If you’re looking to explore some of Italy’s most charming towns beyond Florence without the hassle of planning every detail yourself, this 2-day tour in Assisi and Gubbio might catch your eye. Offered by Bologna Tour & Best Italy Tour, it promises a cozy, well-organized experience that combines cultural highlights, scenic views, and delicious local products. We’ve looked into what this tour offers and what it might mean for your trip, so you can decide if it suits your travel style.
What we really appreciate about this experience is how it balances guided visits with free time, letting you soak in the atmosphere at your own pace. Plus, the inclusion of local tastings and visits to notable sights like the Basilica of San Francesco makes it feel authentic and immersive. On the flip side, the fixed schedule and group setting might feel a bit tight for those who prefer complete flexibility or have specific interests.
This tour is likely best suited for travelers who want a guided, comfortable taste of Umbria—especially those who appreciate cultural sights combined with good food. It’s perfect if you’re short on time but want a meaningful introduction to these iconic towns. Keep in mind, it’s a full, packed itinerary, so be prepared for some walking and a lot of sightseeing.
Key Points
- Comfortable Group Setting: As a private tour, only your group participates, which allows for a more personalized feel.
- Includes Local Tastings: Truffle and typical product tastings make the experience flavorful and memorable.
- Expert Guides: The guided tours of Assisi and Gubbio provide context and insights that enrich your visit.
- Efficient Itinerary: Covers key sights like the Basilica of San Francesco and Gubbio’s museums in just two days.
- Scenic and Cultural: Combines beautiful views with historic sites, offering a well-rounded taste of Umbria.
- Price Reflects Quality: At around $1,153 per person, it’s an investment but includes transportation, guiding, and tastings.
What to Expect from the Tour
While in Florence, here are other experiences we've covered
Starting from Florence
Your adventure begins early in the morning with a private van pickup from Florence. While the drive is just about an hour, it’s a comfortable way to start your day without the stress of self-driving or public transportation. Expect to be picked up at a designated point between 8:30 and 9:30 AM, which gives you a relaxed start.
Assisi: The Spiritual Heart of Umbria
The first major stop is Assisi, a town famed for its religious significance and stunning medieval architecture. Your guided tour will last about two hours, and you’ll visit the Basilica of San Francesco, a UNESCO World Heritage site. This basilica is a highlight of Italy’s religious architecture, famous for its frescoes by Giotto and its spiritual atmosphere.
Walking through Assisi’s narrow streets, you’ll get a sense of its medieval charm. Since the visit is guided, you won’t just see the sights—you’ll learn interesting stories and historical context that bring the place alive. The review from a past traveler mentions that the trip made them admire the “beautiful Umbria,” and the guided tour helps you understand why.
Gubbio: Medieval Charm and Local Flavors
After Assisi, the tour moves to Gubbio, another gem known for its medieval streets and stunning views. The guided tour here also lasts about two hours, with access to local museums. Gubbio’s streets are perfect for wandering, and the guides help you discover hidden corners or local legends you might otherwise miss.
What makes Gubbio especially appealing is the opportunity for a truffle tasting and sampling of typical products. This hour-long stop in the town’s center lets you indulge and relax in the company of your group. Past reviews highlight that the tasting experience is fantastic, with the chance to enjoy local specialties surrounded by greenery.
Relaxed Afternoon & Return to Tuscany
Following the tastings, you’ll have some free time to explore at your own pace—perhaps grab a coffee or soak in the views—before heading back to Tuscany in the late afternoon. The drive back is just about an hour, giving you time to unwind after a full day of sightseeing.
- Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
- The Best tour in Florence: Renaissance and Medici Tales
- Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni
- Florence Electric Golf Cart Tour
- Florence Vespa Tour: Tuscan Hills and Italian Cuisine
- Cooking Class and Lunch at a Tuscan Farmhouse with Local Market Tour from Florence
The Travel Experience: What We Like and Consider

This tour really shines in its combination of expert guidance and local immersion. The guides are knowledgeable, making the history and stories of Assisi and Gubbio come alive. You’ll likely find their insights add depth to your understanding of these towns.
The scenic drive and the chance to taste local products—especially the truffle tastings—are definite highlights. These elements turn the trip into more than just sightseeing; they’re about experiencing the essence of Umbria’s food culture and centuries-old architecture.
However, it’s worth noting that the itinerary is quite full. If you’re someone who prefers to explore at your own pace or has specific interests, the scheduled visits and group setting might feel a bit rushed. Also, since the tour runs for roughly two days, it’s best suited for travelers eager for a quick but comprehensive taste of this part of Italy.
About the Price
At over a thousand dollars per person, this experience isn’t cheap—but it does include transportation, guide services, tastings, and museum access. For travelers short on time who want a seamless, guided experience, this can be a worthwhile investment. However, if you prefer more independent travel or are on a tighter budget, you might consider visiting these towns on your own or choosing a different type of tour.
Who Would Love This Tour?

If you enjoy guided tours that blend history, scenery, and food, you’ll probably find this experience satisfying. It’s especially good for those who appreciate expertly guided visits, want to see Assisi and Gubbio without the hassle of planning transport, and love tasting local specialties like truffle products.
It’s a solid option for visitors who want a structured, comfortable way to explore a slice of Umbria, with just enough free time to soak up the atmosphere. If you’re traveling with a friend or partner who shares your interest in culture and cuisine, this tour offers a balanced mix of both.
Final Thoughts
This 2-day trip from Florence to Assisi and Gubbio manages to combine the convenience of guided touring with authentic, local experiences. The guides’ knowledge and the scenic views are standout features, making it a great way to see these two towns without feeling rushed. The inclusion of tastings adds a flavorful touch that elevates the experience beyond just sightseeing.
That said, it’s a considerable investment, so it’s best suited for travelers who want a comprehensive, worry-free way to enjoy Umbria’s highlights in a short time. If you’re after total independence, this might not be the best fit, but if you’re looking for a comfortably paced, guided adventure with a taste of local life, this tour hits the mark.
DA Florence: 2 days in Assisi and Gubbio
“Just before Christmas together with a group of friends we decided to treat ourselves to a weekend in Umbria.”
FAQ

Is this tour suitable for families with children?
While the tour is generally suitable for most travelers, it involves walking and a full schedule, so consider your children’s comfort with activity and walking.
What is included in the price?
The price covers transportation, guided tours of Assisi and Gubbio, museum access, and local tastings like truffles.
What is the duration of the tour?
The full experience is roughly two days, starting early in the morning and returning in the late afternoon of the second day.
Can I cancel the tour?
Yes, you can cancel up to 3 days in advance for a full refund.
Are meals included?
No, meals are not included, but tastings of local products are part of the experience.
How many people are in the group?
This is a private tour, so only your group participates, providing a more personalized experience.
Is transportation comfortable?
Yes, transportation is via private van, which is typically comfortable and climate-controlled.
What are the meeting points?
Pickups are available in Florence between 8:30 and 9:30 AM, making it convenient to start your day.
Is this tour accessible for people with mobility issues?
While the tour involves walking through towns with cobblestone streets, specific accessibility info isn’t provided, so check with the provider if needed.
If you’re after a taste of Umbria’s charm, history, and flavors in a straightforward, guided package, this tour might just be the perfect fit.
More 2-Day Experiences in Florence
More Tour Reviews in Florence
More Florence experiences we've covered
- Florence: Local Food Tour on a Rickshaw
- Semi-Private Gluten-Free Cooking Class in Florence
- From Florence: Wine Tasting and Dinner in Chianti Vineyards
- Wine Tasting with Cured Meats & Cheeses in Florence
- Florence: Private Michelangelo Tour with Giotto Pass
- Florence: Guided Tour Europe’s oldest pharmacy
- Florence: Accademia Gallery & Statue of David Express Tour
- PRIVATE Half-Day Tour: Chianti Classico Wine Experience.
- Florence: Walking Tour in a Group with a Russian Guide
- Florence: Authentic Pizza & Gelato Experience+Unlimited Wine
- 5 Mornings or 5 Afternoons Sculpture in Clay Guided Workshop
- Viator Exclusive: The Secrets of Gelato and Pizza Making-Florence


