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Hyde Park is happening. Catering to the University of Chicago crowd and its visiting dignitaries, the five-year-old Sophy takes inspiration from hometown literary and musical heroes, whose artworks ornament the walls in the popular and always convivial Mesler restaurant. Taking the title of the first boutique hotel on Chicago’s South Side when it opened in 2018, the property occupies a prime spot on 53rd Street—a vibrant commercial hub lined with shops and restaurants owned and frequented by a diverse population that range from academics to local politicians to the city’s cultural influencers. Former UofC professor Barack Obama’s home (and his under-construction presidential library) are nearby.

It’s all about the playful details at Holiday House, from the love beads that guests receive on arrival to the custom fortune cookies they take home with them. But make no mistake—this 21-and-up property is an upscale, high-style destination. Built in 1951, the 28 rooms and communal spaces were originally designed by pioneering architect Herbert W. Burns, one of the major forces behind Palm Springs modernism. A 2017 update by lauded interior designer Mark D. Sikes reinvented the hotel, giving fresh life to its clean lines with curated artwork and a cobalt, white, and warm wood palette (even the bicycles match). Accommodations are organized as Good, Better, and Best—and the latter is well worth it for the soaking tub and outdoor shower. The pool scene is laid-back and refined—waiters serve rosé flights between guests’ dips in the water—while an honor-system pantry is stocked with such desert “essentials” as sparkling water, straw hats, and potted succulents. Pro tip: Make a reservation in advance for the al fresco Friday night fried chicken dinner, which draws a crowd for its locally sourced chicken, delivered fresh that day and served with comfort-food sides.

Just 45-minutes north of Belize City, Altun Ha is a complex of Mayan ruins dating back hundreds of years. Once the “treasury” for the Mayan people, Altun Ha is one of the most important Mayan sites in the country. Go on a tour of the place with Foolish Dreamzzz, a locally owned operator that will take your group at any size (and the price per person doesn’t change, whether you’re in a group of one or ten). Ask for Kendis Ferguson, the owner and a former history and social studies teacher. He and his company go above and beyond to make sure guests have all their questions answered, and he’ll even make sure you get to climb to the top of the ruins—something not a lot of tour guides in the area make the time to do. The views from there, of course, are amazing.

Grab breakfast at the Sheraton Hotel, located at the south-eastern end of the corniche. This newly-refurbished hotel, also known as The Pyramid of the Gulf because it’s shaped like an Aztec pyramid, offers breathtaking views of the bay and the city. Plus what a better way to start your day than having a scrumptious breakfast at one of the oldest iconic landmarks of the city?

Small and intimate, Hotel Casa Oaxaca feels quintessentially Oaxacan: It’s colonial in style, with whitewashed walls contrasting with vivid pops of carnelian red and fuchsia. It’s surrounded by local vegetation. And it’s filled with Oaxacan handicrafts and art. Common areas invite visitors to settle in and relax, like the on-site library, pool, and terrace with beautifully-made cotton hammocks. The hotel’s seven rooms are arranged around the central patio. Visitors consistently say the service is exceptional, with attention to detail and a “go the extra mile” attitude mentioned frequently as one of the main reasons to return. Another is the hotel’s central location, as it offers an easy walk to many of Oaxaca’s top sights.

Especially after its recent $35 milllion refurbishment, Four Seasons Costa Rica sets the standard for service and luxury in Costa Rica’s burgeoning luxury resort market. Its location is unmatched: perched atop a narrow isthmus, overlooking beaches on both sides, at the very tip of the Papagayo Peninsula. Three swimming pools form the hub of action, spanning the width of the peninsula; on one side of the enormous main pool is an adult pool leading to serene Playa Virador on the Pacific, while the busier family pool leads down to Playa Blanca, where most of the water activities happen—snorkeling, stand-up paddling, kayaking. There’s also an 18-hole Arnold Palmer–designed golf course that’s been tamed from the surrounding jungle. Guest rooms have marble baths, and outdoor terraces or verandas, while the larger suites (one- and three-bedroom) include their own pools. For light dining options, try the ceviche offerings poolside at Bahia or Italian seafood at Pesce. For a splurge, head to Caracol at the golf course for steaks and lobster tail.

When hotelier Sean MacPherson opened the Ludlow he totally nailed the unique spirit of Manhattan’s Lower East Side. The 175-room hotel is the perfect mix of gritty and stylish, cool and calm. Rooms are done up in that signature MacPherson style with unique artisan touches including handmade silk rugs, artisan—crafted Moroccan pendant lamps and Indo-Portuguese-style beds. The “and” factor amenities include bathrobes from cult Paris fashion label Maison Martin Margiela and a Rockstar suite with a 1,100-foot terrace with Williamsburg Bridge views. The lobby is always abuzz, no matter what the hour and features a rotating selection of art curated by Vito Schnable as well as an outdoor “secret” garden that’s perfect for hiding away with your laptop or a good book. Breakfast is included for guests and the warm pastry basket should not be missed. Perhaps the highlight of any stay is the fact you’re right above Dirty French, one of NYC’s buzziest restaurants. Being an elevator ride away from the complimentary herb-seasoned flatbread is reason alone to book a stay.

Nearly hidden behind a tall row of hedges is Delano South Beach, a landmarked hotel built in 1947 and renovated by Ian Schrager and Philippe Starck in 1995. Schrager and Starck wanted Delano to feel like a home; to that end, Starck created a series of discrete “living spaces,” with mismatched furniture, in the hotel’s common areas. Each of the spaces is intended to evoke specific images and experiences from his childhood, such as a wall of nightlights. The Delano’s backyard and pool area are an extension of the lobby’s “living room,” and that’s why a table and two chairs sit in a shallow section of the pool, and why the hotel’s veranda features the kind of comfortable furniture usually found inside a building, rather than outside it. In rooms, guests will find oversized marble bathtubs, said to be a favorite among NBA players because of their seven-foot length, along with Malin + Goetz toiletries.

When Philadelphia‘s battered asphalt and noise begin to tire, head for an afternoon at Longwood Gardens, a verdant hamlet 35 miles West of the city in the Brandywine Valley. 1,077 acres of horticultural magnificence occupy one of Pierre S. du Pont’s many estates, including an impressive conservatory that stretches about 1/2mile. Ornamental gardens and topiaries, which rotate regularly, can be appreciated all year round in addition to seasonal illuminations (the Christmas light display is so well-received, guests must reserve tickets in advance). It’s not only the sheer size of the property that draws in visitors from around the world but the robust display that easily rivals the impeccably manicured gardens of Europe. The indoor children’s garden, treehouses, model trains (seasonal) and concert series make Longwood a great option for traveling families.

Swimming and snorkeling around Xtabi (pronounced “X-tah-bee”) Resort’s underwater caves are a unique experience and a well-kept secret from first-timers. While it’s a great place to stay, overshadowed by places like Rockhouse Hotel, you don’t have to be a guest to enjoy this “meeting place of the Gods” as the name describes. You’ll want to have lunch at the casual, outdoor restaurant first--choices are excellent and include club sandwiches to jerk chicken (even if a tad pricier than from the street grills). After lunch and a rest, change into your swimwear and make your way carefully down the steps until you reach a sandy cove entrance into the sea, beside caves and jutting rocks. Splash in and come out on the front side of the cliffs, where there are ladders to exit or enter as well, if you’re feeling a bit timid. A laid back environment, gorgeous waters--just a tad more jade-colored on this end, for some reason--and underground caves ideal for photo ops make Xtabi a great spot to spend the afternoon. When you tire, climb back up to sip on a Dirty Banana and sunbathe on one of the platforms beside splashing waves.

A trip up to the Dee Wright is a required trek for all my guests who visit Oregon. If you want to experience the power and beauty of the planet, the Old McKenzie Highway delivers an eyeful. Starting in Ponderosa Pine forests and climbing to 5,300 feet above sea level, the road wages a mighty battle to deliver travelers to the top. The structure at the pass is built out of lava from the surrounding flow and towers above the old wagon road that is now Route 242. The road is closed in winter, but it’s a busy corridor during the summer tourist season. The observatory has windows which become frames for the famous peaks easily seen across the barren landscape. On the top deck you can easily see Mt. Hood to the north on a clear day. An interpretive trail gives visitors a great geology lesson on Cascade volcanology. It is a very harsh environment with the blistering heat of summer and the raging snow storms of winter. One can hardly imagine moving though this moonscape in a covered, ox-drawn wagon back when Oregon was just a territory. Nothing like it.

The Florida Everglades is certainly one of the most unusual places to find a winery and brewery, but Schnebly Redland’s Winery excels in both arenas in what some would call “the middle of nowhere.” Guests are greeted by a stunning wine bar ahead, a beer bar to the right and a counter on the left that sells cheeses and snacks. You can also buy any of the selections you’ve imbibed, either bottles of wine or growlers of beer. The wines are unique, made from local fresh fruits like mango, guava and lychee and made on premises. Schnebly’s beers, brewed for Miami Brewing Company, are equally exotic, with brews like the Big Rod Coconut Ale or the Shark Attack Mango Wheat Ale. Tastings start at $7 and go up if you want to keep the glass. Tours of the facilities are available on weekends.

A beautiful drive through the mountainous west coast past the bayside city of Mayaguez opens up to windy roads lined with banana trees. Your destination is the coffee town of Maricao—a small, unassuming city that plays host to festivals, coffee tours, and aquaculture. Also the home to the hidden gem of Salto Curet waterfall. To get down to your starting point, a car with 4x4 is preferred but not always necessary (Going during the rainy season? Drive a truck or SUV). You’ll park in a vacant lot at the bottom of a hill and follow the trail over a river and up the mountain. You’ll eventually reach an abandoned ranger station; at that point you’ll turn left and trek up river. Just a short distance later is the isolated waterfall. Take a swim in the cool water, or hunt down the even smaller trail off to the left that takes you up the rocks to the higher and more roaring waterfall above. This is my most loved waterfall site. It’s secluded and never sees many guests at one time. Bring your camera and a waterproof bag, as it’s likely you will be caught in the rain. It is a rainforest, after all!

With their Paris supper club Hidden Kitchen, Americans Laura Adrian and Braden Perkins regaled guests with a sensational 10-course meal with wine pairings around a communal table in their apartment. The food was nothing short of transcendental; inventive in taste and elegant in form. With such staggering success in relatively short order, it’s no wonder the desire emerged to share their talents with a wider audience.

Their first brick and mortar restaurant and wine bar in Paris opened its doors to immediate praise and the crowds haven’t slowed. Braden and his team apply the same technique, heart and originality to each dish that made Hidden Kitchen a resounding favorite. And even if the prix-fixe dinner in the upstairs dining room exceeds your budget, the ample selection of wines and mini plates in the bar will keep you drinking and nibbling all evening (particular attention goes to the buttermilk fried chicken and celeriac dumplings). And in a recent development, the culinary duo has begun serving American-inspired sandwiches like the Bakesale Betty and Midnight Cuban in the wine bar at lunchtime, Tuesday-Friday. Not to be missed.

The small city of Eupen is the capital of Belgium’s tiny German-speaking community, located in the country’s Eastern Cantons. This unique part of Belgium is far off the tourist map but is well worth a visit for its great food and proximity to the Hautes Fagnes Nature Reserve. But even if Eupen didn’t have these highlights, it would be worth visiting, simply to stay at the stunning B&B Julevi. This beautifully decorated B&B is run by the warm and welcoming Mattens family. The rooms are spacious, particularly the ground floor room, which has its own private sitting room. The dining room and common living room are accented by a stunning spiral staircase, which leads to several upstairs bedrooms. In the summer, guests have access to a small terrace and formal garden, off the kitchen. Breakfasts are fresh and ample and the hosts are quick with suggestions for great places to eat, shop and visit in the area. With rooms ranging in price from 75-95 euro, the B&B Julevi is a steal and a welcome escape from Belgium’s larger cities.