Feeling a little stuck in my trip planning

I think you are being wise to not over plan. That way you can be a bit spontaneous. For example, if you see something on the Venice walking tour that you want to explore further, you will have time. I do like to use Rick Steves' various self-guided walking tours to explore cities, so you might look at those in his guide (I know they are in the Venice guide, not sure about the Italy guide).

Same in Florence & Siena - Rick has nice overview walks you could take just to get a feel for the city.

As to seeing the countryside, Tours By Roberto does an excellent job. I recommend a full day out of Florence. That gives you a day for Florence itself and a day with Roberto. He does a tour that combines a cantina (winery), history, a tiny hill town, and fabulous scenery. There's a fund lunch break at a trattoria you'd probably not find on your own. The group is small, limited to 8 or 9 people, so intimate.

I have driven in Europe but never in Italy. Tuscany is probably the one area I'd want to rent a car. If your whole trip is based on seeing the towns of Tuscany, why not rent a car? Five nights in Florence + Siena gives you plenty of time. Maybe just rent a car few a few days and avoid the cities, just see the towns.

Hi Katie, you have a really nice itinerary! Is this your first trip? I think it's good to plan as if you will go back. There is never enough time to see it all. I would prioritize the things that YOU want to see.

Not sure from what you've written if you're really actually excited to see Florence or not. I do believe there are some that see it as a day trip (via public transportation) from Siena. If you have a rental car, Siena could be a good base (if you get your lodging strategically for driving - others know more about this I'm sure). If you absolutely don't want a car, I'm guessing you can take good countryside tours out of either Siena or Florence. That would save you from a rental car, but we did find driving very easy there (but we gave wide berth to ZTL areas).

As far as Venice, in addition to what you have, I loved the colorful island of Burano. Also, the Doge's Palace was neat to explore.

Thank you Laurel for the excellent idea. I emailed Roberto. I will also look at those walking guides more closely.

Thank you Andrew. Our original plan was to rent a car and spend more time in Tuscany & drive around. But after reading all the nightmares with ZTLs, rental costs, thefts, getting a license, plus wanting to visit wineries & driving, really don't mix. So we decided for the amount of time we'll be there, plus the driver doesn't get to see much, we'd forego it, this time (hoping to be back). It's my first time to Italy also, so I'd like to get one trip down before tackling roads, although I can drive in NYC just as good as any taxi driver, wait, much better actually! I guess it's more fear of the unknown.

Yes Julie, it's our first trip to Italy & hoping not our last, really wanted to see Rome & Pompeii. Next time. The itinerary was really with a lot of advice from this site. Venice wan't even on the radar, I honestly didn't think I'd ever want to see it & now I wonder what was I thinking?? So thank you for the tip on Burano, it does look beautiful & could be a very nice 1/2 day trip. Also, Doge's is right next to St. Mark's so that is pretty doable. Also, thank you for the reminder of prioritizing by what I want to see.

Florence is currently my home screen on my computer. So yes, very excited to see Florence. Just to be in Italy. The coffee, the wine, the food, the gelato!!! Sigh...

Does anyone else feel like if you skip something you are letting people down?

Let me make this suggestion: plan your trip so you COULD rent a car anyway if you get there and then wish you had. What do you need ahead of time that would be hard to do once you arrive? You'd probably want an International Driving Permit (IDP) - costs $20 at AAA. You can even book a car, potentially, for a day trip from Siena without any commitment, then just not take it if you decide not to drive. On the other hand, it would be a shame to get to Tuscany and say, "Gee, wish we could have rented a car!" and not be prepared to do it.

This is how I approached driving in Slovenia on a recent trip (I had driven there before). I reserved a car booking but canceled it when I go there (at no cost); I rented a car the following day just for the day instead of the 2-3 day rental I had originally planned. But I had an IDP with me so I was completely prepared.

I've read enough reports of American tourists driving in Tuscany that I don't think it would be a big deal. I've read the horror stories of drivers straying into the larger cities into the ZTL zones and getting big tickets in the mail later. Clearly there are ways to avoid them. Obviously, staying away from the cities is a good way. Dig up some trip reports from people who have driven in Tuscany and see how they have dealt with it.

Not to sound like I am huge advocate of driving in Europe. I usually prefer to take the train everywhere if I can (I've never driven in four trips to Italy), but in some parts of Europe, having a car and driving really adds a nice dimension and gives you a nicer experience. I'd never want to drive in Italy's big cities or in busy areas, but in rural Tuscany? Doesn't sound like a big hassle.

You might want to plan on having a working smart phone in Italy whether you drive or not. It can come in handy as GPS just for walking directions but of course also if you were to drive.

As u are spending only 2 days in Siena u can see alot of tuscany villages. We took the bus to Pienza, Montepulciano and San Gimignano.
It is easy just have the schedule and go.

Since this is your first trip to Italy, I would stay in Firenze and take the tour with Roberto to get into the countryside. Firenze has a lot to offer (since you'll be at the Accademia, go a couple of blocks further to the Museo of San Marco, I bet your husband will like this small museum, with art painted especially for it; you can see it thoroughly in 60-90 minutes).

Have a wonderful trip!

You are right Andrew H. It could be something I will regret and probably will. For $20, it may be worth looking into for the just in case. Although I hear it may be hard to rent a car for a day. But worth exploring.

JS Pienza, Montepulciano and San Gimignano are some of the towns i would LOVE to experience.

Zoe, you are spot on with the advice of Museo of San Marco, 60 to 90 min is very doable for the hubby, maybe when we first arrive in Firenze. I have emailed Roberto, I think that is my best bet at experiencing the countryside. Maybe my next trip I'll do 5 nights in Rome & the rest in Tuscany countryside. I wish I had a year to travel...sigh.

It's funny, I've been to Ireland three times and my grandmother is from there. She would say, if you had a life time, you wouldn't be able to experience all Ireland has to offer. I have a feeling you'd need two lifetimes to experience all Italy has to offer.

You have let a few people's negative experiences get in the way of achieving your main goal of exploring the countryside!

We always rent a car, have never found the ZTL thing problematic. Car rentals are cheap! Theft? Such a slim to no chance! It is not a license but a small cost permit from AAA. You will regret not renting a car.

Too bad you have given in to the fear mongering found on this site.

Hi Katie! We will be visiting Italy in July and have 4 nights planned in Florence (also staying in Sorrento, Rome and Venice). We also, have 1 full day to explore the Tuscan wine region and smaller towns as the other days will be in Firenze using the Firenze 72 hour card. We have the option of renting a car but since we will definitely be sampling wine, we will opt for a tour package or private tour. I've looked over various offerings and am considering a tour with http://www.tuscanwinetime.com/. If I do not use this company I will use a private driver so that my needs are met for that day. If I were in your shoes, I think I would splurge for the private driver if you can work out an itinerary to fulfill your dream!

Too bad you have given in to the fear mongering found on this site.

Emily, I don't think it is fear-mongering but perhaps more accurately reality-setting. How many times have we seen posts from people who received fine of hundreds of Euro for not seeing a ZTL? It certainly can add stress to a trip to drive in a foreign country, not to mention the expense. The stress and expense need to be balanced against desires.

Personally, I think Americans often assume they have to have a car for the freedom and convenience in travel and many of us have learned that travel without a car in Europe is liberating.

Not sure how expensive it would be to rent a car for just a day in Siena - but you are several months out from your trip, so if you book it now, you'll probably get a good price, and as I said, you can probably book now without any obligation (no fee to cancel car rental last minute). If you don't give a credit card upon reserving the car, there is no fee to cancel. Head over to Kayak.com for example to look for rates. There may be other agencies than show up there.

Just remember that the default (cheapest) rental car in Europe is usually a manual transmission, not an automatic, which you may need to pay extra for.

You are absolutely right Emily. I have let the fear monger get to my head. I really have to stop reading. Although a lot of people do missed those ZTL's & it does cost hundreds in fines. Renting a car in Florence, just isn't an option for me. I have emailed Roberto as a poster previously suggested. The countryside & winery visiting is what I'd really like to accomplish. I don't really have one particular must see town, as I'd love to see them all, but know that's impossible. Drinking & driving is just not optional for me. Since I'll be to tempted to "sample" I'd rather just skip the car this go around. I will probably regret it, but that will just make my plea to go back that much more convincing with the hubby, who by the way can drive a manual. So I'm sure on my flight back, I'll start the conversation....Next year when we go, you can rent a car & we can drive from Rome to the Tuscan countryside. (Since he did forego Rome to fulfill my dream of seeing Tuscany.)

I would definitely recommend doing Tours by Roberto or something similar from Florence and possible Siena. We did the Nude and Food tour by Florence for Foodies last year and it was great! It included spending time in Accademia and then touring around Florence earring food and tasting wine. It's a great value and fun way to see Florence. The same company also does a tour out into the countryside to hunt truffles and then make a meal with them at an agriturismo.