Help for a first timer

Flying in/out of Rome will be fine. Just a bit more traveling back and forth. We recommend Hotel Tiber in Fiumicino for accommodations before you fly home - hotel shuttle to the airport or easy taxi ride. Folks on this forum also recommend the Hilton (I think?) as it is right at the airport.

For first timers to Italy, the usual itinerary is Rome-Florence-Venice and that is pretty easy to do by train. You've got a good amount of time to do that without rushing, maybe 3 nights in Venice, 4 nights Florence, 6 nights Rome? As others have said, make sure you plan for a day of travel between each and you should be fine.

You can do a day-trip to Pompeii from Rome if you are interested in that, or do a short overnight trip to Naples or Sorrento (we really liked Sorrento this spring). Agreeing with previous poster about the Blue Grotto and Capri. It's definitely weather-dependent, and we were not wowed by Capri itself. It's very cool from the water so we would recommend taking the boat tour around the island, if you really want to go there.

We were also underwhelmed by the Amalfi. Again, maybe better by water and in the summer when it's beach weather? We did a day tour by van (Mondo Tours). It was fun, but not quite sure what all the fuss is about.

Simple advice - read Rick's guide and come back with questions

Regarding the Blue Grotto, rough water might keep you from going in on your one Capri day (as it did me), but if you don’t at least try, you’ll definitely not see it. As far as it supposedly being a rip-off tourist trap, it’s certainly a geological wonder, you can’t get in on your own, and I imagine that there’s nothing like it where you live. If you don’t see it on your Italy trip, you’ll miss it, and that would seem to be a shame to be so close, but then deliberately choose to ignore the chance to experience it, because someone else thinks nobody should bother.

Regarding Rome, and potentially flying in and out from different places, you got a great airfare deal, so don’t second-guess your round trip flights. It’s not like you’re having to backtrack two days, or thousands of miles to get back to Rome. One option (which we did eleven years ago), would be to start in Rome (we had a full week), see the other parts of Italy in your plans, then get back to Rome the afernoon before your flight home. We visited Ostia Antica, Rome’s answer to ancient Pompeii that day, then caught a taxi to the nearby Hilton at the Rome airport. We had a very early flight leaving Rome, so being steps away from the terminal was extremely convenient, and worked well for our round trip return.

Alternatively, you’d probably be considering flying to Rome and catching the first train to Amalfi or Tuscany, then looping back to Rome for the final days. Depending on your flight times, I’d still suggest starting off in Rome, then coming back for your flight home just to make your flight the next morning.

First of all thank you so much for all who responded. You were very thoughtful, kind and extremely informative.

Christine, I wanted to answer your questions even though you gave a ton of great info.

The "we" is my husband and myself--in our 50's.
We have both traveled abroad but that experience was limited and we did not plan the trip.
I definitely feel comfortable renting a car and driving until I get to Sorrento or below. I have driven in many major cities with no issue. And I've had people say, it's no big deal, just do it and read so much about how especially Amalfi is a nightmare and don't think of attempting it. We want the freedom to go, stop, see where we want to but don't want to be stupid either.
Tuscany--yes, Florence was my choice. I really wanted to stay in an agriturismo but wonder if that's too far off the beaten path and making things more difficult for myself.
Yes, 13 nights. Due to great deal, no flight changes.
Arrive in Rome @ 9:10am on 26th.

The itinerary days sound very doable to me. I would be good with Pompeii for a day.
I will also use the search feature and read as much as I can. Like I said, I was getting overwhelmed by all the information and trying to find the best way to answer the questions of my trip.

Thank you to all the others who gave their tips. All noted and welcomed. I really appreciate the encouragement about my flight and how I have not made things horrible for myself by going in and out of the same airport.

Thank you this is so helpful. I am not shy about research and staying on top of things, but wow there is so much to choose from.

I am diving deep into the forums now. I may come back for questions. I think having someone say train here, car here, etc is taking some of that overwhelming feeling out.

We spent 11 days in Sorrento in April so I'll comment on that region. Transportation is challenging in the area so I highly recommend you determine your priorities so you don't waste days in traffic or ferries. We used Mondo Tours for a day trip to the Amalfi Coast and enjoyed it, however, of a 9 hour tour, 4.5 were spent in the car getting from place to place. We did a 2nd day trip to the AC ourselves via a ferry from Sorrento to Amalfi and then a bus to Minori. We then walked the path of the Lemons to Maiori and then a bus back to Amalfi. No regrets, but we much preferred our day in Capri with it's spectacular views. We didn't do the Blue Grotto, but that was skipped because my wife tends to get seasick in small rocking boats. Even without the Grotto we had a full day.

By far, my favourite days were spent visiting the Vesuvius explosion sites in Pompeii (2 days), Oplontis (couple of hours), Herculaneum (1 day) and the Archeological Museum in Naples plus a walking tour of Naples (1 day). Capri was next and the Amalfi Coast ran a distant third in enjoyment. The AC is beautiful, and if your goal is incredible views and slow, aimless wandering then it may be for you. But for our go, go, go style of travel, the Amalfi Coast was a disappointment. I wouldn't recommend more than an hour in Positano; you look at the views from above, you look at the views from below, and then you move on. Ravello was my favorite of Positano, Amalfi and Ravello.

I did a trip in 2019 for almost those exact dates! April 26-May 10th :)

In a two-ish week trip I don't go more than 4 places, but I made some visits longer and shorter depending on what there was to do. We flew into Rome and immediately went to Salerno for 5 nights, took a train to Verona for half a day and continued onto Lago di Garda in the evening for 2 nights, Firenze for 4 nights and then ended in Roma for 4 nights. I bet you could do 4-5 nights on the Amalfi/Sorrento Coast (be sure to analyze what you REALLY wanna do and where it would be easiest to get to from), then go up to Tuscany and do Florence/Agriturismo for a total of 6 nights (manage your day trips vs time in Florence to decide how many nights in the countryside vs city), and 4 nights in Roma before leaving. The folks who have gone into more detail have some great ideas!