To connect or not to connect

What you are overlooking is that it would make more sense to reverse the trip. Fly into Venice and home from Rome. The Rome airport has great options for returning but stick with the open jaw. Why waste day returning to Rome? ...... easy trip from the island to the airport on departure day..... Unless something has changed that easy trip is a 4am dash to the airport to catch a connecting flight back to the US.

Someplace I think I read that flying into Venice was easier than flying out. Someone on this forum can speak to that, I’m sure.
I don’t like backtracking but I hate early morning flights even more. The ease of getting to an airport would be my criteria for how I scheduled my flights.
I’ll be interested in reading what the more experienced with Venice departures have to say.
I do try and fly nonstop if at all possible. Is it possible to schedule activities in Rome at the beginning and end of your vacation so you aren’t in a rush to get back to Rome just to fly out the next day?

Our preference is always direct both ways when possible, with priority on direct TO Europe. I never want to get stuck in US but as long as we get to Europe I feel like we are "there".
Last year we flew direct to Paris but had to do a connecting flight home Nice to Paris- then to US- it wasn't that bad and we figured our trip was over - if we got stuck or lost luggage no big deal.

First trip to Italy we flew into Venice - out of Rome-direct both ways. That was perfect.
We just returned from Italy and this time we flew to Rome via Frankfurt- our flight left US late and we were panicking about missing our flight to Rome- we made it just barely and were completely shocked when our luggage got to Rome with us.
Flew home from Venice direct- and while it certainly is easier to arrive in Venice than it is to leave it really was fine. Our flight left at 11- we knew what we were doing and could have easily taken vaporetto/bus to airport without having to get up painfully early but we opted for a water taxi as a splurge- pick up at 7:20 with plenty of time for 11 flight.
However if our departing flight had been any earlier it would not have been as easy.

I would not want to backtrack to Rome and "waste" a night at an airport hotel and a vacation day. If the options you have mentioned are your best price-wise etc- then I'd fly into Rome and out of Venice- (as long as Venice flight is late am) that 2 hour layover at JFK will go quickly- by the time you get thru passport, security, recheck whatever you might only have time for a bathroom break. If I got stuck in NYC we could just take the train home or go stay in city with our daughter! There were worse places to be stranded :)

I would fly into Rome, take the train immediately to Venice (or Florence), and work your way back to Rome, spend all your time there, and fly home. In fact...that's exactly how I did my first trip to Italy, stopping in the same places you mention. Direct flights are awesome - I try to take advantage of them whenever I can.

I see the train to Venice or Florence to start as just another connection that's easier than a connecting flight. There's no reason you HAVE to start in Rome just because you land there, any more than you would have to start your trip at some European airport at your first connection to Venice.

I agree with Andrew H. Fly into and out of Rome. Hop on a train to where ever. Save Rome for the end. I've done it this way, in fact, and would do it again. I refuse to leave anywhere at an ungodly early morning hour; ie, Venice flights. I'd rather spend a few hours on a train riding through Italy than being in JFK airport. YMMV

Into Venice, out of Rome.
Flying out of Venice can be more difficult, especially in early morning. If going by water, tides can be a factor if you are staying on a smaller canal.
Why won’t you change planes in Europe? I have never had a problem with that in many years of travel.

I don’t hate two-segment flights anymore. You can save dollars or miles by taking them, especially code shares with your regular airline. Your hotel room isn’t available at 7 am anyway, and the museums don’t open until 10.

I did have to leave Venice at the crack of dawn, but it was amazing to get a direct flight to EWR. We started that trip with a direct flight to FRA, because we had theater tickets there.

When we started another vacation in Cologne, Lufthansa got us there (2 segments) by noon, with no muss or fuss.

For those saying the flights out of Venice are early, the ones I’m booking leave at 1PM.

I'm with those suggesting direct flights to/from Rome, heading to Tuscany upon landing and leaving your time in Rome until the end of your trip. I've done this multiple times and it works well. An extra 1.5 hours of train travel isn't all that big a deal after a direct flight.

For those saying the flights out of Venice are early, the ones I’m booking leave at 1PM.<<

In that case- don't worry about it- book the flight that makes most sense to you.

I know many here suggest getting on a train on arrival and heading to a diff city (if you have booked roundtrip to Rome for example)- while I am sure it is totally doable I know we would be in no condition to do that. We never sleep on a transatlantic flight no matter how hard we try and we are simply too discombobulated to deal with a long train ride. Train travel is a bit of a no brainer but I still wouldn't do it unless the RT savings were really substantial. I would not be able to sleep on that train ride either making the entire day a wash. YMMV

I will add that IF you can fly TO Venice and home from Rome- that would be the ideal plan IMO- Venice is a great place to get over jet lag- give it 3 nights. We love Rome but it is a big bustling city- perhaps a bit too much for your arrival into Italy-assuming this is your first time?

I just did an ATL to Rome direct with a Venice to JFK to ATL flight home. The flight out of Venice was also around 1pm with a 2 hour layover at JFK. It was fine but.....long. Also JFK was really weird and our terminal was off site in what seemed like an airplane hanger. The 2 hr layover went by super fast. Then our JFK flight to Atlanta was delayed an hour. We parked in the International terminal at ATL but landed at the Domestic. We had to take two shuttles just to get to the International parking ramp. Anyway, by the time we got home it was 11:30pm and felt like 5:30am and we'd been up for 22 hours. So yeah, long. I might not rearrange an entire vacation based on that but just know it's going to feel like 100 years before you get home.

FYI, I just flew in and out of Venice last month - both direct flights to/from the US. Venice Marco Polo airport now has automated passport control with machines that scan your passport (US passports, anyway) and take your picture. The lines moved extremely fast inbound through immigration and outbound through passport control - less than 10 minutes in line each way. Best airport experience I've had in Europe for ages - though this was mid-week in May at a non-busy time. But when I flew in two years ago before they had this, immigration took much longer.

I had a late flight out of Venice home, too. I wouldn't sweat a 1PM flight home at all. You don't even have to get up early. You just get a bus from Piazzale Roma direct to the airport - quick and easy, takes about 20 minutes.

I agree with everyone suggesting to take the direct flight to and from Rome. Once you arrive in Rome, take the train to the farthest location on your list and make your trip backwards, making Rome your last stop and your last city before heading back with a direct flight to the US. You'll have a lot more energy as soon as you arrive than making that extra 1-2 hour train ride towards the end of your whole trip.

I'd be very happy with the departure time you've found from Venice. It is wonderful to start your trip in the city where you land and end it in the city from which you depart. You have that situation (assuming the multi-city tickets are affordable), so go with it!

UPDATE: We decided to start in Venice, but will connect in Rome now rather than JFK. Will finish the trip in Rome and fly home direct.

Thanks for the tips. I feel good about the plan now.