Luxury Italian Highlights: Venice, Florence, Chianti, Rome & Amalfi Coast - 14 Days

Day 1: Arrive in Venice, Guided City Tour

Benvenuti in Venezia! Venice, Italy's "Floating City," is situated in the country's northeast and comprises a unique network of ornate bridges and canals that form the elegant palazzo-lined Venetian Lagoon. It has enchanted visitors for centuries. Arrive in style at your centrally-located luxury hotel by private vaporetto (water taxi), and unwind and relax before heading out to uncover the city's landmarks with a private tour of the city.

You'll start in Piazza San Marco, the heart of the city's cultural and administrative district, flanked by Caffè Florian and Gran Caffè Quadri, two splendid neo-Baroque 18th-century coffee houses that have attracted the city's writers and artists for 300 years. It's a fitting setting for the San Marco Basilica, one of the best surviving examples of Italo Byzantine architecture, featuring exquisite art, gold, mosaics, and marble floors.

Next, skip the queues and venture inside the adjacent Palazzo Ducale (Doge's Palace), built in 1340 for the Doge of Venice, where your guide will reveal the history behind Titian's splendid frescoes and masterpieces. Continue weaving your way through the atmospheric streets and glimmering architecture to the Ponte dell'Accademia, one of the best spots to grab a picture-perfect view of Venice and the Grand Canal as the sun sets. Part ways with your guide and spend the evening dining on delicious seafood or pasta with fresh truffles at one of the city's renowned restaurants. 

Day 2: Explore Venice's Art & Culture, Venetian Boatyard Tour 

Spend a relaxed morning at leisure in Venice. While the city is a haven for art enthusiasts with world-class collections at the Peggy Guggenheim Museum and La Biennale di Venezia Art Museum, there's much to be said for simply strolling the evocative calli (narrow streets) and stumbling across tiny bacari (wine bars), stopping to enjoy a glass of Prosecco and cicchetti (Venetian tapas). After lunch, stroll Venice's exquisite boutiques and galleries in the San Samuele district, while Le Mercerie and Salizada San Moisè should be your go-to for luxury items. 

The beautiful gondole that can be found gliding through Venice's waterways have been used by locals for hundreds of years as the main form of transport throughout the city. This afternoon you'll visit a squero (boatyard) for a private guided tour of one of Venice's most famous boatyards, where you'll learn how the design of these narrow boats has evolved over the centuries. Afterward, head to the inimitable Harry's Bar for a Bellini before spending your final night in Venice sampling regional specialties at one of the San Polo neighborhood's time-honored restaurants.

Day 3: Train to Florence, Guided City Tour

Enjoy one last lingering look across the Grand Canal as you take a private vaporetto to the station, ready for a 2.5-hour direct train to Florence, traveling first class. Tuscany's regional capital is famed for its richness of art and culture, and Firenze's magnificent terracotta-tiled Il Duomo is a testament to the city's incredible Renaissance architecture. After checking into your luxury hotel, you'll get to experience the masterpieces and more with a private walking tour accompanied by a local art historian. 

Start in the Piazza della Republica, once the city's ancient Roman Forum and more recently a hub for Florence's literati. Admire the jewelry shops that stretch across the Ponte Vecchio, a medieval bridge with views over the River Arno, and continue to the Piazza della Signoria. Here, you'll find several Florentine landmarks, Palazzo Vecchio and the Uffizi Gallery, with renowned works by Michelangelo and Leonardo da Vinci.

The highlight of your tour is Brunelleschi's masterpiece, La Cattedrale di Santa Maria del Fiore, known to locals simply as Il Duomo. You'll enjoy a private visit to the exclusive Cathedral Terraces, perched high above the city and normally closed to the public; it's the perfect spot to admire the city's panoramic vista without the crowds. Tuscan cuisine is famous for the quality of its fresh produce, steak, and its exceptional red wines. You'll enjoy both this evening with a dinner at Enoteca Pinchiorri, the city's acclaimed 3-star Michelin restaurant.

Day 4: Accademia Gallery Visit, Sunset River Boat Tour

Florence's Galleria dell'Accademia, founded by the Grand Duke Pietro Leopoldo in 1784, is home to many famous works, none more so than Michelangelo's "David." Created between 1501 and 1504, the 14-foot-high (4 m) marble sculpture became a symbol of the Florentine republic's strength during a time of great political upheaval. Discover the fascinating stories behind the statue's creation and pieces by Botticelli and Tintoretto with a private, guided tour of the gallery.

Afterward, pause for a leisurely lunch in one of the city's neighborhood eateries. Alongside plates of delicious cured prosciutto crudo and formaggi, you'll find flame-grilled bistecca alla Fiorentina, delicious homemade tagliatelle fragrant with porcini mushrooms and freshly shaved tartufo (truffles). Savor a glass or two of brunello di Montalcino, an exceptional local red, and try one of the various riffs on tiramisu. In the summer months, you'll find pistachio and fragole (strawberry) twists to the classic Italian dessert instead of the usual coffee and chocolate. 

Spend the afternoon strolling the elegant cobbled streets, and as golden hour approaches, board a private boat steered by a Renaiolo (traditional boatman) for a sunset ride along the River Arno. It's the perfect way to admire the ebb and flow of post-work city life and Florence's landmarks, such as the Uffizi Gallery, Vasari Corridor, and the Palazzo Corsini, which twinkle in the darkness as you cruise under the Ponte Vecchio and Ponte Santa Trinità. 

Day 5: Transfer to Tavarnelle Val di Pesa via San Gimignano & Chianti Winery Visit

This morning, you'll head out of the city on a private tour of the Chinati Region, exploring the picturesque hilltop towns and vineyards that dot this part of Tuscany. Your first stop is the medieval village of San Gimignano, a UNESCO World Heritage Site located an hour from Florence. It's famous for its historic buildings, Vernaccia wine, and award-winning gelaterias. Explore the city's beautiful squares, palaces, and churches on a private guided tour before sipping a cold drink in the town's enchanting Piazza della Cisterna.

Your next stop is a winery in the Chianti Hills, where you'll tour the vineyards and cellars behind the region's eponymous wine. Made from a minimum of 80% sangiovese grapes, Chianti Classico is made from vineyards within a distinct area that stretches between the cities of Florence and Siena. Learn about the centuries-old production process and then sit down to a tasting of various vintages accompanied by a selection of local dishes.

Afterward, your driver will transfer you to the town of Tavarnelle Val di Pesa, where you'll spend the next two nights in the Chianti countryside at a luxurious bed-and-breakfast with large, elegant rooms, airy balconies, and shaded gardens.

Day 7: Train to Rome, Guided City Tour

Your Italian trip continues apace this morning with a high-speed train to Rome. Travel first class, and in less than 1.5 hours, you'll leave behind the Tuscan countryside for the "Eternal City" and its enticing mix of ancient history, art, culture, and la dolce vita lifestyle that continues to captivate visitors from all over the world. Upon arrival at Termini Station, a driver will whisk you to your luxurious central hotel, where you can savor a drink on the terrace before meeting your guide for a private tour of the city. 

One of the Italian capital's most beautiful panoramas can be found at the top of the Spanish Steps, Europe's longest and widest staircase. As you gaze out over Rome, hear from your guide how the steps feature in religious processions and city traditions throughout the year. Wander down to Piazza di Spagna, where you'll find the Baroque Fontana della Barcaccia and hear tales of popes, emperors, and Ancient Rome as your guide leads you through the maze of alleyways and cobblestone streets toward the dramatic silhouette of the 2,000-year-old Pantheon.

Stop for creamy gelato and continue to Bernini's Trevi Fountain, another Baroque masterpiece where a coin tossed inside is said to seal your return to Rome. Your tour concludes in Piazza Navona, a grand square famous for its Fountain of the Four Rivers and abuzz with sidewalk artists and musicians. Soak up the atmosphere with aperitivo at one of the bars that line the piazza, and as dusk falls, head to dinner in the elegant Jewish Quarter, established in 1555 CE and famed for its leafy cobbled streets and terrific gastronomy. 

Day 8: VIP Tour of the Vatican

See Roman life unfold this morning with a relaxed walk over to the Vatican City Museums: founded by Pope Julius in the early 16th century, the museums are brimming with classical statues and Renaissance gems that continue to fascinate. It's an arresting sight strolling through Bernini's Piazza San Pietro ahead of the crowds, and your 8:00 am start gives you a serene hour to tour the museums and the Sistine Chapel with your guide in private before they open to the public. 

You'll pass through 45 galleries, including the famous Gallery of Tapestries and Gallery of the Geographical Maps, while your guide shares the stories behind the masterpieces before arriving at the magnificent Raphael Rooms and finishing in the Sistine Chapel. Take a moment or two to appreciate Michelangelo's breathtaking frescoed ceiling and "Last Judgement," then view the Papal Tombs and climb the steps to the top of the Basilica. 

As dusk falls, go for a stroll in the buzzy Monti neighborhood, an eclectic area not far from the Colosseum, full of charming enotece (wine bars) and trendy boutiques. Sip Prosecco in the piazza, then find the perfect rooftop restaurant for dinner with sunset views over the city's silhouetted umbrella pines.

Day 9: Exclusive Colosseum & Forum Tour, Afternoon Cooking Class

Follow in the footsteps of gladiators this morning with a private walking tour of Rome's iconic Colosseum. Built by Flavian emperors in 80 CE as the epicenter of Ancient Rome's public entertainment, you'll slip the queues and discover the amphitheater's highlights and the labyrinthine dungeons. You'll also get special access to the arena itself—it's a moment to remember as the custodian unlocks the gates and you imagine the roar of 80,000 spectators calling your name.

Continue your step back in time with a short walk to Palatine Hill, once an exclusive neighborhood for political leaders and emperors, where you'll see ruins of the sprawling palaces. Admire the umbrella pine-dotted views toward the Vatican, Circus Maximus, and the Roman Forum—the focal point of political life in Ancient Rome and your final stop. Explore the forum's vast 2,000-year-old excavations that reveal the temples, squares, and religious sites used by the empire's noble citizens. Meanwhile, your guide will bring the ruins to life with fascinating stories of the political power plays conducted here.

Later on, you'll continue your immersion into Italian life with an authentic cooking class led by a local, who'll guide you through the different types of pasta used in Roman cuisine and the four classic sauces: carbonara, cacio e pepe, alla gricia, and amatriciana. You'll start by preparing the dolce (dessert). Choose from a classic tiramisu or gelato and leave to set as you work on the pasta. Learn how to mix and knead your flour and eggs, then cut or shape your preferred type of pasta. At the end of the workshop, sit down with your teacher and enjoy your creations.

Day 10: Galleria Borghese Tour, Free Afternoon in Rome

Spend the morning exploring Rome at your own pace and follow in the footsteps of locals with the tradition of caffè and a cornetto semplice (croissant) at one of the local bars. Head along the River Tiber to the wisteria-filled back streets of Trastevere to browse the boutiques, wander the shady piazzas, and people-watch. Or stock up on foodie treats to take home with a visit to the vast covered market in Testaccio, where you'll find all manner of cured meats, formaggi (cheeses), artisan pasta, pestos, and chocolates. 

In the afternoon, soak up the beautiful gardens at Villa Borghese, a green oasis in the north of the city, and take a private tour of the ornate rooms of Galleria Borghese, where you'll see sweeping frescoes, Bernini statues, and numerous works by Bellini, Raphael, Titian, Rubens, and Caravaggio. As dusk falls, head to Gianicolo Hill to see the sunset and the twinkling St. Peter's Dome and dine at Armando al Pantheon, a Roman institution, moments from the historic temple. 

Day 11: Train to Naples, Transfer to Praiano via Pompeii, Vesuvius Helicopter Flight

After one last stroll of Rome's cobbled streets and a walk along the River Tiber, you'll take a private transfer to the station and travel first class on a high-speed train bound for Naples, Campania's capital. Your destination is the evocative Amalfi Coast, awash with lemon groves and tumbledown pastel villages that stretch across the rocky coastline. You'll make a couple of stops en route, the first at a winery on the slopes of Mount Vesuvius, where you'll enjoy a tasting of local Lacryma Christi wines made from grapes indigenous to the volcano's unique terrain. 

Your next stop is Pompeii, a fascinating archaeological site that was frozen in time when the ash and volcanic debris that flowed from Mount Vesuvius in 79 CE preserved many of the town's structures in their entirety. Arrive in Praiano, and you'll enjoy one final surprise that's a sure contender for the highlight of your trip: a private helicopter flight over Vesuvius and Pompeii for an aerial view of the sites you explored earlier. You'll land at the legendary Villa Cimbrone, one of the Mediterranean's most prestigious hotels, where you'll enjoy a cocktail on the terrace with views of the coast. 

Day 12: Guided Tour of Amalfi, Citrus Farm Visit & Limoncello Tasting

A quick drive up the coast from Praiano, Amalfi is one of the Mediterranean's jewels, famous for its picturesque whitewashed houses, historical churches, and exquisite handmade paper. Your private guide will accompany you on a tour of the town, where you'll stop for gelato in the beautiful Piazzetta di Sant'Andrea, Amalfi's main square, before wandering up to the top of the town to the Romanesque-Baroque Cattedrale di Sant'Andrea. 

In the afternoon, you'll drive along the coast to a scenic lemon farm, where you'll meander through lemon groves filled with Sfusato Amalfitano lemon trees. See the farmers at work and discover the special qualities of Amalfi lemons and how citrus fruits are used throughout Italian cooking in both salato (savory) and dolce (sweet) dishes. You'll end your tour with a delicious farm lunch using local produce and finish by tasting the farm's own artisanal limoncello (lemon liqueur).

Afterward, your driver will drop you back in Praiano, where the rest of the day is yours to enjoy at leisure. Rent a kayak and explore emerald green grottos and visit tiny hidden beaches or hike one of the area's many walking trails, including the aptly named "Path of the Gods." In the evening, find a scenic spot and people-watch over aperitivi, then head out to dinner and dine on delicious seafood as you savor the picture-perfect Mediterranean views. 

Day 13: Private Luxury Yacht Cruise to Capri

Spend your final morning on the Amalfi Coast cruising in luxury aboard a private yacht as you sail across the azure waters to the island of Capri, known locally as the "Pearl of the Mediterranean." You'll arrive at the Marina Grande harbor, where the day is yours to explore the island at your leisure. Head first to the quaint village of Anacapri perched toward the top of the island. Here, you'll see the sweeping views of the Gulf of Naples and Mount Vesuvius that prompted Emperor Tiberius to build twelve villas on the isle.

Stroll Piazza Vittoria and stop for a gelato before taking the chairlift from Anacapri to Mount Solaro. At 1,932 feet (589 m) above sea level, it's the island's highest point and offers more astonishing views across the bays and over to the Calabrian mountains. When you're ready, make your way back down and enjoy lunch overlooking the coastline. You'll return to Praiano in the evening for a relaxing dinner on your hotel's terrace, the perfect setting to toast your Italy trip.

Day 14: Depart Praiano 

After one last cappuccino and pastry at breakfast, it's time to meet your driver and head to the airport for your flight home. Safe travels! 

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