Savvy Italy travelers, please help a couple first-timers!

With two people and the cities mentioned, train travel would be the easiest and most convenient. A car is best used in the country side away from major cities. The freedom of the car in cities is compromised with finding adequate parking (expensive), avoiding TL zones or you get an expensive reminder of your trip a year later, fuel, etc. Between major cities trains provide more flexibility. Something like 57 trains a day run between Florence and Rome.

You might consider flying into Venice on Oct 1 (arrival day) and flying to Dubrovnik from Rome. Without checking schedules I assume Rome would provide more direct flight options. Spend 3 nights in Venice, train to Florence - Florence is in Tuscany - for two or three nights and on to Rome for the balance. You could easily reverse if the flight schedule out of Venice was better. Steves's guidebooks covers these areas well with many good recommendations for lodging and restaurants. If you are willing to lock into a fixed train schedule you can save considerable dollars with the advance sale, deep discount tickets but those tickets come with restrictions.

When pricing airline tickets look at a three legged flight. You might find considerable saving doing that.

Frank, my apologies. I accidentally posted in Ireland and then re-posted in Italy. I just deleted the Ireland post to avoid further confusion.

The wedding is in Split, Croatia, but we are going to spend a few days in Dubrovnik prior to making our way up to Split.

Thank you very much for your insight!

I agree, use the trains. Use the Rick Steves Italy book for eating and sleeping. You can't miss.

You only have 8 nights on the ground in Italy from the arrival date (Oct 1) to Oct 8 (the night before flying out to Dubrovnik).
Rome is the only place in your itinerary with direct flights to Dubrovnik, therefore Rome should be your last stop. However Dubrovnik is a seasonal summer destination, therefore I'm not even sure there will be any direct flights at all in October, even from Rome. Therefore there is the possibility that you might have a layover in Zagreb.
Frank gave you the most logical itinerary.
Fly to Venice, then work your way south to Florence (in Tuscany), then Rome, by train.
8 nights are a very short time even for just Venice, Florence, and Rome, therefore you may not have time to visit Tuscany's countryside, and especially the Cinque Terre, which is not easily reachable from anywhere. The best you can do to see Tuscany is to spend at least 3 nights in Florence, and take a day trip from Florence. Therefore this is the itinerary that best fits your desires:
Arrive Venice.
2 nights in Venice
Train to Florence (2 hr trip)
3 nights in Florence (this is two full days, one for Florence, and one for visiting the countryside or small Tuscan towns)
Train to Rome (1.5 hr trip)
3 nights in Rome
Fly to Dubrovnik.

Is Rome pretty expensive? We are thinking about skipping it this trip. We don't want to spread ourselves TOO thin...

If we skip Rome, we could focus solely on Florence (with possibly a day trip to Cinque Terre?), wine country and Venice...

It seems that there are direct flights from Venice to Dubrovnik (saw one on skiplagged this morning), so maybe we could fly in to Venice and then fly out of Venice, as well? Not sure on this.

If we cut out Rome, how would this change people's advice?? We would hope to achieve more quality time in Italy by condensing our itinerary, while gaining more flexibility on the back end of our trip in Croatia.

Thanks again for all of the input!

we haven't booked any flights, yet...

open to any suggestions and insight!

Florence is a great home base. Tons to see there and lots of day trips available. It is a small city and it feels that way. Very easy to get around by walking. It's an ideal first timer destination. Rome is wonderful, but it's a big city. If you think you'll make it back some day to Italy, I would say focus on Florence and that general area and go back some day to Rome.

You could certainly start in Florence. Rome can be expensive - probably less so than London and maybe Paris. But the dollar is way up against the Euro things in general are cheaper than a year ago. I think it is hard to do C Terre as a day trip from Florence. First CT is an area and not a specific point so you could have to pick a specific town. Second I think CT works better when you can spend a couple nights in one of the town and do some day tripping to the others.

You could RT out of Venice but that is an extra cost in money and time in returning to Venice. Start it in Florence.

I believe you only have eight nights in Italy before you need to fly to Dubrovnik.

I would have only recommended you visit max of 2 Italian cities flying open jaw. You would definitely make it easier on yourself by eliminating Rome from the mix. IMO, Cinque Terre would eat up too much of your valuable time, and i am not sure if the weather would be ideal in Oct, but others can advise.

Fly to Florence out of Venice or vice versa. Check your flight options using for example Kayak to get the best airfare. Have fun.

Yes I see that Croatia Airlines has a direct flight from VCE to DBV. Kayak shows me a cost of $222 one way for Oct 9.

I don't know what you consider expensive, but prices in Rome will not be substantially different from Florence or Venice.

If you can't increase the overall days of your vacation, skipping Rome will give you 3 more nights for Florence and Venice, if that is want to do. In that case it would be best to fly to FLR then move north to Venice last, since there are flights from VCE to DBV but not from FLR.

If you want to add the CT maybe you could fly to Pisa, spend the first 2 nights at the CT then move via train to Florence for 3 nights, then lastly take the high speed train to Venice and stay in Venice for the last 3 before flying to DBV on Oct 9.
It's your call my friend.

We have taken trips to Italy in September the last two years. Our first trip, we hit the big spots; 2 nights in Venice, 3 nights in Florence, 2 nights in Cinque Terre and 2 nights in Rome. We went into Rome with the mentality that we wanted to see the big sights, but it was important to us to have time in the other places. Rome is a bigger, busier, city, so depending on the pace you prefer you may or may not like this. Our second trip, we spent time in Cinque Terre again (two nights, used as our recovery for jet lag) and then Tuscany. Our first trip, we loved Italy...our second trip, we fell in love with Italy. The smaller towns in Tuscany are amazing. We also have loved our time in Cinque Terre both trips.

If you decide to skip Rome, I would recommend 2-3 nights in Venice, 3-4 in Florence, and 2-3 nights either in Cinque Terre or a Tuscan town. Rome is expensive but not really more so than the other major cities in Europe; in fact we found Venice to be the most expensive in Italy. I would highly recommend train travel; all destinations you mention are 2-3 hours by train, max. If you decide to venture into Tuscany, you will probably want to rent a car. We found the best flight times and prices from where we live (west coast) to be into Milan. Both trips, we flew into Milan but didn't stay there; the first year we took a train to Venice (2 hours) and second trip we went directly to Cinque Terre (3 hours). Some people would probably not want to get off an international flight and immediately onto a train, but it worked for us. After our first two nights in CT, we trained to Pisa, picked up a rental car there, and then drove into Tuscany. If you don't stay in Tuscany, I would highly recommend a day trip into Tuscany; either a wine tour if you would enjoy that or a train trip into a city. We loved both Lucca and Siena.

For hotels, we stayed at La Spiaggia in Monterosso (CT) both years, NH Porto Rosso in Florence, and Anastasia Hotel in Venice. All three were in great, central locations and were clean and friendly.

No matter what you decide, you will have an amazing experience!

09 Oct 2016
Croatia Airlines–OU385
11:15 AM Depart Rome Fiumicino
12:40 PM Arrive Dubrovnik