Best itinerary for visiting Tuscany and Florence

Montepulciano is rather up-and-down all the time.... Consider Montalcino for a hill town that has a flatter central portion. Great wine and food there, too!

Can you arrange to have all of your nights in Roma at the end of the trip? Perhaps like this:

Land in Roma - go immediately by train to Firenze. This will work if your flight gets in early enough.

Firenze - 3 nights

Train to Monterosso - 4 nights

Train to La Spezia, rent a car, drive to Montalcino - 4 nights

Drop car in Chianciano Terme or Orvieto, train to Roma - spend remaining nights

This sounds really good too. Thanks for the suggestions! We’re so excited and I’m loving the planning. I get the best information from the forum, so thanks again.

Kathy

I love Montepulciano as a base for Southern Tuscany, and I prefer its surrounding countryside to that of other cities in the region. You can find beauty almost everywhere, but I think the area around Montepulciano is quite special.

Staying in the city with a car and learning the ZTL zone is a challenge. There are certain lodging places that offer parking. The city center is fairly high up on a hill. Some streets are a very steep walk up. If you stay in the city center, you will get a cardio workout.

I also enjoy staying in the countryside, overlooking the city of Montepulciano. There are some convenient parking lots at the top, making visiting the city center fairly easy and enjoyable. Driving the countryside is a pleasure all its own.

Dropping the car in Florence has its issues. You'll need to be more specific about your plans to do that.

You're covering of a bit of territory for an 11-night visit, and the car offers additional stress. Try to learn the drives on Google Street View before you go. It can help with planning.

We have reservations at Meuble IL Riccio which is just off of the central part of town and it has it's own free parking. I am concerned about dropping off the car in Florence. Our drop off is near the train station. Would you recommend dropping off somewhere closer? Orvieto? Somewhere closer to Monterosso?

Not sure if your questions are directed at me.

Il Riccio is located on the edge of Piazza Grande. It's a good location for a hotel, but it's not the best location for a car. The Riccio's five, free parking spots are located about 800 feet away in a private, outdoor parking area next to the Fortezza. I am assuming the Riccio will give you temporary permission to drop your luggage directly in front of the hotel before you park your car in one of their free spots. You will need to verify this. Cars are normally not permitted in Piazza Grande, but hotels are supposed to get a small timed window, allowing guests to park directly in front to load and drop luggage. If they do grant permission, make sure they give you a print-out paper that says "CARICO SCARICO BAGAGLI" that you can place on your dashboard while you are parked in Piazza Grande.

If the hotel does not have an arrangement with the city (I doubt this is the case), you'll need to drag your bags the 800 feet, to-and-from the parking space.

There will be a learning to curve to find the Riccio with your car and to find their parking lot. Once you do it one or two times, it's a piece of cake. I strongly suggest you follow their recommended route in Google Streetview. Learn how to use Streetview and practice your drives there before you go. Streetview is the greatest driving tool for first-time efforts.

I've been using the car rental offices on Borgo Ognissanti (nearest the train station) since I was in my 20's, pre ZTL. I can make the drive with my eyes closed. Depending on where you research, certain people will scream the horrors of dropping a car on Borgo Ognissanti, and they will insist you drop your car at the airport. If you are not a person who is easily scared, if you are motivated, if you learn Google Streetview, you can figure out the correct route to return your car at the Borgo Ognissanti office. IMO, this is the most convenient place to return a rental, if you have luggage, if you plan to take a train, or you plan to stay at a hotel in Florence. Research the route on your own, and let me know what you find. I'm happy to help you after that.

Thanks for all of the great advice, especially practicing with Street View.

Yes, the hotel did give us the same ticket you described, so we should be able to drop off and then go park. You seem to know a lot about Montepulciano, so do you recommend any restaurants or things to see? We will plan on doing day trips from there, so if there's some that you would highly recommend, we'd appreciate it.

We'll be dropping off the car at:
FLORENCE DOWNTOWN OFFICE
GARAGE EUROPA
VIA BORGO OGNISSANTI 96 - FLORENCE , IT

Which I think is the same one you recommended. Would that be better than driving to La Spezia?

Thanks again!

"do you recommend any restaurants or things to see?"

I prefer knowing people personally before doing so. However, there is no shortage of information available, and one can spend a pleasurable lifetime exploring Tuscany, using Montepulciano as a base. Some visitors have been known to pack up everything and move there.

"We'll be dropping off the car at: GARAGE EUROPA"

You need to contact the local car rental agency office, the company that is supplying your car. (Garage Europa is a public parking garage that leases space to specific car rental agencies.) Determine from where you will be driving (there are many ways to enter Florence) and ask the local agent for specific directions (in writing) to get the car safely to Garage Europa without incurring a ZTL violation. Study those directions. Follow the route in Streetview. Let me know if you have any further questions. PM me if necessary.

Thank you. Your reply made sense about suggesting a restaurant. We love to eat, so there shouldn't be any problem finding something delicious.

Regarding the car, we rented from AutoEurope.com, and the car will be from Hertz. Should I request the directions from Hertz?

Would it be easier to skip Florence to drop off the car and choose another Hertz car rental that has a train connection? The two I thought of was Orvieto or La Spezia, both of which we could catch the train from there, but the trains would probably be fewer and slower.

I'm not sure what you mean by PM. You've been terrific with all of the very detailed guidance. Many thanks.

With a little research, it's not difficult to find delicious food in Italy.

Yes, you need to contact the train station office of Hertz, Borgo Ognissanti, 137/R, to get drop-off directions. It's best to call them. Perhaps they can send you directions via email if you ask. Sometimes, they will simply tell you directions over the phone, so be prepared to write quickly and ask them to spell street names, if necessary.

Hertz
Phone: +39 055 2398205
Fax: +39 055 2302011

"Would it be easier to skip Florence"

What is easy for one person can be an absolute nightmare for someone with little-to-no navigation skill. Changing trains with luggage is something I always try to avoid in Italy. It makes no sense to backtrack to Orvieto from Montepulciano.

It seems you can certainly drive to La Spezia and drop the car at the Hertz location nearest the train station. It's not something I've ever done. I don't think the Hertz office is super close. You may need to take a taxi to the train station from the Hertz office. From La Spezia Centrale, it is a very short train ride to Monterosso.

It is fairly easy to drive to Florence from Montepulciano. Firenze Impruneta is the A1/E35 exit. The route towards Borgo Ognissanti runs along Via Senese. The Hertz office on Borgo Ognissanti is a three-block walk to the train station. It's easy to catch a taxi if you prefer. There is no direct train service to Monterosso from Santa Maria Novella, you either have to change trains at La Spezia or, worse, change at Pisa and then again at La Spezia.

Decisions, decisions.

Yes, so many decisions, but so worth it if I do it right!

I really appreciate all of the help and advice you've given. I know that we'll have a wonderful time, despite the likelihood that we'll make mistakes along the way.

Thanks again for everything!

Kathy

Oops, I forgot. PM is Private Message. You can access that feature in someone's profile.

"the likelihood that we'll make mistakes along the way"

I've been working in Europe for almost thirty years. (My trips aren't vacations.) I get to stay there for weeks at a time. I add personal time when the schedule permits. I still find myself making mistakes, and when they happen, they irk the daylights out of me. Then seconds later reality kicks in. No matter how well you plan, no matter how much experience you have, unexpected stuff happens. The nice thing about experience, you learn how to adapt quickly.

If you don't mind the additional driving time, and you double check on the opening hours of the La Spezia Hertz office, and the cost is within your budget, I suppose the "easiest" choice is to drive directly to La Spezia and drop the car there. That way you deal with only one short train ride with luggage. The amount of luggage you have and its weight can challenge your transportation decisions is a significant way.

I am comfortable driving in Italy because I've been doing it for so many years. If I have a car, I will drive as long as necessary to avoid schlepping luggage onto trains and through train stations. If this were my trip, I'd be driving directly to La Spezia and stopping in a few places along the way. That's my driving style. But all these decisions depend on your day and time of travel. There are numerous variables to consider, which is why a good plan is crucial when trying to create a successful trip.

Thanks again. I have no problem when things go awry as long as my timeline is flexible. I actually enjoy a more serendipitous vacation than every single minute being planned. With that said, I'm leaning towards doing what you would do--go straight to La Spezia and then take the train to Monterosso. What makes this tough is that I won't be doing the driving, my nephew will, so if he doesn't mind the longer drive, we'll do that. If he does, then we have other options that rely on the trains. I'll need to find out more about the Hertz dealership in La Spezia and how close the train is, but that should be easy.

Thanks again for your massive amounts of advice. It's made a huge difference in my peace of mind.