By the glass · CHIANTI WINE TOURS
Classico country starts twenty minutes south of the city and every estate on it will feed you. The 15 below compare how many wineries, how long the lunch is, and whether the price includes the driver who takes the hairpins home.
Ride from Florence to two contrasting Chianti wineries with an English-speaking guide such as Ana, Alex, or John. Tour vineyards and cellars, taste up to seven wines with cheese, salami, olive oil, and bread, then return by comfortable coach in about five hours.
“James Is our guide on the boat Thank you very much”
Leave Florence at 8 a.m. for San Gimignano, Monteriggioni, a Chianti winery lunch, and Siena. You get free time in the medieval towns, three Tuscan wines plus vin santo, and optional Siena guiding and cathedral access. Guides such as Sandro, Marta, and Ilaria are often praised for clear, friendly help.
“Hilaria was our guide, she did a wonderful job, she gave us a lot of information without being overwhelming. The visit to the winery and lunch was delightful. I 100% recommend this tour .”
Ride from Florence into Chianti on an air-conditioned coach, visit two organic family wineries, taste six or seven Tuscan wines with local foods, and return in about five hours. Guides such as Aaron, Alessandra, Cristina, and Maria Luisa have led recent departures, though the guide can vary.
“Way to see the wine country! I’m driving through the terrorist landscape filled with cypress trees and villas was breathtaking! There are miles and miles and miles off vineyards. Our tour guide was versed in several languages, so everyone could understand her words. She was extremely knowledgeable! Thank you for the amazing time!”
Spend nine hours touring Tuscany by air-conditioned minibus, with time in Siena, a Chianti estate, and San Gimignano. Expect five wine tastings, olive oils, balsamic vinegar, and a traditional lunch. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day friendly and on time.
“Marco our tour guide was amazing! He was very knowledgeable and explained everything clearly. He also made sure to talk and connect with many of the people on the tour individually, so it felt very personalized! The tour itself was also incredible - being able to see all the beautiful areas that I did in one day? 10/10”
Travel from Florence by air-conditioned coach to San Gimignano, Monteriggioni, Siena, and a Chianti winery. Expect free time in the hill towns, a three-course Tuscan lunch, three wine tastings plus Vin Santo, and optional guided visits in Siena with guides such as Marta, Sandro, and Riccardo.
“We had the trip at 25/10. Our guide was Riccardo and our driver was Antonio. Riccardo gave us much information about the places we visited while also being very funny and friendly, making the trip even better. The free time in each place was enough to see the top attractions. The meal and the wine tasting were perfect. Aristos and Krystallia Riccardo's Greek Friends”
Leave Florence by tram and coach for two Chianti wineries, seven wine tastings, Tuscan oil, balsamic vinegar, salami, cheese, and bruschetta. Guides such as Luca, Marco, and Alicia keep the day moving, while Monteriggioni adds a compact medieval stop.
“Everything was amazing — the tour guide, the wine tastings, and the amenities. The wines, oils, cheeses, and bruschettas had excellent presentation and were an absolute delight to taste.”
Ride from Florence to two Chianti estates with an English-speaking guide, taste three to four wines at each, sample olive oil and local foods, visit cellars, and enjoy vineyard views. Guides such as Alex, Lorenza, and Cecilia have been praised for friendly, clear explanations.
“We had a fantastic half-day Chianti vineyard tour with our guide, Alex, and our driver, Constantino. Alex was super engaging — he personally checked in with each of us to see if we had any questions or needed recommendations for Florence, which was so thoughtful and appreciated. Constantino was a fantastic driver and made the ride smooth and comfortable. We visited two vineyards, enjoyed delicious wines, and even got to taste freshly made olive oil — a special treat in November! The Tuscan landscape was breathtaking with its fall colors, and it was the perfect morning trip out of Florence.”
Leave Florence by van for a guided two-hour ride through Chianti’s vineyards, olive groves, and country lanes. Guides such as Ben, Filippo, Angus, and Alessio lead the way, with regular photo stops, a support van, and an optional e-bike. Finish with wine, olive oil, and lunch at a medieval castle.
“A truly great experience from the start to the end. Ben was my bike guide for my day in the Tuscany hills. Communication was very good. Information was excellent about the local area. The tour was tailored to me. Wine and food was excellent. I loved the cat too!!!”
Leave Florence by air-conditioned coach for two family-run organic wineries in Chianti Classico. Walk through vines and cellars, taste local wines with Tuscan snacks, and hear stories from guides such as Keiko or Maria Louisa. A cooking class, lunch, and four-wine tasting are available with the upgraded option.
“It was so good, the first winery was a bit stingy with the wine sizes, HOWEVER the second winery had 10/10 wines and a 10/10 son, we accidentally spent $400 on balsamic vinegar, truffle oil and wine because he had good eye contact. ALSO the server (ed Sheerans younger self) was very charismatic and an amazing host. He was so enthusiastic and energetic and just amazing.”
Leave Florence for a six-hour Chianti outing with a guide such as Chiara, Anna, or Abbie. Taste three wines in Radda, browse its small shops, then visit a countryside winery for three more wines, local foods, and an explanation of grape to bottle production.
“It was fantastic. We had a great time. The wine were great, the views, Marina and Luigi... Overall a wonderful time discovering Chianti and its wine.”
Travel from Florence to two Chianti wineries for tastings and a traditional Tuscan lunch, with time in medieval San Gimignano and a photo stop at Piazzale Michelangelo. Guides such as Lorenzo, Daniel, Christian, and Cecilia are praised for local stories, good humor, and relaxed pacing.
“This was part of an end of life trip for me (stage 4 cancer) with my two adult daughters and my oldest daughter’s husband. We are traveling to Venice, Florence, Rome, Catania, Sorrento, Naples. I love wine and wineries and so this was probably the excursion I was most looking forward to. Tour guide was great. First winery—very dynamic host and good wine. 2nd winery-not as personal, great lunch, but not great wine. Trip to San Gimignan beautiful and fun but felt rushed. Driver said he would take my daughter back after last winery to the place that specializes in tiramisu but he did not. Overall good-but we enjoyed the…”
Travel from Florence into Chianti for medieval villages, two wine tastings, and a hands-on cooking class at Agricola Poggio Ai Laghi. Guides such as Marco and Marta add local context, while free time lets you explore Castellina, Monteriggioni, San Gimignano, and Certaldo at your own pace.
“Marco was a wonderful guide for the day in these 3 towns in Tuscanny, we enjoyed it very much! He showed us were to find the most important sighrs in each city, gave us some insider tips on where to eat or drink or enjoy sweet delights. Great tasting of wine, olive oil, aceto balsamico. Nice group size of just 15, new friends were made by the end of the day!”
Ride from Florence into the Chianti hills, visit two different wine estates, taste 3 to 4 wines at each, and sample olive oil, cheese, meats, and other Tuscan foods. English-speaking guides such as Martina, Chiara, and Celeste have made the outing lively and useful for first-time wine tasters.
“It was a wonderful experience in the Toscane landscape. The wine was very good and the people extremely friendly !”
Ride from Florence to Chianti in an air-conditioned Gran Turismo bus, walk among the vines, visit a vinegar cellar, and taste seven wines with Tuscan snacks and olive oils. Guides such as Chiara and Emma add local context, while the five-hour format suits a busy Florence stay.
“The entire experience was excellent. Our tour guide was knowledgeable and provided us with historical facts about the area and the wine tasting experience was wonderful. We highly recommend this tour!”
Meet your English-speaking guide at Villa Costanza and ride into Chianti by air-conditioned coach or minivan. Visit Fattoria Lornano and Casale dello Sparviero for seven wines, olive oil, balsamic vinegar, and local snacks, then explore Monteriggioni before returning to Florence.
“The trip was fabulous, Marco was a fantastic, knowledgeable, engaging host. The wineries were perfect & the wine delicious.”
Pick a bottle and see where it is poured properly.
