Grandmother Needs Help with Trip to Tuscany/Rome - SOOOO many choices

Do you have a guide book, from RS or otherwise? If not, it would be a good start.

The locations within Italy you mention are reached easily by train. Flying would take longer.

You should go from city to city by train in Italy. Florence is where you would base any trip to Tuscany, and it's worth taking a couple of the 11 days in Rome to spend there. You could book a room in an agriturisimo or farm stay for another couple of days if you rented a car. The roads are crooked, but well paved and easily traveled in Tuscany. We saw Siena, Certaldo, San Gimignano and Volterra when we stayed in the country. Many hosts offer cooking classes.

If electing to stay in Florence, it is advisable to head there directly by train from the airport, staying in Rome last.

Hi, crg722, and welcome to the forum -

Florence is the capital of Tuscany and will be the easiest for you to get to by train from Rome. However, to do a cooking class, day trip to Pisa and a wine tour PLUS explore Florence (Firenze) itself, you're going to need more than two nights there. Castle? No, probably not in the plan but there are nice places to stay in Florence. I would also question the wine tour if your granddaughter isn't yet a fan of the grape (I'm guessing she's not.)

Aside from wine, castles and a cooking class, what else are you two interested in and what are you planning to see/do with your 11 days in Rome? Florence is the cradle of the Italian Renaissance so is a goldmine of art and architecture. It is only 90 minutes by fast train from Rome so you don't even want to think about flying but you do need to consider which airport you'll be flying home from. We often recommend that travelers planning to do both Rome and Florence and flying into/out of Rome go directly to Florence by train and end their trip in Rome.

I might also suggest looking at an RS "My Way" tour for the two of you. It manages all of your hotel and city-to-city transport arrangements while leaving the two of you free to explore on your own in between. It does includes more locations than just Rome and Tuscany but if feeling overwhelmed, it might be a good choice so take a look?

https://www.ricksteves.com/tours/italy/my-way-italy

I get newsletters from a place called Let’s Cook in Umbria near Perugia. So, it’s not Tuscany, but they have some mini holidays that combine cooking with sightseeing. The website is https://www.cookinumbria.it/

You need to reorder your days, fewer in Rome than 11, more in Tuscany than 2.

I am loving all these ideas. It is just exhausting trying to figure everything out. I have decided to spend 3 days in Tuscany now - not just one overnight and to take the train from Rome to Florence. I have seen some places in Montepulciano (sp?)i to stay (since waking up and seeing the vineyards/countryside is MY dream). Any recommendations on where to stay (not too expensive - under $100/night)? Also, would it be best if I rented a car in Florence to get to Montepulciano and go from there to see other sites? Then we could go at our own pace. I am looking into flying from Denver to Rome and leaving returning from Florence - seems the airfares are cheaper that way for some reason....... Thoughts? Again, thank you all for helping me an elderly person. I am just wanting to check off the one thing left on my bucket list and give my granddaughter a wonderful memory... My granddaughter is excited about wine tasting also so winery suggestions?

crg722, I think upping your time in Florence is definitely a good idea; two nights is just one day, when you factor in travel time.

And just a gentle note: you've referred to yourself as "an old lady," which I took as a lighthearted comment. Then you added

thank you all for helping me an elderly person.

Umm, we don't know how old you are, but you might not be aware that a good proportion of the folks on this Forum are no strangers to Social Security and Medicare. Not all, by any means, but lots of us fit the "senior" category, and have for years.

And don't worry about safety; you'll be perfectly safe traveling in Italy. Have fun planning, and have a wonderful trip.

A car is really nice in Tuscany, although not needed to "see Florence." When you say "cooking class" and "castle" you are in effect saying you will have a car.

There are still a lot of details to think about, like:
Are you up to driving a rented car in a new place?
Can you drive a standard transmission if they fail to provide the transmission you reserved?
Have you read on this board about:
ZTL
IDP
Collision Insurance in Italy
Medical Insurance for traveling Medicare recipients
COVID-19 cancellation insurance issues
Travel and Cancellation Insurance, taking your specific age into (cost level) account, and whether Pre-existing conditions are included.

Yes I did look at all that. I am good driving a stick shift and actually find driving in new countries exciting.......

So I'm confused: you're not allowing any time for Florence itself?

Maybe we should back up....
How many nights will you have on the ground in Italy, and how many of those are you now planning to spend in Rome? What do you plan to do/see during your stay in the city?

Montepulciano is a ways south of Florence. Call me crazy but I don't think I'd go all the way to Florence on a train just to backtrack by car but since I've not driven it myself, we'll see what the others say. It's also a 2.5 - 3 hour. drive from Pisa (which I'd personally only do if taking a train from Florence, and skip altogether if you only have 2.5 days to spend in Tuscany.)

Wine tasting: it goes without saying that it's safest on a tour with a designated driver unless a 'taste' is really all you're going to have. :O)

I thinking of flying to Florence, staying 3 days in Montopulciano (sp?) and then taking the train to Rome for 8 days, leaving for home from Rome. I was wondering if I should rent a car for the 3 days we will be in Monotopulciano. Like I said, we want to do wine tasting, see Pisa and take a cooking class. Thanks for the help - sorry it was confusing.

I suggest that you not commit to any non-refundable expenses on your forthcoming trip, and look for airfares w/o change fees and with minimal cancellation fees. Epidemics often have waves of intensity, so you can't predict the circumstances in September, especially travelling as a person of higher risk.

I don’t wish to add to the confusion but I think you are shortchanging other parts of Italy.

I also think you truly need to read the RS Italy guidebook. Very insightful regarding sites, and practicalities.

Consider Florence for 3 nights. While in Florence you can train to Pisa but other than the Tower I think somewhere like Lucca or Siena far more intriguing.

I would add at least 2 nights in Venice. It is so unique.

I have friends who own a 1 bedroom rental in the lovely olive tree covered hills near San Casiano Dei Bagni. PM if interested in considering it. Here you’d need a car and it’s a great area not often jammed with tourists.

Help us help you by telling us exactly how many NIGHTS you have in italy.
I am assuming 10 at this point. Rome needs 5 nights minimum.
If you can fly into Florence then out of Rome then at least give Florence 2 full days which is 3 nights. Pick up your car as you leave there and head south to Montepulciano for your Tuscany stay. You can then drop the car in Chiusi and train to Rome.

If art doesn't interest you- then 2 nights in Florence, 3 nights in Montepulciano.

Make sure you have easily accessed legal parking in Montepulciano.
We really loved Montepulciano but be aware it is extremely steep. We will be staying in Pienza next trip. There are lots of lovely agriturismos in the vicinity that you might check out- many offer their own cooking classes.
Wine tasting should be done in town or with a guided tour- you do not want to drive while wine tasting.
Skip Pisa- it's out of the way if seeing/staying in Montepulciano is your goal.

hey hey crg722
how fabulous for you and your granddaughter to travel to italy, you both will have a great and fun time. yes it's overwhelming with planning and researching but you will be happy when all is done, have your list full of what you what to do and see. the folks here are on the forum will give you good bad and ugly. your remark about "an elderly person" gave me a few chuckles. lots of us here are in that category, not knowing your age, but i'm a senior haha
will send you a PM (private message), look in upper right hand corner of page and will say unread message. click it open
like tim says, read up about renting a car. much of the towns a car is useless since you can't drive into town centers, parking "away" from the place you stay, how far is a good question plus you will pay for it. get your IDP (coincides with your driver's license) good for a year, $25/2 passport size photos at AAA and receive same day.
aloha