- 4.9/5 493 Latest reviews
- Destination: Italy
- Duration: 8 Days
- Tour Type: Private & Bespoke
- Tour Style: Classic
About This Trip
This Italy Vacation from Rome to Milan is a perfectly crafted 8-day journey through the country’s most iconic cities, designed for travelers who want culture, comfort, and flexibility. From the ancient ruins of Rome and the Renaissance masterpieces of Florence to the romantic canals of Venice and the stylish elegance of Milan, this classic Italy tour delivers a rich blend of history, art, architecture, and authentic Italian lifestyle. With private guides and seamless train travel, you experience Italy at a relaxed pace while uncovering its timeless charm.
Ideal for couples, first-time visitors, and culture lovers, this Italy Vacation offers customizable experiences such as Vatican Museums, Colosseum tours, cooking classes, gondola rides, and wine tastings. Each destination reveals a different side of Italy—ancient, artistic, romantic, and modern—making this private and bespoke tour an unforgettable way to explore Rome, Florence, Venice, and Milan in one smooth and enriching itinerary.
Summary
DAY
PLACE
HIGHLIGHTS
1 - 2
Rome
Rome Walking Tour, Optional Tour to the Colosseum and Roman Forum, or a Cooking Class
3 - 4
Florence
Florence Historic Center Walking Tour, Optional Tour to Lucca and Pisa or Cinque Terre
5 - 6
Venice
City Center Walking Tour, Optional Tour to Doge's Palace and St. Mark's Basilica or Wine Tasting
7 - 8
Milan
Duomo di Milano, Vittorio Emanuele II
Itinerary
- Day 1: Arrival in Rome – The Eternal City Experience
Begin your unforgettable Italy Vacation in Rome, one of the world’s most historic and fascinating cities. Upon arrival at Rome Fiumicino Airport, meet your private driver and transfer comfortably to your centrally located hotel. After time to relax, join a guided walking tour introducing you to Rome’s iconic atmosphere. Wander through lively piazzas, admire ancient fountains, and enjoy your first taste of Italian cuisine at a local café. For art lovers, an optional Vatican City tour offers access to the Vatican Museums and the Sistine Chapel, showcasing masterpieces by Michelangelo, Raphael, and Botticelli.
Highlights: Private airport transfer, Rome walking tour, historic piazzas, Vatican Museums, Sistine Chapel
- Rome
- Day 2: Rome Exploration – Ancient History or Local Flavors
Today is dedicated to discovering Rome in depth, a cornerstone of any Italy Vacation. History enthusiasts may choose a guided tour of the Colosseum, Roman Forum, and Palatine Hill, where gladiators once battled and emperors ruled. Alternatively, experience Roman culture through a hands-on cooking class led by a local chef. Visit a traditional market, learn to prepare classic Italian dishes, and enjoy your creations paired with regional wine. The afternoon is free to explore Rome’s neighborhoods, shop, or relax.
Highlights: Colosseum, Roman Forum, Palatine Hill, Italian cooking class, local market visit
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- Rome
- Day 3: Rome to Florence – Journey into the Renaissance
Continue your Italy Vacation with a scenic high-speed train journey to Florence, the cradle of the Renaissance. After checking in to your hotel, set out on a private guided walking tour of Florence’s historic center. Discover world-famous landmarks such as the Duomo, Giotto’s Bell Tower, Piazza della Signoria, and the Ponte Vecchio. Learn about Florence’s artistic heritage and the influential Medici family while soaking in the city’s timeless elegance.
Highlights: High-speed train journey, Florence Historic Center, Duomo, Ponte Vecchio, Medici legacy
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- Florence
- Day 4: Florence at Leisure – Tuscan & Coastal Escapes
Enjoy a flexible day to tailor your Italy Vacation to your interests. Explore Florence’s museums, artisan shops, and food markets at your own pace, or join an optional full-day excursion. Visit Pisa to see the iconic Leaning Tower and continue to Lucca, a peaceful medieval town with intact city walls. Alternatively, venture to the breathtaking Cinque Terre, where colorful villages cling to dramatic cliffs overlooking the Ligurian Sea—an unforgettable highlight of northern Italy.
Highlights: Leaning Tower of Pisa, Lucca old town, Cinque Terre villages, Tuscany countryside
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- Florence
- Day 5: Florence to Venice – Romance on the Canals
After breakfast, travel by high-speed train to Venice, a must-see destination on your Italy Vacation. Upon arrival, make your way to your hotel and enjoy time to settle in. In the afternoon, meet your private guide for a walking tour through Venice’s historic districts. Discover hidden squares, artisan workshops, and scenic bridges while learning about the city’s unique lagoon-based history and maritime power.
Highlights: Venice walking tour, canals and bridges, hidden squares, lagoon history
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- Venice
- Day 6: Venice Discovery – Art, Gondolas & Gastronomy
Spend the day fully immersed in the charm of Venice, enhancing your Italy Vacation with memorable experiences. Choose a guided visit to Doge’s Palace and St. Mark’s Basilica to understand Venice’s political and artistic legacy. Enjoy a classic gondola ride gliding through narrow canals, or indulge in a wine and Cicchetti tasting to sample authentic Venetian snacks. The rest of the day is free for photography, shopping, or simply soaking in the magical atmosphere.
Highlights: Doge’s Palace, St. Mark’s Basilica, gondola ride, wine & Cicchetti tasting
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- Venice
- Day 7: Venice to Milan – Culture Meets Modern Style
Travel by train to Milan, the dynamic finale of your Italy Vacation. After hotel check-in, join a guided walking tour showcasing Milan’s blend of history and contemporary flair. Admire the stunning Duomo di Milano, stroll through the elegant Galleria Vittorio Emanuele II, and learn about Milan’s role as Italy’s fashion and financial capital. Optionally, visit Santa Maria delle Grazie to see Leonardo da Vinci’s Last Supper, one of the world’s most famous artworks.
Highlights: Duomo di Milano, Galleria Vittorio Emanuele II, Milan city tour, Last Supper (optional)
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- Milan
- Day 8: Milan Departure – Farewell Italy
Your enriching Italy Vacation from Rome to Milan concludes today. After breakfast and hotel check-out, transfer independently to the airport for your onward journey. For those wishing to extend their stay, Milan offers excellent shopping, cultural sites, and easy access to the scenic beauty of Lake Como, making it a perfect extension to your Italian adventure.
Highlights: Milan shopping, Lake Como extension, end of Italy Vacation
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