map via SevenFiftyDaily
Just a few pointers to give you a hand before you plan your trip!
When you visit Tuscany it can be difficult to decide where to go and how to do it!
Do you blindly pick a tour and hope it is good? Do you rent a car and go it alone hoping for the best? These are common issues for travelers to Tuscany.
Picking a tour off of a third party provider such as Viator, Hotel Beds etc. can be overwhelming at best and it is always a crapshoot regardless of the reviews so you may get a bad guide that day, other guests that are not friendly or are high maintenance, let alone any fun!
The thought of going it alone in a rented car can be terrifying, once you have been in Italy for all of five minutes you will understand why! Also, Tuscany is not like Napa or other wine regions with a main drag where you can just make the rounds popping in and out of several locations, completing three to five tastings in one day, depending on your ambitions;)
Tuscany is bigger than most people think and quite spread out (see map above), you will need to research the wineries and their locations and calculate their scheduled times for wine tours and tastings and how long it will take driving between each location. The majority of the wineries offer lunch also, so I suggest you choose one of them to have your wine tasting experience paired with your lunch, there are many wineries who do a great job at this and you are guided by wine experts or depending on the winery maybe by an Italian Sommelier. If you want to visit any Medieval towns it would be convenient to search for wineries in or around that area. Just getting into the heart of Chianti from Florence by car will take an hour, then you must include parking, rest stop breaks and getting lost (happens to everyone), I strongly suggest WAZE, yes we have it here in Italy and it is a lifesaver!
If you want to book a tour, remember you get what you pay for, the prices have become so ridiculously low in some cases that any decent tour operator cannot offer top quality service at those rates. This applies generally to the large group tours with 50 plus people. These agencies are banking on quantity over quality and most likely you will be shuffled around like cattle. Clearly, your guide will not be able to give you much personal attention and don't try to have a bathroom break off schedule! You may even go to the same wineries as the tours that offer smaller more personal service but the service and what you are offered in regards to food and wine will vary greatly which may give you a bad impression of a valid winery. Fortunately or unfortunately the majority of the wineries cater to tourism and this may include private, small and large groups alike.
Small group tours are a better option, generally, this will include up to fourteen people total with max eight people per van and one guide. Again you won't get the guides full attention because she/he will have to move between vans so again it's just hoping that your van mates and tour buddies are not stick in the muds. Everything will still be scheduled to the minute including yes again, bathroom breaks. You may feel that you would have liked to spend more time in Siena or San Gimignano, or you may need to leave behind that gorgeous leather bag because you just couldn't make a decision in that small space of time, I know this can be very painful, so keep in mind your time is still not necessarily your own, you are part of a group on a tight schedule.
On a positive note, on group tours when it's good it's good! I have had the opportunity to meet the most interesting, amazing and fun clients ever on my tours. This is one of the best parts of my job and sometimes there is such a symbiosis between the group that everyone is laughing and joking and enjoying living that dream under the Tuscan sun for that one moment in time... and it is magical!
Private tours can be a more expensive option if your numbers are below 4 to 6 people, however, for a once in a lifetime experience (hopefully not) it may be worth it for some folks to spend a few hundred euro more. A private tour can be for a couple who wish to see the countryside at their own pace and maybe have a little more of a romantic experience, group of friends and family or a wedding party with a large group of guests who will still get grade A service! The positives on a private tour is that you can go off script in the sense that you will have time to do specialty cheese and jam tastings or wander into the truffle shop to taste some delicacies and enjoy some world famous gelato in the piazza at your own pace and of course you will be given the time to shop if you want to take any goodies home with you.