Updated: December 2017
Best Tuscany Tours and Sightseeing Services:If you travel all the way to Italy, then you better be prepared to spend at least one day in the Tuscany region. Rome and Venice are nice, but the true flavor of Italian wines, cheeses, art, and scenic landscapes are stored in Tuscany and its many small hilltop towns. Planning a tour in Tuscany is no easy task as I recently tried myself. At first I thought renting a car for the day from Florence would be easy and I would drive myself and my wife around the Tuscan countryside sipping wine at beautiful vineyards and eating Italian delicacies in Sienna and Pisa. After searching online and checking with rental car agencies in Italy I realized that rental cars are very expensive in Italy and many of the rental car agencies don't do 1 day rentals. So unless you are staying in a Tuscany villa or hotel for more than a few days, renting a car is not worth $200/day. You are better off using one of the proven Tuscany tour companies or independent guides to give you a complete tour of the Chianti wine region, Siena, San Gimignano, Volterra, and many other wonderful towns located in Tuscany. The fees are not much more and you will get a personalized guide to take you to the best spots without wasting time driving and parking outside the small towns.
Depending on what you want to see or taste, there are a variety of tour operators that can handle your itinerary needs. If you only have a day, like most of us, planning to see at least 2 towns and do some wine tasting is probably all you will have time to do. For a quality map of the Tuscany region, go to http://www.italyguides.it/us/italy/tuscany/tuscany-italy.htm. There are countless tours of all the regions and we suggest going with a smaller company to avoid getting on large buses and being held up by other tourists when the tour should really be about you and your preferences. Our choice was with a private tour operator by the name of Alessandro Cammilli (firstname.lastname@example.org) who is a retired police officer and he knows his way around the Tuscany region. We found his name on message boards online as the most recommended guide you could find. He does lots of customized tours and works with cruise ships that stop along the port cities as well as inland Tuscany tours with local vineyards and all the major stops along the way including Sienna, Florence, San Gimignano, Pisa, and whatever else you want to see. He is truly an amazing guide and host for the day leaving many decisions up to you. If you like an open schedule and don't want to be herded in and out of buses on other peoples schedules, then give Alessandro a try (email him). As for other guided tours in Tuscany, you can try Enjoyflorence.com - they offer wine tasting, driving, and sightseeing tours throughout the region. Lastly, a good small group tour company is located HERE. The Best of Tuscany tour gives you a taste of everything - wine, olives, food, and hilltop towns for about 120 Euros a person. Do your research and go with a trusted tour operator since you will probably only get one chance at one of the most memorable days of your lives.
Tuscany Wine Tours:What better than to get a tour of the Tuscany vineyards by a true wine oficionado. Tuscan-wine-tours.com is run by Rebecca. She offers a perfect Chianti Classico wine tour in the region close to Florence - available as a private tour or in a small group. You get to taste wines like Chianti Classico, a Riserva and an IGT Super Tuscan. Prices range from 240 Euros per person down to 100 Euros. Check out the website for more details on the 4 wine touring itineraries and how to book. Another excellent wine tasting tour in Tuscany is located HERE. They have 1/2 and full day tours with expert guides and exclusive visits to wine cellars that include wine tasting and gourmet Tuscan lunches. Prices are about 120 Euros for a full day - includes transportation to and from your hotel and lunch. You can also search the forums on the Tripadvisor.com site with hundreds of entries from fellow travelers who have done similar tours and can give you references and feedback on who is the best and most reliable.
If culinary delights are more your thing, look into taking some authentic Italian cooking classes while in Tuscany. Tuscany-Cooking-Class.com offer single day and multi-day cooking classes, right outside of Florence (they will meet you in Florence and pick you up). They offer an Introduction to Tuscan Cuisine and an Italian Immersion class, priced from 140-190 euros. Two and three day courses are also offered. They also offer wine tasting tours. Check them out. And yes, they speak English.