Top Siena Day Trips
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Bradley_R, Oct 2026
Extreme fun in Tuscany
Leonardo was a FANTASTIC tour guide. He was extremely personable and knowledgeable. He was very considerate of each of our tour group members wants and needs. The wine was great, the food was great and the camaraderie was even better. We had a wonderful experience and I would highly recommend it!
Peggy_S, Oct 2026
Best day ever!
I cannot say enough about our day with our tour guide, Enrico. He went way beyond the call of duty with giving us the history, taking us to the most stunning views of Tuscany, and stopping at a vineyard for a wine tasting and lunch. He was patient with those new to e-bikes, and he was there immediately when someone needed assistance. The wine tour was interesting and the wine and lunch was fresh and delicious. Be sure to eat the lunch they serve while tasting. You are riding a bike on a country road. Oh, and at the end Enrico called all of us taxis snd even provided recommendations of eateries and sights. Thanks Enrico for a memorable day.
Alicia_H, Sep 2026
Excellent do it!
This was really fun tour and I would highly recommend it to anyone thinking about taking it. It was totally worth the money because you are taken around to three separate cities and it’s an all day eight hour tour. I went with my husband and I would recommend that you take Dramamine or motion sickness medication with you for the ride back if you ever get carsick and go easy on the wine tasting during the day because the curvy roads may make you sick. that aside however, the views from the van were beautiful. the van was clean. The guide Kiko was amazing and told us so much history and he was so kind. We loved visiting the winery and we really loved visiting the artisan at the shop in Volterra. We even bought a few items from him that we will treasure. We loved all three cities. They were very interesting and we had plenty of time in all three. I would highly recommend this tour. We also took the other tour to Pienza and Montepulciano. and we preferred the tour to Voltera/ San Gim. over the other one. That tour was fine. It just wasn’t as interesting.
MARTI_W, Sep 2026
Great Tour
This was a great city tour! We learned a lot about the Siena contrades and the horse race. The Duomo was beautiful! The location to the tour on the app took us right to the starting/meeting point. Leave plenty of time to park and walk to meeting point. Great tour and neat to learn about Siena!
Robert_P, Jul 2026
Informative and Fun
This is a fabulous tour. We requested a guide Giulia for the second time because she is accommodating and adaptable and made the tour of Siena fun, relaxed and informative. She is extremely knowledgeable as we learned about the contrade and especially the famous Palio horse race. I highly recommend this guide and this tour.
Madeleine_R, Apr 2026
So much fun! The farm was...
So much fun! The farm was a definite highlight -- gorgeous views and incredible snacks to kickstart the day! We loved getting to walk around Pienza, and the wine was incredible (though definitely pricey if you wanted to purchase bottles to ship home). All in all a perfect way to explore Tuscany. We also loved our guide Frederico! The perfect balance of informational and letting us relax without pressure.
Regan_F, Jan 2026
We had a wonderful...
We had a wonderful experience with Roberto. 2 wineries and a lunch at a sheep farm that was marvelous. Local meet and cheeses and we even got to see the sheep. Then a stop in Pienza for some sightseeing and a lovely drive back to our hotel. First class experience.
Christina_P, Nov 2025
Great guided experience with Luca
Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in Tuscany.
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Thanks to its prime location in central Tuscany, Siena is an ideal base for exploring the wider region. Siena day trips cover a range of destinations—from the medieval hill towns of San Gimignano and Monteriggioni to the wine capitals of Montepulciano and Montalcino—and save you the hassle of piecing together tricky logistics yourself. Relax with private transport and experience the best of Chianti and the Val d’Orcia, focusing on the villages and castles or sipping your way through the region’s wineries. You can even channel the dolce vita vibe with a classic Vespa or vintage Fiat 500 excursion.
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