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Secreted away on Giudecca Island is the glamorous, lagoon-facing Belmond Hotel Cipriani, originally opened in 1958 by Giuseppe Cipriani, founder of the infamous Harry’s Bar and the creator of that ubiquitous brunch cocktail, the Bellini. The peach-hued 15^th-century palazzo is styled with Murano glass chandeliers and Fortuny and Rubelli fabrics and has a Michelin-starred chef in house and several knockout restaurants all set on manicured grounds. The hotel is kept safe from the prying eyes of paparazzi behind a castlelike wall. No wonder it’s the luxury hideout of choice for celebrities (Mick Jagger is a fan) and the jet set.

If guests do feel like venturing out, the hotel offers one-of-a-kind outings with expert local guides such as a nighttime photography stroll, a visit to area wineries and farms via boat, and a kayak paddle on the lagoon.

Catch the train from Genova Brignole station to Santa Margherita Ligure (about a 30-minute ride, leaving every ~30 minutes) and walk down to the large dockside pedestrian area. You will see the bike rental station just a few steps away from the bus ticket kiosk. For ~5 euros, you can have a bike for the whole day—a perfect option for exploring the fantastic surroundings! While the roads are all paved, they are incredibly narrow, and cars tend to drive quickly. Just be aware and stay very close to the edge for your own safety. Portofino (a 15-minute ride) is a gorgeous town frequented by international tourists and stunning yachts in the summer months. Originally named for the schools of dolphins (Port’Delfino) that often pass this cove, the landscape around the village is breathtaking. If you come in the spring, you can ditch your bike to spend the day hiking the paths up to the perched fort and church, or simply enjoy a gelato while gazing at the quaint fishing boats in the marina.

Two things you need to know about gondola rides in Venice: They’re worth it; and the price is agreed beforehand. Knowing those two things, you can happily hop aboard this traditional Venetian mode of transport and relax, because, touristy as it is, it’s not a rip-off, and it’s a must-have experience. You can pick up a gondola almost anywhere in Venice, and you can see whatever sights you want from one... My own recommendation is to head away from the Grand Canal to the quiet backwater canals where you can really imagine yourself centuries back in time. We engaged our gondolier at the station near Rialto Mercato and asked him to take us across to Cannaregio, a more residential area that still boasts some extraordinary palazzi and churches. We barely met another boat, apart from the odd Venetian getting himself home on his motor launch, and unexpected delights loomed upon us silently and suddenly, like Marco Polo’s house, or the Chiesa dei Miracoli. All in all, much better than joining the heavy gondola traffic in San Marco.

For nearly three centuries, workers serving the nobility at Castello Banfi in Tuscany lived in a small hamlet within the castle grounds. In 2007, however, the stone houses within their tiny village were completely renovated under the direction of Italian interior designer Federico Forquet, catapulting Castello Banfi into a new era of grandeur. Today, the property welcomes guests from November through March in two guest rooms and 12 suites, each with wood-beamed ceilings, countryside views, and bathrooms stocked with “vinotherapy” products made from the estate’s Sangiovese Brunello. A central garden with a pergola, a heated outdoor pool, secluded lounging spaces, and alfresco massage tents offer plenty of ways to take in the surrounding vineyards. If you’re feeling more active, take a cooking class with the chef (held a short drive away at the estate farmhouse), tour the Banfi winery, or venture out to nearby historic towns like Montalcino and Siena.

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.

Spend a day strolling the medieval streets of Cefalù, an idyllic coastal resort town about an hour’s drive east of Palermo. The Norman-era Cefalù Cathedral towers above honey-colored stone houses; a rocky promontory known as La Rocca forms a dramatic backdrop to it all. Step inside the cathedral to see its beautiful mosaics, then get in some souvenir shopping or relax at a café and just people-watch.

Beginning right at the entrance to downtown Cancún (kilometer 0, where the median is also home to a spacious outdoor gym) and tracing the Hotel Zone’s entire northern stretch, this wide, red-paved path is a favorite for runners, in-line skaters, and cyclists in search of outdoor exercise with a merciful bit of shade (the path along Boulevard Kukulcan is lined with jungle flora, palm trees, tropical plants, and a smattering of hotel entrances). Locals especially love working out on the Ciclopista early in the morning and in the evening, when temperatures are cooler.

Blink and you’ll miss this tiny Indian-run eatery serving eclectic international fare between Mitte and Prenzlauer Allee along the trendy Kastanienallee. Notable for its upside-down McDonald’s sign (hence the “W” in the name; Der Imbiss means “The Snack”), the restaurant consists of a service window and a few brightly colored tables, and has quirky Hawaiian and African decor. The food is not only cheap and tasty but also healthy and diverse, pulling off an ambitious mix of Mexican, Californian, Indian, and Italian influences. It’s most famous for naan pizzas—Indian naan breads baked in the venue’s tandoor, with pizza-esque toppings from olives and cheese to artichokes and salmon. The menu also includes filling Indian thali platters, soups and salads, and Mexican-style wraps.

At Little Italy’s Herb & Wood, Chef Brian Malarkey’s wood-fired dishes include roasted parsnips with pickled raisins, parsley-shallot verde, and molten Marin County brie; roasted beets with sherry, walnut pesto, jamón Ibérico, and burrata; and grilled flat bread with whipped eggplant, za’atar, onions, and pine nuts. But the Mediterranean- and California-inspired menu isn’t the only big draw here: The industrial-boudoir aesthetic is equally inviting, with tufted sofas, soft lighting, and feathery fronds under the soaring ceilings of this onetime warehouse. A charmingly tattered edition of Emily Post’s Etiquette book has pride of place on the hostess stand. But the restaurant is unlikely to call guests on any manners infractions except one. In calligraphy at the bottom of the menu, you’ll find the following note: “Substitutions and additions politely declined.”