Logistics/Itinerary for 2-3 days on both sides of a group tour based in San Gimignano


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I've been poking around here and this is great site!

In just a few weeks I am booked for a small group tour based in a villa outside of San Gimignano. I'm looking for advice on my itinerary on 2-3 days on both sides of that tour. So you know where I will have already covered in the Villa Group..., the itinerary includes 1. San Gimignano with a wine tasting at an estate, 2. Chiantigiana - Brolio Castel, Panzano, Montefioralle, Greve, wine at an Estate; 3. Day in Siena; 4. Day in Florence; 5. Certaldo with a wine tasting in or nearby.

I fly in to Florence on a Weds and the Villa Group convenes on Saturday in San Gimignano (I'll have to get myself there). So that gives me 3 nights and at least 2 full days to figure out what to do before joining the Group.

Then the Villa Group ends on a Saturday and I have 3 nights and 2 full days before my flight leaves out of Florence back to California. I want to be efficient in my itinerary so I don't waste time traveling. I'm traveling alone (female, middle age) and I won't have a car but if I needed one I suppose I could rent one. I'm not looking to overspend but willing to pay a little extra for convenience and safety. I don't want to be stressed out. I will be lugging a medium size suitcase and a shoulder bag or backpack.

On the front end I thought maybe I'd fly into Florence and spend time there soaking up the city before the Villa Group. But that's a total of 3.5 days in Florence including the group visit. Is there something else I should consider doing for one of those days? (I've previously been to Pisa and Lucca for a day.)

For the back end of my trip, I'm a major wine freak so I think it would be a shame to miss out on Montalcino and Montelpuciano. Where would I stay - Siena (?) (I will have already had a day there with the Villa Group). But if I do head south to Siena or farther, then I keep getting farther away from Florence where I eventually need to fly from back to California on a noon-ish flight. Is there an optimal way to see these places and get back to Florence the night before I leave Italy?

Thanks for reading through this detailed question, and for hopefully having some advice :) I'm getting totally twisted and overwhelmed trying to figure this out.
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Ciao Pattie, glad you found us!

Sounds like you've been here before and coming back for a longer stay which is ideal to better get to know the area. As a wine enthusiast, maybe it would be ideal to stay at a wine estate, what do you think? Maybe you can consider staying in Florence those first few days before your week starts, and the last few days on a wine estate not too distant from Florence, so you can actually get back into town in time for your flight.

For those first days: you essentially arrive on a Wednesday, I would suggest the rest of your day in Florence and also the following day at the very least. So you could have a day in which to do a day trip - and I would have suggested either Pisa or Lucca (how much do you remember from that trip and what did you see or do?) Also how much have you seen of Florence so far? Because to really enjoy seeing Florence, I always recommend a full 3 days so actually spending those 2 days in Florence, plus your day trip, would not be too much at all. So at that point you could spend both Thursday and Friday in Florence, heading out on that Saturday.

Here's info on getting to San Gimignano from Florence - take bus is the easiest, even with the bus change in Poggibonsi: https://www.discovertuscany.com/san-gimignano/how-to-reach-san-gimignano.html.

As far as the wine estate for after your week, if you head south you run into problems of getting back on time unless you're willing to pay for a private driver to bring you back to the airport straight for wherever you stay at (cost is likely upward of €200). So I would suggest a place closer to Florence, such as Villa Dianella which is just outside Empoli on the road to Vinci. You can do wine tastings and winery tour there, and ask for transfer services to the nearby area if you want to or to the train station so that you can head back to Florence.

Hope this is of help! Another place near Florence with wines/winery is the Medici Villa di Liliano, take a look at my review here.
Thank you Lourdes for your thoughtful reply. This is my first time in Florence and first trip to Tuscany - my one day in Pisa and Lucca was a stop on a cruise that originated in Rome. We saw the leaning tower and walked around Lucca, so it was pretty quick.

I arrive on a Weds., so I think, as you suggested, I'll spend a couple days exploring Florence before I meet up with the group on Saturday. If I do have time for a day trip is there something special I may have missed in Lucca? Or I saw some Vespa tours to the outskirts of Florence, any thoughts on that...?

On the back end, I hear you steering me away from heading south, and thank you for the Wine Estate recommendations. Since I will have had so many visits to Chianti estates already, I had hoped to get into the Brunellos of Montalcino and/or the Nobile di Montepulciano which was why I wanted to head down there. I keep thinking how can I be in Tuscany for 12 full days and not see southern Tuscany!

Here's something I've been weighing...would the main "con" of this be too little time experiencing and too much time traveling? I don't really have a concept of long it takes to get around.:

--Saturday after breakfast at the Villa, get public transportation to Siena (I could probably get a ride to Poggibonsi and catch a bus or train from there).
--Spend Saturday afternoon in Siena. OR should I skip Siena (I'd then just see it on the day trip planned from the Villa) and head all the way to Pienza and stay there? Or maybe you know of a wine estate to stay at in Montalcino or Montalpuciano?
--Sunday - do a group day tour to taste Brunellos
--Monday - check out of hotel and go back to Florence from Siena (or Pienza...?)- is there a direct train to Florence city center? Is it a long trip?
--Tuesday - fly home out out FLR at noon

Thank you for your advice!
Let's say that it can be done, the difficulty is not how far things are because they aren't that far, is that you will have to rely on public transportation and tours to get around.

I'm thinking you can definitely head to Siena (the half day there with the tour won't be enough to see all that Siena has so spend evenings there enjoying the town when the hordes of day trip people leave) after your week in SG and use that as a base. It will actually make it easier to find tours that get you around the Val d'Orcia area: Montalcino/Pienza and Montepulciano are not that far from each other and they can't be reached with trains and you cannot rely on buses for moving around. You will need to use tours and if you base yourself in Pienza, you'll actually have a harder time in finding tours out of there.

So Siena is a better option: https://tours-discovertuscany.partner.viator.com/Siena/d944-ttd there's a few tours here from Siena to all three places, maybe not all on the same day but you could take a look and see what you like best.

Then getting back to Florence from Siena should not be a problem: there is a fast bus that comes back to Florence from Siena (the 131R stands for rapido, you need the R one, not the 131 plain - schedule here: https://www.at-bus.it/it/linee-e-orari/regionali-131r) and from the train station catch the tram T2 line to the airport, takes you right up to the departures terminal. Take a look, you might be able to skip the last night in Florence if you see there are connections that would get you back in time, otherwise do stay overnight in Florence. Trains from Siena to Florence always make a switch in Empoli, so travel time is longer but that is also feasible: https://www.discovertuscany.com/siena/tourist-info/getting-to-siena-without-a-car.html