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In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is different, but all are stylishly simple and feature details such as wood floors, exposed brick, original art work and site-specific installations by local artists, cassette players with mix tapes, well-curated minibars, and Aesop toiletries. For the noise averse, the hotel reminds potential guests that the rooms are located above “an occasionally raucous, whisky-fueled tavern.”

The Jefferson Hotel has been the gold standard for discerning visitors to Richmond (including 13 U.S. presidents) since 1895. Not content to rest on their laurels, the hotel completed a renovation in 2016, restoring its landmarked public areas and refreshing and expanding the guest rooms and suites. The new rooms feel more like posh apartments, with doorbells, foyers to the sitting and dressing areas, and luxury touches like soaking tubs, walk-in showers, and in-mirror televisions. The alligator drawer pulls are a nod to the creatures who used to live in the lobby fountains in the early 20th century. The Rotunda and Palm Court lobbies, with their Tiffany stained glass ceilings, have overlooked many power meetings and celebrations, and provide a magnificent backdrop for decadent afternoon tea or the popular champagne Sunday brunch. The four-star Lemaire restaurant serves a New American menu of Virginia ingredients in their distinctive dining rooms, while the more relaxed TJ’s bistro is open for hearty breakfasts and classic lunch fare. Guests of the Jefferson may work off all that locally sourced food at the 3,000-square-foot gym or in the indoor pool with skylights and an outdoor pool deck.

A popular hangout, Kits Beach—as the locals call it—faces English Bay, and in the summertime it buzzes with beach activities. Volleyball players and Frisbee tossers mingle with sun worshippers, windsurfers and skim boarders. For sand-free dips and swimming lessons, there’s a heated saltwater pool that’s open when weather permits. Also in the vicinity is the Boathouse Restaurant, which serves peel-and-eat shrimp, tasty chowders and fresh grilled fish on a patio with panoramic views.

Many visitors to Peru stay in Miraflores, and for good reason: The neighborhood is where you’ll find most of the better hotels, as well as the top restaurants. Get off main streets to stroll the pretty side streets. Down by the ocean, walk the Malecón seawall and visit the Parque del Amor, or Love Park, to watch paragliders soar and bank overhead. The oceanfront is also home to Larcomar, an open-air shopping mall where you can grab a bite or shop for any items you may have forgotten.

The roots of this Mediterranean Revival-style boutique hotel go back to 1914, when a local grocer created the tropically inspired property to house his visiting vendors. Nearly a century later in 2010, hotelier and style guru Liz Lambert added the place to her mini-empire, reviving the grounds that still feature magnolia, palm, and cypress trees planted by the original owner. Set on a quiet section of the River Walk near the museum corridor, the restored building (which is on the National Register of Historic Places) houses 27 guest rooms decorated in a designer-meets-flea market aesthetic, with bright pops of color and plenty of personality. All are pet-friendly, and feature stocked SMEG fridges, Red Flower bath amenities, custom serape bathrobes, and complimentary coffee and Wi-Fi; suites have sitting areas, terraces, or other perks. Room service comes from the in-house Ocho restaurant, but it’s better to head down and eat there in person to take in the cheery setting, river views, pan-Latin menus, and cocktails that highlight rum (as a nod to Havana) and tequila (an homage to San Antonio’s Mexican roots). A regular calendar of happy hours, musical performances, and cultural events round out life at this vibrant hotel.

Located just two miles north of Port Elizabeth, on an 18th-century sugar plantation and working sea salt farm that overlooks Spring Bay, Firefly Bequia has all the sophistication of its sister accommodations on tony Mustique. Scattered along the hillside to maximize ocean views, the four suites and one two-bedroom cottage are outfitted with king-size four-poster beds, indoor-outdoor showers, and rattan ceiling fans that recall the island’s colonial past. Though it’s a five-minute walk to the beach, you’ll spot the remnants of the plantation’s original sugar mill, a croquet lawn and swimming pool, and the hotel’s resident goats along the way. Upon your return, a cocktail in the stone bar, where green bananas hang like chandeliers, is just the thing to ease you into a star-filled night.

Brunch lasts nearly all day at Crema in Pacific Grove, and you need that time to explore the array of separate quarters in the restaurant’s converted Victorian mansion. Investigate the historic photos, antique furniture, and artistic decor in the downstairs espresso café and wine bar; grab a spot with friends in the garden courtyard or in the dining room upstairs; or keep to yourself in the studious Peacock Room. Once you’ve found your favorite nook, enjoy fizzy and floaty drinks, rich egg dishes, golden waffles, or house favorites like the bacon cheddar biscuits that are football-size and accompanied by honey butter. As the day progresses, Crema is a favorite stop for friends to get together, often over games of Jenga, Battleship, Scrabble, and Yahtzee—all available to borrow from the espresso bar. Pro tip: The goblets of fruity sangria and the Micheladas served with a slice of country bacon are as good in the morning as they are in the afternoon.

If you’re looking for a party atmosphere and excellent people-watching, this restaurant/bar positioned near Hamilton’s harbor is your spot. It serves breakfast, lunch, dinner and late-night snacks. DJs spin and live music is performed throughout the week.

West Loop denizens can get their fill of locally made spirits at this distillery and cocktail bar, where cofounder and head distiller Tremaine Atkinson bottles up just about everything of an ABV nature—with a bespoke spin. Its vodka may be its flagship offering, but it’s proved its aptitude with a handful of other liquors as well, from gin and rum to amaro and limoncello. If you can’t make one of its Tuesday or Saturday tours, swing by anyway for a dram; a full cocktail list pairs up with bites throughout the week and features go-tos like the Cease & Desist, a melding of CH London Dry Gin, Lapsang souchong, ginger, honey, and lemon.

While much attention is paid to the Japanese and Italian influences on Los Cabos cuisine, one of the very best spots in town is an Argentine entry. The low-key, low-lit courtyard restaurant Chamuyo features a dozen or so tables, a long bar, and a traditional Argentine grill. The steak-house menu sends you on a culinary adventure through Buenos Aires dance halls and the verdant pampas. Meat-stuffed Argentine empanadas (markedly different from the Mexican variety) are served oven-baked or fried, and make excellent starters. For your main course, try chef Marcelo Romby’s 22-ounce beef ribs, which he slow-cooks for more than four hours. Pair it with a bottle of Baja red and, if you can, save room for some first-rate alfajor cookies.

For more than two decades, Chef Volker Romeike’s standout restaurant has charmed patrons at the Sheraton Grand Los Cabos Hacienda del Mar with its Pacific Rim concept, ocean views, and dramatic design. Pitahayas—both space and the menu—got an updated look in 2015. A newer focus on blending Mexican and Asian flavors has allowed Romeike to show off his culinary creativity. Duck lumpia (like a spring roll) is served with a papaya salsa; a taro tostada comes topped with carnitas (braised pork); and tuna poke comes with watermelon and chili powder. For special occasions, consider the Cava de Santiago wine cellar, which houses some 400 vintages. The restaurant’s bar also offers Social Fridays, when limitless drinks can be had for a not unreasonable tariff.

Servers, somms, and chef-owner Nancy Silverton all swirl around Osteria Mozza’s centerpiece Mozzarella Bar, where small dishes of freshly imported mozzarella, ricotta, and burrata are plated with pairings like bacon or braised leeks. With eyes closed, white-tablecloth diners attempt to fully savor each bite of cool, moist cheese before it melts in their mouths. These flavors are a tough act to follow, but the restaurant certainly steps up to the plate with signature meals like the Squid Ink Chittara Freddi with crab, sea urchin, and jalapeño. Just be sure to leave room for a rosemary olive oil cake for dessert: The eatery’s Dahlia Narvaez was awarded the James Beard Foundation Award for Outstanding Pastry Chef in 2016. Reservations at least one month out are recommended unless you have the flexibility to take a chance with a walk-in seat at the Mozzarella Bar itself—a one-of-a-kind experience.

This surf-style restaurant elevates local food-truck fare at the new Four Seasons Resort Oahu at Ko Olina. Expect ahi poke, wild-boar hot dogs, and the coolest French fry innovation out there: A heaping platter of slender spuds topped with Parmesan, cherry tomatoes, and wilted arugula for that “It’s healthy, really” feeling! Wash it all down with kombucha on draft—with flavors like pineapple ginger or liliko’i (passion fruit)—and cocktails such as the Castaway, featuring melon vodka, coconut water, and lime juice. Come prepared to lounge outside, as the Waterman wraps around the family pool and also serves its exclusive beach. Food is served 11 a.m. to 6 p.m.

Anguilla’s most social beach is full of local flavor. From visiting boats to residents who flock here for the best island-style bar-and-nightlife atmosphere—home to Johnno’s, Elvis’ Beach Bar, and the Pumphouse—there’s never a dull moment on Sandy Ground’s long, soft strand. The water here is calm, making it an ideal stretch of sand for families as well. Sandy Ground is also the site of Anguilla’s August Monday, the most important day of the summer carnival season, when the entire country seems to be in the same location to celebrate J’ouvert: some folks on the beach, some on boats blasting music. By 1 p.m., the August Monday sailboat race kicks off—the first round of qualifying for the final carnival boat race at week’s end.

The isolated, car-free island of Käringön is a 40-minute ferry ride from Orust, and has less than 100 full-time residents who stay year round, even through the long winter. But it’s a different story in the summer. In the 19th century, the middle classes in Sweden became enamored with the benefits of fresh sea air and started flocking to the small islands along the coast. Today about a thousand visitors arrive daily by ferry or private boat to enjoy the island’s relaxed vibe. Come for a lunch of fresh-caught seafood at Petersons Krog or watch children on the pier trying to catch the little crabs crawling through the seaweed down below. In the cold weather, visitors can take a lobster fishing tour or sample fresh oysters at the Käringö oyster bar, which also has a hot tub that seats six.