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On a quiet white-sand beach within the gates of the historic Hacienda Pinilla ranch, just a few miles from the bustling surf town of Tamarindo, the JW Marriott is an ideal choice for families, offering a wide range of on-site activities for every fitness level—think surfing, volleyball, golf, hiking, kayaking, horseback riding, and the list goes on. The kids’ club provides organized daily adventures for children ages four to 12 while parents steal a few relaxing hours at the oceanfront infinity pool or indulging in beachside massages at the spa. Five restaurants and two bars serve everything from casual burgers for picky eaters to sushi, Asian fusion, and contemporary Costa Rican for those with more refined palates. And all of the 310 guest rooms have balconies or terraces with ocean, garden, or pool views, as well as marble bathrooms with oversize tubs for maximum comfort. Spring for a spacious one-bedroom suite, which has a separate living-room area—a great plus if your little ones are early risers.

Modern luxury meets southern hospitality at the Four Seasons Hotel, where the emphasis on service means no detail is too small. Have your loafers born the brunt of marathon city tours? The hotel provides free overnight shoe shines. Want to impress the little ones? Family-friendly touches such as a mini check-in desk, kid-sized robes, and sponge letters arranged around the bathtub to spell out children’s names won’t disappoint. No one would fault you for hunkering down in your plush neutral-hued room, which couples a marble bathroom, complete with deep soaking tub, separate shower, and C.O. Bigelow products, with sweeping views of Midtown, plus one sweet feature: chocolate-chip cookie delivery before bedtime. But there’s plenty of motivation to venture out, including a spa with an interactive aroma bar, a moody gray lounge inspired by beloved Wes Anderson character Margot Tennenbaum, and Park 75, a seasonal restaurant that utilizes ingredients pulled straight from the hotel’s terrace garden.

It’s not quite Providenciales’s celebrated Grace Bay—the Atlantic surf rolls in with a little too much force for that—but North Beach, on remote, undeveloped Salt Cay, is one of the prettiest stretches of sand in all of the Turks and Caicos. Salt Cay also has the advantage over its more famous counterpart in that just about the only thing on it is the tiny Castaway, whose guests almost always have miles of pure white sand and turquoise ocean entirely to themselves. About a mile and a half from “town” lies a scattered settlement of fewer than 150 people who make up most of the island’s residents. Castaway, which consists of four suites in two beachfront cottages, offers a Crusoe-like experience, except with private dining and Wi-Fi. Each suite has a king bed, to which two more single beds can be added, a full kitchen, and a deck where in season it is possible to watch migrating whales parade by.

After you’ve explored the stunning sea cliffs along Mudjin Bay, get a table on the patio of the Mudjin Bar and Grill to savor the scenery a little longer and enjoy a well-earned meal. The restaurant is part of the Dragon Cay Resort and open every day for lunch and dinner. The menu shows off local flavors such as fried local lobster and conch fritters, along with burgers and chicken wings, but it’s the view overlooking the stunning Middle Caicos coastline that steals the show. (Dinner service requires reservations.)

Third Man Records, the Nashville outpost of musician Jack White’s record label and store, is hard to define. It’s both a retail outlet for vinyl and offices for his label, sure, but it also includes a “novelty lounge” with coin-operated video jukeboxes and whimsical contraptions. What draws the crowds, though, is Third Man’s music venue (decked out with curved blue walls adorned with taxidermy), which regularly holds live performances, shows movies, and hosts record-release events. Visitors also can step into the tiny Record Booth, a refurbished 1947 Voice-o-Graph machine, to record up to two minutes of audio that they can take home on a 6-inch phonograph disc.

Opened in 2012, Hattie B’s is the new kid on the block for hot chicken, Nashville’s most iconic dish. Still, what the restaurant lacks in history it makes up in flavor, proven by the long queues that don’t seem to diminish until the kitchen closes at midnight. The hot chicken, made in the traditional style with a hot cayenne paste, comes in a variety of forms, from wings to dark meat; order the half bird if you want to try a little of everything. Then decide how much you want to crank up the heat, which ranges from mild to “Shut the Cluck Up: Burn Notice.” Half the fun is choosing the sides, which include pimento mac and cheese, Southern greens, baked beans, and extra pickles.

At first glance, this cookware emporium feels like a dusty relic. But dig a little deeper, especially in the basement, and you’ll find just about anything you could need for the kitchen, along with plenty of treasures you don’t—duck press, anyone?—but would love all the same. Knives, copper cookware, and ceramics are the selection’s biggest strengths.

Halifax’s identity is tied to the sea, and its rich maritime history is the central theme of this eclectic museum. Popular exhibits include one dedicated to the role of Halifax after the sinking of the Titanic (the city’s ships helped with the recovery) and the devastating Halifax Explosion, a 1917 ship collision that killed 2,000. Don’t miss touring the CSS Acadia, a naval vessel once used for hydrographic missions.

Via Tornabuoni, one of the most elegant streets in Florence, is lined with many imposing Renaissance palazzi, including a 15th-century beauty owned by the Antinori family, the famed wine producers. The ground floor of Palazzo Antinori is given over to a refined restaurant with a formal dining room—think starched linen tablecloths and waiters in white jackets—suitable for the aristocratic atmosphere. The kitchen relies on ingredients from the family’s estate, so the menu is limited, seasonal, and fresh. Not surprisingly, the wine list is deep, with a selection of super Tuscan blends and wines from the Antinori cellars.

Trattoria i’Raddi, a classic Tuscan trattoria in the Santo Spirito neighborhood, is run by the Outran family. (A few family members are locally famous for playing calcio storico, a historic and brutal sport that seems like a mix of soccer and MMA fighting.) Come here to eat pappa al pomodoro (Tuscan bread-and-tomato stew), pici all’aglione (pasta with garlicky red sauce), and peposa. Peposa is a slow-cooked, peppery beef stew, almost a Tuscan version of chili; according to legend, it was invented by Brunelleschi. The food here is affordable and the prix fixe lunch specials are an even better value.

Via Vittor Pisani, leading up to Milan‘s Stazione Centrale, is a long and open boulevard, lined with modern buildings. It’s quiet, and if you catch it in the right light, it has a vague Ayn Rand/The Fountainhead feel to it. The neighborhood surrounding the train station is less pedicured than other parts of the city and filled with more affordable hotels.

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!

The fashionista’s drinking place of choice, Roberto Cavalli’s chic café makes a perfect pit stop on the designer boutique trail. Perch on a leopard skin pouffe for an excellent cappuccino, decadent pastries and cakes, and savory dishes at lunchtime. Foodie gifts to-go include delicious handmade chocolates, panettone at Christmastime (wrapped in Cavalli’s trademark animal-print paper), and award-winning wines made by Cavalli’s son, Tommaso.

At this speakeasy-inspired cocktail bar near Chiesa Nuova, hipster bartenders pour and shake American classics like Manhattans, Sazeracs and Old-Fashioneds in a smoky lounge. To gain admittance, make a booking and come armed with the secret password, a clue to which can be found on the venue’s website. Once you enter, you’ll be shown to a table or barstool, handed a menu, and asked to fill out a membership card. Service can be slow and snarky, but drinks are worth the wait. Cash only.

When Antonio Marras opened his first showroom and concept store in a residential neighborhood, fashionistas didn’t flinch at making the 10-minute taxi journey from downtown. The Sardinian designer of women’s clothing has earned a following for his fashion-forward style that avoids trends. His collections run the gamut from casual ribbed tanks with hand-sewn sequined flower patches to special-occasion silk jackets and dresses embroidered with Swarovski crystals. Couches and a menu of wine, coffee, and Sardinian sweets invite lingering. Via Cola di Rienzo 8, 39/02-7628-0991. This appeared in the October 2013 issue.