Take Me To: Venice, Florence, and Taormina

Fly into Venice’s Marco Polo Airport with ITA Airways booked by your SmartFlyer travel advisor. The airline boasts a rapidly growing, majority new-generation fleet of Airbus aircraft designed for the modern traveler’s maximum comfort. The enduring magic and romance of Venice will come into view as you take a private, 45-minute transfer from Venice Marco Polo Airport to the freshly renovated Hotel Cipriani. When you arrive at the iconoclastic property, you will be struck by the views of Basilica Santa Maria just across the waterway.

We recommend the Dogaressa Suite, which drips in aristocratic Venetian beauty—named after the “first lady” of Venice…

Overlooking Piazza San Marco, settle into your suite, radiating old-world glamour—perhaps with a hint of Hollywood. The hotel has been a haven for the jet set since the 1950s. We recommend the Dogaressa Suite, which drips in aristocratic Venetian beauty—named after the “first lady” of Venice and filled with the kind of high-touch finishes that will make you feel like royalty. Think velvet Furlane slippers, plush dressing gowns, and rose perfume crafted specifically for the suite.

To kick off your stay, enjoy a casual lunch at Cip’s Club on the water. The restaurant offers classic Venetian fare and cocktails—an ideal spot to melt into la bella vita. And for the ultimate Cipriani treat, be sure to order a Bellini; Giuseppe Cipriani, the founder of Hotel Cipriani, invented this drink. At Cipriani, it’s only served when fresh white peaches are in season. After you’ve sipped and snacked to refuel, explore the gardens before taking the free shuttle to Piazza San Marco for a stroll, or enjoy the property until the six o’clock sunset tour aboard Shirley, Hotel Cipriani’s private mahogany boat. For dinner, enjoy one of the top culinary experiences in Venice, without even needing to leave the hotel. Helmed by Chef Vania Ghedini, ORO is a Michelin-starred restaurant serving up seafood tortellini, blue crab with caviar pairings, and other Italian fineries inspired by the sea.

Before gearing up for a day on the water, start your morning with a cup of coffee following a tennis match on Hotel Cipriani’s clay courts. If you’re keen to improve your game, instructors can be arranged. For art and shopping lovers, take Shirley to the Murano furnaces to witness master glassmakers handcraft world-renowned pieces—a unique chance to see centuries-old techniques in action.

To discover Venice’s hidden corners, go for a private sail on Hotel Cipriani’s Edipo Re, the iconic yacht where Maria Callas and Pier Paolo Pasolini’s romance blossomed. This storied vessel now offers an exclusive route to Byzantine mosaics, seventh-century cathedrals, and endless shimmering waters. For dinner, try the Michelin-starred Wistèria, which serves up a seasonal menu titled Serendipity. End the night with a drink at Hotel Cipriani’s Bar Gabbiano, where you’ll be able to catch some live music as the perfect end to your day.

Now is the time to embrace villeggiatura, the Renaissance Italian tradition of completely disconnecting during the summer months to experience a slow, leisurely pace of life. There might be no better place to do this than Hotel Cipriani’s extra-large pool—the only one in central Venice.

The lore goes that when it was commissioned, the measurements were sent in feet, but it was built in meters. The result was a giant, glimmering respite from the heat right in the middle of the island. Photographer Greg Williams has captured dozens of high-profile faces at the hotel pool. Williams has shot portraits of actors such as Lily-Rose Depp, Nicholas Hoult, and Dakota Johnson, and calls the space “magical.”

Relax in a poolside cabana, enjoy service from Bar Gabbiano, and indulge in fresh fruit, sparkling wine, and poolside mini spa treatments. You have the option to finish the day with a Bacari tour, which will guide you through unexpected bars where locals share the news and gossip of the day over a glass of wine. For dinner, consider Osteria alle Testiere, an in-the-know spot serving up a delectable catch of the day at a small and intimate selection of tables. Get home easily via the hotel’s boat service, which runs every day between 7:30 am and 1 am.

In the morning, enjoy one final indulgent breakfast at Cipriani, soaking up the breeze from your outdoor table. After bidding the Cipriani team farewell and hopping onto your private boat transfer, you can opt for a private car or smooth ride on the high-speed train in Italo’s executive lounge class from Venice to Florence. The train journey takes just over two hours.

…nestled away from the bustle of the city below and the demands of your life, you’ll be able to settle into spaces designed by world-famous artisans.

If you arrive by train, you will be whisked from Santa Maria Novella train station by private car to your next Belmond haven. A quick twenty-minute journey up into the hills of Fiesole, and you’ll arrive at the lush grounds of Villa San Michele. Here, nestled away from the bustle of the city below and the demands of your life, you’ll be able to settle into spaces designed by world-famous artisans. Notably, the entire property has been refreshed following a meticulous 18-month renovation, reopening its doors in April 2026.

Once you’re settled in your suite, you can start the Tuscan arm of your Italian adventure with an early evening to unwind and familiarize yourself with this monastery-turned-hotel. Take a leisurely swim in the panoramic pool overlooking the Arno Valley and Florence, roam the gardens lined with Cypress trees and 200-year-old wisteria, or have an expertly crafted Negroni at Bar Doccia.

Get ready for the evening in your expertly designed suite, reimagined under the creative direction of the Florence-based firm Luigi Fragola Architects. We recommend staying in The Grand Tour, a former residence of Napoleon Bonaparte transformed into a warm, open-layout space with stunning views of the city below and appointed with Tuscan marble, antique pieces, and design touches that beautifully bridge 18th-century decadence with 21st-century ease. Every suite now offers heated plunge pools and private gardens following this year’s renovation.

Tonight, dinner will be at Antesi, Villa San Michele’s ultra-intimate dining experience helmed by Executive Chef Alessandro Cozzolino. With just eight tables and a menu crafted from seasonal ingredients to create dishes using a blend of traditional methods and contemporary techniques, this meal will mark the start of your time in Florence with aristocratic indulgence.

Wake up to gardens and panoramic views that will make you feel as if you’ve been transported to another time. Spend the morning having a quiet, classic Italian breakfast before charging your body in another way. Whether getting a signature treatment from the Villa San Michele Spa by Guerlain or taking a meditation class in the aromatic gardens with Belmond partner La DoubleJ, there are plenty of relaxing ways to ease into your day at Villa San Michele.

After a generative morning, it’s time to head down into Florence with your private driver and guide. Skip the crowds at some of the more well-known attractions in this Renaissance wonder and opt for the in-the-know delights; you’ll be led through less-expected contemporary art on exhibit at Palazzo Strozzi Foundation, which is a perfect contrast to its 17th-century surroundings.

Stop at Santo Bevitore for a classic Tuscan lunch. Spend the afternoon wandering the ancient streets, where you can nab artisanal gelato at Gelateria Della Passera, stop in the Giunti Odeon bookstore, take in the scents of the centuries-old Casa Profumo, and walk across Ponte Vecchio—one of the most iconic landmarks in the city and connecting the city over the Arno River.

After you’ve worked up an appetite strolling the streets—which feel like they are trapped in an earlier time when the Medici family still controlled everything from commerce to the church—head to your dinner at Trattoria Camillo. It’s a local favorite serving the highest-quality Tuscan fare, including a fantastic bistecca alla fiorentina; make sure to order the chocolate torte for dessert. For a nightcap, your SmartFlyer advisor can help secure a spot at Locale Firenze, one of the World’s 50 Best Bars, serving a menu inspired by the Renaissance art of the city.

Today is the day to break out your comfiest shoes because some of the best experiences in Florence are discovered through wandering. Whether it’s your first visit to Florence or you’ve lost track of how many times you’ve visited, the experts at Belmond have a spate of recommendations to bring out a new facet of the city. Start by asking the concierge where to find one of the Fotoautomatica photo booths hidden throughout the city. Make that your first stop so that you can take a memory home with you.

…further proof that in a city filled with art from hundreds of years ago, the spirit of creativity never left.

Then, head to Piazza Pitti, where the market offers the finest display of Florentine craftsmanship, including leather goods of every variety. Take the shopping experience one step deeper by stopping by Antonio Gatto’s hat atelier. Here, you’ll have a front row seat to how each hat is carefully handmade—further proof that in a city filled with art from hundreds of years ago, the spirit of creativity never left. For a taste of some of the home wear offerings in the city, head to the Ginori flagship store to peruse their stunning collection of porcelain dishes.

For lunch, wander over to Trattoria Sergio Gozzi, popular with locals. Here, you’ll make a quick stop for traditional Tuscan fare—we recommend the Tortellacci and Peposo. Follow your lunch with a glass of wine obtained from Florence’s famous buchette del vino. These tiny wine windows, scattered throughout the city, are a 17th-century relic that adds a touch of whimsy to an experience that’s already lovely. Like magic, knock gently and a glass will emerge.

End the day with a relaxed evening at Ristorante San Michele, overlooking the Florentine skyline with a sense of accomplishment at all you saw and explored. Refuel with specialties from the Slow Food Foundation. Dishes are made with the freshest, most local ingredients; think raw-milk pecorino from Maremma, red onions from Certaldo, and Sorana beans.

Start your last full day in Firenze slowly, with a stroll in the garden. The Leonardo Woodlands offer the perfect place for a meandering pace or a brisk, energizing hike, all within Villa San Michele’s grounds.

After breakfast, take a guided tour arranged by your SmartFlyer travel advisor; some favorites include hillside exploration done via Ferrari , or, for those looking to stock up on Italian designs, book a private shopping experience at atelier showrooms, like the two-story Pucci Firenze, or Ferragamo—which can also include a visit to the Salvatore Ferragamo museum.

There are also opportunities to take private, after-hours tours of some of the world’s most famous galleries. Without the crowds and quiet rooms filled with work from all the masters, you can linger at the Uffizi gallery, where Botticelli’s Birth of Venus is on display. Or, gaze up at Michelangelo’s awe-inspiring David at the Galleria Dell ’Accademia. Cap off your customized experience with dinner at the incredibly lush Atelier De Nerli. With deep red wine interiors, you feel like you’re at the bottom of a glass of Chianti—in the best way possible. For a final sweet treat in Firenze, head to Gelateria Vivoli and order the affogato, known as la gran crema al caffè.

This morning, you’ll take a private car transfer from Florence to Rome, where you’ll hop on a quick one-hour ITA Airways flight from Leonardo Da Vinci Airport to Catania Airport in Sicily. The Belmond team at Villa Timeo will arrange for your seamless and private hour-long car transfer to Taormina, which will include stunning views of Mount Etna.

Once you arrive and settle into one of the 21 suites in the ultra-private space, you can relax at the private pool available exclusively to Villa Timeo guests. While lounging poolside, enjoy drinks from Bar Clementina. There is the option to simply order and enjoy or partake in a mixology experience only available to guests of the villa.

Just sixteen guests per evening get the pleasure of dining at this Michelin-starred restaurant on the Grand Hotel Timeo property.

Further sink into the Sicilian pace of life by lounging at the pool before getting ready for an intimate dinner at Otto Geleng, named after the iconic German painter. Just sixteen guests per evening get the pleasure of dining at this Michelin-starred restaurant on the Grand Hotel Timeo property. Executive Chef Roberto Toro helms a tasting menu featuring fresh seafood, suckling pig cheek, and other Sicilian delicacies.

There are countless ways to have a perfect day at Villa Timeo, and sister property Villa Sant’ Andrea; Lido Villeggiatura, Belmond’s private beach club, is designed with a discerning eye for maximum intimacy and refinement and is just a ten-minute private drive from Villa Timeo. But the Timeo team can also arrange for a premium experience catering to your most specific Italian fixations.

For the film buffs, take a day trip to discover the world setting of Francis Ford Coppola’s The Godfather trilogy. You’ll get to feast on the traditional way of life at two picturesque hilltop villages that served as filming locations, Forza D’Agrò and Savoca. As you travel around the winding roads, you’ll have a chance to take in the movie locations, including the Church of Santissima Trinità in Forza D’Agrò, the Church of Santa Lucia, and the famous Bar Vitelli in Savoca.

Your SmartFlyer advisor can arrange for a charter on an Apreamare Gozzo 35—a vessel crafted by the Aprea family, famed master boat builders from Sorrento.

Alternatively, if you prefer to spend your time in Southern Italy on the water, explore the enchanting Sicilian coast on your own private boat. Your SmartFlyer advisor can arrange for a charter on an Apreamare Gozzo 35—a vessel crafted by the Aprea family, famed master boat builders from Sorrento. Depart from Lido Villeggiatura and visit the volcanic Aeolian islands or the streets of Stromboli, which were made famous by the 1950 film starring Ingrid Bergman.

There are other custom experiences your advisor can plan, including a wine tasting, a tour of a local clam farm, or a helicopter tour. Whichever adventure you indulge in, you can end the day in the same blissful way. Unwind at Ristorante Sant’ Andrea, where you can take in a spectacular seaside sunset. Order the authentic Sicilian couscous for maximum cultural immersion. Finish with a drink at Bar Sant’ Andrea, which is open late. We recommend ordering the Scilla E Cariddi cocktail, inspired by the flavors of Southern Italy. At the end of your evening spent by the water, you’ll be escorted back to Villa Timeo by private car.

Start the morning off with a seaside espresso before diving into another dreamy day. Your SmartFlyer advisor will arrange for an ape calessino—the iconic three-wheeled Italian scooter—to take you to every corner of Taormina and beyond. You can drive up to the village of Castelmola, where the quaint main square offers sweeping views of the coastline and a time portal back to a gentler era.

Have lunch at one of the numerous charming cafes in Piazza IX Aprile and indulge in an afternoon sweet treat at one of the many gelaterias lining the square. Wrap the day with an unmissable performance at the famed Greek Theater. Your SmartFlyer advisor can work with the Belmond team to secure seats for one of the sought-after musical performances that bring this archaeological treasure to life.

Come back to your suite to find personalized embroidered pillowcases—a special touch at Villa Timeo and Grand Hotel Timeo—and a detail that speaks to the property’s long history serving kings, princes, and grand dukes.

Spend the morning lounging at Villa Timeo’s private pool and enjoying a last drink from Bar Clementina. Then experience a seamless trip home on ITA Airways, all arranged by your SmartFlyer advisor. With your black-and-white photobooth portraits in hand, you’ll conclude your most intimate trip to Italy yet, feeling rejuvenated and enriched by the culture and surely already hungry for your inevitable return.