Tuscany Day Trip from Rome with Vineyard Lunch and Wine Tasting

Wander through the medieval towns of Montepulciano and Pienza and enjoy a 3-course meal

4.91 (23) ·
Travel Flexibly
· 12h · Rome, Italy

Craving the ultimate Tuscan experience without the hassle of arranging your own experience from Rome? This exclusive day trip from Rome not only delivers everything you need but more: the medieval charm of Montepulciano and Pienza, a 3-course meal paired with exceptional wines, and seamless roundtrip transportation by private coach. With a local, English-speaking guide handling the details, you can simply relax, soak in the breathtaking views, and enjoy Tuscany at its finest.

What You Get With This Tour

  • Expert English-speaking guide
  • Roundtrip transfer from Rome
  • Guided tour of Montepulciano
  • Explore the hill town of Pienza
  • 3-course meal and wine tasting
  • Tuscan Renaissance escape
  • Guide tips

Tour Itinerary

  • 1

    Your tour begins at Piazza del Popolo

    Meet your expert guide and fellow travelers in the center of Rome before boarding your comfortable, air-conditioned coach. As you leave the city, watch the urban landscape transform into the iconic rolling hills and cypress trees of the Tuscan countryside.
  • 2

    Wander through medieval Montepulciano

    Explore this car-free hilltop village famous for its narrow stone streets and impressive clock towers. Your guide will share stories of the noble families who built these palaces while you admire the Renaissance architecture of the San Biagio church overlooking the valley.
  • 3

    Feast at a traditional Tuscan vineyard

    Visit a picturesque winery for a decadent three-course lunch featuring locally sourced ingredients and regional specialties. You will enjoy a guided tasting of several prestigious wines, including the world-renowned Brunello di Montalcino, while overlooking the estate's sun-drenched vineyards.
  • 4

    Explore the Utopian village of Pienza

    Next, travel to Pienza, a UNESCO World Heritage site famously redesigned by Pope Pius II to be the first "Ideal City" of the Renaissance. You will have free time to stroll through its perfectly symmetrical squares, taste local Pecorino cheese, and capture panoramic photos of the Val d'Orcia.
  • 5

    Your tour finishes at Piazza del Popolo

    Relax on the return drive to Rome as the sun sets over the Italian hills. You will arrive back at the original meeting point in the early evening, perfectly situated to enjoy a late dinner in the city after a full day of Tuscan discovery.

Additional Information

Good to know:

  • Accessibility: This tour includes walking tours through hill towns (Montepulciano and Pienza) with narrow, ancient streets. It is not suitable for wheelchair users or those with significant mobility issues. We are also unable to accommodate strollers.

  • Bag Policy: Luggage or large bags are not permitted on the coaches, as there is no storage space and the operator cannot take responsibility for any items left on board.

  • Dietary Restrictions: The meal is a 3-course traditional local lunch. Guests with specific dietary needs should please contact us in advance to inquire about accommodations.

  • Alcohol Consumption: The tour includes a wine tasting and wine paired with the meal. The legal drinking age in Italy is 18 years old.

  • Tour Duration: This day trip typically lasts 12 hours, however external factors may occasionally extend the tour duration slightly.

  • Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can enter sites on time.

Your 12-hour tour includes:

  • Expert English-speaking guide

  • Roundtrip transfer from Rome in air-conditioned coach with Wifi

  • Guided tour of Montepulciano

  • Explore stunning hill town of Pienza

  • 3-course meal and wine tasting (including Brunello di Montalcino)

  • Audio headsets

  • Maximum group size of 50

What to bring:

  • Comfortable walking shoes (for walking through hill towns)

  • Camera

  • Government-issued ID

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Customer Reviews

Natasha H., 23 October 2025

Amy B., 14 October 2025

A scenic, tasty, and one of a kind experience!
Ronnie T., 29 June 2025

I would like to shout out our guide Ana! The tour was an amazing way to get a true experience of Tuscany. Seeing the surrounding towns, learning about the local language and culture, as well as tasting the delicious food and wine! I purchased so many tasty treats to bring to my family back home! Cheers!

Lisa S., 17 June 2025

Great guides, and bus driver. Thoroughly enjoyed the day!!

Great day trip to Tuscany
Jorge R., 26 May 2025

Our one-day trip from Rome to Tuscany was a great experience overall. The planning and execution of the agenda were right on point—everything felt well-organized and thoughtfully timed, with no signs of improvisation. The tour delivered exactly what was promised when we booked it. Our main guide, Chiara, was lovely and helpful throughout the day. In Montepulciano, we were guided by Sarah, who impressed us with her knowledge and genuine passion for the history of the region. A special mention also goes to our driver, Tiziano—we always felt safe and comfortable on the road. The reason we gave the tour 4 stars instead of 5 is due to the lunch experience, which felt a bit disorganized. Some guests were served second helpings while others, including us, didn’t get the chance before our plates were cleared away. Additionally, while we really enjoyed the wine at the tasting, we missed the usual explanations that typically accompany such experiences. A short introduction or some background about the wines would have really enriched that part of the tour. That said, this tour is an excellent way to get to know Tuscany, especially for a first-time visit. We totally recommend it!

Show more reviews

Frequently Asked Questions

What to bring?

Wear comfortable shoes and clothes and bring a bottle of water and a hat during the summer. Appropriate dress is required for entry into some sites on this tour: knees, shoulders and backs must be covered.

Is this tour run by The Tour Guy?

This tour is operated by one of our trusted and vetted partners in Rome.

What if I have concerns about my mobility on this tour?

Unfortunately, due to the transportation involved in this tour, we are unable to accommodate guests in wheelchairs. If you have any doubts about your mobility, please contact our team.

What happens if it rains?

We run our tours rain or shine!

Is lunch included in the price of the tour?

Yes, lunch is included! You’ll enjoy a 3-course meal at a vineyard in Tuscany. Please keep in mind that customers who have not reached Italy's legal drinking age of 18 will not be served alcohol.

What if I have food allergies, intolerances, or other dietary requirements?

Please contact us in advance so we can do our best to accommodate your needs. We will work with our tour partners to provide you with an alternative when possible.

What if I don’t drink alcohol but I’d still like to join a food tour?

Not a problem. Please let us know in the comment box when you book your tour so we can make sure an alternative drink is provided.

Can I bring my kids and do I have to pay for them?

Kids are welcome on this tour and can join for free if under 1 year of age (but won't have a reserved seat on the couch). Children under 14 years old pay a reduced fee. Make sure to select the appropriate number of guests during the booking. If you have small children, please keep in mind that we are unable to accommodate strollers.

Does this tour include hotel pickup?

No hotel pickup is included on this tour. You’ll meet your guide at the designated meeting point in Piazza del Popolo.

Is there any chance the Tour Guy will cancel this tour?

On the rare occasions the tour is canceled, we'll inform you as soon as possible. We will work with you to reschedule your tour when possible or provide a full refund.

How long will the tour last?

This day trip typically lasts 12 hours, however external factors may occasionally extend the tour duration slightly.

Can I bring my luggage with me on the tour?

Unfortunately not, as we do not have a storage space to accommodate items on our coaches. We are also unable to take responsibility for any baggage that would be left on the coach.

Start From: $84.18

Available days Discounted days

Free cancellation up to 24 hours in advance!