Italy · TUSCANY DAY TRIPS
Every trip has one free day too few. These 15 tuscany day trips are worth giving it to — priced and timed so the decision takes minutes, not an evening.
See Siena, San Gimignano, and Pisa plus a Chianti winery lunch and wine tasting on an early start day trip from Florence.
“Unreal. Go on this. All I have to say. With my boys and having the best time. The tour hasn’t even finished and I wanna come back!”
Rome to Tuscany day trip with Montepulciano and Pienza. 3-course farm lunch, Brunello tastings, and an air-conditioned coach.
“The lunch was mediocre at best. 5 measly sips of wine. Probably one glass of wine total. They really needed to have some bottles in the tables. The drive itself was nice and the tour guide was great.”
A small-group 4.5-hour Chianti Classico wine and olive oil tour from Florence, with two winery visits, tastings, and Tuscan snacks.
“This was a great tour. Jonathan was an excellent guide. Very informative and kept us entertained”
One full day from Florence to Pisa, Siena, San Gimignano, and Chianti vineyards, with a guided Siena walk, cathedral entry option, and lunch with 4 wines.
“It was a great trip, I’m a vegetarian and the food was great. We brought our daughter who was 14 months and the tour was great for her.”
Small-group Chianti wine and food day from Florence: 3 winery visits with tastings, a Tuscan lunch, plus Greve in Chianti.
“Our guide, Leo, was outstanding. Shared history with ease, was as friendly as could be, and a good driver (small group, so in a van, not in large bus). The 3 wineries were all charming and the wines/snacks/lunch were well worth it. Found it an excellent value and highly recommend.”
From Florence, bike through Chianti hills and olive groves, then taste wines and olive oil at a medieval castle with lunch.
“This tour was an amazing experience in the Tuscan country side. Angus did a great job leading us through the country side on bikes. He stopped at several points for photo opportunities and share info about the area. The wine tasting and lunch at the castle was a perfect end to the morning. The biking is 12 miles long and you do need to be able to navigate some hills.”
Florence to Chianti and Vernaccia, taste 8 wines at 2 wineries, then enjoy San Gimignano medieval towers on a full-day tour.
“The communication, and experience as a whole was excellent. Emanuele was superb and the two different wine experiences made it even more enjoyable. The views, amazing and finishing off at San Gimignano was a delight being able to have some free time to venture out.”
See Siena, San Gimignano and Pisa plus Chianti wine on a 12-hour coach day trip from Florence, with a guided Siena walk and options.
“My daughter and I had an excellent day! We really loved learning about Siena and the horse race that happens each year. The wine tasting and lunch was fabulous even though it was extremely hot due to the air conditioning not working. (Suggest keeping doors and windows open for air flow) I really adored San Gimignano and would have liked more time there for sure. Many thanks to our guide, Federico and our bus driver, Francisco for ensuring our trip was enjoyable and safe.”
A fast, early Rome day trip to Pisa and Florence by air-conditioned bus, hitting the Leaning Tower, Duomo area, and Ponte Vecchio.
“Highly recommend to people who wants to see Pisa and Florence but may not have enough time to do it all. It's a quick pace tour but you do have enough time to do a little of everything. Museum tickets are not included so pre-plan for that if its a priority for you. My guide was Mary Jo and she was great.”
Self-guided e-bike ride from Florence to Fiesole and a vineyard, with GPS, monastery views, and a stop at Piazzale Michelangelo.
“Well organized, the required phone app was easy to use, John was very helpful in setting it up. The tour itself was a highlight of a two week trip to Italy. Beautiful ride thru the hills and forest outside Firenze”
Chianti day trip from Florence: Monteriggioni, hands-on cooking lunch, 2 wine tastings, San Gimignano, and Certaldo.
“Wine tasting. Visiting Tuscan cities. Enjoyed it all Very good tour guide. Would do it again. Very good tour for money.”
From Florence: Pisa, Chianti wine tasting, San Gimignano, and Siena in one day. Includes lunch and optional Leaning Tower tickets.
“The tour was wonderful, but it was extremely long and was a very large group of people. We were probably 60 people in a two layer bus and it was hot and difficult to travel with so many people. I would spend the money on a smaller tour.”
Small-group Chianti wine and olive oil day trip from Florence with mill tasting, Greve village time, and 3-course Tuscan lunch.
“Informative and great fun. Lorenzo was very caring and knowledgable. Each winery was different but all had some excellent qualities.”
Ride an automatic Vespa from Florence to a Chianti winery for lunch and wine tasting, with scenic countryside roads and small-group safety.
“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.”
Ride a Vespa through Chianti hills from Florence, with safety training, villa lunch, wine and olive oil tasting, helmets, and round-trip transport.
“We had a great time. Your guides were the best funny and kind. Lunch we delicious.. Ben and Philip are the best. Don’t miss out on this tour!!!”
Pick a city, or pick a kind of day.
