Well you can do it, the train is a good idea. I think I might put the Florence days together, then Siena and then Milan. Alt. you could do Siena before Florence. Since the two cities were mortal enemies and the winner was the one to recover first after the black death it is interesting to compare the cathedrals, (one stuck at the point of defeat, the other growing after winning)

This is agressive and I wouldn't do it, but if you like rush then try.

And welcome to Fodors

Hi Bill! Thanks for responding. We are certainly open to different itinerary options! Basically, we want to combine some city time and some country time. Want to EAT, DRINK and soak up just being there. We realize, 5 nights is not a lot of time but its what we have to work with.

Also considering flying into Rome (price dropped today!) 2 nights in rome, 2 nights in Tuscany, 1 night + 1 full day in Rome before flying out.

Loving Italy and your proposed destinations as I do, I wouldn't do this trip. however, it can be done. I think I would cut out one destination, probably Bologna. You say you want to wander. With your itinerary it will be more like race walking if you plan to see much.

Why Milan and Bologna? If you have good reasons, that's fine. Bologna is certainly a great venue for eating, but one can eat and drink well pretty much all over Italy. You won't have time to wander - 5 days is a rush no matter if you stay in one place or travel around. But do you have to fly into and out of Milan? That kind of messes with any ideal short itinerary.

There are a couple of snags in your itinerary.

1. You will have only a few hours of day 1 in Bologna. You arrive at 10:00, need to wait for bags, get to Milan, and then take a train to Bologna. That will take probably 3 hours to get to Bologna, possibly more if you need to wait in Milan for the next train to Bologna. You need to be realistic about the amount of time travel takes.

2. Have you looked at the night train schedule for Florence to Milan? You have a 3 hour connection in Parma at 2:00AM. I would not enjoy sitting in a train station for 3 hours in the middle of the night. This will give you little sleep. The day time trains take 2 hours or less so I would consider them.

Overall this itinerary is too ambitious. You will visit several towns/cities but see almost nothing. Much of your vacation time will be spent getting to and from train stations, packing and unpacking, and on trains.

My choice, with only 5 nights, would be Florence and day trips from there either via public transportation or private guided tour. Siena is an hour away by bus, Pisa is an hour by train. There is other bus service to quite a few Tuscan towns from Florence.

If you stay in the center of Florence within walking distance to the bus/train station you'll have a more relaxing trip and actually get to see a few places in Italy. No need to keep packing/unpacking, finding your way around a new town (always confusing).

Per your info, you have 5 nights in Italy, but your count seems to be off.

Your itinerary 1:
Day 0: Fly from Miami
Day 1: arrive Milan 10 am and take a train to Bologna. Spend "all day" + 1 night in Bologna (Night 1)
Day 2: First thing in the morning take a train to Florence, Spend all day +1 night in Florence (Night 2)
Day 3: Hire a car service to take us around Tuscany, possibly Sienna (Night 3)
Day 4: Tuscany, second night (Night 4)
Day 5: Spend 1 night + 1 day in Florence (Night 5)
Day 6: Take night train (seems like you have no nights left--do you mean an overnight train?) to Milan, spend all of the last day in Milan before flight leaves at 6pm

I avoid one-night stays because they seem to waste time with checking in and out of hotels. Also note that you expect to have "all day" in Bologna, but based on an arrival time in Milano Malpensa, I suspect the soonest you would arrive in Bologna would be about 2:30PM. My rewrite of this itinerary to fit the time you have would include not breaking your stay in Florence into two pieces.

Adjusted itinerary 1:
Day 0: Fly from Miami
Day 1: arrive Milan 10 am and take a train to Florence. (Night 1)
Day 2: Spend all day +1 night in Florence (Night 2)
Day 3: Hire a car service to visit Tuscany, possibly Sienna (Night 3)
Day 4: Tuscany, second night (Night 4)
Day 5: Turn in car and take train to Milan (Night 5)
Day 6: spend all of the last day in Milan before flight leaves at 6pm

For your itinerary 2, again I'm wondering why you are breaking up your stay in Rome. To me it's better to put your days in one place together if possible. with so little time, I would prefer to move less.

Day 0: Fly from Miami
Day 1: arrive Rome airport and travel to Tuscany/Umbria location (Night 1)
Day 2: Spend all day +1 night in Tuscany/Umbria (Night 2)
Day 3: Later in day, drive/train to Rome (Night 3) (or could use this time in tuscany and go to rome in the morning, depending n your interests)
Day 4: Rome (Night 4)
Day 5: Rome (Night 5)
Day 6: fly home

Flying into Rome would work best for you, I think. With such a short amount of time, I would stay in Rome and if you want to see a bit of something else, do a day trip to Florence or a day trip to Orvieto.

If Rome doesn't interest you, go straight to Florence. Do day trip by train to Lucca and Siena or hire a driver to take you around Tuscany.

If you want both, go straight to Florence. Put all of Rome at the end.

When are you going?

If at all possible, wait until you can have a week combined with two weekends to go. You could do more and get more for all the money spent on airfare.

Rather than circling, if you are determined to do several cities - I would do an open jaws flight into the first city and out of the last. It won't cost any more and will save some of your very limited time.

But what I would really do is stay in one hotel throughout and do day trips to see what you want.

If you really want to do Bologna (great food) then stay there and do a couple of trips into the countryside. Or do the same from Florence or Rome.

It may seem like you are doing less, but believe me you will have more time for seeing sights and exploring cities than constantly moving from place to place.

hi winelady

If eating and wine is more important to you than sightseeing, you can have a great trip either landing in Milan or landing in Rome, but you really need to get some guidance about where to go to get excellent food. That is more reliably available on the Chowhound message board for Italy.

For instance, if you landed in Milan and immediately took a train to Parma, you could have fantastic food you would not forget for the rest of your life. (Hotel Daniel in Parma has a terrific restaurant). It is also an incredibly beautiful small town filled with Italian culture, both music and painting. It is such a beautiful introduction to Italy, and with or without a car, you can visit nearby towns and have extraordinary food.

Likewise, if you land in Rome, just press on to Umbria. Spend a night in Orvieto (and drink their lovable wine), but when you are rested, get yourself to somewhere around Montefalco and the good food and wine of central Umbria. You will not lack for spectacular art and history. This is the land of St Francis of Assisi and italy's most glorious frescoes. This is where Hannibal beat the Romans.

5 nights in Italy spend either in the beautiful highly digestible small art cities of the Emilia-Romanga/Tuscany or Umbria is a much more enjoyable trip than being in the overwhelming cities, and while it is true you can always find decent food, even lovely food, almost anywhere you go in Italy, there are some goldmines of great food and cultural beauty, often scarcely changed by tourism (which really helps keep food standards high).

I don't think you will regret shooting past the cities and the conventional tourist spots to enjoy a week in the better food and wine producing regions. The small towns are beautiful.

http://www.telegraph.co.uk/travel/destinations/europe/italy/8965335/Parma-Italy-a-cultural-city-guide.html

http://www.guardian.co.uk/travel/2008/feb/16/top100foodbreaks.citybreaks

http://www.bellaumbria.net/en/itinerary/

http://www.italia.it/en/discover-italy/umbria.html

Rail tickets as low as 9 euros if purchased nearly 120 days in advance....ie Venice to Naples is 9 euros

Wow! Thank you all so much! This is most certainly helpful. I can surely see how I was trying to cram too much in. I think we have adjusted our plan to look something more like this:

-Arrive in Rome around 11am, rent car
-Spend the first 3 days/nights exploring Umbria and possibly Tuscan towns. Plan to stay at one Bed and Breakfast as a home base. Perugia looks like a good location for this. Thoughts?
-Sometime on the 4th day, drive back to Rome. Return car. Check into hotel/BB. Explore the neighborhood, have a late Roman dinner.
-Spend our last 2 days visiting one or two "must see" Roman sites. We know we cannot see it all. We are ok with that.
-Fly out at 8pm of the last day.

Does this sound more do-able? It feels less rushed to me. I like the idea of wandering around Umbria and possibly Tuscany for a few days. With a skeleton plan at least of what towns we'd like to see. There seem to be a lot of self guided driving maps of these areas.

My next questions would be: 1. Where would you base yourself for 3 days of Umbria/Tuscany sightseeing? 2. Which neighborhood in Rome would you base yourself in for a quick 3 day 2 night stay?

Thank you all!!

Considering this is your first trip to Italy, unless you have a lot of international driving experience, I wouldn't rent a car on arrival and immediately head out.

Driving in and out of Perugia every day can be tricky and a bit time consuming. I'd pick a smaller town. In 3 days/nights, you're not going to see a lot of Umbria and Tuscany, so you should figure out what you want to see and then pick a location that makes geographic sense for your day trips. IMO, you should think in terms of Umbria OR Tuscany but not both regions.

If this were my trip and assuming I didn't arrive on a Saturday or Sunday (when car rental office hours

Sorry. I hit the 'submit' button too soon.

If this were my trip and assuming I didn't arrive on a Saturday or Sunday (when car rental office hours would preclude this plan), I'd train to either Orvieto (for Tuscany) or Foligno (for Umbria). If Tuscany, I'd stick to the Val d'Orcia area of Montepulciano, Pienza, San Quirico and Montalcino and also try to see one of the abbeys. If Umbria, I'd see Assisi, Gubbio, Todi and Spello.

Driving a rental car into Rome to drop it off runs a considerable risk of getting hit with one or more fines for driving in the restricted zone.

In Rome I would definitely book a hotel in the historic center - so you can easily walk to as much as possible. As soon as you book the hotel ask them about driving and parking. They will tell you if you can take a car to the hotel or not - or reco where to drop it off and pick up a cab to get there.

We have not found driving into Rome to be as much of a problem as driving into the smaller towns - often just not possible - you need to leave your car in a lot outside the walls. Check for specifics with whatever hotels you book.

There's no need to drive into Rome to return the car unless that's really what you want to do (which I would consider very brave for an Italy newbie!). After your time in Umbria or Tuscany, you can return the car at either Orvieto or Foligno and take the train into Rome.

hi winelady,

This is the way I would do your trip -- but presumably you are smart enough to know that should be taken with a salt shaker! Just giving you my perspective:

-Arrive in Rome around 11am and to directly to Orvieto by train. Check in, get some wine and food and meander or nap or what have you. SLEEP
--- Rent a car and head to either another small town or a farm/winery in either Tuscany or Umbria. (Perugia is a pain with a car, but it is great to visit if you want to go the national gallery of Umbrian Art).
-Sometime on the 4th day, drive to CHIUSI in Tuscany or FOLIGNO in Umbria. Return car and take the train to Rome. Check into hotel/BB. Have Lunch. Begin exploring Rome.
-Spend our last 2 days visiting the Roman sites you personally would be thrilled to enjoy. We know we cannot see it all. We are ok with that.
-Fly out at 8pm of the last day.

In case my above post wasn't clear, I am suggesting your rent your car on Day 2, in Orvieto.

I am also suggesting that when it comes to returning your car, you return it to Chiusi if you are staying in Tuscany, and return it in Foligno (or Orivieto) if you ended up staying in Umbria. Take the train back to Rome.

Where are you finding flights to Miami departing at 8 pm? Most flights to the states depart early morning.

Kybourbon -Hotwire Flight is still listed today, though slightly higher than yesterday, but still not bad at $1080. I love we would get to spend that whole last day before departing, but then we are stuck with a 10 hr overnight layover in Germany. Perhaps we could stay at an airport hotel and get a few hours of shut eye. Not sure yet.

I cannot thank you all enough. These responses are giving me such clarity, and I can really see our trip taking shape.

With the help of your suggestions I think we will indeed take a train to Orvieto straight from landing in Rome. Then rent a car once we arrive. I have kind of fallen in love with this place as a homebase for the country part of our stay http://www.locandarosati.it/ has anyone been? From Orvieto the next day, what would your "cant miss" day trip be? 1-2 towns most I suppose depending on driving distance. Beautiful scenery and a stop at a winery a must

Looking for suggestions on where to stay in Rome too, if you feel so inclined! A lively neighborhood with great (non touristy if possible!!) food, streets to wander, cafes to sit at and within a reasonable distance to great sites. Vague, I know. Hotel or BB with a good bed, good shower and good breakfast

>>>but then we are stuck with a 10 hr overnight layover in Germany.<<<

I wouldn't do this. You can probably book a regular flight from Rome to Miami for not much more and won't have to pay a hotel somewhere you don't want to be. Waste of your short time and money.

From Orvieto (if you are staying there a couple of days), I would visit Civita di Bagnoregio. Also spend some time in Orvieto.
http://www.civitadibagnoregio.it/english/index.htm

I really don't think Orvieto makes a good home base for your interests.

I would head a bit more north to Montepulciano, Pienza and Montalcino (perhaps stay in Montepulciano or Pienza) if you are interested in wine.

I don't think you have time for the countryside and Rome.

I think some of the better known towns of Umbria will be a bit of a drive (over an hour) from the Locanda Rosati. However, I think for your short stay, you can find plenty to see in the area, beginning, of course, with Orvieto (one of my favorite towns).
Bolsena is very pleasant and not on all the tourist maps for some reason. Todi (Umbria) is under an hour (my personal limit for day trips). Pienza (Tuscany)would be a pleasant drive up the SS2, which is a pretty route. I think even towns like Pitigliano and Sorano (Grosetto)come in under an hour's drive.

My overall feeling is that you don't quite have a grasp of how very short a time you have for this trip - so short that a 10-hour layover in Germany makes no sense at all, and so short that staying in Orvieto is not the best decision because you will be in a car trying to get to other places for more time than you will actually spend in other places. Time FLIES when you're traveling through Europe.

I agree that Montepulciano or Pienza (which I love!) would make a better base for you. And though I don't think you have time for Rome, if you need a hotel recommendation, I love the Hotel Modigliani.

Looking back at your interest in wine, food and wandering, perhaps Montepulciano is a better base.
Train from Rome to Chiusi, rent car in Chiusi (note--this would probably be a manual), then drive to Montepulciano. Plenty of wine and food options there. Good town for wandering. Pienza and Montalcino are easy drives. Could return in Chiusi, or if you are interested in Orvieto, return there. Train back to Rome.

My first trip to Italy was a few years ago. I am one of the few people that rush around, cram stuff in and like it. We spent a week of our 3 week trip in Rome with the rest in Venice, Bolzano, Lake Garda, Florence, Montepulciano and Greve and San Sano. We barely scratched the surface in Rome. We're seriously considering spending a month in Rome next year. I could spend another 2-3 weeks in Florence. We also drove a rental car with no issues. Do what you feel comfortable with, but with just a week, I would not leave Rome.

WineLady,
On Sunday I had booked and then within 24 hrs cancelled, a flight home like the one you're looking at with a 10 hr layover. We have spent the night in an airport before, and it is not the way to end a wonderful trip. I don't know why so many flights are like that lately. I was saving $200, but it was just not worth it. Best to keep the layovers to no more than 3 hrs and you'll appreciate the whole vacation more. I rebooked yesterday at some lesser known website. We have typically arranged open jaw flights so we don't have to waste time getting back to a city we've aready seen.

My overall feeling is that you like the 'idea' of spending time in Tuscany or Umbria but have little knowledge about either region. The agriturismo you've fallen for is southeast of Orvieto, not where most people base themselves with limited time to explore Tuscany and Umbria. If you looked at the driving times involved, you'd see why.

I suggest you spend some time researching the regions (include Lazio), locate on a map things that appeal to you and find out the driving times involved. Then, based on how much time you want to spend in the car, figure out a logical geographic base within a reasonable distance.

Alternatively, if this agriturismo is definitely where you want to stay, determine what towns/sights are within a reasonable driving distance from it. For instance, from that location, I would consider Todi, Amelia, Lake Bolseno (also mentioned by someone upthread), Viterbo, Pitigliano and perhaps Tarquinia. Some of these destinations are in Lazio.

Sorry, the agriturismo is SOUTHWEST of Orvieto.

If you want to search driving times from the agriturismo on maps.google.com, type in "Locanda Rosati, Orvieto, Terni, Italy" in the box.

https://maps.google.com/

viamichelin.com will do the same thing.

which you use is a matter of personal preference.

If you end up staying in Locanda Rosati, I recommend that you visit Montefiascone to both sightseee the exceptional architecture but also to drink the absolutely delicious white wine Est! Est! Est! You can combine it with a visit to Soriano nel Cimino, You might find this thread interesting:

http://www.tripadvisor.com/ShowTopic-g194950-i3723-k50559-Soriano_nel_Cimino_a_good_base_for_exploring-Viterbo_Province_of_Viterbo_Lazio.html

I also recommend the 40 minute drive to the Bomarzo monster park, and on the way back a stop in Civitella d'Agliano. Another town that is just about 30 minutes from Locanda Rosait is Torre Alfina, which is a quite impressive castle town.

It's about an hour's drive to Montepulciano from Locanda Rosati, but well worth heading there for lunch one day. It is nice to drive around that area and make a visit to Pienza.

I found it quite difficult to drive in Viterbo.

If you end up deciding to stay someplace, the entire area is filled with lovely vistas, fascinating architecture, good wine and locandas that are just as pretty and well reviewed as Locanda Rosati. Usually it's just a case of more or fewer tourists, more or less shopping.