Italy City Break – 5 Days

By January 22, 2024January 26th, 2024Blog

Explore Italy in 5 days with our city break tour! We start in Rome and visit the charming town of Assisi with its famous St. Francis basilica. See art by Giotto and Cimabue. Next, discover Siena, a UNESCO World Heritage Site known for the historic Palio horse race. 

Enjoy the beauty of Florence, known as the ‘Cradle of the Renaissance,’ and see famous landmarks like the Duomo and Campanile tower. Have a delicious Tuscan lunch in Piazza Santa Croce. Continue your journey to Bologna, Padua, and the stunning city of Venice. 

Take a stroll along canals and visit landmarks like Palazzo dei Dogi and the Bridge of Sighs. Taste the famous wines of Montepulciano before ending your trip back in Rome. Experience the good life in Italy!

Itinerary

Itinerary + Italy City Break - 5 Days

Your journey begins and concludes in Rome! Join our 5-day Italy City Break tour, where you’ll explore Rome and visit 8 other destinations in Italy. This tour package provides accommodation in a hotel, along with a knowledgeable guide, meals, transportation, and more.

Day 1: From Rome to Assisi – Unesco World Heritage Site Palio – Siena – Florence

Day 1: From Rome to Assisi - Unesco World Heritage Site Palio - Siena - Florence + Italy City Break - 5 Days

Begin your lovely journey with a pick-up at 7:15 am from Hotel St. Martin. A comfy coach will take you to Assisi, a small medieval town surrounded by walls. You can explore it at your own pace. Visit the St. Francis basilica to see art by Giotto and Cimabue. Afterward, take your time for lunch (not included). Hop back on the bus to reach Siena, a UNESCO World Heritage Site famous for the Palio, a historic horse race in the shell-shaped town square, Piazza del Campo. Continue your adventure to Florence, where you’ll check in at your hotel. Enjoy dinner and a well-deserved night of rest.

Day 2: Explore Beautiful Florence – Enjoy Lunch at a Traditional Tuscan Restaurant

Day 2: Explore Beautiful Florence - Enjoy Lunch at a Traditional Tuscan Restaurant + Italy City Break - 5 Days

Start your day with breakfast at the hotel, and then venture through the charming city of Florence, often called the ‘Cradle of the Renaissance.’ This city, rooted in Etruscan-Roman origins, flourished during the Middle Ages as a free ‘Comune’ and became even more splendid during the Renaissance, thanks in part to Michelangelo.

Discover numerous landmarks, churches, and buildings, including the awe-inspiring Santa Maria del Fiore, also known as the Duomo. Marvel at its magnificent dome designed by Filippo Brunelleschi. Across a small square, you’ll find the ‘Campanile’ tower (partly designed by Giotto) and the Baptistery, featuring bronze doors imagined by Michelangelo for the ‘Gates of Paradise.’

In the heart of the city, explore Piazza della Signoria, Palazzo della Signoria (also called Palazzo Vecchio), and the Basilica of Santa Croce. Enjoy lunch at a typical Tuscan restaurant in Piazza Santa Croce. Spend your afternoon wandering the cobblestone streets of Florence on your own, or choose an optional short trip to Pisa, one of Italy’s historical Marine Republics. There, explore the Piazza dei Miracoli with the Duomo, Pisa’s iconic ‘Leaning Tower,’ and the Baptistery.

Dinner is at your leisure, and you’ll spend the night in Florence.

Day 3: Explore Charming Bologna, Padua, and Venice: the City of Love

Day 3: Explore Charming Bologna, Padua, and Venice: the City of Love + Italy City Break - 5 Days

Start your day with breakfast at the hotel in Florence, and then head to Bologna. There, you’ll discover the stylish city center with its covered walkways called ‘porticos’ and attractive shopping streets. 

Begin at Piazza Malpighi and walk to Piazza del Nettuno and Piazza Maggiore, the heart of the city. See landmarks like King Renzo’s Palace, Palazzo Podestà, and the impressive basilica of San Petronio, which is one of the world’s largest. Bologna is a paradise for food lovers, so be sure to enjoy a tasty meal at your own pace!

In the afternoon, continue your journey to Padua, where you’ll visit the Sant’Antonio Basilica, a popular destination for pilgrims. Later in the day, arrive in Venice, often called the City of Love and considered one of the most romantic cities globally and unquestionably the most beautiful city built by humans! Check in at your hotel for dinner and an overnight stay.

Day 4: Explore Beautiful Venice – Piazza San Marco, Palazzo dei Dogi, Bridge of Sighs

Day 4: Explore Beautiful Venice - Piazza San Marco, Palazzo dei Dogi, Bridge of Sighs

Start your day with a delicious breakfast, and then get ready for a transfer to Piazza San Marco. Discover the most famous places in the ‘Floating City’: the Palazzo dei Dogi, representing Venice’s impressive history, and the legendary ‘Bridge of Sighs.’ After this guided walking tour, let us treat you to a spritz or a prosecco to top off your visit to Venice’s highlights, all in the company of your tour leader.

In the afternoon, take some time to wander along Venice’s canals at your own pace. Later, return to the hotel for an overnight stay.

Day 5: Venice – Beautiful Tuscany Wine Region – Montepulciano – Rome

Day 5: Venice - Beautiful Tuscany Wine Region - Montepulciano - Rome

Start your day with breakfast, then leave from Piazzale Roma towards Tuscany, famous for its picturesque landscapes, historic churches, castles, and tasty wines. Head to Val di Chiana with a stop in Montepulciano, a medieval town full of history and art. 

This town is renowned for its ‘Nobile’ wine, which you can buy from local wine shops. Montepulciano also hosts a Jazz and Wine Festival every July. Enjoy lunch at a typical restaurant, included in the tour! After lunch, there’s a quick stop for some free time. In the evening, you’ll reach Rome, where the tour comes to an end.

Final Thoughts 

The 5-day Italy City Break tour offers a captivating journey through the rich cultural tapestry of Italy. From the medieval charm of Assisi to the art-filled streets of Florence, the historic landmarks of Bologna, Padua, and the romantic allure of Venice, the itinerary is a delightful blend of history, art, and culinary experiences. With expert guidance, comfortable accommodations, and a seamless travel experience, this tour provides a comprehensive exploration of Italy’s diverse treasures, leaving travelers with lasting memories of the enchanting cities and landscapes.

FAQs

What is included in the Italy City Break tour package?

The tour package includes accommodation in a hotel, transportation, meals, and the services of a knowledgeable guide. Travelers will explore Rome and visit 8 other destinations in Italy, with activities ranging from historical site visits to leisurely strolls along canals.

How flexible is the itinerary for personal exploration?

The itinerary allows for some flexibility, particularly in destinations like Assisi and Florence, where travelers can explore at their own pace. Free time is also incorporated in various locations, offering opportunities for personal exploration or optional activities.

Are meals included in the tour, and is there flexibility in dining choices?

Meals are included in the tour, such as breakfast at the hotel and lunches at specified locations. However, dinner is typically at the traveler’s leisure, providing flexibility for personal dining preferences and exploration of local cuisine.

What type of transportation is provided during the tour?

A comfortable coach is provided for transportation between destinations, ensuring a smooth and enjoyable journey. Additionally, guided walking tours are organized in key cities like Florence and Venice, offering a comprehensive exploration of iconic landmarks with the assistance of a knowledgeable tour leader.

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