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Tuscany question for first time traveler

My husband and I are taking our first trip to Italy this July. Our plan is to fly into Florence for 2 nights, then spend 4 nights in the Tuscany countryside and then 4 nights on the Amalfi coast before heading up to Rome to fly home. My question is regarding our time in the Tuscany countryside. I am torn between spending the whole 4 nights in either Montalcino or Montpucliano or spending one night in Siena on our way down south and hitting Sam gimignano and volterra. Is it worth spending one night there? We would be arriving the day after the horse races so I'm not sure if Siena will be in full swing that day or not. Also we aren't renting a car so we will have car service drive us the whole day. When we get to the southern part we plan to have car service drive us to a few places over the next few days as well. We want to wine taste and relax and not worry about driving. Any thoughts or recommendations? It seems most of my friends recommend montepulciano but I have a hard time driving right by the other spots. I also found a neat Castillo near San gimignano as well if it would make more sense to stay outside Siena. We are interested in walking around small towns, sightsee and eat and drink! Thank you!

Posted by
71 posts

We stayed in San Gimignano at Hotel Leon Bianco and did a day trip to Siena and a day trip to Montalcino. We also stopped in Monteriggioni, which was charming. San Gimignano is delightful, especially when the day trippers are gone. La Vecchie Mura is a wonderful restaurant there with beautiful views of the countryside.

Your decision is going to come down to your personal preference. Regardless, you will have a wonderful time!

Posted by
4105 posts

Since you have a driver, have him take you from Florence to Volterra spend time there first as its larger. Then on to San Gimignano mid afternoon. Most day trippers will be gone by 4:00 and the city is beautiful. Spend the night here if you've found a great spot.

The next day can be spent in Siena
Then a drive to your lodging in Montepulciano.

Posted by
34 posts

We just got back and spent most of our days in Florence and Day Tripped to most of the locations on your list with Train/Bus/Tour options. The day trip thing worked well for us but as someone already mentioned after 4pm when the tourists left many of these towns that are already very nice become even nicer. However, I should mention that we went in December and the weather was pretty much day by day. So we would check a day or so out and see... Oh it will be nice in Pisa/Lucca so we would plan to be there that day. We may not have been able to do that if we had a hard fixed schedule. I should mention that while we watch Rick Steves, rewatch him, listen on podcast, et al... we still IMHO pack a bit on the heavy side and all those transfers can take a toll. This way we only had to pack/unpack a few times and riding the trains... well especially the regional ones can be a pain with a few anvils hanging off of the end of your arms.

Posted by
8063 posts

Siena is a great town for a night. It is lovely in the evening. Nothing more romantic than a drink on the Campo at night under a full moon (or whatever moon you get). I'd do a night in Siena within the walls; no point at all staying on the outskirts. Montepulciano is a great base but I don't know how this works without a rental car.

Posted by
4105 posts

Agree with Janet, you could easily spend a night or two in Siena.

Posted by
63 posts

That’s really helpful. I think we’re staying at Castello Banfi in Montalcino and planning on enjoying the winery and grounds one day there and then getting a driver for a day in montelpuciano and another winery. Then another day we are doing a small group gourmet tour which will drive us around. So we won’t do a ton of day trips but I think we will still see a lot. Planning on doing volterra then San gimignano and then staying in Siena one night first. Thanks for all the replies!

Posted by
15193 posts

Rental car locations are in Florence and Siena only.
If you plan to rent one it makes sense to do so in Florence since you will be there prior to going down to the Siena area. That way you avoid transfers on buses with luggage and all. The Hertz location on Via Ambrosoli (Florence south) and Via del Sansovino are near the A1 freeway entrance to Montepulciano.
If you don’t plan to rent a car at all, to me it makes sense to base yourself in Siena and hire a private driver/tour from Siena to do your day trips to wineries and small villages in the Montalcino/Montepulciano Area.

Posted by
44 posts

Hi, Rachel. I'm was intrigued by your mention of a car service versus renting a car. I'm planning a month-long trip to Tuscany/Venice/Florence in the fall with my 86 year-old mother and a friend of mine (we are both in our 60s) and I was thinking about renting a car for drives in the countryside and Uber/taxis in the cities. But I'd like to explore the option of a car service. How did you identify the service you will use? Is this a car service/tour guide scenario? Thanks in advance for any information. Susan

Posted by
63 posts

Hi Susan - I looked in RS's travel guide and also searched the Travel Forum for suggestions. I am not done planning yet, but I have come across a couple recommended drivers in the area that I am going to consider. Specifically, Alessandra Marchetti Tours was recommended. They have been helpful in their quick responses and recommendations. A day tour of Tuscany is about 400 euro. You should look up their site online and email them if you have specific questions. www.alessandramarchetti.com. I would recommend looking in the travel guides and forum for other recommendations as well and then contacting them to see what type of services they can offer you. Most of them do group as well as private tours which you can choose from depending on your interest and budget. I'm finding that if you plan your home base well, you can still see Tuscany without a car rental. I just don't want to deal with the hassle! I am also happy to provide you with any follow up advice after I actually take the trip :).