Tuscany vacation planning

kathyw-

Looking at your previous posts about this trip-

https://community.ricksteves.com/travel-forum/italy/help-with-itinerary-needed-so-here-goes

questions:
Have you decided to rent a car?

How many nights on the ground will you have?

What are your flight options?
Can you fly into Venice- out of Rome or Milan? or if no Venice in to Milan- out of Rome?
Does the lake region interest you at all?

Christine,
Yes, we will be renting a car once we get to the hill towns. I’m hoping for 13-14 nights there, but we will know more as it gets closer. I’m retired so I’m flexible, she is not. I’ll be flying from North Carolina and she from LA. We can fly into Venice or Florence and home from wherever. I’d like her to have some city experiences and then towns for us both. My first trip was busy, so I would like this one to have some times to relax.
Hmmm, I haven’t thought about the lakes, but I did check out Elba.

Forgot to ask
What time of year?

Does friend have any city preferences?

Hi Kathy, if you can fly into Venice and out of Florence that would be ideal. The reason you want to fly into Venice instead of out of it is because departures tend to be early in the morning meaning you might have to depend on an expensive water taxi to get you to the airport.
If you fly between Venice / Florence and the US there are no direct flights so you’ll need to connect elsewhere in Europe. There are direct flights between Rome / Milan and the US although Rome is closer to Florence by about 15-minutes. Flying round-trip between the US and Milan also works and you cannot fly home from Orvieto. If you go to Orvieto you’ll need to fly home from Rome
If you go to Venice stay three nights so you have two full days. Here’s what I would do:
Day 1 – overnight flight, sleep in Venice.
Day 2 – sleep in Venice.
Day 3 – sleep in Venice.
Day 4 – sleep in Florence.
Day 5 – sleep in Florence.
Day 6 – sleep in Florence.
Day 7 – Siena, sleep in the Tuscan countryside.
Day 8 – day trip to Montepulciano, sleep in Tuscan countryside.
Day 9 – day trip to Pienza, sleep in Tuscan countryside.
Day 10 – day trip to Volterra, sleep in Tuscan countryside.

Well, the last trip was April/ May. I was thinking September/October might be nice, but the days are shorter and also that would affect driving in the dark in the hill towns.
She wants me to plan the trip: she doesn’t care to do all the “touristy things” but loves the thought of exploring villages. I thought about maybe adding some place in Umbria but don’t know if that is feasible due to time constraints, and also not wanting to do too many hill towns.

I can't speak to Venice, never been. We stayed in Montepulciano twice, Florence once. We did quite a bit of driving based in Montepulciano over the two trips, also around September/October. We reached out into San Gimignano and the Chianti area, and over to east Umbria two or three times. Had the odd overnight stay: in Assisi (so we could hit Norcia the next day) and in Sermoneta (for The Gardens of Ninfa, the centre of the universe). Staying off the main drags as much as possible, the driving was for the most part easy and not too busy.

It's a large area. Divide your time between two of three bases: Chianti (if your friend has not been to Florence, look into villages which have bus service to Florence, to avoid driving there), the Val d'Orcia, eastern Umbria. The east part of Umbris is very pretty, driving there not so pretty from Montepulciano. Or, do what we did, just pick one base and relax.

One of the two apartments we rented is no longer available, the other one was from these lovely people: https://www.fontecastello.it/

kathy-

We are reconfiguring our thrice postponed 3rd trip to Italy- can’t even count how many itineraries we have settled on then changed. So many places we want to see and/or return to !

You have to get the big pieces of the puzzle in place first-

Where can you fly in to and out of- usually that means Rome, Venice, Milan for direct/best price.

Where can you pick up/drop off car? Will you need an automatic? Lots of stuff to know about car rental in Italy but set that aside for now.

Strategic use of a rental car is key. Cost-wise/ease of travel.
Car rental offices are closed mid day and weekends in small towns.

Trains are easy.

Staying in the countryside always sounds so lovely until I think of the logistics.- meals, driving, etc.
We like to base in a town where we can enjoy the mornings and evenings. Have dinner “near home”. We don’t drive at night much at home anymore, certainly not going to do it in Italy ;)
I don't want to cook on vacation- we’ll do picnic lunch and dinners now and then but that’s it.
If you want to feel village life, community- stay in town.
Something to think about when considering where to stay and what sort of lodgings.

Important to choose a base that is easily accessible by car with safe/ legal parking.
You won’t be driving IN to any hilltowns- you will be parking outside the walls.

Do you want to repeat places you have seen -Siena, Orvieto, Assisi for example?

If you want a more relaxed trip you’ll want some 3 and 4 night stays.

I think you need to pick your cities first, because that is where you will fly in to and out of.
There is a reason so many do the Venice-Florence-Rome route. It works. You can probably get a little bit of all and still have a laid back time in the middle.

Venice 3- minimum if you arrive here. More of a pain to fly OUT of but not impossible.

Florence 3- minimum but since you’ve been here- is 2 enough this time? Few flights to/from. No direct.

Rome- no minimum or maximum-we love Rome and start or end trips there just to grab a few more days. Easy to fly in and out of.

Milan-haven’t been yet- 1 or 2 nights or head to one of the lakes to start or end your trip. Como or Maggiore. (We had planned to go to Stresa- trip canceled. Music festival there in early September)

It does sound like Tuscany is important to your plan
I’d suggest 2 bases in Tuscany

Pienza makes a good base with a car. Easy access/parking. A flat hill town. 4 nights- visit Montepulciano, San Quirico, Monticchiello, La Foce, B Vignoni, etc- all short day drives, a few close enough to have early dinner in that town if you’d like.

We stayed in Montepulciano which is beautiful but steep and difficult with car. Next trip we are basing in Pienza.

Pick a second base- 3 nights
Volterra and San Gimignano are not really great for access/parking with car but there are lodgings just outside walls. Both towns can easily be seen in a few hours.

Or pick a town in Chianti- Radda, Greve… day trip SG, Certaldo, Siena…

Siena- a pain to drive into. We drove in, parked at hotel, stayed put. Very glad we stayed 2 nights.
Beautiful town, evenings on the Campo, the views

We’ve added Lucca to our next trip. Don’t want or need car there. Good place to drop off car.
Day trip Pistoia, Barga…

Venice-Rome
Venice 3 nights
Train to Florence 2 nights
Get car
Tuscany 7 nights - 2 bases
Drop car- Chiusi
Rome 2 nights-- can’t do it all
Fly home

Rome-Venice
Rome 2 nights
Get car
Tuscany 5 nights
Drop car Lucca
Lucca 2 nights
Florence 3
Venice 2
Fly home

Rome- Milan
Rome 3 nights
Get car
Tuscany 6 nights 2 bases
drop car
Florence 3 nights
Milan 2
Fly home

So many combinations

Gendersen, I’m originally from Niagara Falls NY! Great ideas about Tuscany.
I am reading and rereading all your wonderful suggestions. Seeing the itineraries in print gives me more concrete possibilities than thinking about them. MaryPat, your itinerary makes me breathe easier, haha. Christine, I like the Venice to Rome itinerary. Thank you for the reminder that we can’t do it all. I need to think again about staying in the country vs in town. Last trip, we stayed outside Assisi and felt isolated and it involved more driving.
I’m thinking about returning to Orvieto and then to Rome for flight home.
I do have a question about renting a car: if we go to Siena after Florence, and want to see the city and then visit hill towns, would you recommend staying In Siena for two nights and then renting a car and moving to another base to visit other towns? The country apartment I was looking at is a 30 minute drive to Siena. But where to park?? I remember the nightmare of finding parking in Siena.

I do have a question about renting a car: if we go to Siena after
Florence, and want to see the city and then visit hill towns, would
you recommend staying In Siena for two nights and then renting a car
and moving to another base to visit other towns?

This is where strategic car rental comes into play.
We had wanted to rent in Siena but they could not guarantee an automatic for us, so we picked up car in Florence and went to Siena from there. Yes- it was 2 nights when the car was parked and not used- however we arrived about 4 so did get use of the car on that first day.
We stayed at Palazzo Ravizza which does provide secure parking. The drive into town and to hotel was a bit dicey but once parked it was all good.
Another hotel nearby that also has parking and fairly easy access is Hotel Athena.

I remember the nightmare of finding parking in Siena.

Parking lots surround the town- outside the wall- then an escalator into town.

I mentioned dropping car in Chiusi above. Even though Orvieto might seem simpler there is only a Hertz location there and AutoEurope (which we use for all rentals) no longer deals with that location due to bad reviews.

Christine, thanks for the car rental info. We parked near what I think was the stadium, but I’m glad to hear there is parking around the city. It’s still challenging to say the least.
If we stay in the countryside as opposed to a town, do you think it will be possible to find a driver for winery tours?

This is what I’m thinking so far, thanks to your helpful input:
Fly into Venice- 3 nights
Train to Florence- 3 nights
Train or drive to an Agriturismo close to Siena. We can day trip to Siena, take a winery tour and cooking class while in the area. X 4 nights
Drive to Montepulciano x 3-4 nights. Day trip to Pienza, day trip wine tour, and a day in Montepulciano.

Several options from here:
1. Drive to Volterra and then finish the trip in Florence. fly home.
2. Train to Orvieto x 1-2 nights, train to Rome and fly home.
3. My daughter suggested a flight to Nice, France for a few days on our way home.

I haven’t been to Volterra. Is Lucca worth adding onto that day, or too much?
I’ve been to Orvieto but haven’t done the tunnels and well. I ended the last trip in Rome and was tired because of all the busyness and walking. But 2 nights there would be okay.
Nice is an interesting thought. Maybe get a taste of a new country for the next trip. What do you think? How many nights? 2? 3? Or is this too much changing places?

Someone suggested renting a car in Florence and not Siena.
If we end in Montepulciano and decide to go to Nice, where would we fly out of and also where would we return the car?

Please advise on any part of this.

Fly into Venice- 3 nights Train to Florence- 3 nights Train or drive
to an Agriturismo close to Siena. We can day trip to Siena, take a
winery tour and cooking class while in the area. X 4 nights Drive to
Montepulciano x 3-4 nights. Day trip to Pienza, day trip wine tour,
and a day in Montepulciano.

Is the trip still 2 weeks? This is 2 weeks right here, so unless you've added more you'll need to make your way to your departure airport/city after Montepulciano.

Be careful with "winery day trips"-- you will need a designated driver.
There are plenty of wine tasting opportunities right in Montepulciano.
Here is one:
https://cantinagattavecchi.com/en/prenota/

I see you did ask about driver for winery tours above- have not used myself but RS recommended and good reviews here
www.toursbyroberto.com

Don't miss some of the other lovely small towns in Val D'Orcia- San Quirico, Monticchiello, Castiglione d'Orcia, Montalcino (not our favorite) Bagno Vignoni is a very pretty/interesting place. Another spot often recommended here is Abbey of Sant'Antimo- just south of Montalcino.

Lucca and Volterra on same day seems too much- is that what you meant? Lucca IS a good place to drop your car though if you want to spend the might there then train to Florence. Both Hertz and Europcar are outside the walls.

Nice is very nice, we spent 4 nights and would love to return- not sure it's a good fit with this itinerary--you'll need to see what your flight options are- Rome, Florence, Pisa could be departure airports. From Nice your flight home will likely go thru Paris. For me it would be too much moving around and too many flights- I like to keep my feet on the ground!

If we end in Montepulciano and decide to go to Nice, where would we
fly out of and also where would we return the car?

Chiusi is about an hour- can drop car there and train to Rome or Florence. You will need to spend the night before your departure flight IN whichever city you choose.

Hi Christine. I agree that adding Nice may be too much at the end of a 2 week trip. I’ve tried to limit the amount of times we relocate.
We can add a few days onto the trip if needed, (I’m retired, she is not). You have given two good options for turning in the car. Would you suggest the train from Chiusi to Volterra or drive to Volterra and turn the car in? I think it’s either Lucca or Volterra, not both, and then on to Florence. Which town is your preference?

Volterra doesn’t have a train station

Both towns are quite different
If you are returning to Florence then Lucca probably better choice since you can drop car there then train to Florence

Looking for some direction…

Does this itinerary make sense?

Fly into Venice- 3 nights
Train to Siena
Stay at Agriturismo x 4 nights near Siena.
Rent a car in Siena
Drive to Montepulciano x 4 nights
Drive to Orvieto x 2 nights and return car there
Train to Florence for 3 nights

Or does it make more sense to return the car in Chiusi, take the train to Orvieto and then train to Florence? The only reason for a car in Siena was to visit Civita.

Original plan was to visit Florence after Venice, but I think I would rather revisit Orvieto than go to Lucca.

Your only car rental/ return option in Orvieto will be Hertz

Do you mean Civita Bagnoreggio? That is near Orvieto, not Siena

Christine, I do remember you mentioning previously that the only car rental in Orvieto is Hertz. Is there a reason why so many people use Auto Europe?

Yes, I was talking about Civita near Orvieto. It sounds like the bus there from Orvieto is time consuming. Would you suggest Orvieto or Lucca? I’ve been to Orvieto and it was charming. I read mixed reviews on Lucca as to not much to do there. But at the end of a trip, maybe we won’t want to do too much.

You might find it useful to use this website Rome2rio.com to get better idea of what transportation connections exist between any two destinations you are considering. It allows you to see available options - flights, train, bus, or the driving time between any two sites. I’ve used this a lot to compare train vs driving or to see if any public transport even exists between point A and B. . For example, for next trip, in March, we plan to take a bus from Florence to Siena as it is actually quicker (and cheaper) than a train (due to route train takes). You can also look at where the various stops are, which might point.you to other options/ideas.

By the way, Volterra is known for its alabaster. We enjoyed seeing all that last time, with stops also in Lucca and Vinci (ceramics around there), driving from agriturismo outside Vinci before turning car in at Florence airport (which was in a construction mess the, so turning car in elsewhere sounds easier, but situation in Florence may be better since tram work was completed - will find out in March!).

Thank you for the info Sharon. That site looks like it will be very helpful for figuring out transportation. I did read that the bus was faster than the train from Florence to Siena.
Have a wonderful trip!

AutoEurope.com is a US based consolidator with stellar customer service and usually the best rates

Many here use them for those reasons
Do a search for many many good reviews

They stopped booking with Hertz in Orvieto a few years ago due to bad reviews of that location
I have seen posts here of people who have since booked directly thru Hertz and had no complaints

kathy- Could you clarify exactly when you plan to pick up the car?
From your post it looks like after your agriturismo stay?
If that is your plan I have to wonder what you'll do for 4 days at a rural/remote location- there are so many lovely villages and pretty drives in the area I would think you'd want a car for those 4 nights.

Here is a suggestion-
You will have to change trains in Florence when you travel from Venice to Siena.
Pick up your car there in Florence at the train station and head to your agriturismo 4 nights, then 4 nights in Montepulciano then drive to Orvieto 2 nights- you can visit Civita if you must on your way (or do as a day trip from Orvieto).
Keep the car in Orvieto- there are hotels that have parking (search on booking.com) or you can park in public lot at station and take funicular up.
Then drive back to Florence to return car there. You will save yourself the one way drop off fee (usually about $150) and the cost of those 2 days will likely be a wash- a rental of 10 days is probably about the same as an 8 day rental.

If you must pick up car in Siena- be VERY SURE that you are guaranteed an automatic (if that is what you need) and I would just drive it back there as well to avoid that drop off fee.

Your trip is still so far away but you can play around with AutoEurope.com to see what rental options/costs are. Be sure to filter for automatic (again if that is what you need!). Choose the full insurance rate. Car rental rates have been a bit high this year due to pandemic not sure if they will start to come down and you are 18 months or so out from your trip but it will give you an idea.

You also might want to verify what your flight options might be. Florence doesn't have that many flights and certainly none direct to US so you'll be traveling first on a smaller airline to a location in Europe before you catch your flight to US. Pisa might be better but Rome will always be your best option (from Orvieto you are very close to Rome).

Christine,
I should have you on speed dial! Again, you have make excellent points. I will be able to clarify some of these things when I visit my friend in January: exactly how long a trip she is able to do, what she would specifically like to do and not do, etc.

My latest thoughts were to rent the car in Florence and drive to the Agriturismo: day trip to Siena, stay until evening and then taxi back. There is a cooking class at the farm and wine tasting that we could do. After 3 days in Venice and 2-3 in Florence, we may need a rest day.
My concern is for the number of lodgings this plan involves for a maybe 16 day trip:
Venice 3
Florence 2-3
Agriturismo 4
Montepulciano 4
Orvieto w
Florence or Rome 1-2

What do you think of the above?

So, we either return to Florence after Orvieto or adventure for 1-2 nights in Rome.

The car info is great! I can drive standard, not sure about her.

I have been checking flight from both Florence and Rome just to get an idea. I will have several changes because I’m in NC.

Hi, Kathy. I’m in NC, too! Just reading through, we did a similar trip in 2017. Delta has a nonstop from Atlanta to Venice that arrives about 9:30 in the morning. We splurged on a water taxi from the airport which was fabulous as we basically got a tour of Venice from the water. We only did 2 nights in Venice, then 3 in Florence, 5 nights outside Montepulciano. We had a few more days so added 2 nights in Cinque Terre and 4 in Rome, from where we flew back to ATL. You could skip CT and spend a few days in Rome. There are some lovely, quiet towns near Montepulciano and we spent a few down days by the pool. Happy to be a resource if you need more advice!

As long as you keep several 3 and 4 night stays I think it’s fine

Some places simply don’t need more than 2 nights (Orvieto) and I feel like a 1 or 2 night stay in Rome before departure just means some Rome bonus time
Pick one or two things to see and do that you weren’t able to fit on a longer visit to Rome

Thank you KSinclair for your advice. I’m in Raleigh AND I went to in Italy in 2017 too! We have some common ground. The water taxi ride sounds like it was a pretty amazing way to start off your trip. I appreciate your offer for future help.
Christine- you have confirmed that by staying longer in several places, the itinerary is workable. I’m leaning towards Orvieto and then onto Rome where we will fly home. I am way ahead of the time line, but it helps me to get the ducks in a row early in my mind as well as being able to discuss details with my friend cross country.
Much appreciation for you both.

Yes, do lean towards Orvieto. We just spent 5 days there and found plenty to do. Highly recommend a restaurant called Il Labirinto di Adriano. Get the two mixed antipasti platters.

Nancy,
I was in Orvieto several years ago, but did not have enough time to explore it as much as I would have liked to do. The trip to Civita, although quite an experience, occupied part of the day, not leaving much time for other things. Thank you for the restaurant recommendation!

Kathy, I agree with poster who said 2 nights in Orvieto. Lovely, but as you have put in your itinerary, 4 nights in Montepulciano is a must. The town is lovely, and you can spend the time the Val d'Orcia deserves.

Hello Catherine,
Thanks for passing along some helpful info. I agree with 2 nights in Orvieto. And I’m happy to hear you recommend 4 nights in Montepulciano. In looking at the surrounding towns as well as actually staying in the town, it seemed that 4 nights wasn’t too much. Can you recommend lodging that would offer 2 beds and 2 bedrooms in Montepulciano? After traveling all day together, it’s nice to have our own space at night. That said, a number of places only have 1 bed and a sofa bed (and those may not be so comfortable). I imagine a hotel might be a better choice for the nights in Orvieto (as I believe Christine stated earlier) about being able to check in and drop off our luggage. I’m open to suggestions for lodging there. I stayed at B and B Magnolia in 2017 in Orvieto. Good location, nice owner, remodeling work was being done.

Venice 2N, train to Florence 3N, bus to Siena 3N rent a car the second day. Drive to Montepulciano 2N, drive to Orviet and drop car. Train to Rome 4N. In Siena and Montepulciano you'll want hotel parking. Your third day in Siena you can drive North and check out Chianti.

I’m hoping to arrive in Venice in the morning after a red eye flight ( it’s too early to buy tickets). We will have the rest of that day and the next two full days to enjoy the city. With such a limited amount of time and jet lag, should we use the third and last day to visit Burano, Murano and Torcello or just focus on Venice?