Tuscany & Assisi Small Group Day Trip from Rome with Wine

Exploring Italy’s heartland in a single day sounds ambitious, but this Tuscany & Assisi Small Group Day Trip from Rome with Wine manages to pack in a satisfying mix of scenery, history, and authentic experiences. Designed for those who want to see some of Italy’s most picturesque villages, religious treasures, and natural beauty without the hassle of planning, this tour offers a well-rounded taste of Umbria and Tuscany.

Two features we particularly appreciate are the small-group setting, which means more personalized attention and less rushing, and the delicious, traditional lunch at a family-run winery—a true highlight that speaks to Italy’s love of good food and good wine. The only consideration? With a packed itinerary, you’ll want to be prepared for a full day of sightseeing and moderate walking, especially in historic towns and religious sites.

This tour is perfect for travelers who value rich scenery, cultural insight, and excellent local food but prefer an itinerary that’s manageable rather than overwhelming. If you’re eager to experience Italy beyond Rome’s bustling streets, and enjoy a mix of art, nature, and culinary delights, this trip could be just the ticket.

Key Points

• Limited Small Group: With only 8 participants, the experience feels intimate and flexible.
• Cultural and Natural Highlights: Visit Assisi’s Basilica of Saint Francis, explore charming Montepulciano, and enjoy Trasimeno Lake views.
• Authentic Taste of Tuscany: Experience a three-course lunch paired with local wines at a traditional family winery.
• Comfortable Transportation: Air-conditioned minivan ensures a relaxed journey between sites.
• Flexible Free Time: Ample opportunity to explore towns at your own pace, take photos, and soak up the atmosphere.
• Knowledgeable Guides: Guides are praised for their friendly, insightful commentary, adding depth to each stop.

You can check availability for your dates here:

An In-Depth Look at the Tour Experience

This day trip is crafted to give travelers a comprehensive and balanced taste of the Umbrian and Tuscan landscapes, history, and lifestyle. Starting in Rome, you’ll be whisked away in a comfortable air-conditioned minivan, heading north through scenic countryside. The tour’s small group size—limited to 8 travelers—ensures that everyone can enjoy personal interaction and more flexible pacing.

The Journey Begins: From Rome to Montepulciano

The first major stop is Montepulciano, often called the “pearl of the Val d’Orcia.” This hilltop town is famous for its medieval streets, Renaissance architecture, and, of course, its wine. The itinerary allows about two hours of free time, giving you the chance to wander the narrow streets, browse local shops, or simply soak in the views of the rolling hills and vineyards.

What makes Montepulciano special isn’t just its beauty but also its atmosphere. We loved the way the town’s quiet charm invites wandering without a fixed agenda. One traveler described it as the “Under the Tuscan sun” setting, perfect for photos and just soaking in the vibe.

Iconic Photo Stop: Temple of San Biagio

Just outside Montepulciano, you’ll stop at the Temple of San Biagio—an impressive Renaissance church designed by Antonio da Sangallo the Elder. Its grand stone façade and commanding position make it a favorite for photos, and you’ll appreciate the opportunity for a quick visit and some stunning shots.

The Heart of the Day: Wine Lunch at a Traditional Winery

After exploring Montepulciano, the tour continues with a delightful three-course lunch at a family-managed winery. This isn’t just about eating; it’s about experiencing authentic Tuscan hospitality paired with local wines. The hosts take pride in their craft, and the tasting includes multiple wines that perfectly complement the hearty, flavorful dishes.

As one review notes, the guide’s knowledge about wine and local food added depth to the experience, making it much more than just a meal. It’s a genuine peek into regional traditions, and the relaxed setting allows for conversations that bring the local lifestyle to life.

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Scenic Drive and Lake Trasimeno

Next, the journey takes you to Lake Trasimeno, Italy’s fourth-largest lake. The stop here is brief—about 15 minutes— but enough to capture some peaceful landscape photos. The lake’s tranquil waters and surrounding hills provide a wonderful contrast to the busy towns, making it a perfect moment for reflection or a quick photo.

Artistic and Religious Treasures in Assisi

The final major stop is Assisi, famed for its religious significance and stunning architecture. With a guided tour led by an English-speaking local, you’ll visit the Basilica of Saint Francis and his tomb. The basilica’s frescoes and spiritual atmosphere are highlights, and your guide will help interpret the art and history behind them.

Assisi’s narrow streets and hilltop views make it a delight to explore at your leisure. You’ll have about two hours of free time here to wander, take photos, or visit additional sites if you wish.

Return Journey and Reflection

The tour concludes with a scenic drive back to Rome, arriving at the starting point around 12 hours after departure. Travelers consistently praise the smoothness of the logistics and the friendly, knowledgeable guiding, which makes the long day feel satisfying rather than exhausting.

Practical Details and Value

At $395.36 per person, this tour offers a comprehensive package that includes transport, guided tours, all entrance fees, and a memorable lunch. When you consider the convenience of door-to-door transportation, the expert guidance, and the quality of the experiences, the price becomes quite reasonable—especially given the small-group setting.

The departure from Piazza della Repubblica, with clear instructions to meet in front of Santa Maria degli Angeli, makes planning straightforward. The tour’s focus on authentic experiences, scenic beauty, and cultural insight makes it an excellent choice for travelers who want to see Italy’s countryside without the hassle of self-driving or complicated itineraries.

What to Expect

• Expect a full 12-hour day filled with sightseeing, walking, and photo opportunities.
• Be prepared for moderate walking, especially around towns and religious sites.
• Bring comfortable shoes, sun protection, water, and a camera.
• The tour is not suitable for those with mobility issues or large wheelchairs, as some restrictions apply.
• Since alcohol is not allowed in the vehicle, enjoy your wine tasting at the winery.

Authentic Experiences and Honest Insights

Travelers who have participated in this tour repeatedly praise the knowledgeable guides and the stunning scenery. One reviewer happily remarked that Assisi is “really marvelous,” and the guide’s explanations made the art and history come alive. Another appreciated the safe, relaxed driving, which allowed everyone to relax and enjoy the day without worry.

The wine tasting lunch is often highlighted as a true highlight—an authentic, hearty meal that feels like a warm invitation into Italy’s culinary heart. The views at Trasimeno Lake, along with the charm of Montepulciano and Assisi, provide plenty of photo opportunities and memorable moments.

Who This Tour Is Best For

This experience is ideal for small groups who enjoy cultural sites, scenic drives, and culinary delights. It’s perfect for those who prefer a guided experience but still want some free time to explore on their own. If you’re interested in religious history, art, and authentic rural life, you’ll find plenty to love here.

However, it’s not suited for travelers with mobility issues or those who want a more leisurely pace with less walking. The full day means a commitment, but the variety of stops ensures you’ll come away feeling as if you’ve truly sampled Italy’s heart.

FAQs

Is hotel pickup included? No, you meet the guide at Piazza della Repubblica in Rome. Endpoints are the same as the starting point, with no hotel pickup or drop-off.

How long is the drive between sites? The drive time varies; for example, it’s about 1.5 hours from Rome to Montepulciano, and around 40 minutes from Trasimeno Lake to Assisi.

What should I bring? Pack comfortable shoes, a hat, sunscreen, a camera, and plenty of water. Weather conditions may vary, so dress accordingly.

Are meals included? Yes, the three-course lunch with wine tasting at the winery is part of the package, offering great value.

Is this tour suitable for children? The tour is designed for small groups and includes walking and site visits, so it’s best for older children and teenagers comfortable with walking.

Can I cancel if my plans change? Yes, you can cancel up to 24 hours before the tour for a full refund, making it flexible for changing plans.

Are there any restrictions I should know? The tour is not suitable for those with certain mobility restrictions or large wheelchairs, and certain age and weight restrictions apply.

Is it a guided tour? Yes, an experienced English-speaking guide accompanies you, providing insight and answering questions along the way.

This tour offers a delightful blend of Italy’s landscapes, art, religious sites, and culinary traditions—all wrapped into one well-organized day. Whether you’re seeking beautiful vistas, historical richness, or delicious wine, it delivers a satisfying taste of Italy’s central regions.

You can check availability for your dates here: