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If you research “pretty seaside towns in Greece”, Nafplio often pops up on the search. Located in the eastern Peloponnese, Nafplio boasts narrow, bougainvillea-covered streets, rich-hued neoclassical mansions, wrought-iron balconies and cobblestone and marble streets. It is a popular weekend resort for Athenians due to its waterfront cafes and restaurants, fresh seafood, and pretty boutiques. It is also the perfect base to explore all nearby ancient ruins such as Mycenae, Epidaurus, and Sparta. Sip a cold drink in Syntagma Square, the town center; climb 999 rock steps up the Palamidi Castle for the expansive view; swim in the clear blue waters of the local beaches; and take a sunset stroll along the marina waterfront before dinner.

Along with stylish boutiques and design shops, the narrow lanes of the upscale Khan Market are lined with all manner of eateries, from cafés and cocktail bars to food stalls and fusions restaurants. As of late 2018, the roster also includes Sly Granny, which arrived on a wave of buzz generated from its original Bengaluru location. Through this often-packed bi-level outpost is smaller than the sprawling first location, the concept here is the same: a space “inherited” from a mythical globetrotting grandmother and inspired by her favorite recipes and eclectic style. Here, that translates to a décor of plush velvet sofas, old cookbooks, and crystal bric-a-brac, statement tableware, and bold, quirky artwork in the snug dining room, plus a cozy upstairs bar that converts to a cocktail lounge come dark. Drinks there range from the creative (crafted with ingredients like elderflower, yogurt, or honey-ginger syrup) to the classic (twists on G&Ts and Pimm’s cups), not unlike the style of the food menu below, which starts with pastas, steaks, and burgers, then veers towards tacos, schnitzel, chicken liver pâté, and Kerala-style fish moilee. You won’t need a granny’s encouragement to eat up dishes like bacon-gruyere mac-and-cheese balls, house-cured salmon, chocolate lava cake, and a twist on grilled cheese with ricotta, onion jam, tomato chutney, and two kinds of chilies.

Located in the heart of Bordeaux’s historic district, Vins Urbains draws oenophiles and wine novices alike with more than 250 wines on offer at any time of day. Here, owners Jan and Christelle will guide you through their handpicked vintages, sharing anecdotes about the wines and their makers as they go. Beyond wine, the boutique specializes in produits du terroir like sardine rillettes, white truffle tapenade, and artisanal cheeses, so order something to pair with your wine. Also note that the vaulted cellar downstairs can accommodate groups and special tastings should you want to bring friends or family for a special occasion.

One of Anguilla’s top three beaches, Meads Bay is home to a handful of the best boutique hotels as well as beloved beach restaurants like the Four Seasons, Jacala, and Straw Hat. It rarely feels crowded, and the stunning, near-mile-long white stretch is ultrawide and spacious. Facing turquoise-clear Anguilla waters and a partly rocky landscape on its edges, it’s a favorite for long quiet walks, swimming, and snorkeling, or as a place to enjoy a meal and a drink until the sun sets directly over the sea. Waves can get high in the summer; exercise caution.

With a smart and simple chalkboard menu of cheese plates, salads, sandwiches made with homemade bread, good coffee, and Argentinian wines by the glass, Pain et Vin is a lovely venue for lunch or an afternoon glass of Malbec rosado. The Palermo Soho eatery doubles as a tasting space and shop: look for Friday evening events open to the public, or stop by to choose from the excellent selection of boutique wines to take on a picnic to the park.

Getting to Portofino from Genoa is quite easy. Take the train from Genoa’s Brignole Station to Santa Margherita Ligure, and then catch the 82 bus to Portofino (a 12-minute trip around the bay). While I’m not a huge bus person, this is one of the most gorgeous bus rides I’ve ever experienced. A tiny fishing village with a very posh clientele, Portofino is a wonderful day trip—perfect for walking around, shopping at high-end boutiques, and enjoying an apertivo dockside before heading back to town. Yet Portofino is also covered with trekking trails, so another option is to wear walking gear and come for the breathtaking hikes!

Between Miami and Fort Lauderdale is a local beach town filled with surfers, joggers, and free-spirited beach lovers. The Hollywood Beach Boardwalk moves at a slower pace than those on bustling South Beach and Fort Lauderdale’s Beach Place. Choose from a wide variety of shopping boutiques, restaurants, bars, and experiential beach activities for a fun-filled day by the water. The seven-acre park is eco-friendly and perfect for families. Transportation includes trolley service and boat charters on the marina.

The most rugged, sketchy roads always seem to lead to the best surf breaks. This photo captures the early morning drive over the hill to Cerritos beach in Baja Mexico. Down below I discovered perfect, glassy rights and only a few early risers in the water. In the distance at the point is Hacienda Cerritos, a boutique hotel from which you can stumble out of bed and down to the surf. Mario Beceril, a Baja native, runs a great surf school from the beach for anyone who needs a lesson. mariosurfschool.com

This funky boutique hotel on the edge of the Britomart shopping district goes way back in Auckland history. Built in 1841 as The Commercial Hotel, the DeBrett building survived two fires and two rebuilds plus a stint as a hostel before becoming the quirky place guests experience today. The Housebar has always been the center of hotel life, and today, the intimate wood-and-mint venue exudes its original art deco style and serves classic cocktails and local beers and wines alongside refined pub snacks.

In addition to restoring the bar and adding a glass-roofed atrium that houses the hotel restaurant, DeBretts Kitchen, the current owners affixed contemporary artwork and photography throughout and sheathed the entire building in candy-striped carpeting, custom designed from 100 percent New Zealand wool. Besides the carpet and small-batch minibar selections, no two rooms are the same. Each features unique furnishings from the 1930s on, and every bed has an original screenprinted throw. Two of Hotel DeBretts centerpieces, the chandelier and water sculpture in the restaurant, were crafted by Auckland artists from materials salvaged during the latest renovation. The result is a local experience from top to bottom that gives guests a real taste of New Zealand.

This hotel is on our list of The 11 Best Hotels in Chicago.

Set directly across from the Art Institute of Chicago, this former members-only men’s gymnasium is now the Chicago Athletic Association, which is part of Hyatt’s Unbound Collection. Enter at street level off Michigan Avenue and walk toward the back to find a staircase that leads to the old swimming pool, now a venue for parties and pop-up concepts. Take the nearby elevator to the restaurant, Cindy’s, easily the best rooftop scene in the city, with highly Instagrammable terrace views overlooking Millennium Park, the swooping Frank Gehry–designed bandshell, and Anish Kapoor’s Cloud Gate (aka the Bean).

Park yourself in the second-floor lobby and hang with locals as they tap away on their laptops and sip lattes by the two oversize fireplaces. Walk through that expansive by Roman & Williams–designed room, where light beams in through ornate stained-glass windows, and you enter a warren of table games and darts, all festive and typically open to the public. There’s also the secret six-seat bar, the Milk Room, a relic of Prohibition, and the James Beard Award–winning Cherry Circle Room—a sexy, dark restaurant with a circulating martini cart and a meat-centric menu.

Upstairs in the 1893 landmark, 240 guest rooms reflect the building’s former life, with gym horses as foot beds, working fireplaces in some rooms, plasterwork ceilings, ornate carved wood wainscotting, and a clubby vibe. Some of the rooms are rather small, but the location is hard to beat, and the cozy, wintry ambiance makes it a popular (and fun) place to spend a weekend. And because the CAA keeps an eye on its water conservation, sources its food locally, and adheres to strict recycling standards, eco-conscious travelers can feel good sleeping here.

The 112-room Surfjack Hotel channels 1960’s Hawaii, with vintage upholstery on the headboards, reed ceilings, and midcentury modern furnishings. The onsite Swim Club, with its outdoor pool bar, hosts music events and movie nights. Don’t miss a meal at Mahina & Sun from celebrated Honolulu-born chef Ed Kenney, whose menu showcases island cuisine and ingredients, or a trip to the Olive & Oliver boutique, whose clothing and accessories line are inspired by Hawaiian culture.

Having recently opened its doors to the public, the Factory on Grant Avenue in Norwood aims to be a destination for promoting the arts, crafts, design and a bit of individuality as it hopes to inject some renewed interest in the old neighborhood. The Factory features an artisanal bakery, a glass blowing studio, a screen printing workshop, an art gallery, boutique clothing stores and even a flower shop. Over the years, the popular Grant Avenue in Norwood has declined somewhat, with a proliferation of massage parlors and mini supermarkets. With the new Factory having opened early in 2014, Norwood seems to have a new buzz about it which, hopefully, will lead to other new ventures and establishments popping up too.

Visiting Santiago Achaval and Manuel Ferrer’s boutique winery Achaval-Ferrer is a requisite visit while in Mendoza to sample Argentina’s most awarded wines. Their malbec wines and blends consistently earn high scores from Robert Parker, Wine Enthusiast and Wine Spectator. Started by a group of Argentine and Italian friends, Achaval-Ferrer’s Italian winemaker Roberto Cipressois specializes in small production wines that yield a high concentration of flavors, colors and aromas. Their beautiful 60-acre vineyard, Finca Bella Vista, offers free wine tours and tastings daily. You’ll sample three of their red wines, a sweet dessert wine and homemade olive oil. Chances are you won’t walk out empty handed. Calle Cobos 2601, Pedriel, Mendoza; +54 9 261 553 5565

Tucked into the ancient, magical maze that is Old Acre, the Efendi Hotel looks out onto the city walls and the sea just beyond. Combining two Ottoman palaces, this labor of love from celebrity chef Uri Jeremias—whose nearby restaurant, Uri Buri, is practically a foodie pilgrimage site—took restorers and artisans the better part of a decade to complete under the watch of the Antiquities Authority. The layer cake of history beneath the hotel includes a 12th-century Crusader cellar, where you should head for a wine tasting, and a 400-year-old hammam, where you should book a Turkish bath. Also not to be missed at the Efendi: the 19th-century fresco commemorating the debut of Istanbul’s Orient Express station, the gorgeously preserved ceilings, and the rooftop bar (be sure to go at sunset, when your drinks will be accompanied by a chorus of Muezzin calls). Though you’ll be tempted to linger over the sublime views—and fresh dates—in your room, get out during the day and explore the surrounding alleys, mosques, synagogues, markets, tunnels, fortress, citadel, and port.

It should come as no surprise that Seattle has an umbrella boutique downtown. What might be a surprise is the fact that you can rent umbrellas by the day (and that a single day’s rental might be what you were expecting to pay to purchase one outright). Fanciful, elaborate umbrellas with layers of brightly colored ruffles, asymmetrical shapes, and unique prints hang from the ceiling in an eye-catching display that’s worth stopping in just to see. For a sunny day, a lightweight paper parasol might be just the thing for portable shade (though you’ll find them cheaper in the International District). Locals tote the clear plastic “bubble” umbrella, which has a hemispherical shape to offer more coverage and a transparent material so you won’t sacrifice visibility.