Finishing in Sorrento, where to fly out?

Can you get an open jaw ticket and fly home from Naples instead? It's close to Sorrento and you won't have to backtrack to Rome.

The number of nights you have listed add up to more than a two week trip. More like 15-16 days?

Yes, Naples is the obvious closest international airport to Sorrento.

How much of a pain is it to get to Rome from Sorrento on a Sunday
morning? Would we be better to scrap our last night in Sorrento and
spend a boring night at a hotel near the Rome airport?

It could not just be a pain but too risky; Sorrento is too far away. Naples airport would be a lot closer but I still wouldn't want to be in Sorrento the night before an early or mid-morning international flight from there (been there, done that, wouldn't do it again).

Depending on your flight time, you could stay in central Rome instead of near Fiumicino?

I wondered about flying out of Naples as well. For some reason, Naples worries me; we thought about skipping Sorrento altogether, but everyone really wants to see Pompeii, so we kept this region on the itinerary.

No reason to worry about Naples (I went there alone in my 20s - it was intense but not scary). I would spend at least the last night (if not more), there so you can take in the sites. There is a great Archeological Museum that complements what you will see in Pompeii. The airport is very close to the city center so it should be a breeze even to catch an early morning flight.

We were in Naples July of 2016 as well as Sorrento. I really liked Naples actually.

I too think you should fly from Naples. It would be much easier than returning to Rome.

My suggestion would be that you take a ferry from Sorrento to Naples. There is an area by the "egg" that is a pedestrian only area by the sea full of hotels and restaurants that is about a 15 minute walk from there or a short taxi ride. We returned here for our last night in Italy on a ferry from Capri. We walked but we had stayed there earlier in our trip and knew the way. It is a very pleasant area and much better than any airport hotel. We had a 7 am flight out of Naples and the hotel had a taxi there at 5:15 am.

We stayed at Hotel Royal Continental in Naples but there are a number of hotels there.

We paid less for a beautiful room with a view of the water in Naples than for a very small room in Sorrento.

Beth

If you are able to get a non-stop flight from Rome to your home airport, then I would change the order of your trip to Venice -Tuscany - Sorrento - Rome. I’d rather have a slightly longer drive than a connecting flight. The other benefit is that you could return the car when you arrive in Rome and save a couple of days on the rental.

If you have to get a connecting flight anyway then it you could either fly home from Naples or change your order to end in Rome.

Something to consider, if you are flying from Chicago, is that you can get nonstop flights from Rome but not from Naples. Weigh the inconvenience of a multi stop flight vs. the drive to Naples. Having done a similar trip, I would go from Tuscany to Naples and finish in Rome, dropping the car off in Naples. As mentioned above, Naples has some very interesting sites to visit. It is easy to take the Circumvesuviana train to Pompeii and Herculaneum and to Sorrento, or a ferry to Capri.

It only takes 1:10 to get from Naples to Rome by train. No need to stay near the airport the night before your departure home. Then you can take a cab to FCO the morning of your flight.

Just to add to the confusion, there's a direct air-conditioned bus to the Naples airport from Sorrento (at the train station) if flying out of Naples is a viable alternative.

Yes, the Curreri Viaggi bus departs a few times daily from the Sorrento bus/train station to Napoli Capodichino airport.

http://www.curreriviaggi.it/eng/autolinee.html

We used it March 2017, and for 11 Euro it's great. Had a noon flight, so we took the 8:30 AM bus, and got to the airport at around 10:15. Capodichino is not in a rough area of Naples at all, and why would you care? The bus drops you off at the front door.

FYI, twice we've used Lufthansa for a Naples-->Munich-->Chicago itinerary home. About two hours on the ground in Munich (good chocolate at the airport!), then the 10 hour flight across the pond. Not fun, but Lufthansa is my favorite of the carriers, so they made it bearable.

If flying home from Rome is your preference then I would save Rome for last. Venice, Tuscany, Sorrento, Rome. You can’t trust getting to Rome from Sorrento in time for a flight that morning or afternoon and a boring night near the airport is...boring and a waste of a travel night. Better to have your last night in Rome itself, as part of your Rome visit. Wake up and go to the airport without ad much stress.

However, if your flight isn’t too early you can go from Sorrento to the NAPLES airport that morning. I’d arrange a shuttle or airport bus from Sorrento. If you wanted one night to experience Naples this is when you’d do it, but that’s up to you. I’m interested in Naples but a lot of people avoid it.

Now I am wondering if it doesn't make more sense to hit Sorrento after Tuscany and finish in Rome,

This is what I would vote for

You said "drive". I don't think too many posters here drive from Sorrento to Rome. Most take the faster Frecciarossa train to Rome, and the airport express to FCO. Are you planning to keep a car in Sorrento? If so, think again. Maybe you should budget for cars with drivers for some of your parents' excursions, which Sorrento is well-located for.

You didn't give the likely flight time. Remember three hours to check in, and allowing for traffic in the tunnel to Sorrento and around any big city's airport. Yes, an airport hotel is boring. But the best solution is to select a different flight, before you decide to sleep at the airport. Another idea would be to recover from the jet lag in Sorrento, where touring is not as exhausting as in Venice (or Rome). Then you can indulge your urge to drive and return from Tuscany, dropping the car at the airport and checking in. Possible early rising required, of course. A third approach is to sleep in Rome downtown the last night, and take a cab to the airport in the morning. Do your parents have the stamina for Pompeii or Capri??? If not, maybe you don't need that last night in Sorrento. Honestly, I did not find Sorrento or even Positano to be my idea of "village-Italy". And it's very crowded in the summer. You are already late to have full choice of hotels there. Would your parents consider a different final city?

I would mention that there are a lot of (budget) flights from Naples to England and countries filled with sun-seekers. While I hate two segment flights through London, it is a possibility for Chicago. Make sure you're changing at the SAME London airport!