Italy City Break - 5 Days

We start our charming journey on a deluxe coach from our meeting point at around 7:15 am. We reach Assisi after a few hours, where we begin our tour in earnest. Assisi is a small hill town surrounded by walls, built in the Middle Ages. It is also the birthplace of St. Francis, one of the patron saints of Italy. Here, we will visit the Basilica of St. Francis and see the masterpieces by Giotto and Cimabue.

After the tour of the place, we will have some free time for lunch (not included on the tour). Then, we will board our bus and set out towards Siena, a Unesco World Heritage Site, famed for the Palio, the historical horse race around the shell-shaped town square: Piazza del Campo.

After touring the site, we head towards the city of Florence. After reaching there, we check in to our hotel and enjoy our dinner.

Please note: *Starting from the departure on 30ᵗʰ March 2026, instead of dinner at the hotel in Florence, there will be a lunch in Assisi

After breakfast at the hotel, we set out for our tour of Florence, the cradle of Renaissance, where, with the help of Michelangelo, Italian art reached its pinnacle.

Based on Etruscan/Roman origins, Florence flourished in the Middle Ages as a free “comune” and was further refined during the Renaissance. The city is home to uncountable monuments, churches and buildings. Cattedrale di Santa Maria del Fiore, more commonly referred to as the Duomo, is one of them.

On your visit, you will be amazed by its magnificent dome built by Filippo Brunelleschi. Cross a small piazza to see the “Campanile” tower (partly designed by Giotto) and the Baptistery, with its bronze doors where Michelangelo imagined the “Gates of Paradise.”

In the heart of the city, you will see Piazza della Signoria, also known as Palazzo Vecchio, and the Basilica of Santa Croce.

We will have lunch in a typical Tuscan restaurant in Piazza Santa Croce. We will then spend the afternoon strolling the cobblestone streets of Florence on our own.

As an optional tour, you can take a short trip to Pisa, one of the four main historical Maritime Republics of Italy. There, you will tour the Piazza dei Miracoli with the Duomo, Pisa’s symbol “The Leaning Tower” and the Baptistery.

Overnight stay in Florence.

After enjoying a delightful breakfast in Florence, we head to the elegant city of Bologna. Upon arrival, the charming city center, adorned with its iconic porticoes, invites you to explore during your free time. Begin your walking tour at Piazza Malpighi, leading to the city's heart at Piazza del Nettuno and Piazza Maggiore. Here, you can admire the historic Palazzo Podestà and the Basilica of San Petronio, the largest Gothic church in the world built with bricks. We’ll then reveal why Bologna is often regarded as Italy's gastronomic capital as you dive into its vibrant street food scene, which is as rich and diverse as its culinary heritage. Strolling through the city’s medieval streets, you'll come across an enticing array of food stalls and markets, each offering a tempting selection of traditional and contemporary delicacies. As you explore the charming alleys and lively piazzas, you’ll embark on a culinary adventure that goes far beyond just a meal. With a light street food lunch experience at a local eatery, you’ll have the chance to savor the authentic flavors and unique dishes that define Bologna’s renowned gastronomic identity. In the afternoon, we continue our journey to Venice (Mestre). Upon arrival, check in at your hotel for a peaceful overnight stay.

This morning we head to Piazza San Marco following our breakfast. We then visit the most iconic places of the “Floating City”: Palazzo dei Dogi, a symbol of Venice’s glorious past, and the legendary “Bridge of Sighs”.

After this walking tour, we celebrate our Venice tour with a Spritz or a Prosecco. In the afternoon, spend your time exploring Venice’s intricate canal system at your leisure and return to the hotel in the evening.

After breakfast, we depart from Venice and head toward Tuscany, renowned world over for its wine, landscapes, churches and castles.

We will proceed to Val di Chiana with a stop over at Montepulciano, a medieval town rich in art and history. Known for its “Nobile” wine, on purchase in local wine houses, Montepulciano also hosts an annual Jazz and Wine Festival every July.

We will enjoy a lunch in a typical restaurant and spend some free time sightseeing in the area on our own. In the evening, we leave the place and journey toward Rome, where our tour ends.