Luxury Italy Vacation Packages: A Journey of a Lifetime

A 14 day trip to Italy 
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Take the trip of a lifetime and get swept away by the best that Italy has to offer. Discover the beautiful art, the rich culture and the fascinating history. Perfect for the first-time visitor, this comprehensive tour includes the country’s highlights: Rome, Florence, Tuscany, Venice and Milan. Soak up the Renaissance in Florence, visit breathtaking ruins in Rome and sip Chianti wine in the sunny Tuscan countryside. Every day in Italy is a wonderful new discovery!

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General Information

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Detailed Itinerary

Places Visited 

Rome, Florence, Tuscany, Pisa, Chianti, Venice and Milan.

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1 - Begin Your Tour in Rome, Italy

Upon arrival in the Rome airport, you will be greeted by your driver who will take you to your hotel. In the afternoon, you’re free to explore this amazing city at your leisure. Rome is famous for its historic monuments, like the Colosseum, the Roman Forum, Vatican City. However, Rome is a real city and has a distinctly modern feel. It bustles with traffic jams, fashionable people, colorful outdoor markets, lively piazzas, the best restaurants, late-night bars and a hopping club scene.

Day 2 - Guided Tour of the Rome’s Important Sites

In the morning, you’ll take a tour of classical Rome. Your tour begins at the Colle Oppio with a panoramic view of ancient Rome’s most vital social center. Once inside the Colosseum, your guide will talk you through the bloody past of the amphitheater and share tales of gladiators. After a brief stop at the Arch of Constantine, you’ll visit Palatine Hill where you’ll enjoy a great view of the Roman Forum and Nero’s Circus Maximus where chariot races were once held. Walk along the “Via Sacra” or “Sacred Way”—the main path of the Roman Forum that was the site of ancient festivals and triumphal processions. The tour ends at the temple of Julius Caesar, where visitors from around the world still leave flowers and candles today in his memory.

In the afternoon, enjoy a guided tour of Rome’s most famous piazzas, monuments, and fountains. Stroll through Rome’s cobblestone alleyways, and discover some of the world’s most famous sites, including the Pantheon, Piazza Navona, and the Trevi Fountain—don’t forget to toss in a coin. Then, visit Rome’s two most famous public spaces, the Piazza del Popolo and the Spanish Steps with their stunning views and lively atmosphere. The Pantheon, once temple to Roman gods, is a 2,00 year-old building that has one of the best preserved and largest brick domes in the history of architecture. Your tour concludes with a coffee stop at the stylish Caffarelli Terrace, a magnificent place with spectacular views of Rome’s historic center.

Day 3 - Guided Tour of the Vatican City.

Today you’ll take a guided tour of the most important place in Christendom: Vatican City. Your tour guide will take you through the Vatican Museums, which house one of the world’s most extensive art collections. You’ll see the ancient statue collection of Julius II as well as the papal apartments decorated by Raphael. Stare in awe at the stunning Sistine Chapel, and take in all you can of this monumental masterpiece by Michelangelo since photos are absolutely not allowed when you’re inside. The highlight of the tour is a visit to Saint Peter’s Basilica, the most glorious and grandest church on Earth. Inside the basilica, you’ll see more masterpieces, including “La Pieta” by Michelangelo and Bernini’s adorable cherubs. Finally, step outside the basilica to view the expansive Saint Peter’s Square, where the pope appears to give his blessings on Sundays and Wednesdays at midday.

Day 4 - Travel from Rome to Florence & Guided Tour of the Uffizi Gallery

After breakfast, you’ll take the train to Florence. Enjoy a private transfer from the train station to your hotel in Florence. This afternoon, visit the Uffizi Gallery—one of the most important art museums in the world. The Uffizi offers a visual tour of art history from the Middle Ages to the Renaissance. At the museum, you can admire the highlights of medieval art by Giotto and Cimabue. Most people visit the museum to see the masterpieces of the Florentine Renaissance by Botticelli, Michelangelo and Leonardo da Vinci. Their paintings show the changes in living and thinking inspired by the Florentine Renaissance. You’ll have the afternoon and evening at leisure to explore Florence on your own.

Day 5 - Visit the Accademia Museum in Florence & Leisure Time

After breakfast at your hotel, you’ll take a guided tour of the Accademia Museum to admire Michelangelo’s famous sculpture of “David.” Michelangelo spent three years carving this statue from a huge block of rough marble. When you see the sculpture’s intricate details and realistic expression, it appears that it is made of human flesh rather than stone. This statue of David shows his strength and courage, and it became the Florentine symbol of power and invincibility. You will also find a copy of the “David” statue along with other important Renaissance sculptures at the Piazza della Signoria, which would be a wonderful place to visit this afternoon. This lively central square of Florence is a hub of cafes, restaurants, upscale boutiques and people watching. You’ll have time for a leisurely coffee stop at an outdoor cafe, shopping at the boutiques, or just hanging out with the locals in the piazza.

Day 6 - Tour of Siena and San Gimignano

Today you’ll enjoy a full-day tour of Siena and San Gimignano. This excursion through the delightful hills of Chianti takes you through the lovely scenery of vineyards and olive trees. When you arrive in Siena, a tour guide will show you the old city center. Then you’ll go for a walk along the small medieval streets, admiring the impressive palaces and ending up at the splendid cathedral with its vibrant interior. The tour concludes at Piazza del Campo, one of the most beautiful medieval squares in the world. After lunch you’ll visit the tiny hilltop city of San Gimignano, famous for its numerous towers that were built by wealthy families during the Middle Ages. San Gimignano has a fascinating history and boasts many beautiful frescoes and other art treasures. On your way back to Florence, you’ll stop at Monteriggioni, a charming walled medieval village.

Day 7 - Leisure Time in Florence & Guided Tour of Pisa

This morning you’ll have free time to explore Florence. In the afternoon, you’ll take a scenic drive through the Tuscan countryside to the university city of Pisa, famous for its architectural marvels. There, you’ll enjoy a guided tour of the Piazza dei Miracoli, where you’ll find the famous Leaning Tower and other important monuments. Then visit the cathedral, a masterpiece of Romanesque design. If you’re interested in continuing your walk, you can keep going until you reach the Piazza dei Cavalieri, the site of the Scuola Normale, one of the world’s oldest and most famous universities.

Day 8 - Wine-Tasting & Scenic Tour of Chianti Region

After breakfast, enjoy your leisure time in Florence. In the afternoon, you’ll take a day trip to Chianti. Enjoy the scenic ride through the Chianti countryside, one of the most famous wine regions in the world. You’ll visit a winery in a magnificent medieval castle, where you can visit the gardens and the splendid wine cellar filled with barrels of the Chianti Classico wine. Your visit includes a wine tasting and a snack, followed by a visit to a beautiful Romanesque church nearby. For dinner, you’ll be treated to a special meal in the magical atmosphere of an old village among the hills. Indulge in the delicious hearty Tuscan cuisine that pairs perfectly with fine Chianti wine.

Day 9 - Travel from Florence to Venice

After breakfast, you’ll take the train to Venice. Enjoy a private transfer by boat from the Venice train station to your hotel. The afternoon is at your leisure to discover this magical city, where beauty surrounds you everywhere you go. Ornate Byzantine buildings and exquisite churches line the canals and piazzas in a show-stopping decorative display. The city’s Byzantine architecture gives it an exotic feel and hints at the influence from Islamic world. Beginning in the 13th century, Venice established a flourishing spice trade in the Near East. You won’t find any cars on the narrow streets and elegant piazzas of Venice, making the city a peaceful retreat that takes you back in time. Enjoy your strolls through the quiet streets, allow yourself to get lost, and be prepared to be dazzled by your discoveries.

Day 10 - Guided Tour of Venice & Gondola Ride

This morning you’ll take a guided tour of Venice’s most important sites. The tour begins at Saint Mark’s Square and will include visits to St. Mark’s Basilica, the Doge’s Palace, the Bridge of Sighs and the Piombi Prison. You can appreciate Venice’s Byzantine heritage when you see the dazzling gilded mosaics of Saint Mark’s Basilica; admire the exquisite pink and white marble facade of the Doge's Palace, and get a glimpse into what life was like in the Piombi prison, where Casanova was held prisoner. In the afternoon, enjoy an atmospheric gondola ride through the city’s peaceful small canals and discover the secrets of Venice. Afterwards, you’ll take a walk through the charming residential neighborhood of Castello, where you’ll stop at a piazza for gelato. Then you will take a boat ride along the Grand Canal, an unforgettable Venetian experience.

Day 11 - Tour of Venetian Islands & Evening Opera Performance

Today you’ll take a boat tour of Venice’s less-visited sites, including the island of San Giorgio Maggiore, the Saint Elena Gardens and the Lido. Departing from Ponte della Paglia near San Marco Square, your first stop is the island of Murano, world-famous for its glassware and factories. The next stop is the island of Burano, known for its lacemaking and pastel-colored fishermen's cottages. From there, you’ll sail a few minutes away to the island of Torcello, the first settlement in the lagoon. The Cathedral of Santa Maria dell'Assunta with its magnificent Byzantine mosaics and the 11th-century Church of Santa Fosca are visual evidence of the island’s historic importance. In the evening, enjoy a classical opera performance in the incredible setting of Palazzo Barbarigo Minotto, a 15th-century Venetian palace facing the Grand Canal.

Day 12 - Travel from Venice to Milan

After breakfast, you’ll have free time to explore Venice. You may want to visit the Accademia Gallery to see the masterpieces of Venetian art. The many churches of Venice are also worth exploring. There are 137 churches in Venice, many of which are magnificent examples of Neoclassical and Baroque architecture and are filled with the masterpieces of Tiepolo, Bellini, Veronese and other famous artists. In the afternoon, you’ll take the train to Milan and will be provided a private transfer from the Milan train station to your hotel room. In the evening, enjoy dinner on your own at a nearby restaurant serving authentic Milanese cuisine such as pumpkin ravioli or risotto.

Day 13 - Guided Bus & Walking Tour of Milan

After breakfast, you’ll take a guided bus and walking tour of Milan. The itinerary includes a one-hour walking tour with visits to La Scala, the city’s famous opera house, and the Duomo, considered by many to be one of the most most striking gothic cathedrals in the world. You’ll also get to view the world-famous "Last Supper," painting by Leonardo da Vinci. As you walk around the city, you’ll get a feel for its energy. Milan is busy metropolis, Italy’s economic engine, home to Italian stock market and center of international business. This city is also the world’s fashion capital, where the fashion industry, theater and cinema flourish. The afternoon is at your leisure to browse the designer boutiques, visit the museums or explore the hidden neighborhoods of this stylish city.

Day 14 - Tour Concludes & Depart from Milan, Italy

Your tour concludes this morning. After breakfast at the hotel, take a private transfer to Malpensa airport for your return flight home.

Price

Price 

Zicasso recommends the following guidelines for customized Italy tour packages, excluding international flights:

  • 5-star: USD $450 - $1,000+ per person per day

The customized package will include hotels, airport transfers and other transportation within Italy, guided tours or activities, unique experiences, trip planning, and 24X7 support during your trip.

Please inquire for a custom quote. The price is customized based on final hotel choices, travel dates, and other custom preferences.