Montepulciano Wine Tasting and Assisi Private Day Tour from Rome

Traveling from Rome and exploring two of Italy’s most intriguing spots in one day sounds ambitious, but this private tour makes it surprisingly doable. Designed for those who want a blend of scenic countryside, historic sites, and a bit of indulgence, it offers a taste of Tuscany’s wine culture alongside the spiritual beauty of Assisi.

What really drew us in are the personalized experience—a private driver and guide means less waiting and more tailored exploration—and the chance to sip wines in an ancient cellar, paired with local cheeses and cured meats. We also appreciate the visit to Assisi, especially for its iconic basilica and the significance of Saint Francis’ legacy.

However, this is a full-day adventure that involves quite a bit of driving and some organized time constraints. If you’re looking for a relaxed, unhurried pace with a lot of free time, this might feel a bit rushed. It’s best suited for travelers who enjoy a structured itinerary that maximizes sightseeing without sacrificing comfort.

If you love combining food, wine, history, and stunning views in one trip, this tour is a very solid choice. It’s especially ideal if you prefer a private experience that skips the larger group chaos, and the price reflects the level of personalized service and exclusive access.

Key Points

• Private transportation and guide provide a personalized, comfortable experience.
• Wine tasting includes at least four wines paired with local cheeses and cured meats.
• The itinerary covers both stunning Tuscan views and Assisi’s spiritual sites.
• Timing is tight, so be prepared for a full day with lots of sights packed in.
• The price is on the higher side, but largely reflects the private service and exclusive visits.
• Booking in advance is recommended, with most travelers booking about 88 days ahead.

What to Expect from This Tour

The Journey Begins: Rome to Montepulciano

The day kicks off with hotel pickup in Rome, in a luxury vehicle, setting a tone of comfort and ease. Your private driver will take you on a scenic drive through Italy’s countryside, giving you glimpses of rolling hills and vineyards—perfect for snapping photos and settling into the rhythm of the day.

Montepulciano: A Medieval Jewel with Breathtaking Vistas

Your first stop is Piazza Grande, the heart of Montepulciano, perched high on a hill. We loved the way this town combines medieval charm with Renaissance elegance—think ornate palaces, ancient churches, and winding cobblestone streets. The views over Val d’Orcia and Val di Chiana valleys are genuinely breathtaking, offering those classic Tuscany landscapes that make your camera work overtime.

During the roughly three hours here, you’ll stroll through the streets, admire the architecture, and visit a historic wine cellar. The cellar is quite the highlight—an ancient space where you’ll taste at least four different wines, expertly paired with local cheeses and cured meats. The guide’s explanations help you appreciate the wines beyond just tasting; you learn about their origins and what makes Montepulciano wines special.

Assisi: A Spiritual and Artistic Treasure

Next, the journey takes you to Assisi, a town renowned for Saint Francis. The main draw is the Basilica of Saint Francis of Assisi, a UNESCO World Heritage site filled with frescoes by Cimabue and Giotto. The basilica is deeply moving, especially considering it’s the burial place of Saint Francis himself.

You’ll also visit the “Porziuncola”, a tiny chapel where the Franciscan movement began, making it an important pilgrimage site. The guide points out the significance of this humble space in religious history. Plus, you’ll see the Basilica of Santa Chiara, another key religious site in Assisi.

The visit to Assisi is about three hours, giving you enough time to absorb its spiritual atmosphere and appreciate its art and architecture. Keep in mind that dress code requires knees and shoulders to be covered, so plan accordingly.

End of the Day: Comfortable Return to Rome

After a full day of sightseeing, your private chauffeur will bring you back to your hotel in Rome, typically in the evening. The smooth, private transfer ensures you can relax after a busy day, reflecting on the day’s highlights.

What Makes This Tour Stand Out

The Personal Touch

Unlike large group tours, the private nature means you get tailored attention and flexibility, which is especially valuable at sites like Assisi, where crowds can get overwhelming. The guide (not available on Sundays due to masses) is knowledgeable and friendly, making the experience educational as well as enjoyable.

Wine and Food Pairing

The wine tasting is more than just a sip of wine; it’s paired with local cheeses and cured meats, giving you a true taste of regional flavors. The visit to a centuries-old cellar adds a sense of history to your tasting experience, making it more memorable than just sampling wines at a restaurant.

Scenic Views and Cultural Depth

Both Montepulciano and Assisi are places that invite awe—Montepluciano with its panoramic vistas, Assisi with its spiritual and artistic aura. We found that the views from Montepulciano’s piazza are particularly stunning, making it the perfect photo stop.

The Practical Side

Duration and Pace

The tour lasts around 8 to 9 hours, which is quite full. While the itinerary is well-organized, it’s worth noting that you’ll spend a significant part of the day on the road. If you’re not a fan of long bus or car rides, this might be a bit tiring.

Cost and Value

At approximately $1,140 per person, the price is certainly on the higher end. However, it includes luxury transportation, private guide, all entrance tickets, and a comprehensive wine tasting. For travelers seeking a premium, hassle-free experience that combines several highlights, the cost can be justified.

Booking in Advance

Most travelers book about 88 days ahead, which suggests it’s a popular choice. Planning early ensures you secure a spot, especially during peak seasons.

Who Is This Tour Best For?

This experience is ideal for travelers who want a personalized, seamless day exploring Tuscany and Assisi without the hassle of self-driving or arranging multiple tickets. It’s suited for those who appreciate wine, history, and art, and want a comfortable, structured day.

If you’re a bit pressed for time but want to see both regions, this tour packs in a lot, but be prepared for a busy day. It’s not designed for leisure or slow sightseeing, but rather for those eager to maximize their Italy experience with a touch of luxury.

FAQs

Is transportation included?
Yes, the tour includes pickup and drop-off in a luxury vehicle with private transportation, making the journey between sites smooth and comfortable.

Can I participate if I have mobility challenges?
Most travelers can participate, but since the tour involves walking around towns and sites like the basilica, some mobility considerations may be necessary. It’s best to check with the provider if you have specific needs.

What’s the focus of the wine tasting?
The tasting features at least four wines paired with local cheeses and cured meats, providing a taste of Montepulciano’s renowned wine tradition.

Is the tour available on Sundays?
Yes, but note that the guide will not be present during Mass inside the basilica on Sundays, which might limit some explanations.

How long do we stay in each location?
You’ll spend about 3 hours in Montepulciano and roughly 3 hours in Assisi, with travel time included, making it a full but manageable day.

What should I wear?
For visits to religious sites like the basilica and Porziuncola, knees and shoulders must be covered. Dress comfortably but respectfully.

In the end, this private tour offers a well-rounded experience—beautiful scenery, a good dose of history and spirituality, and the chance to savor excellent wines. It’s a bit pricey, but the privacy, convenience, and quality make it a worthwhile choice for those wanting to get a lot out of one day without the stress of planning every detail. Whether you’re a wine lover, history buff, or spiritual seeker, this journey provides a meaningful snapshot of Italy’s diverse charms.