-colored villa set directly on Treasure Beach, this Jamaican-owned guesthouse is a gem, and feels more like a vacation home than a hotel. There are six spacious guest rooms and two larger suites, each with their own patios or balcony with a glorious sea view. The interior is intricately decorated with carefully chosen African-themed paintings and sculptures, and the owner—who returned after many years in the US—takes pride in providing true Jamaican hospitality. There’s a bar and no restaurant on site, but that doesn’t prevent the large kitchen and staff cook from taking your daily orders for breakfast and dinner, dishing out excellent local specialties that are served poolside with the sea in front of you. It’s one of my favorite places to stay and get away from it all.

With a 20-foot waterfall, a deep turquoise pool, and underwater caves, the Irie Blue Hole is a special find. You’ll need to hire a guide in nearby Ocho Rios to bring you up the mountain to explore this off-the-beaten-track place, but it’s one of Jamaica’s most stunning swimming holes. The lush setting, surging blue waters, and options for cliff-jumping will keep you there for hours. This gorgeous blue hole is now attracting more visitors, but it never feels too crowded. Yet!

Because it’s a major cruise port there are plenty of tacky restaurants on St. Thomas, but it doesn’t take a lot of effort to get under the skin of the island and find places where the locals eat. One such restaurant, Gladys’ Cafe, serves up traditional Caribbean fare and is known as one of the best on the island. Skip the a la carte menu and instead get one of the lunch plates including curried chicken or goat served with red beans and rice, mac and cheese and fried plantains.

Café Monarch is to dining what the monologue is to theater, meaning a one-man show. Chef Chris is the guy who will cook your food. He’s also the guy who will take your reservation, field your order, and, quite possibly, bus your table. It’s a small and intimate place that’s been compared to the Secret Garden. I get that. The entire spot measures only 500 square feet and it’s some serious face time with one of Scottsdale’s best chefs. It’s a labor of love where the menu changes daily.

Tucked amongst the galleries in downtown Scottsdale’s art district, Frank & Lupe’s is a charming hacienda with delectable, down-home Mexican food. Its shaded back patio is one of the best places to sip ice-cold Tecate or margaritas on a nice day. No doubt one of the restaurant’s shining stars is the carne adobada burrito plate, a warm tortilla wrapped around pork marinated in red chili sauce, vinegar and oregano. It’s on the spicier side, but a nice dollop of sour cream balances it out nicely.

There’s no better way to get the perfect pair of cowboy boots than to get them made to order, and that’s Heritage Boot’s specialty. These boots are made by hand by artisans from Leon, Mexico that have been making boots for generations. There are timeless pieces with the best quality skins, imported from Europe, and the attention and love for detail shows with every piece. Stop by to check out the fun art work that decorates the store or to place your order on first pair of hand made Cowboy boots!

When I first found this store, I was overwhelmed. This place holds so many treasures, you’ll need several trips to look through everything. Franky’s is one of the most popular thrift/vintage stores in Puerto Rico, and likely only one of a few. The proprietor provides a lot of his items as props for movies being filmed in PR—like the recent Rum Diaries movie. If you like vintage, then you’ll love shopping here. It’s on the corner of San Francisco Street, right behind the little plaza as you enter Old San Juan.

There’s a powerful love for the 80s in Chile and in no other club does this shine through like at Blondie. The nightclub is tucked away in a retail shopping center in a gritty area of La Alameda. You’ll hear anything 80s from New Wave to techno, goth rock, and theme nights like Pet Shop Boys, Bowie, Madonna, even 90s nights. There are also live concerts from local rock bands like Lucybell. A favorite place to party with the gay community and university students. Alameda 2879 (Metro ULA)

After New Year’s, tomatoes become the king of vegetables and flood the markets with no end in sight (until March). Many of the shirt-soakers hail from a dusty country town near the coast called Limache. These tomatoes hold a place in most Santiaguinos’ hearts and nearly every restaurant, joint, and household will be making copious amounts of “Ensalada Chilena” (Chilean tomato salad) at this time of year. The ingredients are simple: perfectly ripe tomatoes cut into slices or wedges (no skin), tempered onions, chopped cilantro or basil, a drizzle of olive oil and a pinch of sea salt. Heaven.

Chilean “completos” are hot dogs piled high with the works--usually mashed avocado, chopped tomato, optional sauerkraut, and an obscene amount of mayo (maybe 1/3 cup). Actually, eating them is a feat of gravity without the toppings winding up on your shirt, or the ground. Chileans are passionate about their completos and no place draws them in like Dominó, an old-school soda fountain with locales peppering the downtown. Locals crowd around the counter to scarf down these dogs with Coca-Cola or freshly made juice. Various locales throughout downtown (see website)

Located above Explore Booksellers off of Main Street, Pyramid Bistro is Aspen‘s first restaurant serving sustainable food with integrity. Martin, the head chef and owner, prides himself on preparing the freshest food from raw, nutrition-dense ingredients. This is the optimal place to eat if you are gluten-free or vegetarian. You can’t go wrong with one of their amazing salads, delectable stir fries, or house specials like Indian Spiced Red Lentil “Gallette” or Caraway Dusted Petaluma Duck Breast. Dining in a historical Victorian House only enhances the experience.

One of the first things I like to find when visiting a new destination is a place to take a good walk. Winding through the city’s waterfront neighborhoods, the design of the HarborWalk allows the public to connect with the cleaned and restored Boston Harbor. The section in South Boston and Fort Point Channel takes you along some of the city’s best views of sparkling high rises, as well as plenty of good restaurants to stop in. Take time to people watch and grab a bite. Their interactive map shows the visitor just where they can connect to it.

Owned by brothers James and Adam Roth, this quaint wine and gourmet food shop welcomes customers to sample a handful of seasonal wines or beers every Thursday and Friday evenings and Saturday and Sunday afternoons. The wines and beers are usually paired with artisanal cheeses and/or charcuterie from their gourmet food section. Ask to be on their email list so as to find out what specials and promotions are happening. Beer tastings are held on Thursday evenings, and wine tastings take place on Friday, Saturday, and Sunday afternoons.

Tree-Guys Pizza Pub is a great place to stop in for a pie and a beer. With the usual array of pizza choices, there’s no shortage of great eats right at your fingertips. Connected to the pizzeria is Hi-Fi Lounge (the pub) where you can belly up to the bar on any given night and sample their daily drink specials. From draft beers, to Bloody Marys, to choice tequila, there’s no shortage of libations at this local watering hole. Come for some pizza, stay for some drinks—the Tree-Guys insist.