Spend two weeks experiencing Italy's cities and Amalfi Coast in luxury. Start with a private tour of Venice to see ornate palaces and visit a traditional gondola workshop. In Florence, dine on world-class food and wine and go on a hot-air balloon ride above the Tuscan hills. Dive into history with priority access to the Vatican and a private tour of the Colosseum, then soak up the sunshine and ocean views on the gorgeous Amalfi Coast.


  • Tour a traditional boatyard to see how gondolas are made
  • Go on a luxurious wine tour in the Tuscan countryside
  • Dive deep into history with a private tour of Rome's Colosseum
  • See the incredible Mt. Vesuvius crater and Pompeii ruins from a helicopter
  • Take a private luxury yacht to Capri Island on the Amalfi Coast

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Venice, Private Guided City Tour Venice
Day 2 Bacaro & Private Squero Tour in Venice Venice
Day 3 Venice to Florence, Private Guided City Tour Florence
Day 4 Private Guided Accademia Gallery & Boat Tour Florence
Day 5 San Gimignano & Chianti Wine, Transfer to Tavarnelle Val di Pesa Tavarnelle Val di Pesa
Day 6 Hot Air Balloon Ride, Afternoon in Siena Tavarnelle Val di Pesa
Day 7 Tavarnelle Val di Pesa to Rome, Private Guided City Tour Rome
Day 8 Priority Access Vatican Tour Rome
Day 9 Private Colosseum & Forum Tour, Afternoon Cooking Class Rome
Day 10 Private Galleria Borghese Tour, Free Afternoon in Rome Rome
Day 11 Pompeii & Mt. Vesuvius Helicopter Flight, Transfer to Praiano Praiano
Day 12 Guided Tour of Amalfi & Limoncello Farm Praiano
Day 13 Private Luxury Yacht to Capri Island Praiano
Day 14 Goodbye Italy!  

Detailed Itinerary

Day 1: Arrive in Venice, Private Guided City Tour

Gondola on the Grand Canal
Gondola on the Grand Canal

Welcome to Italy! Arrive at Venice Airport before meeting your driver to transfer to the city center to board a water taxi to your hotel. Venice in northern Italy is famous for both industry and tourism. With nicknames like "Queen of the Adriatic," "City of Water," and "The Floating City," it's clear that the city's myriad canals are its main draw. Stretching across 117 small islands in the marshy Venetian Lagoon along the Adriatic Sea, the city has long been a commercial and cultural hub, thanks to its strategic placement. Silk, grains, spices, and art were traded through the Middle Ages, making Venice very wealthy.

The city is also famous for its many beautiful historical attractions, such as the Piazza San Marco and San Marco Basilica, the Grand Canal, and the ornate Doge's Palace. The Lido de Venezia is a famous luxury destination that attracts actors, critics, and other cinema industry celebrities. In the afternoon and evening, head out for a private guided walking tour of the city's top sights. Start at Piazza San Marco (St. Mark's Square), the heart of the city's cultural and administrative district. The piazza is also home to the Palazzo Ducale (Doge's Palace), a Venetian Gothic palace built as the primary residence for the Doge of Venice in 1340. 

Adjacent to the palace is the San Marco's Basilica, originally the Doge's personal chapel. The building is one of the best surviving examples of Italo-Byzantine architecture and features a stunning collection of Byzantine art, gold mosaics, and beautiful marble floors. 

The palace is also connected to the next-door prison by the infamous Bridge of Sighs, which has joined the two buildings since the 16th century. The bridge features a small window onto Venice's harbor and earned its grisly name from the prisoners' sighing as they got one last glimpse of the city on their way to execution. While most visitors gather outside the bridge to look in, you'll get the best sense of history from inside the bridge, looking out from the same window as the doomed medieval prisoners.

Day 2: Bacaro & Private Squero Tour in Venice

Open-air restaurant on a canal
Open-air restaurant on a canal

Enjoy a free morning in the city. Pick from the following suggestions, then head out to explore before lunchtime: 

  • Discover art at the Ca' Pesaro Galleria Internazionale d'Arte Moderna, Peggy Guggenheim Collection Modern Art Museum, and La Biennale di Venezia Art Museum
  • Explore San Giorgio Maggiore, one of Venice's smaller islands that stands separate from the main canals  
  • See an opera show at the Teatro La Fenice 
  • Haggle for produce at the busy Mestre market, held every Wednesday and Friday
  • Go shopping for luxury items on Le Mercerie and Salizada San Moisè 
  • Browse textiles, craft shops, unique boutiques, and galleries in the bohemian San Samuele district 
  • Rent a kayak and explore Venice from the water 

For lunch, head to a traditional bacaro, a Venetian wine bar, to try the Cicchetti—little bite-sized snacks accompanied by a glass of wine. The seafood in Venice is always fresh-caught, so try the fried squid skewer or the creamy salted codfish canapès. The mozzarella in Carrozza (a fried cheese sandwich), various cold cuts, and other delicacies are also delicious. 

In the afternoon, take a private guided tour of a traditional squero, a small boatyard where tradespeople build and repair gondolas. This squero was founded in 1884 by an expert local craftsman who changed the classic shape of the gondola boat. These changes were permanently adopted into gondola construction and handed down over the generations to keep the art alive. You'll learn about the art and science of traditional gondola construction and see how the beautiful boats are constructed using a combination of carefully selected natural wood for ultimate longevity. 

Afterward, enjoy an evening stroll in the city center, then find the perfect restaurant by a canal for a delicious meal.

Day 3: Venice to Florence, Private Guided City Tour

Ponte Vecchio bridge
Ponte Vecchio bridge

After breakfast, head to the train station to catch a train to Florence. Florence is Tuscany's regional capital and its most populous city. Long considered a cultural capital and the "Jewel of the Renaissance," Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, a terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's "David" sculpture. 

Spend the day exploring the top sites with an art historian on a private guided walking tour. Start in the medieval city center in the Piazza della Repubblica, one of the city's main squares. It has been the city center since Roman times. See the Colonna della Dovizia, also known as the Column of Abundance, that marks the point where the cardus (north-south oriented road) and decumanus maximi (east-west oriented road) met and also where the Roman forum stood.

Continue to the Piazza della Signoria, the city's political center since the Middle Ages, where ceremonial events, rallies, and festivals are celebrated. Here you'll find several iconic Florentine landmarks—Palazzo Vecchio and the Uffizi Gallery, which houses works by Michelangelo and Leonardo da Vinci. The square's centerpiece is the Neptune Fountain, a popular meeting place. 

See the Ponte Vecchio bridge, a symbol of Florence's power over seven centuries. The bridge houses buildings and shops, which merchants and shopkeepers have occupied since the Middle Ages. Arrive at the Italian Gothic Cathedral of Florence and climb the 400+ steps to reach Giotto's bell tower. Enjoy a private and exclusive visit to the Cathedral Terraces, which perch high above the city traffic and are generally closed to the public. From here you'll have a bird's-eye view of the whole city. 

For dinner, head to Enoteca Pinchiorri, Florence's 3-star Michelin restaurant, then stroll through the city back to the hotel.

Day 4: Private Guided Accademia Gallery & Boat Tour

Ponte Vecchio at sunset
Ponte Vecchio at sunset

Meet your art historian guide in the morning and visit the Accademia Gallery for a private tour. The Galleria dates back to 1784 when the Grand Duke of Tuscany, Pietro Leopoldo, reorganized the Academy of Arts of Design in Florence into the modern Academy of Fine Arts. The Galleria was specifically designed to house valuable works of art, and its spectacular architecture is impressive in its own right.

Among other masterpieces, the Galleria is home to one of the Renaissance's most iconic masterpieces, Michelangelo's "David." This incredible 14-foot tall Renaissance sculpture, which depicts the Biblical hero, was created between 1501 and 1504 and became a symbol of the Florentine republic's strength during a time of massive political change. Much like David facing the mighty Goliath, the Republic was threatened at the time by stronger states, not to mention to Medici family regaining power. 

Enjoy lunch and spend some time shopping for souvenirs or simply enjoying the city's ambiance.

Later in the afternoon, board a traditional boat piloted by a Renaiolo, a traditional boatman, for a sunset ride on the Arno River. The 45-minute trip on a traditional boat will take you down the Arno from Piazza Mentana, pass under the Ponte Vecchio and Ponte Santa Trinità, and navigate by the Uffizi Gallery, the Vasari Corridor, Palazzo Corsini, and the 10th-century San Jacopo sopr'Arno Church. 

Day 5: San Gimignano & Chianti Wine, Transfer to Tavarnelle Val di Pesa

Landscape in Chianti region, near Siena
Landscape in the Chianti region, near Siena

In the morning, head to the Tuscan countryside to explore the Chianti Region. Your first stop is the medieval village of San Gimignano, a UNESCO World Heritage Site located an hour away 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 grabbing a coffee in an open-air café. 

Continue to the Chianti Classico wine region to visit a typical Tuscan winery. This winery blends centuries-old knowledge with a modern approach to create environmentally-friendly wine cultivation. As part of the project, weeding and chemical topdressing have been eliminated from the growing process, and the waste that the company produces is recycled into organic fertilizer. 

Enjoy learning about the winery and the unique characteristics of the local climate that have made the region unfavorable to most crops but ideal for growing wine grapes. The Chianti wine, made primarily of Sangiovese grapes, is the local staple. Tour the cellars and vineyards, then enjoy a wine tasting accompanied by a delicious Tuscan lunch of pasta, cured meats, cheeses, and local desserts. Enjoy the evening in the town of Tavarnelle Val di Pesa. Spend the night in a luxurious Relais, an exclusive bed and breakfast with large, elegant rooms, airy balconies, and shaded gardens.

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Day 6: Hot Air Balloon Ride, Afternoon in Siena

Siena Cathedral and medieval Old Town
Siena Cathedral and medieval Old Town

Spend a relaxing morning enjoying the peace and serenity of the Tuscan countryside. Kick back on the patio with a good book and a cup of coffee, go for a stroll on a quiet lane, or explore one of the town's many historical landmarks. For the experience of a lifetime, enjoy a private hot air balloon ride over the rolling hills, olive groves, and ancient hamlets of the Tuscan countryside. Break for a gourmet picnic lunch, then drive to Siena for an afternoon in the medieval hilltop city. The city is unique, recognized as a UNESCO World Heritage site as the perfect embodiment of a medieval town.

See the magnificent Cathedral and Town Hall on the Piazza del Campo, the iconic trapezoidal square where the famous Palio horse race takes place twice a year. Visit the Gothic Cathedral of Santa Maria Assunta, an impressive building filled with treasures by Pisano, Donatello, and Michelangelo and frescoes by Pinturicchio. Enjoy a typical Tuscan dinner of local cured meats, pecorino cheese, and panforte, then return to your Relais in the countryside.

Day 7: Tavarnelle Val di Pesa to Rome, Private Guided City Tour

Palazzo Montecitorio
Palazzo Montecitorio

In the morning, make your way to the Florence train station, then take the high-speed train to Rome. Arrive, then head out for a private guided tour of the historical center of the Eternal City. 

According to legend, Rome was founded by brothers Romulus and Remus in 753 BCE atop Rome's Palatine Hill. The long-time center of the mighty Roman Empire, Rome boasts nearly 3,000 years of architecture, history, and culture. These days, Italy's capital is considered one of Europe's top cities thanks to its ancient monuments, incredible art masterpieces, and cosmopolitan vibe. It's a center for fashion with a buzzing food culture and has a growing nightlife scene. 

Visit the Piazza di Spagna, the Fontana di Trevi, and the Piazza Navona (originally an ancient stadium), which now houses Bernini's Fountain of the Four Rivers and the Egyptian obelisk. End your evening with a stroll to the neighborhood piazza for gelato and some people watching.

Day 8: Priority Access Vatican Tour

St. Peter's Square and the Vatican
St. Peter's Square and the Vatican

Today, you will visit the Vatican City museums and Sistine Chapel, and other top sights for an exclusive guided tour of the city's incredible art and history. Start at the Vatican, where you'll get an 8:00 am start, giving you a one-hour lead on the rest of the crowds. See the Pio Clementio Museum, Gallery of the Candelabra, Gallery of Tapestries, and Gallery of the Geographical Maps

Continue to see the magnificent Raphael Rooms, ending in the breathtaking Sistine Chapel to see Michelangelo's Genesis ceiling frescoes and his Last Judgement altar fresco. Continue to St. Peter's Basilica and Square and experience the magic of Renaissance art as you learn about the masterpieces' intimate details and untold stories. In the evening, go for a stroll in the buzzing Monti neighborhood, an eclectic area in the city center full of hip wine bars and trendy boutiques, then find the perfect rooftop restaurant for dinner with sunset views.  

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

The ancient Roman Colosseum
The ancient Roman Colosseum

In the morning, meet your archaeologist guide and dive into the history of the Roman Empire with a private guided walking tour of the Colosseum, the world's largest amphitheater (tickets included). You'll explore the main complex and the Belvedere, the recently opened third ring with a view of the arena, and the Imperial Forums up to the fourth and fifth rings.

Walking through the ancient amphitheater is like taking a trip back in time to the days of the Roman Empire. The Colosseum held 50,000 spectators and was the central venue for gladiator fights at its prime. Learn about ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian Emperors who built the Colosseum. Continue to the Roman Forum and Palatine Hill, built between 46 BCE and 113 CE. Walk along the ancient Roman street Via Sacra to see the Temples of Vesta, Antonino, and Faustina. See the ancient Basilica Julia and Aemilia and experience the grandeur of the Roman Empire.

Enjoy some time to yourself, before partaking in a 2.5-hour afternoon cooking class to learn to make traditional Roman pasta specialties. You'll learn to make Cacio e Pepe, Carbonara, and Amatriciana—all Italian favorites. Start with great local ingredients (pecorino cheese, fresh meat, and eggs), then make the perfect sauce with fresh market vegetables. Form the homemade dough into the classic pasta shapes and combine everything for a delicious meal. Once you're finished, sit down to enjoy your creations for dinner paired with the perfect glass of wine.

Day 10: Private Galleria Borghese Tour, Free Afternoon in Rome

Galleria Borghese
Galleria Borghese

Today is a free day to explore the city. Head to Galleria Borghese, one of the world's premier art museums, for a private guided tour to see works by extraordinary artists Bernini, Caravaggio, Canova, and Rafaello. The gallery's highlights include sculptures and paintings from Cardinal Scipione Borghese's collection (1579-1633). Admire Caravaggio's most important paintings, including "Boy with Basket of Fruit," and see Bernini and Canova's sculpture collection, boasting works such as "Apollo and Daphne" and "David." Rafaello's "Entombment of Christ" is also a must-see. 

Walk through the ornate rooms and explore the splendid frescoes, stories, and masterful techniques behind the masterpieces. End the tour with a peaceful stroll around the Villa Borghese gardens, enjoying its beauty and calm far from the chaos of the city. Other suggested activities include:

  • Visit the Museo Nazionale di Castel Sant'Angelo history museum 
  • Tour the Renaissance Villa Farnesina  in the Trastevere district
  • Head out of the city for a day at the Ostia beach for miles of sand and warm sea 
  • Visit the historic and fascinating neighborhood of Testaccio to see the giant Monte Testaccio, an ancient pile of discarded olive oil jars from the 2nd century CE
  • Spend an afternoon at the Musei Capitolini, the oldest and one of the best museums in Italy

In the evening, return to the Trastevere neighborhood for dinner at an osteria or a trattoria, followed by drinks at a trendy wine bar.

Day 11: Pompeii & Mt. Vesuvius Helicopter Flight, Transfer to Praiano

View from the Villa Cimbrone terrace
View from the Villa Cimbrone terrace

In the morning, board a high-speed train to Naples, then make your way to a winery on the slopes of Mt. Vesuvius. Sample local wines and discover how the area's volcanic soil produces terrific regional wines, then transfer to Pompeii. The UNESCO World Heritage Site has been frozen in time since the 79 CE eruption of the nearby volcano, which covered Pompeii in ash and preserved it entirely. Explore the city's ancient roads, storehouses, baths, and temples as you learn about life in ancient Rome. 

In the afternoon, take a breathtaking helicopter flight over Mt. Vesuvius to see the crater, the Pompeii city ruins, and the dramatic Amalfi Coast. Remember to bring your camera—this is one of the trip's highlights! Land at the legendary Villa Cimbrone on the coast for a leisurely cocktail on the panoramic terrace and enjoy the cool ocean breeze as you relax in the lush terraced gardens. Take in the sunset views of the coast, then transfer to your accommodation.

Day 12: Guided Tour of Amalfi & Limoncello Farm

Positano in the evening
Positano in the evening

Start your morning with a quick drive up the coast from Praiano to Amalfi. The town of Amalfi is a jewel of the Mediterranean coast, famous for its white-washed buildings, historical churches, and paper-making industry. 

Go for a private guided walking tour through the town to see the sights and soak up the atmosphere. Stop by La Piazzetta di Sant'Andrea—the square at the heart of the city—to see the Duomo and the Romanesque-baroque Cattedrale di Sant'Andrea. Once one of Italy's four central Maritime Republics, Amalfi is now primarily a resort town. Stop by the Paper Museum to learn about the flourishing local paper industry, which brought a stream of wealth and skilled artisans to the area. 

In the afternoon, continue to a traditional limoncello farm and learn about the family tradition of preparing special meals and regional dishes with unique local lemons. At the end of the tour, enjoy a memorable lunch where every dish is made with the famous Amalfi Coast lemons. 

The rest of the day is free—try your hand at windsurfing in Praiano, rent a kayak and explore emerald green grottos, tiny hidden beaches, and impressive sea caves, or hike on one of the area's many steep hiking trails. In the evening, check out Praiano's nightlife at the Africana and Music on the Rocks nightclubs, or find a quiet romantic restaurant for dinner on a terrace with a view of the Amalfi Coast.

Day 13: Private Luxury Yacht to Capri Island

Private yachts moored near Capri Island
Private yachts moored near Capri Island

Spend the day aboard a private yacht enjoying the sunshine, summer villas, and clear blue waters of Capri Island, known locally as the "Pearl of the Mediterranean." Capri sits on the south side of the Gulf of Naples and is a popular destination. Ancient Romans used the island for summer villas for the Empire's rich and famous, while the Greeks called Capri the "Isle of Sirens."

In the morning, board your private luxury yacht to Capri. Go for a guided walking tour of the island's main attractions. See the principal harbors (Marina Grande and Marina Piccola), walk along the Belvedere of Tragara (a villa-lined promenade with panoramic views), and explore the ruins of ancient Roman villas. Head up the hill to see Anacapri, the Piazzetta, Augustus' Garden, and the best views of the Faraglioni Rocks. You'll return to Praiano for a relaxing dinner with a view in the afternoon.

Day 14: Goodbye, Italy!

Little details of life in Rome
Little details of life in Rome

Time to say goodbye to the country of love! After one last cappuccino over breakfast, your driver will transfer you to the airport for your connecting flight home. Safe travels!

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Map of Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome & More - 14 Days
Map of Luxury Italian Highlights: Venice, Florence, Amalfi Coast, Rome & More - 14 Days