Italy · TUSCANY COUNTRYSIDE DAY TRIPS
This is the list to send a friend: 15 tuscany countryside day trips worth the money, each with its price, its traveller verdict and the one thing to check before you commit.
Tuscany day trip from Florence with guided Siena, Chianti winery lunch and wine tasting, San Gimignano towers, and Pisa with optional Leaning Tower climb.
“Great experience all around and beautifully coordinated. Very unique. Manolo was the best tour guide ever!”
Florence to Siena, Pisa and San Gimignano in one day with Chianti lunch, wine tasting, and guided time in key squares.
“I would recommend visiting San Gimignano first..we were too tired to enjoy and walk through the beautiful city. Our guide Alesseo was sweet and informative and our driver Michel was excellent!”
A full day loop through Pisa, San Gimignano, Siena, and Chianti with optional Pisa tickets, a Siena guide, and wine-lunch.
“I enjoyed every moment of this tour. Barbara is an amazing guide and told us everything about the places we visited and where to find the best gelato and coffee (and bathrooms😅). For the Siena tour, Chiara was an amazing tour guide and the lunch at Poggio Ai Laghi was paired with some of the best wines I tasted. The whole tour was an amazing experience and I recommend it to anyone who wants to see the highlights, just so they can visit those places by themselves again and fully enjoy everything about Toscana.”
Small-group Chianti Classico tastings from Florence, with two winery visits, vineyard tours, and food pairings, plus scenic hillside drives.
“Leonardo was a wonderful guide, so knowledgeable and so kind, the wineries were exquisite! Would highly recommend this tour!”
Florence farm class makes pizza, fresh pasta, and gelato with a wood-fired oven, Chianti tastings, and sweeping Tuscan hill views. Recipes included.
“15 out of 10 experience. Luca, Chris and Erika we're fantastic and know how to keep everyone engaged while showing you how to make delicious food. We opted for the pasta class which included making three different pastas with different sauces and homemade gelato. We were a group of 6 ranging in ages from 28 - 67 and a range of cooking skills. My mother has been making homemade pasta her whole life and even she learned some new skills! It was educational, delicious and fun. We all had the best time - it was one of the top highlights from our trip to Florence over the holidays. P.S. Walkabout…”
One long Florence day trip covering Siena, San Gimignano and Pisa, with optional winery lunch and wine pairing, plus guided stops.
“Get ready to walk a ton but you will see lots of things. A great way to see different sized towns, learn history, and enjoy wine in the middle.”
Rome to Montepulciano and Pienza with Tuscan farm lunch, wine tastings, and Val d’Orcia views by air-conditioned coach.
“It was such a beautiful and lovely tour. Our tour guide is Anna and the driver is Luca. They make such a great team! We love all the places included in the tour. Food and drinks were excellent.”
Go off-road from Florence into Chianti or Val d’Orcia for guided tastings, olive oil and cheese stops, and a classic Tuscan meal.
“Gloria and Roberto were amazing guides. Not only were the wineries diverse, but the knowledge shared was informative and interesting. Gloria also took the time to answer questions and ‘get to know the group’. Roberto was a smooth and careful driver.”
Florence market tour plus a Tuscan farmhouse cooking class, pasta from scratch, and a 4-course lunch with Chianti wine.
“Such a fun experience! We did it over the summer and decided to do it again! The pasta was terrific, gelato was excellent and the staff (Gloria and Luca) were amazing! Will definitely do it again on our next trip! Thank you!!”
Full-day Tuscany tour from Florence: guided Siena, Chianti winery lunch and wine tastings, San Gimignano towers, Pisa sights and Leaning Tower.
“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 Tuscany day trip from Florence with San Gimignano towers, Chianti winery lunch and wine tasting, and guided Siena highlights.
“It feels very rushed in last portion of tour. We had a guide that walked entirely too fast and our chronic knee and back pain were exacerbated trying to keeep up. Guided tour wasn’t really necessary… save yourself the expense. Meal was delicious! We thoroughly enjoyed San Giiagmano wish it was longest stay of tour.”
Ride a Vespa through Tuscan hills from Florence, stop at scenic landmarks, then enjoy a hearty estate lunch with wine in a small group.
“So much fun and Chris was a really friendly , knowledgeable guide . Thankyou so much for a very special day !”
Small-group Chianti tasting from Florence with 2 renowned estates, 6 wine and olive oil samples, and Tuscan bites in under 5 hours.
“Rapha and Sergio provided a friendly and informative tour out to two Chianti wineries in a comfortable bus. The Tuscan landscape and villas dotted around the hills did not disappoint, and the wines were paired with generous antipasto plates. Great tour with fellow travellers from all over the world. Five out of five stars.”
Florence to Tuscany in one day: Siena, Chianti with 5 tastings and lunch, then San Gimignano towers. Guided, small-group tour.
“The guide was very informative and engaging. We had a fantastic day and got what we wanted, history, fantastic surroundings and wine yard.”
A full-day Tuscany loop from Florence covering Monteriggioni, Siena, San Gimignano, plus Chianti wine tasting with local snacks.
“The trip was amazing! The tour is well organized and super worth it! A must if you visit Florence and want to visit other cities. 100% recommend it!”
Every kind of day out in the country, and the best of each.
