14-day itinerary for late Aug-September 2024

Welcome to the forum!

First question- are you up to traveling on your arrival day?
If you could that would eliminate the one nighter/split stay in Rome- put all your Rome nights at end of trip.

Can you fly IN to Venice, out of Rome? Or vice versa? Or out of Naples?
That would open up a lot of itinerary possibilities. This is what's called a multi-city ticket (not 2 one ways)

Siena- I think it is worth 2 nights but don't see where in your itinerary to take from, so one is fine.
It makes sense to stop there on your way to Florence. From Siena to get to Venice you'll have to go back to Florence anyway to catch the train.
There is a bus from Rome to Siena that will be your best tranportation as it is direct (Flixbus I think.
(Otherwise same as above- train to Florence then bus to Siena)

Sorrento/AC is absolutely worth the time- actually 4 nights if you could- it takes a lot of time and hassle to get there- make it worthwhile. The train from Venice to Naples is almost 6 hours then you have to transfer to local train to Sorrento so that first day is mostly travel.
Have you considered staying in Salerno?- it is actually ON the AC whereas Sorrento is not. Direct fast train from Venice and to return to Rome. Less expensive lodging, less touristy, great restauarnts, access to Paestum, easy access to Amalfi, Positano, Ravello by ferry or bus. (Capri is a bit far- substitute Ravello)

So -if you want to travel onwards (I am guessing not because you are coming from west coast)
Arrive
Bus to Siena 1 night
Bus to Florence 3 nights
Train to Venice 3 nights
Train to Sorrento (Or Salerno) 4 nights
Train to Rome 3 nights

Another option
Train to Florence on arrival- 4 nights with 2 day trips Pisa/Lucca and Siena
Train to Venice 3 nights this might not work with Regatta?
Train to Sorrento (or Salerno) 4 nights
Rome 3 nights

Or - same as you have but with the 1 night in Siena
Rome 3 nights
Siena 1 night
Florence 3 nights
Venice 3 nights
Sorrento or Salerno 3 nights
Rome 1 night

PS: The AC is beautiful but getting to/from is chaotic, inefficient and frustrating. It is no more gorgeous than the Oregon coast (and that is from a California girl).

My first impression is that you're doing a lot of backtracking. Also, five locations and 14 nights is a lot, especially with the distances involved. You need to perhaps condense, not add destinations. Three nights is two full days. You also need some time to slow down, nurse a cold, adjust for weather, do laundry, recover from the heat.
Is there any way to change your flights and fly into Venice and out of Rome, on an open jaw, or multi-city tickets?
If not, I'd highly advise that after landing in Rome, you jump on a train and go straight to Venice or Florence. Then , put all the Rome nights on the end.
Sorrento/ AC, which you name as a priority, has massive infrastructure issues and is always congested. Moving about is time- consuming and frustrating. Neither public nor private transportation is efficient. It will take most of the day to get to Sorrento and get settled, so at least another night in the AC is advisable. Also, the AC will be very crowded, there's no shoulder season anymore.
Many folks are now taking the train from Naples and staying in Salerno instead of Sorrento, as the crowding isn't as bad, and the train service to/ from Naples and Rome is much more dependable and comfortable.
Lodging availability will be tight, and make sure you have air conditioning. You are right to secure lodging asap.
I'm so glad you and your daughter will have this time together. Knowing the realities on the ground, you can have a memorable trip. I know planning is overwhelming for your first adventure- enjoy!

It appears you will be relocating five time in fourteen days. In addition, some of the places are north of Rome and some are south. Each time you relocate it will consume about three quarters of of day. It's checking out, getting to a train station, waiting, the train ride, getting to the new hotel, and checking in. That will put a serious crimp in the time you have to explore and enjoy.

If possible, consider flying in to Venice, moving on to Florence, and finishing up in Rome and flying back from there. Save the places south of Rome for another trip. That way you'll have plenty of time to enjoy three great cities and do some day trips from each.

Just offering something to think about.

Thank you all for the detailed responses!
I'm looking into changing the flight to arrive in Venice. If not feasible, I'll try take the train from Rome to Venice in the afternoon. Have already checked and there are several direct trains that afternoon. I may wait to buy the rail ticket once I land in FCO (just in case any of the flights is delayed or canceled).

I do like the idea of less cities with more time to enjoy them. So, skipping the south for a future trip is definitely looking more tempting.

It always so nice when the OP considers the advice given and updates us on the itinerary modifications. Mllj2026, thanks for the update.safe travels!

Pat,
I'm most grateful!

It turns out that changing the flight from PDX to arrive in Venice is NOT feasible (every flight option entailed a minimum layover of 11 hrs at a USA airport...ugh). But looking at OMIO, there are cheap flights from FCO to Venice Marco Polo airport that I could take in the afternoon (if my flight is not cancelled or delayed). I would probably wait to buy this 1-way ticket once my flight from Newark lands at FCO. My daughter is flying from Germany after visiting with friends from college. She could meet in Venice, instead.

Honestly, I wouldn't mind skipping the south for now. I come from Puerto Rico, and live in Oregon. So, I've had my share of gorgeous coastlines and beaches. ;-)

Much rather enjoy Venice, Florence/Tuscany, and Rome. :D

Mllj2016, yes, those connection times are horrible!
One last idea, could flying into Milan work? It's closer to Venice than Rome.
In any case, have a wonderful trip!

Pat,
I'll look that up.
Thanks so much!
Maria

Did you look at Delta flying into Bologna?

Are you flying on Delta from Portland? If you can adjust to the PDX-AMS flight that would give you many more options to fly directly to Venice from AMS and then home from Rome. You mentioned you have a layover at Newark and then buying a one way ticket at FCO. You may pay a premium for purchasing a same day ticket (or not, no way to know). Even if it costs a bit to change your overseas flights, it would be more efficient to fly to where you want to start (Venice) and home from where you end (Rome).

FWIW I have never been to the Amalfi Coast but I wouldn't choose go there in the heat of August or the height of summer tourist season. Fewer stops and more time in each will be a much better first time in Italy experience.

CL,
I bought the R/T ticket a while back, and changing it would be prohibitively expensive. The most affordable option for me is to fly from FCO to Venice on a 1-way flight. I've already priced all options and this is (by far) the most affordable and painless alternative. I rather do this than take a cab to the Rome Terminal station to get on a train (a very onerous and risky option considering traffic).

I rather do this than take a cab to the Rome Terminal station to get
on a train (a very onerous and risky option considering traffic).

I'm not sure why you are worried about this?

You buy your train ticket to Venice once you land so you give yourself plenty of time to catch it.

You can take a taxi fixed rate 50 euros to Termini-it has never taken us more than 45 min in the day time to get to the center from FCO
OR
Even easier and cheaper you can take the Leonardo Express from FCO to Termini for 14 euros. Takes 32 min runs every 15 min- no need to book in advance
Lots of people do this without problems. It will save you some money and the hassle/expense of getting from VCE in to Venice.

The train ride is relaxing, you grab lunch to carry on at Termini, you snooze a bit, you arrive in Venice - you walk out of the station and BOOM! there is the Grand Canal- it's the best way to arrive in Venice.

Thanks for the idea, ChristineH!

Honestly, after an 18-hr journey (from the time I arrive at PDX, layover, and second flight), I'm not sure I'll have the energy to deal with another 5 hrs of travel.
I will definitely keep this in mind as a backup plan.
I really appreciate your feedback!

Honestly, after an 18-hr journey (from the time I arrive at PDX,
layover, and second flight), I'm not sure I'll have the energy to deal
with another 5 hrs of travel.

I don't blame you.
I'd stay the 1 night in Rome after all that travel.

There are decent hotels close to Termini
Hotel Sonya
Hotel Aberdeen

Plan to walk around a bit --from Hotel Sonya it's about 20 min to the Colosseum, see it from the outside, then up to Trevi Fountain, have a nice dinner near there and back to your hotel to get a good night's sleep.

Hop on a fast train to Venice in the am