Open Jaw, or saving money

No brainer. Open jaw. You'll save so much time not having to go back to Rome. The only way I wouldn't do open jaw is if you're traveling in a logical circle and not going out of your way to get back to where you started.

It's only 1.5 hours by train between the two cities and you only have to backtrack once to Rome to catch the departing flight. The value of the time loss + cost of 2 train tickets is < than $300. Yup, it's a no-brainer - round trip is much, much cheaper and the time savings isn't a whole heck of a lot. That's why a lot of people do round-trips to/from Rome...there are no direct flights to Florence.

How does the flight connection out of Florence compare to the connection out of Rome - same layover, same flight times? Sometimes it's very different as well as a difference in price.

If you round trip to/from Rome, then you'll need an extra train ride obviously - how much will that reduce the savings of doing the open jaw flight? You can check prices now for about three months out to see what best train prices might be on Trenitalia Florence to Rome.

If you do the round trip to/from Rome, personally I'd take the train to Florence immediately upon landing in Rome (there are a few direct trains a day but otherwise you'll need to change between in Rome between the airport), start your trip in Florence, take the train back to Rome and end there so you don't split up your days in Rome.

That $150 savings is off set by the additional fare getting to and from and for the Leonard Express to the airport. So the savings could be less than a hundred per person. And time does have value. What are your dates?

PS -- This is really strange. We almost always fly open jaw and rarely find it to be more expensive. Without any info from you I just did a quick check, mid-July Denver to Florence and Rome to Denver was $225/person cheaper than a RT to Rome. That surprised me but I double checked and it is correct. That is the biggest difference we have seen in a long time. Give us you dates and cities.

The mention of layovers is a good point. IF we did the Rome round-trip both legs could be direct flights (we're flying out of Montreal, as we live in Vermont. Driving 2 hours up to Montreal is not a big deal and will be saving us incredible amounts of both time and money. Flying out of Burlington, VT is...not cheap

IF we fly out of Florence we may have a layover in either Munich or Zurich, both listed to be around 1.5 hours.

I would select the $300 cheaper roundtrip upfront especially if it is to echo Agnes it involves a direct transatlantic flight to and from Rome.

If you can fly direct both ways to/from Rome, I'd do Rome round trip almost for sure - no point in adding an extra layover at an airport if you can avoid it. Just another chance for a delay. And obviously it won't save you time; flying to Rome and taking the train to Florence may wind up saving you time..

You have to add the cost (in time and money), of the return to Rome. Round trip may still be your best bet, but consider ALL costs.

As others have said, if you do decide to do RT to Rome, travel immediately to Florence and put all your Rome time at the end.

Open jaw. The cost of getting back to Rome will offset a lot of the difference. Then you loose a night of your trip because you usually can’t get from Tuscany to Rome on the same day you fly out (too much risk).

Then you loose a night of your trip because you usually can’t get from
Tuscany to Rome on the same day you fly out (too much risk).

That assumes total inflexibility in allocating days between the two cities; yet, there's no evidence this is the case. The OP can get back to Rome a day earlier (and spend it there) so as not to inflict any risks on the day-of-departure.

Are you sure you are pricing this correctly? You use multi-city option and not two one way tickets. I just priced open jaw Montreal to Florence on Oct 10 and return from Rome on the 24th for $28 US dollars/person less than RT to Rome same dates. That is very close to what we typical find when pricing open jaw tickets. The difference is rarely more - both ways - than a few dollars.

I've never had good luck at the Florence airport, so that may be coloring my view here. But if the train ticket to return to Rome is less than $300, and if you can score non-stop flights out of Rome, I'd pick the Rome option myself.

My first thought was as the poster who said "open jaw, no brainer". However, when I got to the information about the actual flight details, I agree that a round trip to Rome would be better. I would definitely go for saving the $150 and getting direct flights over stopovers. Even if I use up that savings getting back to Rome for the return trip, a short train trip is worth it to get that direct flight home.

I would prefer not to split Rome - why change hotels one extra time? It also adds one extra travel day to an already short stay. More contiguous days together seems to make it easier to schedule things.

Flying direct to Rome and then taking a train to Florence doesn't seem more daunting to me than flying to some other European city, connecting to another flight, and then getting from Florence airport to the center of town.

This falls under Rule of Travel #2: Spend money to save time.

Unless the money savings is redonkulous (which $150 pp is not, imo), fly open jaws because it will save valuable vacation time which you can use to explore more Italy or not feel as rushed. Yes, you may have layover time on your flight home, but it's a travel day regardless.

Personally, I'd rather the direct flight home - if you throw layovers into the mix, then you are risking (albeit minimally) delays. The less time I spend at an airport, the better.

I don't think you'd have anywhere close to a $300 saving by the time you factored in train tickets. But the convenience and ease of direct flights in both directions certainly might be worth a lot. Since arrival days are a blur due to jet lag anyway, I'd head straight to Florence, then return to Rome in a few days for the remainder of the trip. It's less than 2 1/2 hours. Bonus points if you land in time to catch the direct train from Fiumicino.

Unless the money savings is redonkulous (which $150 pp is not, imo), fly open jaws because it will save valuable vacation time which you can use to explore more Italy or not feel as rushed. Yes, you may have layover time on your flight home, but it's a travel day regardless.

But it may not save any time - it may be faster to fly to Rome and train to Florence. We don't know what time the flights arrive in Italy. Assuming the trip starts in Florence (my suggestion if round-trip to Rome), all that really matters is what time you get to your hotel in Florence to start the trip, after planes, trains, taxis, whatever.

Ah, I did not realize Florence-Rome was the open-jaw option being discussed. I should have read closer. Florence-Rome is barely open jaw, about as much as I open my jaw for the dentist. Rome-Venice would be a different story.

I would not and have not made any visit like this as an open jaw trip. These are not cities very far apart. Quicker, and more relaxing, to head back through the airport you know versus the one you don't. I actually prefer round-trips, as my RT flights are specific ones I pick for ease. I also really enjoy trains through the country side or overnight trains. I have yet to purchase a small cheap flight to get back to my RT city, but would do that rather than open jaws. I love returning to the city that I already know, and it has been less expensive for me to take this approach as well...although that is not a deciding factor for me when it comes to flights. There is no right or better way, just what fits your style better. YMMV

"IF we fly out of Florence we may have a layover in either Munich or Zurich, both listed to be around 1.5 hours."

My first thought was spend the money to fly open jaw BUT your layover time would have me going back to Rome for the direct flight instead of trying this connection. These connection times are too short for me. I'll do a 2 hour layover on domestic travel but going for an International leg, I'd want 3 hours between arrival and departure. I have NOT flown out of either of these airports, it's just my general rule for a non-stressed transit.

Have you considered Pisa to fly out of? The airport is larger than Florence, and may have more options.

I made the "no brainer" comment. I did not consider the lack of non-stops from Florence. That would make a huge difference for me too.

I really appreciate everyone's thoughtful input and shared experiences. I'm looking at the dates of Saturday, September 29 - Friday, October 12th. Flying out and into Montreal, and now leaning towards flying in and out of Rome. The cost difference has minimized since my first search, but it is still nearly $100/person. It really is less about the money and more about the experience, and the idea of flying direct both directions is very tempting. We may not save money, but we would hopefully save time and potential headaches.

I'd do the round trip. Open jaws can be great, but it often doesn't work too well when using smaller airports. Also, unless you're planning on spending a night in Montreal upon your return, you've got that drive back to Vermont to deal with upon your return. Who know if they'll be 'extreme vetting' or whatever when you're trying to cross the US border to get home. That's on top of having to go through Canadian immigration when you enter Montreal.

The money is so close it doesn't matter, logistics are what matters. Open Jaw is a misnomer in this case because you will just be flying in/out of Rome plus another flight to Florence which might not even save much time. I would R/T Rome with an itinerary of:
Land in Rome and take train to Orvieto for two nights. Rent a car and tour Tuscany (I like Montepulciano as a base). Drop car in Siena for a few nights and then train to Florence. Train to Rome for how ever many nights before you fly home. Hertz has offices in Orvieto and Siena. For a first time visit, save Rome for last so it's less of a culture shock.

I'll jump on the "Two direct flights and train the rest" party. You board the train at close in Florence S.M.N. station to Tiburtina and make the easy transfer to the regional train to the airport, or to Termini and the more expensive Leonardo Express to the airport.

From Florence airport you need a taxi to the airport, go through the gauntlet of check in, security, then immigration at your transfer airport, possibly more security (true flying to the USA, I don't know about Canada) walking to the new gate, waiting around for boarding. Now true, that will all take place at Rome airport, but only once.

But in the end, it really depends on each individuals preferences. I think 3 hours on a train beats 1 hour on an airplane, but that is just me.

Edit - One last thing. Consider traveling to Florence immediately after you land. Then return to Rome for the 2nd half of the trip and you will be right by the airport for departure.

“Open jaws” is really like into Venice, out of Naples, where the time and distance involved are considerable, so the jaw is wide open. Florence and Rome are close enough that we are really discussing “open lips”. I think the ease and speed of direct flights carries the day here, and adjust your itinerary as you must.

I have done both, open jaw and round trip but mostly round trip. Open jaw is not an option if on the return I have to change planes 1-2 or 3 times. I fly both legs non-stop.