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.
Your trip can be personalized on a private tour, depending on which region you would like to see, one of the most popular is a 9 to 10 hour day which includes Siena, San Gimignano, and Chianti, and to really put the icing on the cake is the winery and lunch! What you definitely want to avoid is to be taken somewhere overly commercial where their main intention is to sell you their product which unfortunately we also have here in Tuscany.
Choose the subregion, If you are a Brunello or Nobile fan then Montalcino, Montepulciano, and Pienza may be a good option, this is a great itinerary for those staying in Siena because of the greater distance from Florence, however, from Florence, it is still doable!
I put these two options together for logistical reasons, for instance, it would be a wasted day to go to Luca, then back to Castellina in chianti-classico for lunch, you would have no time for Siena or San Gimignano. I mention these two because they have become the must-see stops, however, there are many charming Borgi(medieval towns) that are just as beautiful and not swarming with tourists so this may be a more pleasing option for some travelers. With the boost in travel to Italy in recent years, it may start becoming the thing to do to go off the beaten track and ditch the crowds, everywhere is dreamy here so you can still make your friends just as jealous on Facebook;)
If you don't mind a bit of a drive then maybe you would like to travel out to Bolgheri where the best Super Tuscans hail from and book a charming B&B, that you could coordinate with a beach day as well;) The possibilities are endless, so it can all be all created for your personal preference!
So I guess the point is that you should first decide what type of tour you would like to do, group or private and what your budget is and then go from there. If you can get some first hand knowledge from friends who have been to the region this is always helpful, however the best case is to use someone in the area or a trusted travel agent to help you navigate through it all!