11 Days Art & Architecture in Rome, Florence & Milan

After arriving in Rome, your private guide will meet you and transfer you into the city to begin your time in Italy. Once checked into your accommodation, head straight into the heart of Ancient Rome for a guided visit to the Colosseum.

Entering the Colosseum with your guide gives you the chance to better understand the building’s scale and history rather than simply viewing it from the outside. As you walk through the ancient amphitheater, your guide will explain how gladiator contests, public events, and spectacles once took place here before tens of thousands of spectators. You’ll also hear how the structure was engineered nearly 2,000 years ago and why it remains one of the most important landmarks from the Roman Empire.

After the tour, continue around the ancient ruins, taking in views over the Roman Forum before walking farther into the historic center. Spend the rest of the afternoon exploring Rome’s streets, fountains, and piazzas with your guide before stopping for dinner in one of the city’s traditional neighborhoods.

Today focuses on Vatican City and some of Rome’s most well-known historic landmarks. Begin the morning at St. Peter’s Basilica before continuing into the Vatican Museums with your guide. Inside, you’ll walk through galleries filled with sculptures, paintings, maps, and Renaissance artwork before reaching the Sistine Chapel.

After time in Vatican City, continue back to central Rome to explore the city’s Baroque side. Walk between the Spanish Steps, Trevi Fountain, and the surrounding streets filled with cafés, boutiques, and historic buildings.

The rest of the afternoon is flexible depending on your interests, whether you prefer more time visiting churches, galleries, or simply walking through different parts of the city with your guide.

Today focuses on seeing a different side of Rome, away from the larger landmarks and busiest tourist areas. Start in Trastevere, one of the city’s best-known neighborhoods, where narrow streets are lined with restaurants, cafés, apartments, and small local shops.

Walk through the area with your private guide, stopping at small piazzas, older churches, and local food spots along the way. This part of Rome is best explored on foot, with many of the streets too small for traffic and full of places you would likely miss on your own.

Later, continue toward Campo de’Fiori and the surrounding streets, where your guide will take you through busy market areas, small bakeries, wine bars, and local cafés spread across the neighborhood. There will be plenty of time to stop for lunch, coffee, or more walking through the surrounding streets before returning later in the day. 

This morning, leave Rome behind and travel north with your private guide in your Mercedes V-Class. The drive into Tuscany passes vineyards, olive groves, small hill towns, and countryside roads as you make your way toward Siena.

After arriving, spend time exploring SieSiena’sstoric center on foot. Walk through the old streets with your guide before reaching Piazza del Campo, the large main square at the center of the city. You’ll also see Siena Cathedral and smaller streets filled with cafés, bakeries, and local shops.

There will be time to stop for lunch before continuing onward to Florence later in the afternoon. After checking into your accommodation, you can spend the evening walking around the historic center or enjoying dinner near Piazza della Signoria.

This morning, meet your private guide and head into the center of Florence to start exploring the city’s historic landmarks. Your first stop is the Florence Cathedral area, where you’ll see the Duomo, the Baptistery, and the large square surrounding the cathedral before continuing through the nearby streets on foot. 

Continue through the center with your guide, walking between Palazzo Vecchio, Piazza della Signoria, and the streets surrounding the Uffizi Gallery. Along the way, your guide will explain how Florence developed during the Renaissance and how the Medici family shaped much of the city.

Cross the Ponte Vecchio later in the day before exploring the Oltrarno district, known for artisan workshops, smaller cafés, and quieter streets on the opposite side of the river.

Today, your private guide will take you between two of FloFlorence’sst important museums. Start at the Accademia Gallery to see MicMichelangelo’svid up close before continuing on foot through the historic center toward the Uffizi Gallery later in the day. 

Inside the Uffizi, see works by Botticelli, Leonardo da Vinci, Raphael, and other major Renaissance artists while learning more about FloFlorence’sle in Italian art history.

Between museum visits, continue walking through FloFlorence’sstoric streets, with time for coffee stops, lunch, and visits to smaller churches or piazzas throughout the day.

Today, your private guide will take you out of Florence for a day exploring two historic Tuscan cities. The first stop is Pisa, where you’ll spend time around Piazza dei Miracoli, seeing the Leaning Tower, the cathedral, and the baptistery before exploring more of the city on foot. 

After time around the square and surrounding streets, continue onward to Lucca, a smaller Tuscan city surrounded by Renaissance walls. Spend time walking through the historic center, passing churches, bakeries, local cafés, and quiet piazzas.

Return to Florence later in the afternoon through the Tuscan countryside.

Today, travel north from Florence to Bologna with your private driver. After arriving, begin exploring the citcity’sstoric center, known for its long covered porticoes, brick buildings, and medieval towers.

Walk with your private guide through Piazza Maggiore and the surrounding streets before continuing into Bologna’s historic market areas, where food stalls, bakeries, cafés, and delicatessens fill the center of the city. You’ll also spend time exploring some of the covered porticoes and smaller side streets that make Bologna so well known. 

The afternoon gives you time to explore more of the city on foot or stop for dinner at one of Bologna’s traditional restaurants.

Today, your private guide takes you through parts of the Emilia-Romagna region, stopping in Parma and Modena along the way.

Begin in Parma, where you’ll walk through the historic center and see piazzas, churches, cafés, and local food shops known for Parma ham and Parmigiano Reggiano. Continue onward to Modena later in the day, another city closely connected with Italian food culture.

Spend time exploring the streets and markets with your guide before returning to Bologna in the evening.

Leave Bologna behind and continue north toward Milan in your Mercedes V-Class. After arriving, begin exploring the historic center with your guide.

Visit the Duomo di Milano and spend time around the cathedral square before walking through the Galleria Vittorio Emanuele II and the surrounding shopping streets. Later in the day, continue into the Brera district, known for galleries, cafés, and smaller historic streets.

Milan also shows a more modern side of Italy compared with the cities visited earlier in the trip, with newer buildings and business districts sitting alongside historic architecture.

Before leaving Milan, spend your final morning with your private guide exploring more of the city center, including the streets around Sforza Castle, local cafés, shopping areas, and smaller historic corners you may not have seen earlier in the trip. 

Walk through parts of the historic center you may not have seen the previous day, including the area around Sforza Castle and nearby streets filled with cafés and local shops. There will also be time for lunch or final shopping before leaving the city.

After your time in Milan, your private guide will transfer you to the airport or onward destination, bringing your Italian art and architecture journey to a close.