Italy · SIENA TOURS
Every trip has one free day too few. These 15 siena tours 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!”
Tuscany in one day: Pisa’s Piazza dei Miracoli, Siena, UNESCO San Gimignano, and Chianti lunch with wine tasting, guided in English.
“Our guide was excellent. Luca made sure to connect with everyone. I was interested in the art but also the history. Luca, was available to answer questions as we walked to the site. i would request him.”
One day tour from Florence to Pisa, San Gimignano, Chianti wine lunch, and Siena, with Leaning Tower tickets and optional guided walks.
“Barbara was an amazing guide! She made an already amazing tour even better. Sienna was very nice. Poggio Al Laghi, the winery was very nice! Great cuts and cheese plate & a great pasta dish! The host was cool & funny. San Gimignano... what can I say.... ot was absolutely stunning & the highlight of the tour for us. It was quite, gorgeous, had midevil vibes and AMAZING views. It's one of those places that you want to move to for a few months after visiting. Pisa was overall forgettable. I highly recommend this tour!!!”
Florence day trip to Siena, San Gimignano, and Pisa with a Tuscan winery lunch and optional wine pairing, plus cathedral and tower time.
“Amazing day trip, with great guides sara & Gaia. Got to see pisa in daylight and night time. Food and wine lovey at the vineyard. Highly recommend”
Full-day Tuscany tour from Florence to Siena, San Gimignano and Pisa, with Chianti vineyard lunch and wine tasting, small group feel.
“Sara was informational and warm. Our guide in Sienna was helpful to understanding the local art and history. Enjoyed the friendly rivalry between Florence and Sienna. While we felt hurried, each stop was just the right amount of time. Each site felt like a day unto itself.”
11-hour coach day trip from Florence to San Gimignano, Monteriggioni, Chianti and Siena, with lunch, wine tasting, and optional Duomo entry.
“Great experience with an opportunity to see a lot! My only recommendation would be that if you have the cathedral guided tour, have it start when you arrive in Sienna so you have a little bit more free time.”
One-day Tuscany loop from Florence: Pisa, San Gimignano, Siena and Chianti views, with optional lunch and wine pairing.
“Hilary was fantastic.Kept everything on schedule and kept everything interesting fun and fresh”
Small-group Tuscany day trip from Florence to Siena, Chianti winery with five tastings, and San Gimignano, plus truffle lunch.
“Marco was brilliant and we had a lovely day, with his guidance! We did sort of think that it would have been nicer to see San Gimignano earlier in the day, because after the travel and winery everyone is starting to flag and it was one of the key reasons we picked this tour.”
Skip-the-line entry to Siena Cathedral and Piccolomini Library, with a QR-code audio guide. See Pinturicchio frescoes and the mosaic floor.
“Only that it felt quick. Over too soon. Self guided so that had something to do with it.”
Florence to Siena, San Gimignano, and Monteriggioni in one day with Chianti tasting and estate snacks, led by Ciaoflorence guides.
“Nice day trip from Florence to Siena, San Gimignano and Monteriggioni. The bus was comfortable and the guide was knowledgeable of the areas. The weather was foggy so it made for some nice pictures. I recommend this tour seeing these beautiful cites and culture in Italy.”
Siena Cathedral Complex pass with audio guide. See crypt, Baptistery, Piccolomini Library, Museo dell’Opera, and the Facciatone viewpoint for $21.
“We had a lovely time in Siena, the cathedral was beautiful!”
Florence to Siena, San Gimignano, Monteriggioni and Chianti in one day, with a guided Siena walk and a 3-wine tasting.
“Sara and Lorenza were great tour guides. Mario a safe bus driver. Bus was comfortable. Knowledgeable professional and most pleasant”
Florence to San Gimignano, Siena and Chianti for UNESCO sights plus a guided cathedral option, lunch, and a guided wine tasting.
“Absolutely loved San Gimignano… by far the favorite party of this trip. If I was to do it over I would skip the winery and stay here for more time. sienna was lovely as well. The wine tasting and lunch was average but the small towns were definitely the highlight. Aaron and Alexandra were great hosts and very knowledgeable!”
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 day trip from Florence to Siena and San Gimignano with a winery lunch, guided walking tours, and free time for towers and gelato.
“Very enjoyable experience with professional tour guides. Really a perfect day with low stress and good pace.”
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