5-Day Best of Italy Trip with Assisi, Siena, Florence, Venice and more

The 5-Day Best of Italy Trip with Assisi, Siena, Florence, Venice, and more offers a well-rounded introduction to northern Italy’s most iconic destinations. Priced at $1,157.59 per person, this tour packs in five days of sightseeing, combining guided tours, free time, and convenient logistics. Departing from Rome, the journey takes travelers through Umbria and Tuscany regions, visiting Assisi, Siena, Florence, Bologna, Padua, and Venice. The tour features four nights in centrally located 4-star hotels, some meals, skip-the-line entrance fees, and a deluxe coach with onboard Wi-Fi.

What sets this trip apart is the expert guides who lead walking tours, share insights, and ensure a smooth experience. The hotels’ central locations allow easy access to the cities’ top attractions, making it a practical choice for those wanting to see a lot without the hassle of planning every detail. The tour is especially suited for those with moderate physical fitness, as it involves walking and a tight schedule.

One important consideration is that hotels in Venice are not in the city center but still provide convenient access, and city taxes are paid directly at each hotel. During high season, the tour operates in English only, which travelers should keep in mind if they prefer multilingual guides. The trip delivers great value for a moderate budget and offers many highlights for first-time visitors to Italy.

Key Points

• Includes five top Italian destinations over five days from Rome to Venice.
• Accommodation in four-star hotels located centrally in Florence and Venice.
• Guided tours feature skip-the-line tickets, walking explorations, and expert local guides.
• Comfortable transportation on a deluxe coach with Wi-Fi and onboard headsets.
• Some meals are included, such as breakfasts, lunches, and dinners, with a special light lunch during the Venice segment.
• The tour operates in English only during high season but is also offered bilingually in Spanish, Portuguese, and French.

Starting the Journey: From Rome to Assisi and Siena

The tour begins early from Hotel St. Martin in Rome at 7:15 AM, heading into Umbria. Your first stop is Assisi, famous for its hilltop setting and the Basilica of St. Francis. The Basilica Papale e Sacro Convento di San Francesco is rich in artwork and frescoes, with the remains of Saint Francis housed inside. The complex showcases architectural beauty and interior decorations of exceptional value.

Next, the journey continues to Siena, where a guided visit covers the Piazza del Campo. This sweeping square is renowned for its unique shell shape and Palio horse races. Afterward, the tour heads to Florence, where guests check into a 4-star hotel and enjoy a welcome dinner. The day’s highlights set the tone for Florence’s artistic treasures.

Exploring Florence’s Art and Architecture

The second day begins with a visit to the Duomo di Firenze, an icon of Renaissance architecture. The cathedral’s tiled dome, designed by Brunelleschi, offers photo-worthy views. The bell tower by Giotto complements this imposing Gothic church. Guided by local experts, visitors learn about Florence’s artistic heritage and the city’s role during the Renaissance.

Later, the Piazza della Signoria reveals Florence’s political history, with sculptures such as Michelangelo’s David (original in the Accademia Gallery) and Ammannati’s Neptune. The square has been the political heart since the 14th century. The day concludes with a visit to Basilica of Santa Croce, the burial site of Michelangelo, Galeazzo Galilei, and Rossini. The Gothic church offers artistic and historical insights during the guided tour.

Crossing into Emilia-Romagna: Bologna and Padua

On the third day, the tour moves into Bologna, with a guided visit to Piazza Maggiore, the city’s central square. Here, the Palazzo del Comune and Basilica di San Petronio define the urban landscape. The main church is one of Europe’s largest, despite being unfinished. The square is a hub of medieval architecture and public life.

Next, the group visits Basilica of St. Anthony in Padua (not available from March 24, 2025, onwards). This unique church blends Romanesque, Gothic, Byzantine, and Moorish styles. It is a significant pilgrimage site, with frescoes, artworks, and the tomb of St. Anthony. The light street food lunch experience in Bologna during high season enhances the day’s culinary appeal.

Discovering Venice’s Iconic Sights

The fourth day immerses travelers in Venice’s elegance. The group explores Piazza San Marco, often called Europe’s most beautiful square, surrounded by the Basilica, Palazzo Ducale, and the Clock Tower. The Basilica features marble, mosaics, and five grand portals.

A highlight is the Ponte dei Sospiri, historically regarded as the last view prisoners saw before incarceration, according to legend. The 35-minute visit offers a glimpse into Venice’s history of justice and intrigue. The day also includes free time to stroll through Venetian alleys, visit glass factories, or relax in the city’s enchanting ambiance.

Final Stop in Montepulciano

The last day begins with a visit to Piazza Grande in Montepulciano, perched 600 meters above sea level. Famous for wine production, the town offers breathtaking views of Tuscan hills, olive groves, and vineyards. Visitors can admire the Renaissance Palace’s tower and enjoy panoramic vistas of the Sibillini Mountains and Cimone.

This stop provides a relaxed conclusion to the tour, allowing guests to appreciate Tuscan scenery and the town’s historic charm. The tour then returns to Rome, ending at the original meeting point.

Logistically Comfortable and Well-Organized

The entire trip is conducted on deluxe coaches equipped with Wi-Fi, making navigation and communication straightforward. The guides lead walking tours in each city, often providing headsets for clear listening. Hotels are centrally located, ensuring easy access to main attractions, though the Venice hotel is outside the city center, which might require extra time to explore.

The tour includes some meals, such as breakfasts, lunches, and a welcome dinner in Florence. A light lunch and Spritz & Cicchetti experience in Venice add to the culinary experience. Entrance fees are prepaid, allowing skip-the-line access to key sites, saving time and hassle.

Practical Tips and Considerations

The tour operates in English during high season, with bilingual options in Spanish, Portuguese, and French. Travelers should be prepared for a busy schedule with moderate walking involved; it is not suitable for those with mobility issues.

Hotels are subject to availability, and city taxes are paid directly at the hotels. The itinerary is strict, aiming to maximize sightseeing within five days, so flexibility and good walking shoes are advised.

Who Will Enjoy This Tour Most

This 5-day itinerary is perfect for first-time visitors or those with limited time who want to experience Italy’s top cities efficiently. The combination of guided tours, free exploration, and comfortable transport makes it appealing for travelers seeking convenience and value. History buffs, art lovers, and foodies will appreciate the carefully curated stops and local guides.

Frequently Asked Questions

What is included in the tour price?
The price covers five days of guided sightseeing, four nights in 4-star hotels, some meals (breakfasts, lunches, dinners), skip-the-line entrance tickets, deluxe coach transportation, and onboard Wi-Fi.

Are all hotels centrally located?
Hotels in Florence and Venice are centrally located for easy access to attractions, but the Venice hotel is not on the main island, which might require some commuting.

What meals are included?
The tour includes breakfasts on all days, lunches on three days, and dinners, including a welcome dinner and a light lunch with Spritz & Cicchetti in Venice.

Is this tour suitable for travelers with mobility issues?
No, the itinerary involves walking and a tight schedule. It is not recommended for travelers with mobility challenges.

Can I cancel this tour?
Yes, cancellations are accepted up to 6 days in advance for a full refund. Cancellations less than 6 days before start incur fees, with no refunds less than 2 days prior.

Does the tour operate in multiple languages?
During high season, the tour is conducted in English only. Bilingual options in Spanish, Portuguese, and French are available.

Are additional costs likely?
Some optional activities, such as museum guided tours, gasoline tours, or gondola rides in Venice, have extra charges not included in the base price.

What is the group size?
The tour accommodates up to 45 travelers, facilitating a personalized yet group experience.

What should I pack for this trip?
Bring comfortable walking shoes, clothing covering shoulders and knees for church visits, sunscreen, and an umbrella for potential rain.

How long is the tour?
The core experience lasts 5 days, with approximately daily schedules that balance guided tours and free time.

Who is the tour provider?
This experience is offered by Gray Line I Love Rome by Carrani Tours and can be booked through Viator.

This 5-day Best of Italy Tour offers a comprehensive glimpse of Italy’s most beloved cities, blending guided insights with free exploration. It stands out for expert guides, prime hotel locations, and skip-the-line access to key attractions. While busy schedules and hotel location outside Venice are considerations, this trip remains a value-packed option for first-time visitors eager to experience Italy’s highlights in a short time.