DAY TRIPS FROM ROME · ITALY
The best of Rome, in one place.
The 15 most popular tuscany & montepulciano day trips in Rome, with prices, run times and the booking platform for each. The ones worth fixing your days around, and what each actually gets you once you are through the gate.
Rome to Tuscany day trip: Montepulciano walk, Pienza UNESCO free time, Tuscan farm lunch with Brunello tasting, coach comfort.
Most Popular“Enjoyable and beautiful countryside. We enjoyed the stories of the guide and the visit to the Christmas market in Montepulciano.”
Rome-to-Tuscany day trip packs Florence highlights and Pisa’s Leaning Tower into a tight, bus-powered 14-hour plan with bilingual guidance.
“Lisa is our tour director, she is very knowledgeable, friendly, and very helpful. She take time and wait for everyone in the group.”
Ride a prebooked high-speed train from Rome to Florence, then head to San Gimignano for a family winery lunch and wine tasting.
“Had an amazing tour with an excellent guide! Highly recommend it to anyone looking for a great experience!”
High-speed train to Florence and Tuscany wine country. Guided Renaissance walk, family winery lunch and tasting, plus San Gimignano towers.
“This tour was our favorite part about our 8 day visit to Italy. Our guide, ANTONIO, was absolutely wonderful. He was so kind, personable, flexible, accommodating, fun, & charming. We saw amazing sights in Florence & so much enjoyed the visit to the quaint, family-owned winery. The best part was the visit to the small…”
Guided Siena and San Gimignano day trip from Rome with winery tasting, lunch, and historic sights in a small semi-private group.
“We had a great time. My wife 😍 needed to walk slowly with a cane and she was not rushed or left behind like many other tours. Our guide kept everything at her pace. Great job!”
Rome to Tuscany in 12 hours: Montepulciano and Montalcino, DOCG tastings, friars refectory lunch, Wi-Fi, and film spots.
“I thoroughly enjoyed this tour everything I experienced was amazing.”
A private Tuscany wine day from Rome with Montepulciano, Bagno Vignoni, a Montalcino winery tasting and lunch, plus UNESCO Pienza.
“Viator outsources tours which most time is ok. In this case we have to recommend not using this tour company or guide. This experience was nothing short of horrific. What should have been a VIP small group turned to a nightmare. We were a party of 5, there was another couple and our last pick…”
Tuscany & Pitigliano day tour from Rome with hotel pickup, small-group winery tastings, hill towns, and a three-course lunch.
“Ziggy was an amazing guide. He kept us informed every step of the way regarding times of arrival at the different stops, answered all our questions and gave us dinner recommendations once we arrived back in Rome. Highly recommend this tour if you are wanting to get out of Rome for the day!”
Private Montepulciano and Pienza day tour from Rome with hotel pickup, underground cellar tastings, and UNESCO cheese stops.
“Such a stunning day! The two towns were beautiful! We had enough time to explore. The restaurant recommended was stunning!”
Private day trip from Rome to Pienza and Montepulciano in Val d’Orcia with tastings, guided stops, and comfy pickup in a dedicated vehicle.
“Our tour guide was very informative, kind and helpful. The cheese tasting in Pienza was delicious. We also learned about the cheese aging process. Pienza is a small country town where you imagine sitting and sipping coffee all day. The lunch was good afterwards and my husband and I throughly enjoyed learning about the wine…”
Full-day Rome to Tuscany wine tour with tastings at 2 wineries in Chianti and Vernaccia, plus San Gimignano and Florence free time.
“This was a great experience, we had our train tickets sent to us (we came from Rome). They were messaging us that day to make sure we made it to the train and that we were okay. Then, we met with the rest of the group and tour guide in Florence, about a 25 minute…”
Private Tuscany day trip from Rome to Montepulciano and Pienza, Nobile wine tasting, cheese stops, and hotel transfers in 10 hours.
“Marrow was very knowledgeable about all of Roma and Tuscany region. My family loved the tour and would recommend to others. Must try wine and relaxing trip. The views were awesome.”
Private Tuscany day trip from Rome with Siena and San Gimignano plus a family winery lunch and wine tasting, with hotel pickup.
“Amazing trip! The vineyard owner was so friendly and welcoming and treated us like family! Loved this !!!”
Sample classic Tuscan bites and Chianti wines on a Florence food walk from Oltrarno to Santa Croce with family-run tastings.
“Amazing experience! Don't miss this! Highly recommend”
Rome to Siena and San Gimignano for a full-day Chianti wine tour with a cellar visit, 10 tastings, and a local lunch.
“Monica and Luigi were excellent! This was our favorite tour during our stay in Rome. Siena and San Gimignano were interesting and beautiful. The history of Siena is fascinating. Our wine tour and lunch were spectacular - VERY generous amount of different wines and delicious locally sourced food. I would do this again!”
From the Colosseum and the Vatican to the trattorias of Trastevere and the day trips beyond the walls.
