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  • Bodden Town Road, Bodden Town, Cayman Islands
    For a true taste of local life, head to Bodden Town—the Caymanian capital before George Town rose to prominence in the 1800s—and pull over at the roadside fish fry where the likely queue tips you off to the impending tastiness: Grape Tree Café. Granted, on any given day, the crowd may include as many chickens as humans (the former seem to love nothing more than strutting from palm-shaded table to palm-shaded table on Grape Tree’s patch of beach sand). Atmosphere aside, the big lure here is the array of fried fish: snapper, mahi-mahi, swai, and wahoo—served with fritters, cassava, sweet potatoes, and breadfruit.
  • 297 Shore Rd, Chatham, MA 02633, USA
    Every story about Chatham Bars Inn surely features the veranda, a wide porch with companionable groupings of wicker armchairs and table service that alleviates the need to fetch your own drink—so you never have to look away from the serene view of sailboats and swooping seabirds.

    Chatham Bars Inn excels memory making and, in addition to spaces like the verandah that make you feel you’re part of a generous and grand tradition, this Cape Cod resort has created intimate places (a small library, a settee in front of a fireplace, a private deck outside your cottage, chairs arrayed around a fire on the beach) where your private traditions will be forged.

    It faces the aptly named Pleasant Bay, calm waters sheltered from the Atlantic surf by barrier islands. And you’ll find it’s impossible to forget where you are: The fleet of sailboats and fishing boats and runabouts keep the ocean top of mind while the creative menus in the dining venues (centered around the catch of the day and the seasonal produce from their own eight-acre farm) are likely the most locavore of any property of this caliber.

    Originally built as a private hunting lodge, the inn has been in business since 1914, which means many guests have been coming here since childhood. This curated version of a Cape Cod beach vacation is a decades-long habit for those guests—and one that new arrivals may be inspired to adopt. Pride of place is strong here and guests get caught up in it, too. While you don’t have to shuck the clams or dig the potatoes yourself (though those could probably be arranged upon request), you will never feel insulated from the experience of this distinctive part of New England.
  • Skoura, Morocco
    The beloved Dar Ahlam resort has taken its show on the road with Route du Sud, a six-night driving tour to five destinations with three private retreats that showcase the shape-shifting landscapes of isolated southern Morocco, one property at a time. The first stop is the hillside Maison des Arganiers, two and a half hours from Marrakech, in a rocky landscape facing miles of argan groves; next comes La Maison de l’Oasis, nestled in an oasis of palms; and the final private destination is the dramatic La Maison Rouge, which sits at the edge of a red canyon. Along the way you have beach picnics, nomadic campouts, and scenic drives through dramatic desert dunes.
  • More and more cruise ships are arriving to the well-known Greek islands for day exploration. And while that is a boon to the local economies; crowded restaurants and beaches are not what you have come to experience. Some of these popular islands actually have very few year-round residents as the cruise visits are seasonal. So that “real Greek” town that you came to see, really isn’t. The solution? Try one of the lesser-know but equally beautiful Greek Islands like Ios in the Cyclades Islands. Here you’ll find five-star hotels, mom and pop inns, historical monuments, miles of sparkling beaches, dynamite restaurants, vibrant mountain towns, incredibly reasonable shopping, breathtaking vistas, and local wines, but most of all Ios can be your own paradise. The island of Ios is still a place where real people live and work, but there is plenty of support for tourism (sometimes it’s party central at Mylopotas Beach) and you will find true hospitality, safe streets to wander and new activities like the recently opened hiking path system. Imagine walking at your own pace to archeological sites, beaches, churches and mountain villages just like the early inhabitants did for centuries? The Greek Cultural Mountaineering Club of Fyli has long wanted to repair and connect the ancient paths and a few months ago the project was completed with the help of volunteers and the Municipality of Ios. Over thirteen kilometers of paths are open and well-marked by signs connecting other paths and old roads of Ios for you to enjoy. Not a hiker? The shopping is sublime. Not for the collectors of designer handbags but those desiring handmade leather sandals, precious gem jewelry and smart local-style clothing designs. Lounging by the pool is always a favorite. Stay at the elegant Liostasi Suites and you will be pampered like a jet-setter. Wish for a low-key stay? The Pavezzo Hotel and Suites is painted in beautiful colors and embellished by flowers offering family-style rooms, rooms for one or two and vantage points with sea views set on the side of a mountain with cooling breezes and the friendliest owners. If you are a fan of Greek cuisine there are many terrific restaurants, some right on the ocean like Drakos Taverna at the end of Mylopotas Beach. A favorite in Chora, the town above the Ormos harbor which is completely accessible on foot, is Elia. Visit the cathedral and one of old windmills the island is famous for while wandering the maze of winding stone streets that spill down from top of the hill. Or down in Yialos by the harbor pop into one of the very casual tavernas. Be sure to visit the food shop called Mosenta at the port to watch them create, and for a taste of sesame seed and honey cakes. They also package local wild herbs and make a great body cream that is made from their own honey and olive oils. Insider Tips: Go in Fall for peace and quiet and best rates on rooms. There is no airport so take the ferry from Pireaus, Athens or Santorini. Images Kurt Winner Photography
  • 132-140 Rue des Rosiers, 93400 Saint-Ouen, France
    Marché aux Puces de St-Ouen, aka Clignancourt, is Europe’s largest flea market and the city’s favorite place to find a bargain. Exiting the Métro at Porte de Clignancourt, those in the know pass by the counterfeit designer-goods hawkers, avoid the parking lot with camper vans full of cheap goods, and head under the overpass to Rue des Rosiers. Groups of stalls form smaller flea markets, each with its own specialty, so shopping can feel like walking through a museum where you can actually buy things. The market called Serpette draws serious dealers looking for mid-century marvels, but shoppers who head as far as Jules Vallès market may score some true bargains. Of course, this is France, where food matters, so there are plenty of local cafés to choose from. Ma Cocotte is trendy chic, La Chope des Puces has live jazz with moules frites, and Chez Louisette draws a crowd nostalgic for French tunes with its simple steak frites.
  • Lima District 15001, Peru
    Every day at noon at the Plaza de Armas (also called Plaza Mayor), trumpets blare, drums pound, and cymbals crash as the guard changes outside the presidential palace. Enjoy the Spanish fanfare like a local: from a plaza bench with an ice cream cone. The Plaza is also the site of festivals, concerts, and the much-loved annual National Pisco Day when the fountain spouts free high-proof grape brandy for all.
  • 717 Orleans St, New Orleans, LA 70116, USA
    This gem right off Bourbon Street is close to the action but far enough (and insulated enough) to make you feel like you can get away from the frenetic pace of the city’s most famous avenue at a moment’s notice. Guest rooms are well-appointed and comfy, with plantation-shuttered windows, plush beds and sleek bathrooms. Plus, every guest gets a voucher for a welcome drink in the hotel’s smoke-free bar, the Bourbon O. Be sure to catch live music there on Friday nights, as well as bartender Cheryl Charming, whom a local magazine named Mixologist of the Year in 2014. Back at the hotel, the Roux on Orleans restaurant can satisfy breakfast, lunch and dinner desires, and a heated saltwater pool makes lazing about in a lounge chair all day very, very easy. But if you want to be the ultimage envy of Bourbon Street revelers, make sure to reserve a balcony suite; it features a porch overlooking all the boozy revelry below and lets you party above the action.
  • 4 Yawkey Way, Boston, MA 02215, USA
    Nothing defines Boston quite as much as the town’s devotion to sports (10 championships since the turn of the century doesn’t hurt), and with all due respect to the five-time-Super-Bowl-champion Patriots, it’s Fenway Park, not Gillette Stadium, that’s the temple of sports fandom. Opened in 1912, the quirky green bandbox between Lansdowne Street and Yawkey Way is almost as famous for its obstructed-view seats as it is for its fabled Green Monster wall in left field, but that’s a price Sox fans gladly pay in exchange for maintaining Fenway’s historic layout. It’s both intimate and loud on game day even in years when the Sox aren’t contenders (tickets are often hard to come by, so plan ahead); the old ballpark also is open for one-hour, behind-the-scenes tours that take you inside and atop the Green Monster. You’ll be able to stroll around the field (the warning track, not the grass), and visit the press box, the Pesky Pole, and (on days with no games) the dugouts and bull pens.

  • Piazzale Michelangelo, 50125 Firenze FI, Italy
    One of the best views of Florence can be savored from the Piazzale Michelangelo, a short walk across the Arno River from downtown Florence. For a fun afternoon head to the square and enjoy an enchanting panorama of the city, followed by a relaxing alfresco lunch at one of the nearby restaurants. The Piazzale Michelangelo is also worth a visit at night to get a very different glimpse of Florence. The lights of the Duomo and the buildings surrounding it make for a magical nighttime scene.
  • Pariser Platz, 10117 Berlin, Germany
    Napoléon and his armies marched through it; revolutionaries and Nazis gathered beneath it; the Berlin Wall ran right behind: It’s safe to say that Berlin’s iconic Brandenburg Gate, completed in 1791, has pretty much seen it all. Designed by Carl Gotthard Langhans, who drew inspiration from the entrance to the Acropolis in Athens, the gate is best approached via Unter den Linden, the tree-lined boulevard that runs between the gate and the former Royal Palace. You can combine a visit here with nearby sights such as the Reichstag, Tiergarten Park, and the Memorial to the Murdered Jews of Europe. Since 2016, an impressive high-tech museum at the gate has offered a history of the city through the perspective of the iconic structure.
  • 5900 Lower Honoapiilani Rd, Lahaina, HI 96761, USA
    When eating at the Sea House Restaurant, it’s hard to decide what is actually better: the view of Molokaʽi across the water, or the Molokaʽi sweet potatoes used in the frittata. Either way, both combine for a memorable breakfast on the island’s northwestern corner. Opened in 1963 when tourists were just discovering Maui, the Sea House restaurant celebrated its 50th anniversary in 2013—thereby making it one of the oldest restaurants in West Maui. Even with the history, fame, and ocean views, it’s one of the island’s most affordable restaurants. Most items on the breakfast menu will cost you $12 or less, and when you’re done with your meal, you can splash in the waters of protected Napili Bay. The Sea House sources many of their ingredients from local Hawaiian farmers (such as the Molokaʽi sweet potatoes), and they also follow traditional fishing calendars when choosing their fish for the menu. This is a great option for beginning the day on the island’s northwestern coastline and is a filling starting point for later adventures toward Honolua Bay and beyond. Or, just relax on the sands of Napili beneath the shade of a rustling palm. After all, there are only three hours between the end of breakfast and the start of the Sea House happy hour—an affordable menu that starts at 2 p.m. and has been voted one of the best on Maui.
  • San Pedro, Belize
    Hol Chan Marine Reserve, located just a few minutes’ boat ride from San Pedro, is the place to go for snorkeling in Northern Belize. This small, protected area (Hol Chan means “little channel” in Mayan) is home to part of Belize’s barrier reef, which is the second largest in the world (after Australia‘s reef), and the largest healthiest. There are many tour operators out of San Pedro that can take you out for a half-day of snorkeling the reef, and you’ll see colorful coral, rainbow fish, and manta rays, among other marine life. Make sure your guide brings you to Shark Alley, where nurse sharks come to feed on the fish scraps boats leave behind. There, you’ll be able to swim mere feet—or even inches, if you dare—from the creatures.
  • 111 S Grand Ave, Los Angeles, CA 90012, USA
    This bowed silver building stands out among the skyscrapers of Downtown L.A. (though it now has an equally interesting-looking neighbor in the Broad). Those stainless-steel curves have a purpose, though. Architect Frank Gehry designed the Walt Disney Concert Hall with top-notch sound quality in mind, and the result is an architectural landmark that doubles as one of the most acoustically advanced concert halls in the world. The venue is home to the always impressive L.A. Philharmonic, a 100-piece orchestra that puts on concerts ranging from classical to jazz, contemporary, and world music throughout the year.
  • 207 Banff Ave, Banff, Alberta, Canada
    Dining at the Grizzly House is an experience. As soon as you walk in, it’s obvious the place hasn’t changed much since it first opened decades ago. The interior is dark, and the wood-paneled wall is lined with taxidermy trophies. But the novelty of cooking at your own table makes up for it all. The food ranges from decadently simple—cheese, oil, and chocolate fondues—to exotic, like rattlesnake or alligator meat. The only thing more novel than preparing your own food is the rumors of the restaurant’s history as a swingers’ joint. Whether the stories are urban legend or not is hard to say, but telephones at each table that allow you to call any diner in the room seem to suggest there’s some truth to the gossip.
  • Jacob Bontiusplaats 1, 1018 LL Amsterdam, Netherlands
    This funky spot stands out among Amsterdam’s many urban “beach bars.” You can laze away a sunny afternoon at one of the picnic tables or chairs set up on a wide stretch of sand. Cocktails and beer slake your thirst, while decent pulled-pork tacos, burgers, and poke bowls keep hunger at bay. If the weather isn’t agreeable, the café—located inside a converted warehouse—strikes all the right hipster notes: Think distressed, graffitied concrete walls; leather sofas; vintage television sets; and groovy lighting. An adjacent warehouse hosts all sorts of events, from flea markets to film screenings to dance parties.