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West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above). She then opened Little Goat, a retro diner, across the street. Graham Elliot Bowles keeps it simple at his casual g.e.b, where each dish has no more than three ingredients. On a more elegant note, the prix-fixe menu at Grace, from chef Curtis Duffy, features dishes such as kampachi with coconut, lime, basil, golden trout roe, and pomelo presented in a cylinder of frozen ginger water.

Cabo’s first-ever microbrewery, Baja Brewing Co. has a cantina located on the rooftop terrace of Cabo Villas Beach Resort & Spa. Take in views of Land’s End with a pint of the flagship Cabotella blonde ale and a wood-fired pizza made with beer yeast dough.

Tsukishima is a neighborhood best known for one of Tokyo’s local dishes, monjayaki. This casual dish is similar to Osaka’s savory okonomiyaki pancake but with much more liquid, making it great fun to cook. Diners are seated around a hot iron grill and prepare their own monjayaki after the staff help you with your first one. An ice-cold beer hits the spot as the table heats up. There are a variety of flavors, like seafood, pork, or house styles. A popular combination is mochi, mentaiko (spicy roe), and cheese. At night the main street is open only to pedestrians and is an interesting area to wander and explore.

It’s not often that one comes across a double-decker theater. In fact, the Elgin and Winter Garden Theatre Centre is the only still-active stacked theater, and has been designated a National Historic Site. Built in 1913 by American architect Thomas W. Lamb for the Loews theater group, the two venues were meant to serve two separate markets. Today, they frequently host live performances, musicals, and films. The Winter Garden is especially unique, featuring a decorative ceiling hung with dried leaves, a touch that transforms the room into a magical land.

There’s no shortage of great eateries in the New Zealand capital—reputedly Wellington has more cafés and restaurants per person than New York City—and Field & Green is a popular option for the city’s discerning diners. With a versatile menu bylined European Soul Food, it promises ever-changing weekly dishes that could include house-made pasta with wild mushrooms and blue cheese, or baked eggs with spicy lentils and mint yogurt. These hearty but sophisticated flavors are the ideal sustenance for daytime explorations of the city’s harbor attractions, and the good-value, Wednesdays-to-Saturdays three-course supper menu can be partnered with local Wellington craft beers or New Zealand wines.

Feel instantly cool when you slip through the unmarked wooden doors and enter La Factoria. Garden lights hang from the graffiti-covered walls (designed to look artsy-shabby with a stylish restraint), seductive music plays, and the liquor bottles behind the bar are lit from beneath to add to the glow. The flattering amber light in this neighborhood bar invites whispered conversations and lingering glances. La Factoria, which introduced San Juan to the craft cocktail when it opened in 2013, encourages experimentation. Take your time enjoying your drink of choice, but be sure to wander a bit further into the sprawling building where you’ll come upon separate spaces with different moods: a wine bar, a speakeasy, a dance floor.

One of Bermuda’s most historic resorts—there’s even a 300-year-old sea captain’s cottage on the property—Cambridge Beaches is a traditional rose-hued confection that matches its four pink-sand shores. Though an English country club vibe prevails in many of the public spaces (think tennis whites and croquet on the lawn), the rooms are anything but stuffy, outfitted with vibrant coral and lime-green sofas, zebra-striped rugs, and in some rooms, private plunge pools. Relaxation can be found in the marine-sourced treatments on offer at the Ocean Spa, but if you’re looking to excite the palate, the acclaimed Tamarisk restaurant plates up local takes on creole specialties, from the iconic Bermudan fish chowder to fresh-caught lobster baked in garlic and coconut oil.

The centerpiece of a vast resort, golf club, and residential community complex, Rosewood Bermuda sits on 240 acres of waterfront land overlooking Castle Harbour, Harrington Sound, and the Atlantic Ocean. The recently refurbished resort is anchored by the Manor House, where 88 guest rooms blend classic cottage-style architecture and modern interiors that continue to set the standard for today’s luxury seekers: think canopy and four-poster beds, plantation shutters, and colonial-era antiques, all set against a cool white backdrop. Spring for a deluxe poolside room, which also has access to a private poolside daybed. Just don’t expect too much down time. Three on-site restaurants and two bars are beyond selfie-worthy, treatments at the spa incorporate local ingredients like cedar and juniper, and hotel guests receive membership to the 18-hole Roger Rulewich–designed golf course, tennis courts, and a beach club that sits on an exclusive stretch of pink sand for the duration of their stay.

Part of the University of British Columbia, this museum houses one of the finest collections of Northwest Coast Aboriginal art, including bentwood boxes, feast dishes, totem poles, and canoes from the Haida and Coast Salish people. Some of these artifacts are displayed in a soaring grand hall with views of the Point Grey cliffs. Visitors can also look forward to a respectable European ceramics collection, with earthenware and stoneware from the 16th to 19th centuries, and a rotunda with works from Haida artist Bill Reid, including the massive Raven and the First Men, made out of laminated yellow cedar.

A tour of St. Nicholas Abbey is a chance to explore one of the finest so-called great houses of Barbados. Not an actual abbey, the well-preserved Jacobean plantation mansion in the northern parish of St. Peter dates from the mid-17th century and is filled with antiques. On the mahogany tree–dotted manicured grounds, visitors can also see the old steam mill and rum distillery that are still in operation; the output from the latter, and other local products, are sold in the gift shop.

The great macaron debate may forever wage on, but from the first time I tucked into a small box of Pierre Hermé’s diminutive cookies, perfectly crisp on the outside and melt-in-your-mouth soft on the inside, I knew I’d remain loyal to his interpretation. Perhaps best known for his unique flavors—foie gras and chocolate, lemon and fennel, vanilla and basil, among many others—it’s his Ispahan croissant, with rose almond paste and crushed raspberry flakes, that really keeps me going back.

The Common becomes extraordinary on winter evenings when the Christmas tree is up and soft lights seem to hold back the twilight chill, but the truth is there’s no bad time to visit the nation’s oldest public park. The former cow pasture has been a focal point for Boston’s history and culture since its inception in 1636—a site for riots and rallies from the Revolutionary War to the Vietnam War era as well as weddings, hangings, and burials. Summer splashing and winter skating at the Frog Pond are local traditions, and you can spend hours wandering from landmark to landmark (like Augustus Saint-Gaudens’s famous bas-relief Memorial to Robert Gould Shaw and the Massachusetts Fifty-Fourth Regiment, or the Soldiers and Sailors monument atop Flag Staff Hill). Or you can just laze in the sun on the park’s west-side lawn.

From the dusty street, the Hotel El Convento in León, Nicaragua, beckons with its stately façade and red Spanish-tiled roof. Step inside and you instantly feel at home amidst ornate period furnishings that are surely a far cry from the building’s humble beginnings as the 1639 San Francisco Convent. The elegant Restaurante El Victoriano offers an indoor-outdoor retreat centered on the hotel’s manicured, tropical courtyard—an example of the colonial hacienda style found throughout León. The restaurant is a meeting place for people from all walks of life—aged former Sandinistas who now hold positions of leadership, locals splurging on a fine meal, or foreign students from one of the city’s many Spanish language schools seeking tranquility and an excellent cup of coffee.

Italy’s beloved region of Tuscany brings to mind bucolic vineyards, rolling hills, and roads lined with towering cypress trees. But there’s plenty else to delight and even surprise travelers. Consider the quaint town of Punta Ala: located along the southern Tuscan coast, it’s under the radar of most travelers, yet the go-to summer escape of generations of Romans and Florentines.

Punta Ala strikes a balance between relaxation and understated elegance that encourages lingering, and the same goes for its premier place to stay: Baglioni Hotel Cala del Porto. Set against the backdrop of the Mediterranean Sea and with two adjacent beach clubs (La Vela and Alleluja), the hotel’s 38 airy rooms offer views of the gardens and marina. In the heart of Maremma, Hotel Cala del Porto is perfectly located for day boating trips out to the island of Elba, wine tasting at notable Tuscan wineries, and some of the best golfing in Italy. The regional park Bandite di Scarlino beckons with hiking trails ideal for early morning risers.

This spot near Eagle Beach is pure Caribbean. The live music is infectious, the plates come piled high, and the tables are situated outdoors, under the sky or a tin-roof overhang. Plus, there are more local patrons than visitors. While the atmosphere is laid-back, the menu is full of sophisticated presentations, from island favorites to international dishes. Popular picks include the crab cakes, almond-dusted grouper, and lobster ravioli. The wine list is also excellent, as is the craft beer selection. Note: Reservations are recommended. The restaurant is closed on Sundays.