Begin your Italian adventure in Rome and drive into the picturesque Umbria region, where you’ll visit Assisi, a charming hilltop town and UNESCO World Heritage Site. From there, journey into the heart of Tuscany, exploring the historic streets of Siena and the artistic treasures of Florence, including the iconic Duomo. Continue your journey through northern Italy, stopping in Bologna and Padua before arriving in the enchanting canals of Venice.

Enjoy two nights in 4-star accommodations in both Florence and Venice, with hotels centrally located for easy access to each city’s top sights. Most breakfasts and lunches are included, and your guided experience features walking tours, skip-the-line access to major attractions, and insights into Italy’s art, history, cuisine, and culture.

Day 1: Rome – Assisi – Siena – Florence

Departure: 7:15 AM from Rome

Begin your journey north to the Umbrian hill town of Assisi, a medieval gem and UNESCO World Heritage Site. Explore the town’s charming streets before visiting the Basilica Papale e Sacro Convento di San Francesco, the sacred resting place of St. Francis. This remarkable basilica is a masterpiece of art and architecture, featuring two harmoniously connected buildings adorned with priceless frescoes and intricate interior decorations that celebrate the life of the saint.

 

Next, continue to Siena for a guided tour of its famous Piazza del Campo, renowned for its unique shell shape and historic significance, including the world-famous Palio horse race.

In the evening, arrive in Florence, check into your centrally located 4-star hotel, and enjoy a welcome dinner to begin your Tuscan adventure.

Day 2: Florence

Spend a full day discovering the artistic and cultural treasures of Florence, the capital of Tuscany and the cradle of the Renaissance.

1. Duomo – Cattedrale di Santa Maria del Fiore
Begin at the iconic Duomo, with its breathtaking dome engineered by Brunelleschi and the elegant bell tower designed by Giotto. Florence’s historic center is filled with museums, palaces, and churches that house some of the world’s most important artistic masterpieces. Don’t miss Santa Maria Novella and Santa Croce, two of the city’s most significant churches. When you want a break from galleries, take a leisurely stroll through the charming streets and squares of Florence to soak in the atmosphere.

 

2. Piazza della Signoria
Next, explore Piazza della Signoria, the heart of Florence’s political and civic life since the 14th century. This historic square has witnessed key events, including the return of the Medici family in 1530. Admire the famous sculptures that tell Florence’s political stories, from Michelangelo’s original David (housed today in the Accademia Gallery) symbolizing the strength of the Florentine Republic, to Ammannati’s Neptune Fountain celebrating the maritime ambitions of the Medici.

 

3. Basilica of Santa Croce
End your day at the magnificent Basilica of Santa Croce, rebuilt in 1294 for the Franciscan order by Arnolfo di Cambio. This church is the final resting place of Florence’s most illustrious figures, including Michelangelo, Rossini, Machiavelli, and Galileo Galilei. A memorial to Dante is also here, though his sarcophagus remains empty, as he was buried in Ravenna after his exile.

Day 3: Florence – Bologna – Venice

Depart Florence and travel north toward Bologna, a city famed for its rich history, medieval architecture, and culinary delights.

1. Piazza Maggiore & Piazza del Nettuno
Begin your Bologna exploration at Piazza Maggiore, the vibrant heart of the city, where centuries of history unfold among grand palaces and churches. Adjacent is Piazza del Nettuno, created in 1565 to showcase the striking Fountain of Neptune, which gives the square its name. 

 

2. Basilica di San Petronio
Visit the imposing Basilica of San Petronio, Bologna’s main church, which dominates Piazza Maggiore. Though largely unfinished, it is one of the largest churches in Europe, and its vast size makes it the fourth largest in Italy. The basilica’s grandeur and architectural details provide a remarkable glimpse into Bologna’s religious and cultural history.

Day 4: Venice

Experience the magic of Venice, a city of elegance, romance, and unparalleled beauty, where churches, palaces, bridges, and squares reveal centuries of artistic and cultural brilliance.

1. Piazza San Marco
Begin at Piazza San Marco, often called “the drawing room of Europe,” the vibrant heart of Venice. Marvel at the majestic Basilica di San Marco, with its five ornate portals, intricate marble decorations, and dazzling mosaics that hint at the splendor within. Nearby, admire the Palazzo Ducale, a symbol of Venice’s golden age, and the Torre dei Mori, also known as the Clock Tower, a centuries-old engineering marvel that once kept time for the city. Explore the Napoleonic Wing, home to the Correr Museum, which showcases Venice’s rich history and art.

 

2. Ponte dei Sospiri (Bridge of Sighs)
Cross the famous Bridge of Sighs, steeped in legend. During the Serenissima, prisoners would sigh as they crossed it, glimpsing the outside world one last time before imprisonment—a poignant reminder of Venice’s fascinating history.

Day 5: Venice – Montepulciano – Rome

Depart Venice and travel south through the scenic landscapes of Tuscany to the charming hilltop town of Montepulciano, renowned for its namesake wine.

1. Piazza Grande, Montepulciano
Arrive at Piazza Grande, the heart of Montepulciano, perched 600 meters above sea level. Take in panoramic views of rolling Tuscan hills dotted with olive groves, vineyards, and iconic cypress trees. From the tower of the Renaissance-style Palazzo Comunale, you can see as far as the Sibillini Mountains and the Cimone, making it a perfect spot for photos and reflection. Enjoy the opportunity to stroll the historic streets and, if you wish, sample the famous Montepulciano wines that have delighted visitors for centuries.

 

2. Return to Rome
In the evening, conclude your unforgettable journey as you return to Rome, bringing with you memories of Italy’s art, history, cuisine, and breathtaking landscapes.