nicolemarie1

Hi everyone! I'm planning a trip to Italy in September w/ my boyfriend of 8 years. We are flying into Milan and then renting a car and driving to Cinque Terre (3 nights), driving to San Gimignano (2 nights), Montepulciano (2 nights), Florence (1 night.... wish it could be longer. Ditching the car in Florence) and then Venice (2 nights).
We are planning on doing some day trips to Lucca, Pisa, Siena, Pienza, Montalcino and the Val D'Orcia!

Desperately in need of a tour guide that can personally show us the Tuscan countryside! Any recommended wineries with lunch?
Also, if we have the option to do 2 nights in Florence and do 1 in Venice, is this better? Do you prefer Venice over Florence or vice versus?

I would appreciate any input you have to offer. We are in our late 20s and are big foodies!!

TDudette

Welcome to Fodor's, nicolemarie1. With all the sites you have on your list, I think you need more than one visit! 😁 Have you looked at Rick Steve's guided tours yet? All the schlepping for travel, tickets, etc. add to the time it takes. Also, do a search here. Go back to the general Europe forum and see the airplane icon by 'Display Trip Reports' for ideas.

P_M

You need to seriously revise your plan unless you just want to drive past everything. You'll barely get to a new place when it's time to leave. If you insist on keeping this itinerary then nobody can help you. Please take that in the helpful spirit in which it was given. By trying to see too much, you'll end up seeing nothing but the road.

nicolemarie1

I absolutely appreciate the feedback! Our flights have been booked into Milan and leaving from Venice so we must start the trip in Cinque Terre and end in Venice.
However, I am happy to reroute parts of the trip in the middle. Would you recommend to just have one home base in the Tuscan countryside? Should we opt to drive from CT to Siena or Montepulciano and just reside there for 3-4 days and do day trips from there?

uktravelover

Hello Nicolemarie,
You don’t have to go to the Cinque Terre just because you are flying into Milan. The drive to Florence from Milan Malpensa airport takes around 4 hours, from Milan Linate airport it’s about 3.5 hours. You can do it by train from central Milan in less than 2 hours.
If you want to pick up your car at the airport and won’t be too jet lagged then one option would be to drive to Lucca or Pisa for an overnight stopover then to a location in Southern Tuscany or Northern Umbria to use as a base for 4-5 nights and do day trips from there. Where you choose probably depends on your interests, but some options to look into are Arezzo, Cortona, Montepulciano, Castiglione del Lago, Chianciano Terme. You could then drive to Florence for 2-3 nights before catching the train to Venice for 3 nights.
Good luck with your planning.

Jean

Comments/observations in no particular order:

Ten nights in 5 different hotels. IMO, ugh, for what is presumably your first trip to Italy.

It's a shame you booked your return flight from Venice without planning to spend any significant amount of time there. It's an outlier in your Liguria/Tuscany itinerary. And I'll guess that your departing flight leaves at the crack of dawn...?

Unless you're flying into Milan from somewhere else in Europe (IOW, the same time zone), driving 4+ hours to the CT after landing is a very, very bad idea. Take the train. Bonus: You won't have to figure out where to park the car near a CT town for 2 days. You won't want to drive between the CT towns. Trains and ferries are much easier. You could rent a car in La Spezia at the end of your time in the CT.

If you were thinking of seeing Pisa and Lucca as a day trip from the CT, that would involve more than 4 hours of driving, not counting finding parking and walking around. (You could train to Pisa in about 90 minutes, then to Lucca in 30 minutes, and back to the CT in 90 minutes. No parking issues.) If you were thinking of stopping in Pisa and Lucca on the way from the CT to San Gimignano, it's still 4+ hours of driving, not counting parking, walking and sightseeing. Actually not much time sightseeing. If you want to climb the Leaning Tower, you need to make timed reservations in advance.

If you were thinking of seeing Siena as a day trip from San Gimignano, then why are you staying in SG (where you only have one full day)? You should stay in Siena. More to see by far.

You could stop in Montalcino and Pienza on the way from SG (or Siena) to Montepulciano, but you won't have much time in either place. Montalcino, Pienza and Montepulciano are all IN the Val d'Orcia, so the Vd'O is not a separate destination.

You need to learn all about ZTLs, which are limited traffic zones established in almost every Italian town of all sizes. During most hours of most days of the week, you can't drive INTO any historical centers of towns, including all of the CT towns and the Tuscan towns you mention as overnight stays and day trips. You park outside of the towns and walk in and out. That means every stop takes a bit longer than you might think.

https://mominitaly.com/ztl-in-italy/

A one-way car rental will be more expensive than a round-trip rental. If that extra cost doesn't bother you, consider skipping Florence on this trip and driving Montepulciano to Venice, returning the car in Venice. Both Florence and Venice need more time than you're giving to either, but I think the logistics of driving Montepulciano to Venice and returning the car there are easier than returning the car in Florence and making another hotel stop. FYI, if your only time in Florence would be on either/both a Sunday and Monday, many of the most famous and popular sights will not be open.

Unless the rental car driver is a EU citizen/resident, they need to have an International Driver's Permit. You may never need to show it, but it is required.

bilboburgler

great advice from Jean, to reinforce, read about ZTLs, don't drive on the first day.

mjs

i think it might even be difficult to drive by all of the places listed in your itinerary. You might start talking about your boyfriend in past tense. Since you are flying into MXP and out VCE it makes sense to at least spend 3 nights in Venice which will give you two full days. I agree that driving in a foreign country after a long flight is probably not the best of ideas and a train to the CT is safer. After 3 nights in the CT you are then left with four nights. I would rent a car at La Spezia as suggested above and drive to Siena. Stay at the Palazzo Ravizza which is in town within the city walls with free parking if you book directly with the hotel. Four nights gives you 3 full days and if you give one day to Siena you have 2 full days to drive out to where've you want to go within reason. Drive to Venice where you will drop the car off. Alternatively you can train from the CT to Florence, stay in Florence, spend 2 days in Florence and one day with public transport to somewhere else in Tuscany like say Siena. There are other options including skipping the CT but the above two options i have outlined would work.

Jean

Another vote for Palazzo Ravizza if you decide to drive to and stay in Siena.

SusanP

Yes, Palazzo Ravizza is great. In addition to parking, I had a room with a gorgeous view out across the Tuscan countryside.
On the other hand, since you mentioned a tour guide for Tuscany, you could go to Cinque Terre by train, then to Florence and stay there for four nights with a couple day trips. www.hillsandroads.com are very good. If you know where you want to go, they will tell you what is feasible, or if you're not sure, you can tell them what your interests are and they can suggest an itinerary. Just another option. Then it's an easy train to Venice, where I agree you should stay three nights.

Jean

I like SusanP's suggestion of staying in Florence (but - disclaimer - Florence is my favorite Italian city so I'm biased). You could see Pisa/Lucca in a single day trip by train and on another day take a guided tour with transport to SanG and Siena (or even DIY using public transportation... easy). However, I think the Val d'Orcia towns would have to wait for another trip to Italy. They're just too far from Florence unless the driver sticks to the very boring autostrada to reach the area and return. But, good news, you could substitute a lovely and relaxing tour of Chianti including a tasting/tour at a winery and a great lunch in a small town, etc. For Chianti, you really need a guide/car.

This idea might end up saving you money. The cost of a one-way car rental for a week, plus fuel and tolls, plus parking fees, would likely cover all of the train fares and the tours

But do research what you want to see/do in Florence before you plan multiple days away from the city. There is a LOT to see in Florence.

nicolemarie1

Thank you all so much for the input and advice. I really appreciate you taking the time to comment some wonderful ideas & substitutions for my trip. I will definitely re-address our current itinerary plan.

lauramsgarden

Hi Nicole, it sounds like a wonderful trip. We spent 3 nights in Venice, but it wasn't our favorite part of the trip (although our favorite part of Venice was a trip to Murano and other lagoon islands). ON the other hand, we only had a day trip to Florence and if we are ever so blessed as to return I would definitely want several days in Florence. The art was phenomenal. We visited the synagogue there. In general we have had luck using guides from Tours By Locals (although I wouldn't recommend the one we used in Tuscany but I loved the one we used in Venice.) Check out my trip report from October 2021. Let me know if you want more details. Have an awesome time.

lauramsgarden

Hi again, I started reading through my trip report (thank you for the excuse to revisit the memories) , we did not get to the Uffizi in Florence (I would go back just for that) but did go to the Palazzo Piti and was blown away - really worthwhile and not as crowded. In addition to the beautiful hilltop fortified towns, Siena was wonderful and we spent an awesome day there.

I know you asked about farmhouse lunches: here is the excerpt from My trip report about the wonderful Farmhouse experience we had - but sadly nowhere to I mention the name of it - maybe you can track it down by location : We then stopped at a farmhouse restaurant owned by a friend of the guide. It was probably my favorite moment so far. The owner said he had no idea how old the building was but hundreds of years. It was located in the Val D'Orcia, a Unesco world heritage site where farmers actually can't disturb the landscape (I'm not sure if I understood correctly, can't figure out how they make a living in that situation). We sat with other guests at long wooden tables. They made some special dishes for my husband (gluten free), but the rest of us were served a kale soup that was a revelation - cooked for two days with bread and beans. I scooped up every drop. Then a tagliateri pasta with ragu, then pork with pumpkin and potatoes, and chocolate cake with homemade vanilla, citrus icecream. It was so incredibly beautiful there, and just a fun relaxed place.

kybourbon

I would take the train Milan to Florence instead of driving on arrival. Spend a night or two in Florence, pick up your rental car (Florence airport is close), pick either CT or Val d'Orcia (you don't have time for both). Drop the car back in Florence and catch the train to Venice. That way you don't have a big drop off fee for dropping in another location.

There used to be a bus from outside Milan Cadorna station to Siena non stop. I'm not sure it still exists as many things disappeared during the pandemic.

Every place you listed you are not allowed to drive in (ZTL) except for the country side - Val d'Orcia. You will be surprised how much time it takes figuring out where you can park, how that particular parking area/place works, etc. Italy is not forgiving when violating ZTL's and they have cameras everywhere.

rosetravels

With 10 nights, and given your interests, I'd land in Milan, spend a day and night to rest, and take the train to Florence. I would skip the CT for this trip. Go again! After a few days in Florence rent a car and stay at an agriturismo in Tuscany near Pienza/Montalcino/Montepulciano. That whole area is extraordinary and there are good (ie delicious) farms to stay at, especially near Pienza. Then return the car and take the train to Venice for a bit.

1 nt Milan
3 nights Florence
4 nights Val d'Orcia (day trips to visit Montalcino, Montepulciano, Siena, etc)
2 nights Venice