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A honeymooner’s dream, the 40-acre Grand Wailea hails from the era of the Hawaiian mega-resort. From its perch over the Pacific, the hotel offers an impressive collection of original art (much of it created by locals specially for the property), 40 acres of lush tropical gardens, and over-the-top water features among the nine swimming pools, including slides, caves, a Tarzan swing, swim-up bars, and a canyon with an enclosed “lava tube.” The resort even boasts Humuhumu, a Hawaiian-inspired restaurant set in a man-made lagoon, and 780 guest rooms, all of which include a private patio or balcony. Opt for accommodations on the Napua Club level for a more intimate “boutique hotel within a resort” feel.

Among the small shops and restaurants that line Elmwood Avenue, Thin Man Brewery stands out in more ways than one. In a literal sense, its second-floor balcony extends over the street, offering guests the perfect place to sip pints in the sun. More figuratively, its beer selection is among the best in the city, with more than two dozen brews on tap, including the Prairie Paradise (a coconut-and-vanilla imperial stout from Prairie Artisan Ales in Oklahoma) and the Taras Boulba (a pale ale straight from Belgium). Thin Man also brews a few of its own beers on-site—if they have it, be sure to try the Pills Mafia pilsner. Since opening in 2016, the brewery has become so popular that there is now a second location in Black Rock, in a collaborative space with Tappo Pizza.

A key component to the mastery of a skill is knowing when to break the rules. As its name implies, Jovanina’s Broken Italian breaks away from the traditional rules and expectations of Italian cuisine with the measured confidence of a master. Owners Jennifer and Jake Linzinmeir bring years of restaurant experience, both in the kitchen and in management, to Jovanina’s, which allows them to find an approachable balance of new flavors and classic dishes to the menu. The airy ground-floor space feels festive, with whitewashed brick walls along one side and a bar running the length of the other; a downstairs wine-bar dining area has a quieter, more intimate vibe. Try any of the handmade pasta specials or go with the favorite: a brick-oven pizza topped with fennel sausage, smoked mozzarella, and caramelized onions.

Once the hip newcomer, this craft cocktail lounge is now a King Street veteran that attracts a more mature crowd than the line-up-outside adjacent clubs catering to the college set. Locals meet here for half-price happy hour (Wednesdays feature bourbon) and before shows at the Charleston Music Hall nearby. The stock of spirits is impressive, as are the intricate ways they’re mixed, like a “Macho Man Dandy Savage,” with house-infused dandelion gin, honey, and yellow Chartreuse. The mixologists here have a history of winning local bartender competitions. Complementing the flavors are the gorgeous environs in an historic building that features exposed beams, leather furniture, and a swanky rooftop garden that’s a welcome respite just off the buzz of King Street below. It all sits atop The Macintosh, chef Jeremiah Bacon’s stunning seasonal fare restaurant that shares a mutual owner.

A restaurant inside Heidelberg Castle was never going to be modest or inexpensive, and Scharff’s Schlossweinstube is nothing if not upscale. With classic parquet flooring, sparkling chandeliers, and stucco ceilings, it’s romantic and refined, its Baroque decor only outdone by its Michelin-starred fare. Informed by classic German and French techniques, head chef Martin Scharff serves local favorites like Swabian ravioli, as well as roast duck, unique dishes such as veal kidneys, and a delicious cheesecake with raspberry sorbet, all perfect for pairing with an extensive selection of international wines.

If you’re not looking to splurge, try the neighboring Bistro Backhaus, with a more rustic appeal including vintage furnishings, a huge baking oven, and a casual menu of coffee and cake. It also features a shaded terrace and the same wine list as Scharff’s.

Dating back to 1843, this massive museum has grown and modernized over the years, especially with the addition of the Neue Staatsgalerie (New State Gallery) in 1984 and a modern hall specially built in 2002. Spanning some 96,875 square feet of exhibition space, the collection focuses on early Swabian panel painting and 19th-century Swabian Neoclassicism, but also includes modern pieces like Oskar Schlemmer’s Figurines for the Triadic Ballet, Matisse’s famous Back Series, and a Joseph Beuys room that was installed by the artist himself. Other highlights range from Dalí’s Raised Instant and George Grosz’s The Funeral to Miró’s Bird with a Calm Look. Opt for a guided tour to ensure you see everything, then visit the museum shop and the Fresko café-restaurant. Note that, on Wednesdays, you can visit the permanent collection for free.

Nestled on beautiful Playa Dorado in Puerto Plata, this elegant hotel features 50 stylish suites, complete with neutral decor, flowering orchids, and private furnished balconies. Some suites can be connected, but for even more space book the penthouse, which includes three bedrooms, a large living room, and a freestanding outdoor tub. In addition to a pristine beach, Casa Colonial boasts a sleek rooftop pool, a restaurant that serves fine French-Caribbean cuisine, and a spa with a treatment gazebo above a tropical pond. When staying here, don’t miss the chance to explore Puerto Plata and its charming main square surrounded by Spanish colonial and Victorian buildings, as well as the more-than-500-year-old remains of Fort San Felipe. Fifteen minutes from the resort, you can also swim in freshwater lagoons in El Choco National Park.

Steps from the sand on Princess Margaret Beach, Jack’s Beach Bar is the perfect spot for an alfresco lunch, happy hour on the terrace, or both. It’s a good choice for dinner, too, although landside access is tricky, with lots of stairs and rough terrain that’s difficult to navigate in the dark. Whenever you come, look forward to local ingredients, prepared with an international touch. Pair the tropical quinoa salad with the catch of the day, or opt for the famous fried chicken, served with your choice of mango chutney, smoky barbecue sauce, blue cheese dip, or Mama’s Hot Sauce. If you’re having too much fun on the water, order something from the delivery menu and Jack’s will bring it directly to your boat—the restaurant delivers up to almost two miles from the beach.

About an hour’s flight from Panama City is David, the capital city of Chiriquí province. From there, it takes another hour by boat through lagoons, mangroves, wetlands, and estuaries to reach Cala Mia’s dock on the island of Boca Brava. Upon arrival, guests find a low-key resort, where 11 bungalow suites feature modern amenities like air-conditioning. Also on site are thatched-roof “ranchos” with hammocks and cushioned seating for unwinding in view of swaying palm trees and the nearby shoreline. The resort’s Point Sur restaurant offers a four-course meal each evening that revolves around local fish and seafood, including lobster caught just off the premises. During the day, guests can take guided hikes in the nearby forests to see howler monkeys and tropical birds, or go island-hopping with a boat captain in search of white-sand beaches.

Situated off the eastern shore of Long Island, The Chequit is old school in an elegant way. The hotel occupies a big white building, surrounded by grassy lawns, impeccably maintained hedgerows, and towering deciduous trees, and features bright, homey rooms, complete with large windows that let in plenty of natural light. While all the rooms have been refurbished, those in the main house retain much of their original architecture, lending them a certain vintage charm. The Chequit operates on a bed-and-breakfast model, and guests can either take their morning meal in the lobby or opt to have a lighter option sent straight to their room. While the target audience here is weekenders seeking an escape from New York City, the hotel is also a popular spot for weddings and retreats, with two meeting rooms and full catering services available from on-site Red Maple Restaurant.

Sitting on 40 acres in the quaint town of Stone Ridge, Hasbrouck House is a lovely boutique getaway, featuring 20 one-of-a-kind rooms spread out over three structures. Rooms are bright and homey, with wooden floors and plush beds. Some even feature vaulted ceilings, stone fireplaces, and deep, freestanding bathtubs. Although it’s not a spa retreat, Hasbrouck House does offer a variety of massages that can be enjoyed either in a cozy treatment room or your very own suite. For many guests, however, the highlight of a weekend here is dinner at on-site restaurant Butterfield, which offers a seasonal menu inspired by fresh produce from the Hudson Valley. Come in the summer and you’ll also have access to the 55-foot-long swimming pool, nightly bonfires, and outdoor movie screenings and concerts.

A larger, more luxurious alternative to an inn-style getaway, the ocean-facing Gurney’s Montauk Resort offers gorgeous views, plush accommodations, and top-notch amenities, including a whopping 2,000 feet of private sandy beach. The spa is the star attraction and includes a Finnish sauna, steam room, Roman bath, and saltwater swimming pool, all of which are only open to guests to maintain a quiet, exclusive ambience. Other property highlights include a salon, fitness center, and selection of restaurants, ranging from Scarpetta Beach (which serves Italian cuisine) to Tillies (a more casual bistro with hearty American fare and brunch specialties on weekends). Not surprisingly, the guest rooms and cottages are especially luxe, with lovely wooden floors, walk-in rain showers, and big windows with sweeping sea views.

Somewhere between private villa and luxury hotel room, the suites at Pietermaai are as close as you can get to a chic, European pied-a-terre in the Caribbean. Plus, they’re located just a stone’s throw from Curaçao’s liveliest restaurants in the up-and-coming Pietermaai district, the popular Punda shopping area, and the atmospheric Floating Market (which doesn’t really float). The loft-like suites are outfitted with kitchenettes, wooden floors and shutters, and an outdoor sitting area. Some have a plunge pool or duplex layout, and the two-bedroom penthouse apartment is oceanfront. When not relaxing in their rooms, guests can take a dip in one of the hotel’s small pools, surrounded by lush gardens, or set off in search of sand with beach towels provided by the hotel.

Like all of the best Spanish tapas restaurants, Barrafina has no tables. In London’s Covent Garden, all the eating is done at a long marbled bar, lined with red leather stools, and there are no bookings: you get here first, you get served, all the while watching the chefs at work. The idea is that it’s just like being in Spain (the inspiration for Barrafina was Barcelona’s Cal Pep), and it really is: the atmosphere is chaotic and the food comes from all corners. One minute you’re eating a ortiguilla (a type of sea anemone found in the Balearics) in a paper cone, the next a chicken wing served in a Canarian mojo picón sauce.

The large, leafy patio of this mezze restaurant in bohemian Exarchia was once the local schoolyard. Now cozy couples and animated gaggles of friends gather beneath the flowering bowers to enjoy some of the most honest and comforting food in town. Order as many dishes as you can fit on the table and share them all. Rather than traditional Greek fare, the menu is a tasty Mediterranean pick-and-mix. Try the cracked wheat salad with green apple, mint, and dried figs; meatballs seasoned with cinnamon and clove; and mini lamb kebabs. The high-ceilinged, well-lit classrooms make charming dining rooms in cooler weather. Service is unfailingly friendly and relaxed.

A school-turned-mezedopoleío serves delicious meze including bakalyaro (walnut-crusted fish fillets) and pita topped with yogurt and smoked eggplant. Bonus: a patio surrounded by bougainvillea.