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From the outside, San Giorgio looks like one of Greece’s ubiquitous whitewashed homes. Inside, traditional Greek textiles and locally made furniture adorn the 33 unfussy rooms. Most feature rough-hewn wooden dressers, large circular jute rugs, and beds canopied with mosquito netting. Some have terraces with views of the Aegean Sea. Guests can relax during the day in cocoonlike hanging swings near the pool or take a 10-minute walk to the popular beaches Paradise and Paranga. In the evenings, it’s not uncommon for DJs such as Bob Sinclar or David Guetta to make guest appearances in the hotel’s open-air lounge.

This honky-tonk-inspired bar has a hometown feel and a country vibe, and has great local beers on tap—like Grand Cayman’s classic premium lagers, the CayBrew and Caylight. Don’t miss out on the Thursday night Rock & Roll Bingo: It can get rowdy and is a lot of fun. Lone Star Bar and Grill is well known for its BBQ, including Texas-style ribs as well as barbecue chicken and burgers. When you get the munchies after a few beers it’s a nice break from the gamut of seafood offered at other establishments.

One of the delights of Valparaíso is exploring the colorful hillsides that ramble down towards the sea. Take the century-old funicular elevators Ascensor Concepción (Turri) or El Peral near the main plaza, constructed between 1883 and 1911. Once high into the hills of Cerro Concepción & Alegre, explore the meandering alleyways and cobblestone streets on foot. There are boutiques, cafés, mom-and-pop shops, old school bakeries, bars, restaurants, art galleries, and church bells tolling. It often feels more like a small village than a city. Climb up and down the many staircases often lined with bright graffiti. In the distance, the bay gleams in sunlight and the busy port never tires. At dusk, the lights twinkle like fairylight. Grab a table at a spot like Café Turri for a view of the sunset and a cocktail.

There’s a reason chef Tony Maws has developed a cult following at Craigie on Main. For years, the cozy restaurant has been turning out beautiful food in a space that feels like it might be your friend’s dining room. Its commitment to regional, organic sourcing has been called a tad obsessive, but once you’ve eaten there, you’ll appreciate the attention to detail. The menu is created only after the best of the day’s ingredients have arrived; the wine, beer, and cocktail list also features the same local flavor. If you want the full experience, the chef’s seasonal tasting menu is a must. The corned-beef hash on the brunch menu is one of the reasons the restaurant regularly ends up on “Best of Boston” lists. (House-made doughnuts in a pool of golden caramel sauce don’t hurt either!)

At Maui Brewing Co. in Kihei, visitors can take hour-long tours of the brewhouse, cellar, and packaging line, then adjourn to the tasting room with views of Haleakala and Molokini. There, they can sample beers, ciders, wines, and specialty cocktails while playing board games or simply taking in the vistas. Also on-site at the brewery is a restaurant with 36 craft and specialty beers on tap, plus a menu of burgers, fish tacos, and pizzas with MBC’s Bikini Blonde lager in the crust. Go for the live entertainment or the twice-daily happy hours, when you can enjoy steep discounts on house beers, classic cocktails, pizzas, and select appetizers.

I wouldn’t recommend doing the Ute Trail hike on your first day in Aspen, especially if you come from sea level, but it is definitely a must see. Known as one of the harder hikes in Aspen, it is short but sweet. You traverse up the side of Aspen Mountain on steep switchbacks and just when you think you can’t do one more switchback and your lungs are about to burst you come to a precipice with one of the best views of the town of Aspen. It should take anywhere from 30 minutes to an hour to get to this point. From here you can keep hiking to the top of Aspen Mountain and take the Silver Queen Gondola down, which is about another hour and 30 minutes, or trek down the way you came on the Ute Trail.

Fringe just oozes character. From the moment I walked past the racks of vintage clothing and battered cowboy boots outside the shop, I knew I had to go inside. The interior is like a hip warehouse of sorts—a large but cozy space full of vintage furniture, clothing, art, and lots of unclassifiable goodies. The owner also carries carefully selected body products such as Kai fragrances. The shop is best known for its vintage signs, many of which have been carefully restored and are alone worth a look. Fringe is located on a fun section of 21st Street at the south end of Midtown Sacramento. Next door is the lovely It’s All Yoga studio and a large antiques store. Around one corner is Sacramento Beekeeping Supplies and around the other is the Vietnamese Buddhist restaurant Andy Nguyen’s (all vegan).

A brief description of Skansen—a 75-acre open-air museum with historic buildings and a zoo—doesn’t convey just how much fun it is. You can easily spend a happy half-day here, looking at wolves, reindeer, moose, seals, and other Nordic creatures, then popping into old buildings that have been brought here from all over Scandinavia and reassembled. In some you can talk to people in costume who are playing the roles of the original inhabitants. Elsewhere you can watch glassblowers at work and visit old-fashioned stores. Open since 1891, it remains one of Sweden’s top tourist draws.

Located on East Beacon Drive, off of Route 12 in the town of Rodanthe, is perhaps the most famous beach house in the Outer Banks. The Inn At Rodanthe was the actual setting for the movie based on Nicholas Spark’s prized novel “Nights at Rodanthe” starring Richard Gere and Diane Lane. Designed to have the look and feel of a traditional seaside inn, it features six bedrooms and suites, balconies providing stunning views of the Atlantic, and the famous blue shutters and house sign so prominently featured in the film. One can rent the house through Sun Realty and I’m sure you’d have an amazing stay. Or if you’re driving by, the house is easy to spot with beachgoers parking their cars along the street and coming out to take pictures.

One of the great things about the Caribbean is that its rich history was often written at beautiful, easily accessible locations. One of the best places to learn a bit of that history is pictured above. That’s the beach at Columbus Landing in my home island of St. Croix. It was here, in 1493, that Columbus sent ashore a small contingent of his men to scout for fresh water. What they found instead were a group of Indians who weren’t too keen on visitors. What’s the whole story of Columbus and his less than stellar (to say the least) track record throughout the region? That may take a bit more book learning, but feeling what these new visitors may have felt coming ashore in this corner of paradise starts on these sands.

For the past 10 years, Mario, the owner of VEBorange, has been selling DDR (East Germany) collectables and other German antiques. Most items in the shop on Oderberger Strasse are objects made and sold between 1950 and 1980, making this a great place to find kitschy and totally unique goods. When I visited on a sunny Saturday afternoon, Mario was tinkering with a Sputnik relic from the CCCP. Not everything that he collects or receives ends up on the shelves. Behind the counter are the things deemed interesting or noteworthy—things that might fit in a museum. If the nearby Mauer Park turns out to be too disappointing for you, head over to VEBorange (a short three-minute walk away) to find truly unique and special items. You can find everything from old Soviet war medals to clothes and furniture.

The weekly flohmarkt (flea market) in Friedrichshain’s Boxhagener Platz is a popular spot where locals meet up for shopping, drinking, or just a bit of fun each Sunday. While the Mauer Park flea market gets most of the tourists, this one is far less touristy. You’re much more likely to find a good deal on used books, cool T-shirts (some by local designers, even!), music records, and knickknacks. Because the market is relatively small, it’s quite enjoyable to take a stroll through the stalls and then enjoy a picnic on the grassy area in the middle of the square. Many cafes and restaurants are situated on the streets bordering Boxhagener Platz so you won’t be bored for things to do. The market is open Sundays during daylight. On Saturdays in the same area you’ll find a fresh food & produce market.

Castle Ho’s motto, the owner of lovely boutique 1861, is quite simple. “Women who love being women and dressing the part.” Such is the premise of her work, and it definitely transposes into her boutique. The store is decorated in what seems to be a vintage fashionista’s dream: airy space, high ceilings,Vvictorian inspiration, and soft eggshell, champagne and pastel pink hues everywhere. No boys allowed! The multi-brand store focuses on feminine, timeless pieces first and foremost, and incorporates up-and-coming designers into the mix, like UK-based Emily and Finn and Torontonians Pink Martini, along with Montrealers lines Coccolily and Arti Gogna. Don’t be fooled by the perfect, fairy-tale decor; the prices are more than fair and very few things are over $100 in the store. Guilt-free, stylish shopping? I like.

The nightclub Chalet is located on the busy nightlife-riddled street of Schlesische Strasse. Just steps from one of Berlin‘s longtime hipster nightclubs, Club der Visionaire, Chalet is relatively new to the scene. Open since 2012, the club is run by the same legendary Bar25 crew (now closed down, sad face here). Chalet is located in what appears to be a run-down house, but really that’s par for the course in Berlin. Thankfully the yard out back is a small oasis. All weekend long, you’ll find Berlin’s trendiest folks hanging out in the Chalet courtyard. A night out at this club feels a bit like a house party—just with a small cover at the door. My photo above was taken at 6am on a Sunday morning...so hopefully you get the idea.

RedRocks is a small eatery in the Columbia Heights neighborhood in Washington, D.C. It’s located just a couple blocks off the main commercial area hugging 14th Street. While there are plenty of chain restaurants peppering 14th Street, it’s worth straying a couple blocks to come to RedRocks. This is a neighborhood bistro that’s all about casual dining—perfect for unwinding from a day of sightseeing or shopping along 14th. Neither the atmosphere nor the food is pretentious. I come for the wood-fired pizza, and nothing satisfies me more than their Neapolitan pizza topped with house-cured sausage and pepperoni. You can come here with friends and just hang out to eat and drink and have a good. Sometimes simple pleasures are the best! Metro stop: Columbia Heights