Top Tuscany Overnight Tours

Driver was very nice and gave us some history about Tuscany Swell

We did the 2 day Chianti bike tour from Florence to Sienna. Despite the near 100 F temp., we were able to ride out of the city walls and immediately enjoy the views of rolling hills full of vineyards and olive trees. On our occasional stops, our knowledgeable guide Giovanni shared interesting facts throughout the ride. On the first day we lunched at a rustic, family owned farm and in the evening relaxed at a beautiful villa. On our second day, we lunched at a scenic winery. Giovanni was really good at adapting to our level and interests! Then we rolled into Sienna. What a great way to travel to Sienna, the next stop on our trip. It was an amazing experience despite the heat. Just be sure to make sure your e-bike fits you before you head out on this 2 day adventure—both the seat height and the distance to your handlebars since you’ll be on your bike for a while! The 4 of us are just casual bike riders but with the e-bikes we scaled amazing hills and experienced beautiful views! Highly, highly recommend!

My husband and I took the two day bike trip from Florence to Siena. Our Guide was Alejandro and we were assisted on the route by a lovely young woman whose name I have forgotten and by Gabriele — a total gem. Every detail on this tour was carefully thought through. Alejandro is a an attentive and expert guide. He was easily able to help my husband and I even though we have different levels of experience on bikes. (I felt completely safe even though I’m not the best bike rider. And on day 2 Alejandro brought me a padded seat for my bike — so thoughtful!) The areas we rode through were incredibly beautiful. We were delighted to see the changes in topography as we rode from Florence, through the Chianti region, and into Siena. In addition to being funny, kind, and at the same time utterly professional, Alejandro was knowledgeable about all of the plants and trees that we saw and gave us lots of interesting facts about the flora and fauna. He also had lots to say about the historical significance of the sites we were seeing. Now I must rave about the two wine tastings that we did. We Like Tuscany partners with several small wine producers, and on each day we were blown away by the wines and the food and the decor! Alejandro has a personal relationship with the people who run these small wineries. Being on a tour with this kind of an insider was very special. I think the best way to sum this up is that I am now trying to figure out a way to organize a whole family reunion around a bicycle trip in the area with Alejandro and the team at We Like Tuscany! It was the highlight of our 5 week trip to Europe. I simply cannot recommend it highly enough!

My husband and I went on this tour for our anniversary. It was absolutely incredible! We got to have our free time in each place and got great recommendations from our tour guide, Elisa. Elisa was so sweet and answered all of our questions! We had a great time with the others on the tour too, and wish we could have been on a longer tour with them.

Beautiful Countryside! Great trip. Our tour guide, Mario was wonderful. He customized our days to suit our needs. He was thoughtful, kind and very knowledgeable about the areas we visited. A memorable two days.

We very much enjoyed our time with Mau.. in fact, we went back for seconds after we had been to the area earlier that same year. This time we toured the Chianti region, had a wonderful lunch and tour at Casa Emma and concluded at San Giminiano for walking/shopping/gelato, etc. Mau is an excellent guide with a great command of the history and interesting anecdotes to keep our 12yr old engaged. When we return to Tuscany, we will absolutely hire him again. Highly recommended!

We booked the 2 day e-bike Tuscany tour. From checking in until saying good bye to our guide Jacopo, the experience was wonderful. Riding the e-bikes through the hills offered beautiful views and a pleasant way to see the area. The e-bikes made climbing the hills very comfortable. Our 1st stop for lunch at the winery/farm was more than we expected. Warmly greeted by the owner upon our arrival and enjoyed a tour of their lovely grounds. We were served a tasty lunch. Almost everything served to us came right from their farm. A tasty and relaxing experience. Jacopo is everything you would want in a tour guide, informative, interesting, alert and kind. He made this experience wonderful and took fantastic care of us. It's a fun way to explore the region.

We did the two day bike from Florence to Siena. I booked it because we hadn’t been to Tuscany and wanted to see some countryside outside the cities, some friends had done a 12 hour van tour but that’s not really our style. I stumbled upon this company and this trip and listened to reviews and booked it. SO HAPPY I DID! Just an amazing way to see the countryside; the guiding is top-notch and they take care of everything from portaging luggage to delicious food and wine. Alessandro was so perfect- great knowledge of the area and biking but also just lots of fun. They’ll tailor the trip to the needs of the group and the weather or season. Our night in the villa outside a tiny Tuscan town was not too fancy but just spectacular. Tuscany is hilly and steep, we are bikers but chose e-bikes and it was really the way to go- still getting good exercise but way faster and frankly just more fun on vacation! If you’re not really a biker an ebike would be a great way to try it too as your guide will be so helpful and the assist is very useful in the hills. Hundreds of happy reviews are not wrong here, it was most definitely a highlight of our trip to Italy and you should book it!

We did the cycling tour during a couple of relatively rainy days towards the start of the winter season, it was just the two of us and a guide but the weather generally held off and we saw great views of Tuscany including a number of small villages. The food was some of the best we have had in Italy at the stops for lunch.We do not cycle regularly at home and are probably of average fitness, the ride was a good challenge but not too difficult. In the case of worsening weather or any difficulties, there is always someone with the company van driving the same path and stopping at regular checkpoints. Overall we thought this was a better way to see Tuscany than a hiking tour, and this was why we booked it, but it would be ideal if at a time with better weather.Our guides were particularly great! Cossimo was undergoing post-graduate studies in Italian history at the time and had plenty of passion and insight into our surroundings. Andrea was also always super friendly, knowledgeable and approachable.

Our trip through the rolling hills of Tuscany was a marvellous experience. Our guide was in tune to our abilities and experience and adjusted the pace accordingly. The scenery was stunning!

The two days I spent biking through the Tuscan hillsides were the highlight of my vacation in Italy. The views, the food, and the guide were all top notch. Although a day trip is also a tour option, I highly recommend the overnight trip, as it offers a "less touristy" way to see the region. Our guide Bill was fantastic in accommodating the different experience levels within our group, and worked to let us go at our own individual pace. Lunch Day 1 was a three course meal with wine pairing, which was delicious. After lunch, we biked the rest of the way to the hotel. The hotel had AC and a swimming pool, which was much needed after biking in 100 degrees. Lunch Day 2 was in Gaiole in Chianti, which was also charming.Now, the biking part... I have never been cycling, so maybe some of this is obvious to those who aren't rookies like myself. I am a runner and fairly active, so the endurance needed to cover the mileage was a non-issue. However, the ride is hilly, so an e-bike is an option for those who need it. The hardest part for me was the bike seat- literally. I have never experienced pain like that in my life. If you are like me and think to yourself, how bad can it really be? Bad. Bring or rent a seat cushion. Diaper rash cream is also a must for chafing.If you are on the fence deciding if this tour is for you, do it! You won't regret it.

Cycling through Tuscany on this 2 day trip with my wife was the highlight of my time in Italy. Our guide Cossimo was fantastic and having e-bikes made the ride very enjoyable. No problem on the hills! There were many nice stops along the way, two great lunches with wine, and an overnight stay at a nice villa with a pool.

The 2 days of cycling thru Tuscany with my wife was the best 2 days of our 16 days in Italy. Our tour guide, Andrea, spoke excellent English and was an awesome tour guide. He is from the area and was an wealth of information and a very genuine and sincere person. The food for lunch and dinner that was included in the tour was amazing. The Villa that we stayed in overlooked the hills of Tuscany and was absolutely gorgeous. When the day comes that we visit Italy again this tour will definitely be included in our trip. Our driver, Edoardo, was also great and was a pleasure to talk to.

We had an awesome time on this two-day trip. Feddie was our tour guide and Cosimo assisted with the bags, equipment, and both were great. This was a really fun way to see Tuscany.

Highlight of our trip to Italy was the bike tour through the Tuscan countryside. Funny that the other couple on the tour lived 2 subway stops away from us in Toronto! First day was relaxed and Bill walked us through the tour, safety etc and stopped a few times to introduce us to the country-side, trees, plants, farms. We rode Kona hybrid style bikes as this was a more relaxed tour. The cars were not a problem as they are used to the many Italian cyclists always on these country roads. Before lunch we stopped at a Classic Winery (owned by a family who did business with the Medici's and involved with Trevi fountain!). Bill took us through the wine making process and we had a wonderful white table cloth lunch and wine tasting. Then a bit of work in the afternoon and a long hill before we got to the hotel. Everyone made it through.Hotel was a tiny local-owned place but had a relaxing pool to cool off in. We were actually worried about the heat at 32C in the cities was roasting us. In the country side on bikes, no problem. Dinner was fantastic as was breakfast.Last day we had to cover more mileage but made stops for photos on the roadside and in scenic towns. Lunch was at a little town and we feasted on ravioli with truffle sauce (same place as the luxury bike tours). Right near the end it started thunder storming but van was there to pick us up before going into Sienna.Amazing value for a 2-day bike tour!Recommendations: - Should be in reasonable shape and experienced on a bike - If afraid of climbing hills or keeping up, get the e-bike - you still have to work but it helps when you need it. - For the ladies, the seats are a bit narrow so ask for a ladies seat in advance or bring one.

My husband and I had the best time on our 2 day bike ride through Tuscany. While my husband and our guide Davido rode their traditional bikes, I opted for the electric bike . The best decision I made. I am no cyclist and the electric bike made it very easy ( especially on the hills). I could just enjoy the beautiful scenery and countryside. Our guide was fantastic and we had such a pleasant time with him- the first day with other riders and the second day - just us. The food we stopped for was fabulous and the accommodation was nice too. Very quiet, very Tuscan. It was really a highlight of our Italian holiday. thank you xx