Florence · TUSCANY COUNTRYSIDE TOURS
Every Florence trip has one free day too few. These 15 tuscany countryside tours justify the slot, priced and timed so you can decide in minutes and get back to the fun part of planning.
Small-group Chianti Classico tastings from Florence, two winery visits, wine and olive oil pairings, plus time to shop in the hills.
“Wonderful, very nice, wine is great, beautiful landscape, guide and driver very nice, bus arrived on time, sufficient time on every stop. Plenty of wine and cheese”
San Gimignano, Monteriggioni, Chianti winery lunch and wine tasting, plus Siena with optional cathedral access, all by coach from Florence.
“We had a day trip to San Gimignano and Siena. The tour was amazing and well-managed. All thanks to Alessandra and Enrico. The lunch and wine tasting experience were good. The guided visit to Siena was merged with another language, thus, making it difficult to understand.”
Full-day Tuscany trip from Florence to Siena, San Gimignano and Monteriggioni, with Chianti tastings, snacks, and guided sightseeing.
“A jam packed day in Tuscany. Well organized and great value for all the sights plus wine tasting. Roberto was excellent”
Full-day Florence trip to Val d'Orcia’s hill towns with Brunello and Vino Nobile tastings, Pienza, and a Gladiator filming stop.
“Overall a bit underwhelming experience. The tour guide Jarromo was knowledgeable and friendly. But one of our seat was a jump seat and one was the last seats. Both were very uncomfortable and the jump seat ahead had no ventilation. This is a long trip we a lot of driving and the organizers should leave some seats open to make everyone comfortable. Also, after seeing Montepulcino and Pianza visiting Montalcino was a bit repetitive and dropping that may nicely experience crisper. Was tasting was nothing special. Actual visit to a vineyard would be a better unique experience. Also it’s a lot of climbing and walking on the hills. So, caution…”
Val d'Orcia day trip from Florence with Brunello and Vino Nobile tastings, Pecorino cheese in Pienza, plus medieval hill towns.
“Our host Roberto was amazing. So well organized and full of great information and he kept a great pace to the day. Nice coach transportation and great wines sampled with lite snacks. Enough personal time to walk about the three towns and have lunch in Piensa. Overall very worth the full day excursion. Highly recommended.”
Ride a vintage Vespa from Florence through Tuscan hills, stop for skyline photos, then enjoy prosciutto, cheese, and Chianti.
“Leo (leoni) was amazing! Friendly and informative and most of all, safe. Allowed for some fun in the Vespa and also great stopping points. We had our own group of friends totaled at 8. Would absolutely book again! I heard from the whole group of other guests with different guides that they were all amazing as well!”
Ride a Vespa through Chianti Rufina country roads, then enjoy a family winery tour, lunch, and wine tasting from Florence.
“We loved this tour so much. Dejan, Alexa, Luca, Marcelo and the whole tour staff kept us laughing. Although we didn’t all drive Vespas since some of were very incompetent vespa drivers (me), we enjoyed the ride on the back of a tour guides bike around the beautiful chianti countryside. No one wants to check in to the hospital on vacation, so thank you for keeping us safe. The wine tasting was really delicious. Grab a few bottles before heading back to your vacation lodging. I would give Tuscany Cycle 10 stars out of 5. Truly a beautiful memory I will never forget.”
Florence to Tuscany farm day: vineyard walk, organic wine tasting, and hands-on fresh pasta class with lunch or dinner, plus limoncello.
“Such a great experience! Loved Christina our guide-so genuine & knowledgeable! Even in the pouring g rain we had an amazing time! Wine tasting superb and pasta making was so fun!!”
Florence to Val d'Orcia: Brunello and Nobile tastings in Montalcino and Montepulciano, Pienza lunch, castle stops and views.
“Great day in Tuscany. I want to say thank you to Simona and the wineries for making our experience wonderful. Simona went above and beyond to help make it a great day. Thank you Simona. Ci rivediamo presto speriamo!”
Drive a restored vintage Fiat 500 through Tuscany from Florence, with photo stops, safety training, and Chianti with cheese and ham.
“Mano the Tour guide was excellent and very informative 10 out 10 for the whole tour and here team 👍”
Sunrise hot air balloon over Chianti from near Florence. One-hour flight, prosecco toast, and a hearty breakfast included.
“I highly recommend this experience to anyone considering the balloon flight, The balloon basket was larger than I expected meaning there were more people on the ride, but this did not impact the quality of our experience. It was an amazing experience. The flight was seamless, our pilot very friendly, professional and very skilled at piloting our balloon. It is an incredible way to experience Tuscany and I highly recommend it.”
Florence day trip to Monteriggioni and Val d'Orcia, with medieval walls, the Templar Museum, Pienza cheese stops, and optional wine tasting.
“Amazing day trip into the tuscan countryside. Val d'Orcia is pure heaven! We didn't opt for the wine tasting so we had free time in all 3 towns, which suited us perfectly. There was just enough time to get a great taster of each town if you only have one day to experience it from Florence like we did.”
A small-group day trip from Siena to San Gimignano and Volterra, with pilgrim-road walks, saffron lunch, and alabaster artisans.
“Tour guide was awesome. Communicated well. Has great knowledge of the area. Friendly and safe.nnnnnnnn”
Horseback ride through Siena’s countryside past vineyards, rivers, olive groves, and cypress roads, with training for all levels and optional tastings.
“Horseback riding was our favorite activity to do while in Italy! We were so grateful for Giulio for his passion and enthusiasm on the tour, and his patience, and kindness with five of us. He made us feel safe and comfortable on each of our horses and the ride through the countryside was incredible and so beautiful. All of us had only been on a horse a couple times, but the horses were very well-behaved and made riding easy. We also were hesitant about getting to and from the farm but Giulio even helped us arrange a taxi back which was very much appreciated. Highly recommend!Read more”
Escorted Florence day trip to San Gimignano, Monteriggioni, and Siena, with a Chianti winery lunch and wine tasting. Go your own pace.
“Everything was amazing. I liked that they spent quite long in San Gimignano even though its small as its so beautiful. Also they get there early morning to avoid crowds. Siena was also stunning. Hosts Ricardo and Fabiana (I may have got these names a bit wrong as writing from memory) were great. They have stressful jobs to manage such large groups but they both did a great job remaining calm and friendly all the time.”
Every kind of day out, and the best of each.
