Balance your travels between the city and countryside with this week-long itinerary. In between the art and history found on the busy streets of Milan and Florence, you'll also visit the peaceful villas of Lake Como, the seaside towns of Cinque Terre, and the vineyards of Chianti.


  • Scope out the fashion scene in Milan
  • Visit the luxury villas of Lake Como
  • Take in the seaside views from Cinque Terre
  • Tour the artistic landmarks of Florence
  • Taste the famous vintages of the Chianti wine region

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Milan, Afternoon of Art & Culture Milan
Day 2 Private Tour of Lake Como Milan
Day 3 Private Full-Day Milan Tour Milan
Day 4 Train from Milan to Florence Florence
Day 5 Day Trip to Cinque Terre Florence
Day 6 Full-Day Chianti Tour: Winery & Steak Poet of Fiorentina from Florence Florence
Day 7 Depart Italy  

Detailed Itinerary

Day 1: Arrive in Milan, Afternoon of Art & Culture

Naviglio Grande canal in the evening
Naviglio Grande canal in the evening

Welcome to Milan! From the Milano Malpensa or Linate airport, you'll transfer to the city center to check in to your hotel. Milan is known as the non-official capital of Italy, the place where everything happens. The city is a center for business, shopping, fashion, and culture, as well as medieval art and beautiful architecture. Many of Milan's old monuments and buildings were destroyed during World War II bombings, and the new construction and modern architecture give Milan a sophisticated vibe. Because of this, Milan is known as Italy's "new" city and represents modern Italy. 

Spend the afternoon exploring Milan's art and culture. You can learn about Leonardo da Vinci's works and scientific and technological advancements in the Leonardo da Vinci National Museum of Science and Technology or visit the Pinacoteca di Brera fine art gallery, located in the Palazzo Brera. You might also consider a stroll around the bohemian Brera District to see art academies, galleries, and fine dining restaurants and bars, or shop for luxury brands at the Via della Spiga, Via Sant'Andrea, and Via Montenapoleone shopping streets 

A visit to the 16th-century Royal Palace, a sprawling neoclassical palace turned art museum, is a great way to explore the city's history and art. Although the building suffered significant damage during World War II, it has been beautifully restored and is now a renowned cultural center. In the evening, head to the Navigli at Porta Genova, Milan's ancient network of canals and passages used for transporting goods and supplies across the city. At night these streets transform with crowds of locals and tourists meeting friends at restaurants and aperativo bars. Come for the buzzing energy, stay for the wine bars and people watching.

Day 2: Private Tour of Lake Como

Springtime in Bellagio,
Springtime in Bellagio, "The Pearl of the Lake"

After breakfast, head out for a full day on Lake Como, Italy's third-biggest lake. The area is known for its upscale resorts, dramatic landscapes, and views of the Alps. The lake's unique location gives it favorable weather conditions, with most of the cold winds blocked by the Alps to the north. As a result, Lake Como's warm climate has drawn visitors for thousands of years to its temperate shores. 

Thanks to the mild weather and pretty setting, the lake has long been a popular destination for the elite to build extravagant summer villas and lakefront palaces. You'll get to visit Villa Carlotta in Tremezzo, which boasts Japanese-style gardens, Villa Melzi in Bellagio with its wealth of historical Napoleonic relics, or Villa D'Este, a hotel of international renown. There's also Villa Balbanello in Lenno, an elegant and refined villa with a manicured garden draping over the rocky lakefront terrace. Villa Monastero has an eclectic style and a garden full of exotic trees, balustrades, and Venetian wells. 

Continue your tour in the city of Como, which lies on the southwest branch of the lake. Tour the Gothic 14th-century Cathedral of Como, sprawling Villa Olmo park and exhibition halls, and the Museo Didattico della Seta (Museum of Silk) with your local guide to learn about the region's historic silk industry. See the sights with a ride on the funicular railway and enjoy the views as you stroll on the waterfront promenade. 

After a full day, catch a transfer back to Milan in time for a relaxed evening stroll to the neighborhood wine bar.

Day 3: Private Full-Day Milan Tour

The Last Supper by Leonardo Da Vinci
The Last Supper by Leonardo da Vinci

Spend the day discovering sights and history in Milan on today's private tour. Start in a vehicle to see panoramic views of the city, then continue on foot to see the city up close. The driving tour starts at Foro Bonaparte, built to celebrate Napoleon's victories, to see the Arco della Pace (Arch of Peace), the Santa Maria delle Grazie, and Sant'Ambrogio churches, as well as the San Babila and Fontana Piazzas. Drive by the Corso Venezia, a luxury shopping street in the Quadrilatero della Moda district. 

Leave the car behind and walk with your guide to see the 18th-century Neoclassical Teatro alla Scala and the iconic gothic Cathedral (local tip: head to the roof for panoramic views of the city). The Cathedral took nearly 600 years to complete, and its shiny marble facade and striking late Gothic architecture make it the symbolic monument of Milan. The massive church is the largest in Italy and the fourth-largest in the world. Stroll through the airy halls of Galleria Vittorio Emanuele II, a spacious indoor shopping mall famous for its ornate architecture and skylights, which now houses historic restaurants, bars, and trendy shops. 

Continue to the Castello Sforzesco, a 15th-century castle and fortress which now houses a prominent art museum and works by Leonardo da Vinci.

Plan your trip to Italy
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Day 4: Train from Milan to Florence

Ponte Vecchio and Florence skyline
Ponte Vecchio and Florence skyline

After a leisurely breakfast, depart your Milan accommodation and transfer to the train station for your trip to Florence. The trains in Italy are fast and comfortable, so sit back, relax, and enjoy the views on your journey. 

Arrive in Florence, then check into your hotel. After settling in, head out for lunch at a quiet café. Join a local guide for a walking tour of the city's sights in the afternoon. Start at the Duomo (Cathedral of Santa Maria del Fiore), one of Florence's most famous landmarks, then continue to the Galleria dell'Accademia to see Michelangelo's famed David sculpture. Afterward, head to the Church of San Lorenzo and the Medici Chapels to see the colorful Chapel of Princes and the New Sacristy, famous for Michelangelo's Dawn & Dusk and Night & Day statues. 

Wrap up your tour with enough time to find the perfect neighborhood wine bar for a relaxing evening in the romantic city.

Day 5: Day Trip to Cinque Terre

Town of Manarola
Town of Manarola

In the morning, depart by private vehicle for a full day on the Cinque Terre, a section of the Italian coast famous for its medieval villages, stunning cliffs, and beautiful hiking trails. Start in Riomaggiore, one of the five villages that make up the historic Cinque Terre region. Walk along the beautiful Via dell' Amore to enjoy the coastline and sea views. The views along the cliffs are exhilaratingly stunning and worth the walk. Continue to Manarola for some free time. The tight-knit village has a main street lined with shops and a quiet harbor full of brightly-colored wooden boats that fishers take out for a day's work on the sea. 

From here, take a 15-minute boat ride up the coast to the town of Vernazza, a small resort town located at the mouth of a river and naturally protected from wild sea swells by a rocky promontory. This natural wave break protects the harbor, making it the only docking point in the Cinque Terre. Enjoy lunch on your own time as you explore the local cuisine and savor regional delicacies. 

From Vernazza, make your way to Monterosso, the final town on the Cinque Terre. The city's medieval center remains nearly perfectly preserved, with its ancient tower-houses and network of carrugi (narrow alleyways that lead from the sea to the cliffs above the town). Monterosso is also renowned for having the best gelato on the Cinque Terre (make sure to try some!) and breathtaking views of the sea. After the day's sightseeing, follow your nose to the neighborhood bakery to sample the local focaccia with pesto for a delicious snack you won't find anywhere else. 

Day 6: Full Day Chianti Tour: Winery & Steak Poet of Fiorentina from Florence

The perfect glass of Chianti
The perfect glass of Chianti

Hit the road today with your private guide to explore the romantic region of Chianti. This large region is located between Florence and Siena and is famous for its unparalleled beauty and peaceful countryside. Each part of this incredible region is full of vineyards, wineries, medieval towns, and winding rural roads. The Chianti region is renowned for producing delicious red wine of the same name. The region's unique characteristics and local climate are unfavorable to most crops but ideal for growing wine grapes. The Chianti wine, made primarily of Sangiovese grapes, is the local staple. 

Visit the famous Castello di Verrazzano. Spend the morning learning about the winery and touring the cellars and vineyards, then enjoy a wine tasting accompanied by a delicious Tuscan lunch of pasta, cured meats, cheeses, and local desserts. Then meet the legendary butcher Dario Cecchini, nicknamed the "world's best butcher" for another authentic Tuscan experience. The 8th-generation butcher of Antica Macelleria Cecchini is known as the "Poet of Fiorentina"—the famous Tuscany T-bone steak—and you'll find him behind the counter of his butcher shop in the heart of Chianti, in Panzano, every day of the week including Sundays.

The walkway behind the counter is raised, so Dario looks much like a large, smiling giant, a benevolent and friendly man who loves entertaining locals and visitors with his recitations of verses of the Divine Comedy. For a real taste of the butchering process, taste his Chianti Butter (lard cream flavored with herbs and spices), and the "Sushi of Chianti" (thinly sliced raw meat). 

Day 7: Depart Italy

Little details of life in Rome
The little details add charm to life in Rome

After one last cappuccino over breakfast, head to the airport for your connecting flight home. Have a good trip!


Map of Cities and Nature in Italy: Milan, Lake Como, Florence & Cinque Terre - 7 Days
Map of Cities and Nature in Italy: Milan, Lake Como, Florence & Cinque Terre - 7 Days
Written by Sonya Pevzner, updated May 5, 2022