First trip to Italy itinerary

First,

Welcome to the boards and congrats on your upcoming trip! My husband and I traveled to Europe in 2010 when we were both in our 20's so I think I can offer some advice.

The easiest mistake to make when planning a trip is planning too many things to do. (I know this because I learned the hard way!)

Now, to start. Most travelers who have been to Italy will tell you Rome, Florence and Venice will require minimum of 3 days / 2 nights each to see. If my count is correct you have 17 cities and 11 days. If you plan to do anything more than run from place to place you'll want to cut this list in half or even less. Given your short timeframe, you'll really need to decide if you want to focus on 1 area of Italy (For example Tuscany) or if you want to see the big cities of Venice, Florence and Rome. Doing both enjoyably in such a short time really isn't possible.

Here's what I would suggest:

If you land in Venice and Fly out of Rome your itinerary could look like this:

1: Land in Venice, go through customs, shuttle to Venice from Airport and get settled and do a little exploring and have dinner.
Sleep in Venice

2: Explore Venice (pick max of 4 sights to see with the knowledge you can add more if you find you have time at the end of the day. Sleep In Venice

3: Explore Venice (Pick another 2-4 sights to see.) Wrap up any shopping, dining or wine tasting "musts". Sleep in Venice

4: Morning train to Florence. Explore Florence (Plan 4 sights to see.) Sleep in Florence.

5: Explore Florence (Plan 4 sights to see.) Sleep in Florence.

6: Pick up a rental car and relocate to a centrally located Agriturismo. Explore Tuscany. (Perhaps San Gimignano and Volterra?) Sleep in Agriturismo.

7: Explore Siena. Sleep in Agriturismo

8: Drop off your car and catch a train to Rome. Explore Rome ( Plan 2 sights to see). Sleep in Rome

9: Explore Rome (Plan 4 sights to see.) Sleep in Rome.

10: (IF - and ONLY if you're bored in Rome, plan to take a day trip on this day to Orvieto. Sleep in Rome.

11: Wrap up any Shopping, wine or dining "musts". Sleep in Rome.

12: Fly Home.

Regarding transportation. Most of the cities on your list are well connected by train. Trains are ideal when possible.
The exceptions are the Tuscan hill towns which are not connected easily by train. If you are comfortable driving a manual transmission car (stick shift) you can manage those efficiently. Just be sure you have your international drivers permit and understand the potential problems with ZTL zones when driving in italian cities (a quick search of these forums for "IDP" and "ZTL" will give you lots of info.)

Thanks for your suggestions!

I think I'll skip staying in Florence and add extra days elsewhere, maybe I'll do a daytrip to Florence from Tuscany instead. What do you think of this itinerary? I think the next part will be deciding where to go in Tuscany.

Land in Venice 1: Land in Venice, go through customs, shuttle to Venice from Airport and get settled and do a little exploring and have dinner. Sleep in Venice.

Venice 2: Explore Venice (pick max of 4 sights to see with the knowledge you can add more if you find you have time at the end of the day. Sleep In Venice

Venice 3: Explore Venice (Pick another 2-4 sights to see.) Wrap up any shopping, dining or wine tasting "musts". Sleep in Venice

Tuscany 4: Pick up a rental car and relocate to a centrally located Agriturismo. Explore Tuscany. (Perhaps San Gimignano and Volterra?) Sleep in Agriturismo.

Tuscany 5: Explore Tuscany. Sleep in Agriturismo

Tuscany 6: Possible day trip to Florence by train? Sleep in Agriturismo

Tuscany 7: Explore Tuscany. Sleep in Agriturismo

Rome 8: Drop off car in Orvieto (see Oriveto a bit) and catch a train to Rome. Explore Rome ( Plan 2 sights to see).Sleep in Rome

Rome 9: Explore Rome (Plan 4 sights to see.) Sleep in Rome.

Rome 10: Explore Rome (Plan 4 sights to see.) Sleep in Rome

Rome 11: Wrap up any Shopping, wine or dining "musts". Sleep in Rome.

Home 12: Fly Home.

I don't disagree with the Back2Italy's advice at all, but just want to offer a somewhat different perspective.

While Rome, Venice, and Florence have some of the things you are interested in, they are places where art and architecture are the primary draw. You don't necessarily have to see any of them. You could base yourself in one or two of the smaller towns on your list, or in an agriturismo in the countryside somewhere, and with a car you can make your way all over Umbria and Tuscany, take a cooking class, do wine tasting, fall in love with pecorino cheese, and maybe fly in and out of Rome and catch whatever interests you most about that city in the first few or last few days.

Just some food for thought.

I agree with the idea of staying in Tuscany with a possible day trip to Florence. I think you do not need to be a lover of history and art to love Italy... The food ,wine, scenery and people are just a few of the reasons to enjoy the country. You would probably enjoy some time in CT as well. I prefer smaller towns and villages and driving around having picnics in the countryside instead of always visiting another museum among hordes of tourists.

As its your first time I would perhaps forget the Tuscan countryside for 2 reasons:
Firstly the time of year, late October is not the best time (Spring Summer better).
Secondly to avoid the stress of driving and parking - potentially eating up time and causing arguments.
How about this ...
Rome (4)
Florence (3) with day trip to Siena
Bologna or Verona (1)
Venice (3)

Since Art and Cathedrals are not your thing, I bet you would like the Cinque Terre. We stayed a few days in Riomaggiore, (my favorite of the towns) and visited the others through hiking and trains. It was a lot of fun and so easy to see!

You have a good list. I agree, you don't have to love art and architecture, but how do you know you don't until you are surrounded by it? The architecture and art in public places may surprise you. Stay away from the museums if you want, but art is everywhere - even in the foam design on a cappuccino. Enjoy!

Thanks for all of your advice! :)

I would like to see Cinque Terre but I don't think I'll have time for it this trip, I was also thinking it might not be a good idea for October if it rains.

Djp_syd, I agree it probably isn't the best time to go, but I was looking forward to seeing Tuscany the most out of everything, including Rome, so I really don't want to cut it out of this trip. Would it make it any better if I moved the trip to the first week of October and left on October 5th instead of the 12th?

Fly into Venice 2 nights.
Train to Florence to see the David, make a reservation.
Train to Siena (I know the bus is recommended) 3 nights. Stay outside the city walls close to the train station and car rental agencies, we loved Hotel Italia.
Rent a car your last two days in Siena and day trip in Chianti.
Drive to Montalcino, Pienza, Montepulciano and pick one for 2 nights.
Drive to Orvieto for 1 or 2 nights. Great shopping in Orvieto and a good place to drop the car.
Train to Rome for the remainder of your trip, fly out of Rome.
The time between Venice and Rome will be your least expensive for food and lodging. Great scenery and food. Take a food/ wine class in Siena and it will teach you what to look for while touring the countryside.
Don't discount art and architecture, until you have been to Italy you don't know what art and architecture really are. At least I didn't.

That itinerary sounds good Richard, thanks!

I'm thinking about flying into and out of Milan. I see that Emirates has round trip non stop tickets for $696. Has anyone flown Emirates before? I'm not sure how long it would take to get to Venice and Rome by train from Milan though?

If you can move the trip up a week that might help... however, I was there two years ago during mid-late October and we had absolutely beautiful, warm,summery weather every day but one (some rain). boat trip to CT was amazing, walked on the beach, etc... and few crowds. Met some people who were there the week earlier and it was unseasonably cold and rainy most days. So... you know it is unpredictable, but given the choice I would probably try for as early in Oct. as possible. When I dream of returning to the Italy I love, it is the Tuscan villages and countryside that call me, not the museums or cities (I do enjoy and appreciate them, but they don't have my heart)

Similar to Richard, how about this ...
Rome (4)
Florence (2)
Pick up hire car in Florence
Montepulciano (1) via Chianti
Siena (1) via San Gimignano
Drop off hire car in Siena
Venice (3)

A week is not going to make any difference. You can get great weather in October and you can get average weather in September. Luck of the draw. Cross your fingers.

I am very knowledgeable on Bologna and Siena. Should you need recommendations of hotels/restaurants and sites other than churches....let me know.