Venice and Tuscany - 50th Birthday Trip

Welcome and Happy Birthday!

If you mean staying in Montepulciano for 12-14 nights- that's probably too long.
Montepulciano is lovely but does not have good transportation links. Train station there is not even in town. You would need a car to visit any of the Tuscany villages- really from wherever you choose to base, as there are few towns accessible by train. Bus is an option but limited routes and schedules, so I'd say a car is necessary at least for part of your stay.

Be careful with winery visit- you will need a designated driver
All drivers will need an IDP- get at your local AAA.

You might consider 2 bases- one in Val d'Orcia like Montepulciano or Pienza, another further north like Siena or a Chianti town or even Lucca..

From Venice train to Florence to pick up car- your choices there will be better than a small town like Siena.
Then head to your northern pick for a base for 3 nights? then Montepulciano or Pienza for 3-4 nights. That leaves 3-4 for Venice and 1 night to stay in whatever your departure city is.

Have you determined where you wil fly home from?

You'll def need a car in Tuscany - but we have found parking can be tough in many areas. How long will you be in Venice?

We had something similar planned, but we have now changed it to a week on our own thru Venice, Florence, and Sorrento and then a tour of Tuscany with Tauck. We did look at the Rick Steves Tuscany tour also that looks very good too. You could look at that tour for ideas. We are going in October. I'll be interested to continue to follow this thread. We are flying into Venice for 3 nights (we have been before, but it's one of our favorite cities), then taking the train to Florence to meet up with our tour for a week. The tour ends in Rome (where we have been, so we are taking the train to Sorrento - another favorite city). You will love Tuscany - we've been to a few places, but are excited to see more. What a great BDay trip !!

Thank you Christine! Love your ideas! We are planning to stay in Venice for 3-4 nights. Flying to Venice and out of Florence or Rome.
We have driven in Italy before so thank you for reminding me about the international license, had totally forgotten about it.
My best friend lived in Perugia for many years so we have visited the Umbria and Tuscany region a few times but this time we really want to focus on food/wine once we leave Venice.

@Chinalake - We are not big in joining tours, day tours yes but not multi-day as we like to enjoy things at our own pace especially in Italy where you can sit somewhere for hours and not be rushed out. We love Tuscany and Umbria, so much to see and enjoy. Good luck planning your trip, sounds like you are ahead of me in terms of planning :) thank you for replying,

I agree with Christine. Take a direct train from Venice (Venezia S. Lucia) to Florence (Firenze SM Novella): https://www.trenitalia.com/en.html and rent a car at the train station. Read up on ZTL zone laws so you don’t get stuck with a hefty fine that Florence is notorious for. A few seconds in a bus lane is costly. You can then drive along the Chiantigiana (SR222 road) through the Chianti wine country: https://lovefromtuscany.com/scenic-drives-in-tuscany/.
I’ve read that you should never leave luggage in your car in IT. I did not have problems but if you do, make sure it’s locked in the trunk. Do not leave anything visible in your car when parked.
Siena is a good place to sleep which is magical after the tourists leave. From Siena drive through Val d’Orcia which is full of well-kept farm houses with many scenic landscapes. You can stop in Montalcino if interested in its winery.
I would sleep in Montepulciano over Pienza, but do visit Pienza’s old town that makes a good day trip from Montepulciano. Sleep in Montepulciano a minimum of two nights. Another good day trip from Montepulciano is Cortona.
From Montepulciano drive up to San Gimignano for a half day then to Volterra which is another scenic drive. Sleep in Volterra for two nights.

Mary Pat, thank you!!! absolutely love your tips! I can't wait to see San Gimignano again! In one of my trips to Italy I visited a lot of the small villages and San Gimignano is one I always said I would go back to. Agree on Montepulciano over Pienza, I have been to Pienza but haven't been to Montepulciano so I rather stay there. When visiting Tuscany, did you rent Airbnb or stay in hotels? I have always done day trips either from Perugia or Florence so I never spent overnight in these smaller villages. Thank you again for your help!

If you have a base in the northern part of Tuscany -Siena or Chianti-I would visit SG and Volterra from that base
It’s over 1.5 hours from Montepulciano
You might even choose to base in Volterra

Make sure you have secure accessible parking wherever you choose to base

did you rent Airbnb or stay in hotels?

I stayed in hotels in the city center. The great thing about Airbnb’s is you can do laundry without finding a laundromat during the day. This is crucial for packing light.