Does this Italian itinerary look feasible? I appreciate any and all suggetions

6/10/2023 Monday - Rome - Drive to Rome from Assisi and drop car off
at Rome Train Station

Are you sure about driving to central Rome? Are you comfortable handling traffic like this? https://www.youtube.com/watch?v=cVDOKGhHBJw

Consider renting the car outside of Florence. Perhaps closer to your destination. It’s more practical unless you’re stopping off somewhere close to the city of Florence.

Consider not renting a car at all since all your destinations are served by public transportation. You will save a lot of money as well as hassle.
You have a lot of destinations with very short visits. Add a week if you can or eliminate the southern part and concentrate on Venice, Florence, Siena, and Rome.

Right. I don't see any need for the expense and hassle of a car. With the exception of Amalfi, all of your destinations are served by rail. There is a learning curve to driving in Italy; requires some advance homework. You also can't take a car into many historic city centers, and leaving anything you can't afford to lose in an unattended car is not advised.

Take boat to Capri or charter pvt. boat

No need to charter a private boat if your goal is hiking the island. Take a ferry. Go as early as possible.

6/15/2023 Saturday - Amalfi - Take taxi early morning to Ravello and
then to Amalfi - Can we kayak in afternoon?

You have to get to Amalfi from Sorrento first before taking a cab to Ravello. (Edit: you'd not thinking of cabbing directly from Sorrento to Ravello?) As you'll have luggage with you, you'll have to have your accommodation store your bags or find a baggage storage service as i'm sure you don't want to sightsee with it. By the time you do all of that, get to Ravello, sightsee and then return to Amalfi, I wouldn't think there'd be enough of the day left to kayak but happy to be corrected if wrong.

How costly would it be to take taxi the entire way from Amalfi to
Naples?

Very, depnding on what ;expensive' means to you. As noted in this recent thread, just the cab ride from Amalfi to Ravello is running 40-50 euros one way. Taxis are expensive in this region.
https://community.ricksteves.com/travel-forum/italy/very-limited-bus-service-in-ravello

Maybe we should just stay in Sorrento the whole time???

That's an "up to you" question. From Sorrento, you can travel to Naples on the local commuter train or by ferry. Circumvesuviana train will drop you in central Naples but will be very busy and while serviceable, is a battered, unlovely thing. Ferry will drop you at the port from where you'll need to take taxi or bus to your accommodation. If you're in Amalfi you'd need to take a SITA bus, ferry or cab to Salerno and train from there to Naples, or ferry from Amalfi to Naples. Your choice.

It also is up to how much packing up and checking in and out of hotels you want to do. It's a personal preference with no right or wrong but we lean towards having a base when possible and doing our day-tripping from there, especially as it allows us to drop the bags once and not have to deal with storage and whatnot. While not recommended for ALL situations - for instance I don't recommend day-tripping the Cinque Terre from Florence - it works for many others.

Some links to local bus routes/schedules (these could change a bit by next summer):
https://www.ravello.com/sita-bus-schedule/

One more thing... You'll want a Plan B should weather interfere with Path of Gods or Capri.

For me this itinerary seems very rushed and that you are trying to visit too many places in too few days. But, only you know if you will be comfortable at this pace. I also agree with the suggestion to just stick with public transportation in the Sienna to Assisi to Rome part of the trip. Can you eliminate any of these places? Maybe your one night stopover in either Siena or Assisi as you are allowing yourself very little time there. Certainly Venice and Florence need more time.and you are giving yourself very little time for actually seeing and doing things. Seems like a good portion of your trip will be taken by travel time from place to place. When planning remember that two nights in one place actually gives you one full day of siteseeing. I understand the desire to want to see it all but could you better prioritize which are most important to you? Right now you are trying to see 8 places in basically 13 days as your first and last days are overseas travel days. I think that maybe you are underestimating the distances and travel times. It is doable and if this is your usual travel pace and you know you like that pace, then go for it. But, if you have not done a trip like this before, I think many of us here will advise slowing it down a little and eliminating something. Another thought is that this is next June, and the Italian summer season is filled with tourists and all of these places will be crowded so whatever you decide to do make reservations and be prepared for crowds. Good luck with your plans.

You barely have enough time to do Venice, add one day.

You have one day in Florence, that is just plain silly. You need 3-4 days there.

sienna and Assisi are great, but conserve time and do them on another trip.

Rome, ou have three days there, suggest 4-5.

Your Naples area plans are not bad, but did you have not set enough time to do all that you plan. Skip Salerno.
Also, look for tours instead of expensive taxis.

Do you have a special interest in Assisi?
If not save for another trip
No need for car at all

Add a night to Venice
Stay in Florence 4 nights and day trip to Siena (note spelling)

Research bus and ferry options in Amalfi area
Taxis are outrageously expensive

I agree with Geo. Try to focus on a region instead of the country top to bottom. You’ll love Venice and Florence and Rome. I spend 4 to 5 nights in each and never get bored. I find it’s a richer experience. It takes time to acclimate to a place. You’ll be surprised how time flies.

Fast Trains are easy between the three. If you want to see more than the three places spend a few days in Verona. it’s on the same train line between Venice and Florence. Verona is incredibly charming. From there You can take day trips via fast train to Bologna and Vicenza. You could drop Rome and add Lake Garda about an hour away from Verona. Hop on the ferry and visit the small towns on the lake.

Pair Rome with Tuscany or Amalfi or Pulgia, etc.

Buon viaggio,
Terry

I've been to Italy a bunch of times. One important thing about enjoying a visit there is deciding in advance you just will NOT see a bunch of cool things. You don't have to see every single wonderful sight in your 2 weeks: concentrate on 3 places, maybe 4, and I guarantee you will still have an amazing time, and probably even a more amazing time, since you can slow down, breathe, and enjoy the ambience without having to rush to the next site. Maybe skip those wonderful places in the South and don't go south of Rome?

I'd echo what the others say about not renting a car in the big towns. I'd also strongly recommend you should try to see at least one smaller, quieter town off the super crowded tourist path. Venice, Rome, Siena, Amalfi coast, and probably Assisi are all great places, but they will will be PACKED with tourists in June.

There are a few somewhat less crowded places you could choose from that are still accessible by train: maybe consider Cortona or Orvieto. There will still be plenty of tourists there, but fewer than those other places, and you will fall in love with them, especially at night when the crowds disappear. Or if you really want to get away from the tourists, maybe rent a car for just 3 or so days and go some place in Umbria that is less off the beaten path, like a few nights in Todi or Sansepolcro, then return the car at the end of that.

It appears there are major relocatons five or six times in less than two weeks. Every time you change locations you will lose at least one half to three quarters of a day. It's not just the actual travel time, it's also packing up, checking out, getting to the train station (or doing the car rental paperwork), finding the new hotel, and checking in and doing a bit of unpacking. In addition, the last day is the departure day so that's a "lost" day. The first day may very well be "lost" also due to possible late arrival, getting to the hotel, checking in, and jetlag. Trying to cover all you've planned in the amount of time you have might be more than possible and still ENJOY the trip. You might want to consider staying in only only three places with day trips from them. You'll certainly want good memories of people, places, great food, and such. Not just a blur of train stations, hotels, and driving. Not being critical, just offering food for thought.

I would agree that there are too many destinations. I'll also agree that the time allowed for Florence is tragically short: I like the suggestion to skip Assisi, train to Florence from Venice and day-trip Siena from there.

The reason I didn't advise replacing the AC with, say, smaller hill towns or a different city is that the OP has a keen interest in some specific outdoor activities such as hiking Path of the Gods and kayaking, thus I understand their choice. Looking at their past posts, it appears that they've hiked, biked and/or kayaked in Poland, Switzerland, Austria, Denmark and Norway as well. In one previous Norway thread she said, "We would like to spend more time outdoors than in museums." OK, that helps.

I'd probably stay all 4 nights in one coastal town versus two but that's just me.

Maryanne/natique2, can you tell us anything more about yourselves that might help us to make the best suggestions for you? And is it just you and your husband this time or are your adult children going too?

A suggestion for Rome: IF you can fit it in - and your time there is awfully short - take a look at 'hiking' a long flat piece of the Appia Antica? That has been our favorite day in Rome thus far, and one we're going to repeat. The 'road' passes through countryside adorned with crumbing tombs and monuments along the way. As well, you can visit the remains of an Emperor's private circus, catacombs and some other interesting things. Take a look? We started our walk pretty far out, at Casal Rotondo, and walked into Rome versus the other way around. You could start closer in, though. Bring beverages and a bag lunch or snacks.

https://www.parcoappiaantica.it (click the orange "translate" button at bottom of the page)
https://www.parcoappiaantica.it/smart-info-ita-eng/
https://www.parcoappiaantica.it/wp-content/uploads/2021/11/Mappa-completa-del-Parco-dellAppia-Antica-ITA.pdf

Here's a brochure that maps the stuff along the way and tells you, in English, what you're looking at. :O)
https://www.parcoappiaantica.it/wp-content/uploads/2016/05/AppiaAntica_eng_2015.pdf

We spent 11 days in Sorrento in April so I'll comment on this portion of your itinerary.

• You'll take a train from Rome to Naples and then board the Circumvesuviana train to Pompeii and Sorrento.
• Once you reach Naples, transportation gets frustrating and will be slow. I'd recommend getting an early start, to give yourselves more than 2 hours at Pompeii. We spent 2 days and a total of 12 hours there, but you know your level of interest more than me.
• Capri. Good choice, we enjoyed far more than the Amalfi Coast. There is a ferry that leaves about 8am that will be far cheaper than a private charter.
• There is no easy, fast, or non-frustrating method to tour the Amalfi Coast; especially in June. I don't know how much a taxi will cost but it won't be cheap. We took a cab from the Sorrento train station to our hotel which was a 10 minute walk away (it was raining) and it cost 24 Euros. You'd think that was because we got ripped off, but that is the cost for taxi service in the region, cost will likely be 150 Euros +/-. You don't say if you're staying in Amalfi but I assume you are and that is why you need a taxi. I'd be more inclined to not waste time and do day trips from Sorrento.
• There is a couple of kayak rental and tour companies in Sorrento. Once will take you to the ruins of a Roman Villa nearby. We actually hiked the 30 minutes to it instead of kayaking.