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Just 50 miles north of the highest peak in the Atlas Mountains, Marrakech is a vibrant city that will let you dip into buildings from the 14th century just as easily as you can modern-day shops. When visiting Marrakech, spend a relaxed, dreamy morning in Jardin Majorelle before heading off to galleries, a museum dedicated to and the former home of fashion designer Yves Saint Laurent, or to snake charmers and other so-very-Marrakech wonders. Nicknamed the “Red City” for the clay used in many of the building, Marrakech is the best Moroccan city for an immersion course in the country’s culture, before you head off to explore the rest of Morocco.

There’s no need to fly all the way to Italy to try the pie that earned first place at the 2007 World Pizza Cup. Just head to North Beach and Tony’s Pizza Napoletana, where chef-owner Tony Gemignani was the first American to win the title. Gemignani serves only 73 of the prize-winning Margherita pizzas a day, but the seven ovens in the kitchen make a broad selection of styles, including Sicilian, Roman, New York, St. Louis, and even a Detroit-style pie—a square pizza made with Wisconsin brick mozzarella cheese. To find Tony’s, either follow the scent of baking crust or look for the line of eager customers awaiting entry to the no-reservations corner eatery.

For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

If you’re looking for a break from the beach and the noise, head to Konoko Falls Park (formerly known as Coyaba River Garden) for a quiet picnic, swim, and nature walk through beautifully manicured gardens. The Mahoe tiered waterfalls—a smaller, just-as-picturesque version of Dunn’s River Falls but rarely crowded—cascade through the park, and an on-site museum showcases the history of Jamaica’s first inhabitants, the Taino. The park offers gorgeous views of Ocho Rios’s bay below. Climbing and swimming in the falls, at your own pace, is great fun.

Walking through the narrow streets of Boston‘s North End might have you thinking about a delicious Italian meal. Take the time, however to explore the area on Hanover Street where the surrounding brick buildings suddenly give way to a park where Paul Revere stands guard. Commemorating his ride to warn the colonists of the impending British Invasion, the statue stands in front of a small park leading to the famous Old North Church. The setting is a perfect spot to relive the beginning of the American Revolution, and after exploring, leaves you in a location filled to the brim with restaurants and cafes to recharge before moving on.

San Francisco’s seven hills and extensive coastline offer plenty of impressive views; why not enjoy them with a delicious meal or bubbly drink? The Burger Bar on the top floor of Macy’s and the Rotunda at Neiman Marcus overlook Union Square. Bay-side eateries like Epic Roasthouse offer travelers water views, while the Cliff House (shown) and the Beach Chalet are right on top of Ocean Beach. To see the city glittering at night, visit the Top of the Mark bar at the Intercontinental Mark Hopkins Hotel or the Americano at the Hotel Vitale, in full view of the Bay Bridge’s Bay Lights.

Que Bonita offers furniture from the Sierra Madre, textiles from Guatemala, Peruvian ceramics, Native American jewelry from the Southwest—all on the way to (or from) Mt. Lemmon on Tucson’s northeast side. This family-owned gallery/furniture/clothing store has been in Tucson for three decades. When in southern Arizona, check this place out for items from all over Latin America. (It’s only a couple doors down from a good pub, and next door to a hotel, too!)

Stroll inside the Errol Flynn Marina, located right in Port Antonio town, for a waterfront respite along manicured lawns and sailboats. Enjoy an afternoon “I-Scream” cone from the on-site Devon House, a household name in Jamaica. There are public benches by the water, as well as bars and restaurants. If you can, stay long enough to enjoy the sunset.

All of Mexico City‘s neighborhood markets are fun to browse, with their rows and rows of colorful stalls and equally colorful characters, and you can’t go wrong ducking into any one of these mercados as you come across them in your wanderings. Mercado Medellín is particularly favored among expats from other parts of Latin America, as it specializes in foodstuffs from Caribbean and Central and South American countries. This is also a superb market to visit if you’re hungry. Vendors sell everything from Colombian ajíaco to Cuban ice cream, so don’t hesitate to graze your way through the treats on offer.

Adventurous souls should plan on a moonlit dip in the bioluminescent Glistening Waters, also known as Luminous Lagoon. Boats leave from a marina, located an hour north of Montego Bay, on scheduled night tours. As your tour boat speeds out into the dark of night, you’ll spot fluorescent blue streaks in its wake—bioluminescence that’s created when living microorganisms (in this case, dinoflagellates) are disturbed. You can jump in for a swim, too, and glow in the dark as you splash about. It’s an amazing phenomenon to witness, and it’s said to exist in only five lagoons or bays in the world. Back at the marina, the Glistening Waters restaurant offers beautiful views, as well as pre-cruise drinks and food.

This is my favorite Scottsdale resort because it gets Southwestern style down without being kitschy or over-done. There are no cheesy dream catchers or Kokopelli statues here – just a color palette as bright and breathtaking as a desert sunset. Four Seasons Resort Scottsdale is perched in the city’s northern half, and surrounded by miles of Saguaro cacti and rugged rocks. Its location adjacent to Pinnacle Peak Park is perfect for hikers and if you crave more of an adrenaline rush, check out the high-octane tours from Arizona Outback Adventures. At Proof, the resort’s American canteen, dinner is practically a cross-country road trip with home-style comfort food inspired by, and sourced from, the 50 states. Plus, there’s a hearty list of wine, microbrews, and small batch and craft distilled American spirits. The Spa at Four Seasons also celebrates the resort’s sense of place with treatments like the Sonoran Honey Body Polish and Jojoba and Prickly Pear Polish.

Tippy’s Restaurant is the place to be on the north end of Eleuthera. Located on the beach, the restaurant features amazing views and a cool, laid back atmosphere. The food is excellent and is a nice mix of seafood and American cuisine. On the weekends Tippy’s is almost always packed with people, many of whom are there to listen to the live music and to enjoy a fun evening out.

Though few tourists venture to Kingston, the capital and hub on the eastern coast of Jamaica, music fans should make the day trip to visit Bob Marley’s former home, now a museum dedicated to Marley’s life and impact on the world. A guided tour of this museum takes about an hour and a half and includes a 20-minute video presentation. Even devoted reggae fans will likely learn more about Bob than they ever knew. Exhibits include multiple awards, guitars, and his bed with an engraved headboard depicting a lion.

Few venture this far east in Jamaica, but those who do will find one of the most authentic sides of the island, and the most secluded of getaways. A charming fishing village about thirty minutes past Port Antonio, Long Bay is as peaceful and scenic as it gets, with just a handful of affordable, casual guesthouses perched atop dramatic cliffs and overlooking a long stretch of deserted beach. No frills here, just nature and culture. The fresh ocean air, the roadside fresh seafood shacks and friendly locals will have you staying longer than you planned. Be sure to drive along the coastal highway and head as far as Manchioneal, another stunning fishing village that feels thousands of miles away from the touristy side of Jamaica.

The Grand Central Oyster Bar celebrates its 100th anniversary this year as a New York institution. Located in the lower concourse of Grand Central, it serves over 25 varieties of oysters daily. There is a huge menu of American seafood—chowder, fried clams, lobster rolls, clams casino—whatever you are looking for, they will have it. The Oyster Bar is also famous for its architecture—the beautiful arched tile ceilings are the hallmark of famed Spanish architect Rafael Guastavino, who left his unique stamp across NYC. Take your pick from three different seating areas: a series of old-fashioned, U-shaped counters which seem to be popular with tourists and locals; the oyster bar, which would be perfect for singles or those dining in pairs; and the saloon-type restaurant in the back, popular with the business crowd. Wherever you are sitting, it will be bustling with activity. While there are several other oyster bars in the city, the Grand Central Oyster Bar offers a piece of New York history. It’s like stepping back in time, a retro celebration of old Americana that generations of locals, tourists and travelers have visited over the years. My suggestion is to stop in for fresh oysters and cold beer at the bar.