Tuscany Day Trips

If you were to base yourself in Florence or Siena, there would be a lot of good options. Two tour companies you could check in with are Walks of Italy and Tours by Roberto, and I’m sure there many more.

hey hey catherine
come&seeitaly.com
withlocals.com/florence
getyourguide.com/florence
stop at a tourism kiosk in a piazza and see what they offer. we did a tuscany tour with sergio (scenicwinetoursintuscany.com) it was an okay tour. wanted to go to places i looked at but didn't happen. lots of these tours go to places they have agreements with, to me like a pay off. plan a private tour and inform them what you want to see and do, will be a different price (more expensive).
thecrazytourist.com/15-best-day-trips-florence look at where the tours go, what's included and how long. it's your decision
when we were in geneva a year ago, we saw a taxi driver at there station and asked for a 2 hour around the city and some outskirts. we paid about 80E for it.
in italy and time you want a taxi. either call them or wait at a station. do not hail them down. learned our lesson. ask the host/hostess if they know of someone. leave early since a lot of people want to tour the tuscany area and will be crowded in the main cities everyone wants to see.
good luck with whatever your decision is
aloha

I can second the recommendation for toursbyroberto.com having very much enjoyed a joinable tour from Florence to Montalcino late April 2019. It was a pick-up near the Duomo 08:30 and drop off return 16:30 and a fabulous day spent visiting two very different wineries in Tuscany plus a brief Montalcino visit. Comfortable drive in a late model Mercedes van with photo stops along the way, personable driver/guide and an excellent pranzo (extra charge) at one of the wineries. Opportunity to purchase vino as well as olio from friendly, gracious and hospitable folks who live their passions. In Siena, Anna Piperato (sienaitalytours.com) is a fantastic guide you should contact for a custom tour of her city.

I third the recommendation for Tours by Roberto. He picked us up in Montepulciano, and others in other places. We had a great day with him exploring off-the-beaten-track places, and a wonderful lunch at a winery. No more than 8 people in the group and he is passionate about sharing his region.

www.toursbyroberto.com

There is public transportation within Tuscany, it's just not conducive to seeing several small towns in a day. Often times bus schedules are geared to working people and school children, not tourists. But if you really have two weeks you could certainly visit quite a few towns. The problem with tours is that they all go to the same places at the same time leading to the places you want to see being very crowded from about 10:00 to 4:00pm. With a little research, and if you don't mind changing hotels every few nights, you could do a great trip where you spent about 24 hours in each of several towns, being there in the evenings and mornings when it's uncrowded and lovely.

Here are two websites that might help - https://www.tripsavvy.com/tuscany-train-travel-guide-4135538
https://lovefromtuscany.com/basics/getting-around-tuscany/

I would spend 3-4 days in Florence. One good day trip from there is Pisa and Lucca, done by train, easily combined in one day.
I would also spend at least 2-3 days in Siena.
Then pick several more smaller towns and see if you can't piece them together to hop from one to the next.

You will find tour companies, but I would look at logistics and consider staying in a small town in addition to Florence, just to mix things up. Once you get a list of companies, cross reference locations and see if you have any outliers that a different base would facilitate a visit to.

My fifty cents is Sienna would be a better city base to spoke out from because it’s a little smaller and more central to Tuscany than Florence. But definitely go to Florence for two nights after your time in Sienna. Research your selected tour operators pick up points relative to your sleeping place and bus size. We did a cattle call style wine half day tour from Florence to Greve and two Wineries, large bus. Had to hike a fair distance to find the pickup spot past the train station, was not easy. The tour was fine and exactly as advertised for the price but nothing more. We also slept in Lucca before Florence and it’s a good town to visit and/or sleep for 1-2 nights.

Seeing small towns where you want to spend only 1 to 3 hours looking around can be tough via public transportation. First, bus and train service to such places tends to be infrequent; second, it usually links the town to the nearest major city (Florence being primary in Tuscany), so visiting two small towns in a single day is often challenging. Seeing three in one day is like winning the trifecta at the racetrack. Very often it works out to a choice between grabbing a snack-food lunch and leaving the little town more or less when you want to or having a nice Italian lunch but having to cool your heels for an extra two or three hours.

Taking a tour that goes to multiple places you want to see will be a lot more efficient, but it comes with cautions:

• Most tours in Tuscany will depart from Florence. It will be a lot tougher if you don't spend any nights there.

• Tours are considerably more expensive than buying tickets on buses or regional trains.

• When tourism initially opens up, tours may be less frequent than before--perhaps only during peak season or only a few days a week.

• When you take a tour, you're stuck with a fixed schedule that may not align particularly well with your own interests. I never know how much time I want to spend anywhere until I'm actually there.

I really prefer sightseeing on my own - doing the reading, planning and scheduling I've found can be part of the fun. That said, for the past 3 years I did look into day tours. They would give me the more comfortable transportation to places distant from my home base. That would be a major plus. But here's the problem: I travel alone. Every excursion cancelled me a day or two before the tour saying they don't take singles. Huh? I don't remember seeing that on their web site and when I made the reservation it was clearly for one person. At least they didn't charge my credit card. So, be careful and make sure they will accept you as a single traveller.

In 2018, we took a great day long wine tour that left from Florence. Todd does a great job with his small tour groups.

https://tuscantrails.com/daily-chianti-tours

I was just about to recommend Tuscan Trails myself. Our tour was 6 years ago and we're still talking about it.

hey hey catherine
i agree with acraven, robert, and collins about these tours.
some of the cities/villages will be crowded with other tourists going to all the same places with limited time to roam, get back on bus to next stop.
prefer smaller tours, make sure they do allow singles (any tours) full or half day, look at transportation (car, van or bus), more time on bus than exploring, the cost of tour, what's included and what's not, read fine print and reviews, days open and times, white or red wine.
italyxp.com
tuscanwinetour.net
italysbestrome.com
are you staying in florence for 2 weeks or seeing other areas of italy? we did a prosecco tour outside venice that was one of my favorites. loved the lush green views, villages/towns, vineyards/wineries.
aloha

you can always take the train, From Florence to Pisa: these are important railway destinations and have great connections to each other.. think about the idea of getting a boat from Florence and around the Tuscany region, it is great as you can visit Cinque Terre which has the known national Park and you can dock into the towns of your choice .. there are many different services such as Busfox.com (here you can check the schedules throughout the day and where to make stops at) but there may be no service during the weekends and the other boat service i had in mind was Seamaster yacht charter or BednBlue which has skipper charters with boat rentals worldwide that will help you visit places without the need of you driving, you will just have a professional take you to all the Tuscany regions you want, all at a good budget.