Tuscany & Assisi Small Group Day Trip from Rome with Wine

Exploring Tuscany & Assisi with a Small Group: An Authentic Day Trip from Rome

Travelers often dream of a day immersed in Italy’s scenic countryside, historic towns, and delicious wine—but the reality can sometimes fall short if you’re in a big, crowded tour group. This particular small group day trip from Rome promises not only a handful of iconic locations but also a more intimate, genuine experience. With a friendly guide, cozy transport, and well-chosen stops, it’s a well-rounded introduction to some of Italy’s most beloved treasures.

What we really love about this trip? First, the small group size guarantees a more personal touch, making it easier to ask questions and soak up the atmosphere. Second, the combination of scenic viewpoints and cultural sights—like Trasimeno Lake and Assisi’s basilicas—feels thoughtfully balanced. Third, the delicious Italian lunch paired with local wines truly enhances the experience, giving you a taste of Tuscany’s culinary pride. The only caveat? With a packed 12-hour schedule, some travelers may find the timing tight, especially if they like savoring each stop at leisure.

Ideal for those seeking a combination of history, nature, and gastronomy, this tour offers a great taste of Italy beyond Rome’s city limits. If you’re after authentic scenery, engaging guides, and the chance to sample regional wines, this trip could be just the ticket.

Good To Know

• Intimate Experience: Small group size (limited to 8 participants) offers a personalized, relaxed atmosphere.
• Diverse Highlights: Combines scenic lake views, charming towns, and religious sites for a well-rounded day.
• Authentic Food & Wine: Enjoy a three-course lunch with wine tasting at a family-run Tuscan winery.
• Comfortable Transport: Air-conditioned minivan makes long drives comfortable and stress-free.
• Expert Guidance: An English-speaking guide with positive reviews, including mentions of knowledgeable and friendly hosts.
• Flexible Itinerary: Well-planned stops with scenic photo opportunities and free time in key locations.

You can check if your dates are available here:

A Deep Dive into the Experience

Starting Point and Transportation

Your adventure begins at Piazza della Repubblica in Rome, where the guide will be waiting outside the Santa Maria degli Angeli e dei Martiri church next to a black van. The transport itself is a highlight—an air-conditioned minivan that ensures comfort during the long drive through Italy’s scenic landscape. Traveling in a small group keeps the journey intimate and allows for meaningful conversations or just relaxing with the countryside flying by.

Montepulciano: The Tuscan Gem

First stop is Montepulciano, often called “Under the Tuscan sun” in many films and travel stories. Here, you get roughly two hours of free time to wander the medieval streets, browse local shops, or simply sit with a gelato while soaking in the views of rolling hills and vineyards. The town’s atmosphere is relaxed but lively, and walking through its narrow alleys feels like stepping into a postcard.

A key photo stop is at the Temple of San Biagio, a stunning Renaissance church with a striking façade that dominates the countryside. According to reviews, many travelers appreciated the chance to snap pictures of this architectural marvel against a backdrop of lush landscapes. One reviewer, Claudio, mentioned that the guide’s explanations made the visit even more memorable, and the driver’s smooth, safe driving allowed everyone to relax and enjoy each moment.

The Culinary Experience: Wine & Lunch

No visit to Tuscany is complete without savoring its food and wine, and this tour delivers with a three-course lunch at a traditional, family-run winery. The meal includes local specialties and a wine tasting that lets you sample regional vintages. Guests describe the experience as a highlight; Claudio expressed gratitude for the “incredible” wine and the attentive service, noting the opportunity to enjoy authentic flavors in a cozy setting.

The timing for lunch is about 1.5 hours, giving you enough time to indulge without feeling rushed. The guide’s insights on wines and local culinary traditions help you appreciate each sip and bite, making it more than just a meal but an educational experience.

More Great Thing To Do Nearby

Trasimeno Lake: Serene Scenic Stop

Next, a quick scenic drive takes you to Lake Trasimeno for a 15-minute photo stop. This peaceful lake, with its calm waters and gentle hills, offers a perfect moment for reflection and picture-taking. Reviewers appreciated this stop as a chance to connect with nature and enjoy a calmer pace amid the busy day.

Assisi: The Spiritual and Artistic Treasure

The final major highlight is Assisi, home to the revered Basilica of Saint Francis. You’ll enjoy a guided tour by a friendly, knowledgeable local who brings the site’s religious and artistic significance to life. The basilica’s beautiful frescoes and the tomb of Saint Francis resonate deeply, especially for those interested in religious history or stunning religious art.

Guests, including Tadea, praised the guide’s attentiveness and how the tour balanced historical context with accessible storytelling. You’ll have around two hours here to walk, explore, or relax in the charming town streets. Many find Assisi to be a peaceful, inspiring ending to a long day.

Returning to Rome

The drive back is about 2 hours and 20 minutes, giving plenty of time to reflect on the day’s sights or chat with fellow travelers. The tour concludes back at the starting point, Piazza della Repubblica, around evening time.

Why This Tour Works for You

This experience blends scenic beauty, cultural richness, and culinary delights in a way that feels genuine and manageable. The small group size makes it ideal for travelers who prefer a more personal, relaxed atmosphere over large bus tours. The balanced itinerary means you get a taste of Tuscany’s most iconic towns, a tranquil lake, and Assisi’s spiritual sites—all packed into 12 hours.

The value for the price comes from the combination of guided insights, quality transportation, included meals, and exclusive photo stops. It’s perfect if you want to maximize your day without the hassle of planning every detail yourself.

Who Might Not Love It?

Because of the packed schedule, this tour might not suit travelers who prefer slow, unstructured exploration or those with mobility issues. It also requires comfortable shoes and moderate walking, especially around Montepulciano and Assisi. If you’re a big fan of spending more time at each site to absorb every detail, you might find the pace a little quick.

Final Thoughts

This small group day trip from Rome truly captures the essence of Italy’s diverse regions—combining scenic vistas, historic towns, and authentic cuisine in one seamless experience. The personal guidance and thoughtfully chosen stops make it a wonderful way to see Tuscany and Assisi without the stress of self-organizing.

It’s especially well-suited for travelers who value intimate group settings, expert guides, and a mix of cultural and natural sights. The inclusion of a wine-tasting lunch elevates it from a simple sightseeing tour to a full Italian experience—delicious, authentic, and memorable.

If you’re after a day that balances history, scenery, and gastronomy, this trip offers excellent value. Just pack comfortable shoes, your camera, and a sense of adventure—you’ll leave with a fuller heart and plenty of photos.

FAQ

Is hotel pickup included?
No, the tour starts at Piazza della Repubblica in Rome, next to Santa Maria degli Angeli church.

What should I bring?
Comfortable shoes, a hat, camera, sunscreen, and water are recommended.

How long is the overall tour?
The entire experience lasts about 12 hours, with the start time depending on availability.

Is the tour suitable for children or seniors?
It’s best suited for those comfortable with moderate walking and a full schedule; it may not be ideal for very young children or those with mobility restrictions.

Are dietary restrictions accommodated?
This isn’t specified, but since the lunch is at a family-run winery, you might want to clarify dietary needs when booking.

What is included in the price?
Transport, a three-course wine tasting lunch, guided tour in Assisi, entry fees, and a small group guarantee are included.

Can I cancel?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is it suitable for people over 264 lbs?
The tour notes certain weight restrictions and may not be suitable for those over 264 lbs (120 kg) due to comfort and safety considerations.

Will I have free time at each stop?
Yes, you’ll have enough time to explore Montepulciano and Assisi at your own pace, plus brief photo stops at Trasimeno Lake and San Biagio.

This day trip offers a well-rounded taste of Italy’s heartland—beautiful towns, serene lakes, historic sites, and hearty regional food. It’s ideal for travelers wanting a guided yet intimate experience that balances sightseeing with genuine local flavor.

You can check if your dates are available here: