First time to Italy 14 days

From Naples, if you book early, you can get a ticket on a high speed "freccia" train for a reasonable price, which would take between 1:05 and 1:17 travel time. I am looking at the beginning of June and the prices are about 28 to 30 euro.

A plane would probably be more expensive, and when you consider time spent in security waiting, and the time spent getting from the airport in Rome to downtown, I think the train is a much better option.

I think you can have a wonderful trip to Italy doing it on your own. Italy is extremely user-friendly for American tourists, even those [of us] with limited Italian language skills.

I have flown in to Rome and out of Milan, on separate trips, so I won't opine on your flights. I would consider saving Naples and the Amalfi Coast for your next trip, for a more leisurely pace.

But I will highly recommend Tuscan Trails for a wine tour while you are in Florence. The owner, Todd, is an American Ex-Pat and I can only describe him as the best history teacher you wish you ever had, with wine.

You need to start making hotel, train, and tour reservations ipso fasto.

http://tuscantrails.com/

Flying into Venice and out of Naples puts you on a straight line course, eliminating any backtracking.
The downside is you'll most likely have 2 flights with interconnecting flights.

I like your itinerary. We have actually done exactly that. I wouldn’t change a thing.

It depends on how important Rome is. Rome is far easier to fly home from because most direct flights leave around noon to early afternoon. Easy getting home. Flying from Naples will mostly likely mean an early morning flight to a connecting city such as Rome or London, etc. Much longer flight home. The train between Naples and Rome is about two hours.

For most cities we have always had good luck booking local tours through the local TI.

It is a decent schedule, a bit busy, but will give a good taste Italy in preparation for your return trip.

You'll have more flight options (to the US, at any rate) if you fly out of Rome at the end of your tour.

As far as specific tours go, what's the most important thing for you to see/do while in Italy? History? Food? Art? A little more information will make it easier to make suggestions.

Train to Naples . . . Amalfi Coast 3 days . . . train to Rome. More details please. Are you thinking of staying in Naples? Are you aware of the time it takes and the transportation options to the Amalfi Coast? What do you want to see and do in those 3 days.

Count exactly how many nights you will be in Italy. Subtract 1 and this is the number of days you have. The day you land doesn't count because you will probably by wiped out and jetlagged. The day you leave doesn't count because you need to leave your hotel about 4 hours before flight time, much more if you aren't sleeping in the city you're flying home from (Naples or somewhere else?) The rule of thumb is that you use about 1/2 day each time you move. If you have 12 nights on the ground, I think you really don't have time for the Amalfi Coast.

I recommend passing on Naples/Amalfi Coast. Three days in Rome is not enough and 3 days in Florence is not enough to do Florence and do day trips into Tuscany.

The internet will show you a plethora of tours, but you can check TripAdvisor under Things To Do in each city and pick your places.
You won't need a tour to visit the Vatican and Sistine Chapel, however do some research on the site prior to visiting. It took over a century and a half to build St. Peters and the site of the plaza at St, Peter's was formerly Nero's arena where many Christians were murdered. Get a guidebook.

A tour for the Coliseum, Palatine Hill and Forum is a good idea. There is so much more in Rome.

For Venice, if looking for affordable B&Bs or hotels, look for places near the main train station.

We are looking at 14 days on the ground. I have taken into account for the air travel when planning itinerary. Since this is our first time to Italy and probably only time, it is important to us to see the most but yet enjoying Italy at a comfortable pace. It is also important to enjoy the coast of Italy. I have debated between the Amalfi Coast and CInq de Terre. I welcome any recommendations between the two.

We took our first trip to Italy in 2017 and did it ourselves. You asked about city tour recommendations. We took 2 Walks of Italy tours (recommended by others on the forum) and for us they were a good compliment. They have several in each city, but our choice was the VIP David & Duomo Tour in Florence and VIP Doge's Palace Secret Passages/Basilica tour in Venice. Depends on your interests if maybe another of their tours would work for you. When we went, you could get a 10% discount if you had a Rick Steves' guidebook. Also recommended by RS is Alessandro Schezzini for his chiccheti/bar tour, https://www.schezzini.it. He is a hoot and we had a great time.

We will be flying into Venice and out of Naples on our upcoming trip. We got a good deal. But you have the right idea which is, if you need to fly back from Rome, make Rome last. If you get a good airfare from Naples, you can just put Naples last. I don't like to take a train into a city on the day my flight to the mainland leaves - ends my vacations with travel stress.

We are also staying three nights in each town. Enough to have two full days, but understanding that we absolutely cannot see everything in that amount of time.

I agree with the others as far as eliminating Naples and the Amalfi. Since you want to see the coast, why not consider a day trip from Florence to the Cinque Terre? Add more time to this area to see Tuscany and the coast. We have been to both the Cinque Terre and the Amalfi. While we preferred the Amalfi, it was primarily due to the glorious weather we had there as opposed to 3 days of rain in the Cinque Terre. Nonetheless, the CT is lovely albeit crowded due to cruise ship travelers. You can add another day in Venice or Rome if need be. You won't regret the extra time in either. Venice is magical, and Rome is loaded with must see's. Enjoy the planning. There are tons of websites that supplement Rick's guidebooks.

Take a nice bus ride from Sorrento to Rome .. drops u off at the main terminal... the train from Rome to Florence is faster then the bus ... we usually take buses as if your visiting a hill town chances are the trains go by at the bottom of the hills... San Marino is it's own country on the east side ... look at it on YouTube... fabulous!

Florence-Sorrento will take 4Hr28m.

Sorrento to Rome 2Hr53m.

So both will consume a half day by the time you check out, get to the station, then repeat the process in your arrival city.

I think your itinerary is good as is. I would not drop Naples/Amalfi coast in exchange for Cinque Terre. In my opinion, Naples/Sorrento and Amalfi have more to offer. I think the flow of your trip is fine. None of these locations are that far away from each other. Your only long transport day is Florence to Naples or Sorrento, and it is not that long or involved. I've done that journey from Florence to Sorrento and the sit down after days of sightseeing was very welcome and I enjoyed watching the landscape from a train. Stick with your gut on what you want to see.

You have 14 days. I'm assuming that includes your 2 travel days. So you really have 12 nights to plan an itinerary. Always think in terms of nights not days. You lose half a day each time you travel between cities. In other words 3 nights = 2.5 days. If you think this will be your one and only trip then keep the itinerary but do go from Florence to Rome then Rome to Naples. Since your time is limited, hire a private car to take you from Naples to where you are staying on the Amalfi coast. Fly home from Naples. You save the time backtracking to Rome.

If you can add a few extra days it would be better and add them to the Amalfi coast and Rome. If you can't, and you think you may get back to Italy someday then drop either Venice or Naples/Amalfi Coast. If not, then plan ahead and enjoy your trip

This is a short trip and lots of miles. I'd skip Naples and add days to Rome. It really deserves it.

If you choose to do your original itinerary and can get a flight out of Naples that fits your budget, do that and eliminate back tracking to Rome.

Another option is after Florence/Tuscany, spend 2 nights in a Cinque Terre town and add one more day to Rome. Reduces time spent traveling but being a more 'compact' area to cover. This gives you a 'coastal' experience, with less train time.

In late June both the Cinque Terre and the Amalfi Coast will be packed with tourists. If you stay in Sorrento, you may spend as much time waiting in line for buses and traveling on them than actually seeing the towns or hiking. People here on the forum who are familiar with the CT say you can avoid the worst of the hordes by staying in one of the other coastal villages, maybe not quite as beautiful, but a lot more pleasant.

Take into account that if you spend 3 nights in a place, you have only 2 days to see it. A lot of time on your "travel" days will be used actually travelling - packing, checking out, getting to the train station, then getting to your hotel, checking in and unpacking. Each new place means time for getting oriented as well. A string 4 3-nighters is not a relaxing pace.