Suggestions for private tours out of Florence around Tuscany?

Try
www.toursbyroberto.com

Recommended by RS

Second to Tours by Roberto. Booked with Roberto in May and it was great day. He took 6 of us picked us up/dropped us off in Florence. I think it was $900 for the day.

hey hey dennis.w.burke6
with october being a time with harvest and festivals going on, be prepared for places being busy
tuscan-wine-tours.com
many different wine tours for you to check up on. friends did the super chianti wine tour and absolutely love it plus meeting the famous butcher, dario cecchini, and having lunch at his restaurant.
tuscanyexperiencetours.com
few different tours in different areas of tuscany, you pick where
florencetown.com
under destinations, florence & tuscany, wine tours
tuscantrails.com
read up what he offers with chianti tours
italyxp.com
under destinations, tuscany and view all kinds of tours listed.
maybe a tour in a fiat 500, wine safari in chianti, day tour to san gimignano, siena, chianti & monteriggioni
our group of 4 did a private tour couple years ago was good and bad. winery & owners were great, countryside was beautiful, thought we could pick places to see but nope. san g was pack with many tour buses dropped off same time, was so crowded trying to roam around in stores, stopping at cafe with long lines, with a given time to spend in these places, siena was another crowded place that sometimes get upclose and personal with parking farther away with so many cars and people. they go to places that are kickbacks to them, my own opinion which it is worth the extra cost for smaller private tours. go to other unknown places and wineries that were much better with the atmosphere and calmness.
educated-traveller.com
wine windows of florence. very interested area in florence, couple years ago our pedicab driver took us by this with story and history behind it. they were not open yet but people have renovated, sit and enjoy with people watching and having a glass of wine.
just some options for you to research which at times is half the fun. enjoy
aloha

2019 we spent three days w/ Roberto and were most satisfied.

In May, we booked a wine tasting tour from Florence with airline points. I had also looked online and found nothing that resonated with me. We're not fond of tours but this one ticked the boxes. We wanted to see the countryside without driving. Be part of a small group in a little van, not a big bus. We wanted to visit at least two wineries and have some kind of eating experience included. We felt we could deal with it this offering and the price was right. However, when we got to the meeting point, nobody was there. We were told it was cancelled because of COVID and got our money back. I'd bet that happens a lot. We missed it but did other fun things that day. Maybe Roberto would have come through for us but it didn't seem like the option we wanted. Good luck.

This is amazing!

Thank you ALL! I really appreciate the suggestions!

We leave Friday for our trip so happy to circle back with you afterwards but we are using Luca with Hills and Roads for the majority of our day tours around the Tuscany area and he has been fabulous to work with thus far on putting together the itinerary and helping with suggestions to plan out the days we are travelling with him. If specific to wineries and less on the sightseeing I would check out Grape Tours Tuscany. My parents did their four elite tour offerings back in 2015 and still rave about them to this day. My husband and I have thus arranged for three of the four elite tour days with them for San Gimignano, Chianti and Montepulciano regions.

Oh that would be great if you could keep me posted, Amanda