Exploring the highlights of Umbria and Tuscany on a 5-day tour through Italy seems like an incredible way to immerse ourselves in the country’s rich history, culture, and cuisine. From the spiritual charm of Assisi to the medieval beauty of Siena and the artistic treasures of Florence, this itinerary promises an unforgettable journey. And with the opportunity to savor the culinary delights of Bologna and get lost in the romantic canals of Venice, it’s bound to leave us with memories that’ll last a lifetime. Shall we dive in and uncover the best of what this captivating country has to offer?

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Key Points

This 5-day tour covers the highlights of Umbria and Tuscany, including Rome, Assisi, Siena, Florence, Venice, Bologna, and Padua.
The tour includes guided visits to iconic landmarks like the Basilica of St. Francis, Piazza del Campo, the Duomo, and St. Mark’s Square.
Travelers will have a mix of guided tours and free time to explore the local cuisine and culture in each destination.
The tour provides four nights of accommodation in 4-star hotels and includes transportation in an air-conditioned vehicle with Wi-Fi.
The tour is suitable for travelers with a moderate fitness level, with a maximum group size of 45 and optional tours available.

Tour Overview

This 5-day tour offers an ideal introduction to the highlights of Umbria and Tuscany, with a mix of guided tours and free time to explore.

With 280 reviews and an overall rating of 4.3, the tour includes four nights of accommodation in 4-star hotels, some meals, and entrance fees.

The tour kicks off in Rome, then takes you to Assisi, Siena, Florence, Venice, Bologna, and Padua.

From the Basilica of St. Francis in Assisi to the canals of Venice, this tour provides an immersive experience of Italy’s history, art, and culture.

Looking for more options in Rome? We've reviewed plenty of other experiences.

Itinerary Highlights

As we embark on this journey, we’ll begin in Rome and travel north to the serene town of Assisi, where we’ll visit the Basilica Papale e Sacro Convento di San Francesco d’Assisi, the resting place of St. Francis.

Next, we’ll head to Siena and explore the picturesque Piazza del Campo.

On day two, we’ll spend a full day in Florence, marveling at the Duomo, Piazza della Signoria, and Basilica of Santa Croce.

The following day, we’ll visit Bologna and Padua before arriving in the enchanting city of Venice, where we’ll see Piazza San Marco and Ponte dei Sospiri.

Day 1: Rome to Assisi and Siena

On the first day of our Best of Italy Tour, we depart from Rome and make our way to the historic town of Assisi, the birthplace of St. Francis.

Our guided visit to the Basilica Papale e Sacro Convento di San Francesco d’Assisi provides a glimpse into the life and legacy of this revered saint.

We then explore the charming medieval streets of Siena, admiring the stunning Piazza del Campo, known for its unique shell-shaped design.
Our tour guide shares the rich history and cultural significance of this Tuscan gem, leaving us eager to discover more of the region.
As the day draws to a close, we look forward to the adventures that await us on the next leg of our Italian journey.

Day 2: Full Day in Florence

After an early breakfast, we make our way to the historic heart of Florence, eager to explore the wealth of art, architecture, and culture that the city has to offer.

We begin at the iconic Duomo, marveling at its intricate Renaissance facade and climbing to the top of the dome for panoramic views.

Next, we stroll through the picturesque Piazza della Signoria, home to impressive statues and the Palazzo Vecchio.

Later, we visit the Basilica of Santa Croce, admiring its stunning Franciscan architecture and the tombs of renowned Italians like Michelangelo.

With ample free time, we can discover Florence’s charming streets, sample local cuisine, and immerse ourselves in the city’s vibrant atmosphere.

Day 3: Travel From Florence to Bologna, Padua, and Venice

We depart Florence early this morning, eager to discover the historic cities of Bologna and Padua on our way to the iconic city of Venice.

Our journey takes us through the lush Emilia-Romagna region, known for its delectable cuisine and cultural treasures. In Bologna, we explore the majestic Piazza Maggiore and admire the stunning Basilica di San Petronio.

Next, we venture to Padua, where we visit the Basilica of St. Anthony, one of Italy’s most important pilgrimage sites.

Finally, we arrive in the enchanting city of Venice, ready to be captivated by its canals, bridges, and timeless charm.

Discover the rich history and cuisine of Bologna and Padua
Marvel at the Basilica di San Petronio and Basilica of St. Anthony
Prepare to be enchanted by the iconic city of Venice

There's plenty more to explore in Rome

Day 4: Exploring Venice

Awakening to the gentle lapping of the canals, we eagerly set out to explore the enchanting city of Venice.

Our first stop is the iconic St. Mark’s Square, where we marvel at the grand Basilica and the Doge’s Palace. We wander through the maze of picturesque bridges and alleyways, stopping to admire the intricate architecture and soak in the lively atmosphere.

Later, we board a traditional gondola for a romantic ride along the famous waterways, gliding past centuries-old palaces and under the Bridge of Sighs.

With free time in the afternoon, we dive into Venice’s culinary scene, savoring the region’s renowned seafood dishes.

Day 5: Return to Rome via Montepulciano

Departing the enchanting city of Venice, we make our way back to Rome with a stop in the charming town of Montepulciano.

Along the way, we’ll visit the Piazza Grande, a picturesque town square surrounded by medieval and Renaissance architecture.
Montepulciano is renowned for its robust red wines, so we’ll have the opportunity to sample some local vintages.
Before reaching Rome, we’ll take in the stunning views from the hilltop town, providing a fitting end to our immersive journey through the heart of Italy.

Inclusions, Logistics, and Traveler Information

Although this tour includes an air-conditioned vehicle, onboard Wi-Fi, and licensed local guides, city taxes must be paid directly at the hotels upon arrival or check-out. The tour doesn’t include hotel pickup, and it’s not wheelchair accessible, requiring a moderate fitness level. Here’s a quick overview:

Inclusions	Exclusions
– Air-conditioned vehicle – Onboard Wi-Fi – Licensed local guides – Skip-the-line tickets	– Hotel pickup – City taxes – Some meals

The maximum group size is 45 travelers, and rates don’t include city taxes. Optional tours, like a Venice gondola ride, are available. Cancellations incur varied fees, so plan accordingly.

Frequently Asked Questions

Can I Extend or Customize the Tour Itinerary?

Yes, you can extend or customize the tour itinerary. We offer flexibility to accommodate your preferences, whether you’d like to spend more time in certain cities or add additional destinations to the tour.

Do I Need to Bring Any Specific Documentation?

We recommend bringing your passport and any necessary travel documents, as they’ll be required for hotel check-ins and to enter attractions. Plus, have your travel insurance information on hand just in case. Let us know if you have any other questions!

Are There Any Age Restrictions for the Tour?

The tour does not have any age restrictions. We recommend it for travelers of all ages who can participate in moderate physical activity. Just be sure to let the tour operator know of any special needs when booking.

Can I Book Additional Activities or Excursions?

Absolutely! The tour offers optional activities like a Venice by night tour and gondola rides that you can book separately. These add-ons allow you to customize your experience and see even more of Italy’s highlights.

How Do I Get to the Meeting Point From the Airport?

We recommend booking airport transfers or taking public transportation to reach the meeting point at Hotel St. Martin in Rome. The tour doesn’t include hotel pickup, so getting to the starting location is up to you.

The Sum Up

This 5-day itinerary offers an immersive and well-rounded experience of Italy’s cultural highlights. From the spiritual charm of Assisi to the artistic treasures of Florence, the culinary delights of Bologna, and the romantic canals of Venice, we’ll explore some of the country’s most beloved destinations. With guided tours and ample free time, this trip promises unforgettable memories and a deeper appreciation for the enchanting beauty of Italy.