Seeking guidance with itinerary

Have you booked your time at Borghese Gallery? If so, great, if not, do so ASAP. They limit the number of people at one time. You can also take a (small) group tour led by a guide from the museum. We found it great two years ago. Otherwise, use the tour printed in Rick Steves’ guidebook.

Day 5 - if you’re open to another food tour, look at Eating Europe’s Testaccio morning tour, in Rome’s foodie hotspot Testaccio neighborhood.

There are several other palaces/museums, with history and art. One that doesn’t get as many visitors (no crowds, excellent experience) is the Doria Pamphilj Palace. The noble family still lives there, and the Prince even narrates the audio guide to their massive private art collection.

If you see one church, make it the Basilica di San Clemente - an old church on top of a much older church on top of a pagan temple. Book the underground archaeological visit before you get there.

Visiting the Baths of Caracalla (south of Circus Maximus) on our last trip was a special treat - it was an enormous complex when it was operating in ancient times, and the mosaics and what’s left of the structures is amazing.

We did Scooteroma in Rome. We have a Vespa at home. It was exhilarating to go around Rome on a Vespa. It was safer to ride in Rome than here. Car drivers in Rome are aware of scooters.

https://scooteroma.com/

You might consider visiting Ostia Antica, which was the port of ancient Rome. You can reach it by public transport from Rome. The site has been beautifully developed, and you can see the remains of houses, shops, even a cafe. There are also the remains of apartments, baths, and a theater.
We have been there twice; once, 40 years ago with my brother as a guide. (He’s an art historian, specializing in late ancient Rome.). This time my daughter, who lives in Rome, booked a private tour, which was really excellent.

Be careful timing things down to the hour. Both times we've been to Rome, rain set us back a day. Make sure to stay flexible.

Looks like you have 4 nights in Sorrento. I didn’t find Sorrento at all interesting. It’s basically just tourist shops and restaurants.

If the reason you want to go to Capri and the AC is for postcard type scenic views, then I recommend 2 nights in Capri and 2 in Positano instead of 4 nights in Sorrento. The time you spend in Sorrento would be much better spent in Capri, Positano or Amalfi. If you stay in Positano, from Positano take the full day and visit Amalfi and Ravello. In Ravello go to both Villa Cimbrone and Villa Rufolo for great views and gardens. In Capri go to Giardini di Augusto, Villa San Michele and Monte Solaro and do a couple of the scenic walks. Stay in Capri, not Anacapri.

Capri and the AC need more hours than a day trip each.

My reasoning behind using Sorrento as a home base was ease of travel from the port to Pompei and Capri on the boats. Perhaps I was wrong. Would it be better to cut the AC/Sorrento visit in half, sleeping in Sorrento by 2 nights, May 24 and 25, and Postino 2 for 2 nights? I have a free day in Rome, I could also cut short 1 night in Rome and spend an extra day on AC. What do you suggest?

All of my comments are for Rome.

On your Day 4, Sant Angelo (which isn't hugely interesting, IMO) is closer to Saint Peter's. You might want to visit it on your Vatican day.

For people-watching, visit these piazze, and if you can, spend leisurely time at a cafe - Piazza della Rotonda (where the Pantheon is, also good for a short visit); Campo d'Fiori (site of a farmers' market in the mornings; lots of musicians in the evenings); Piazza Navona.

I second San Clemente, it's fascinating. And one of my favorites, because I love Caravaggio, there's Church of San Luigi dei Francesi, which has three of his paintings (the Cycle of St. Matthew); another one is in the Basilica of St. Augustine. Also Chiesa di Sant'Ignazio di Loyola, the dome is trompe d'oeil and is a fun optical illusion. These three churches are close to Piazza Navona. Basilica of Santa Maria del Popolo is a little further away, but has two more Caravaggios. It's a special thing, I believe, to be able to see paintings like this in situ, in the place that they were painted to be in (vs. a museum). If you don't visit the Fine Arts Gallery when you visit the Vatican, but like paintings and can put up with the crowds, circle back to visit there (this is separate from the Raphael rooms, which I'm guessing you will definitely see on your tour of the Vatican Museums). Michelangelo's sculpture of Moses is also a bit of a further walk, it's at San Pietro in Vincoli (St. Peter in Chains).

If you like mosaics, I can give you a different list of churches that have mosaics. These are some of the oldest churches in Rome, with the oldest mosaics (there are some great mosaics in San Clemente).

Spend some time in Trastevere; it's an interesting part of Rome, and good for walking around and people-watching. The sculpture of Saint Cecilia in the Basilica of Saint Cecilia is, IMHO, amazing. It looks like it could have been sculpted last year. Also wonderful mosaics in Basilica of Santa Maria in Trastevere.

The Trevi Fountain is packed, packed, packed with tourists and isn't that pretty IMO, but if you're in the area, wander by (though be careful, I've been told that pickpockets know there are many distracted tourists in that area).

In terms of food, I would suggest that if you are into food, you should book your dinner restaurants a couple of weeks in advance, especially for Friday and Saturday nights. If you have any interest in gelato, there are many gelaterias, but Giolitti is always my favorite.

Enjoy!

Also, would it be easier to visit Ravello and Amalfi from Postino if I dont have a car?

There are no boats to Pompeii. From Sorrento the usual travel method is the Circumvesuviana train, which has a stop right near one of the entrances to the excavations. It's sort of a rattletrap train without air conditioning and can be crowded. The Campania Express runs four times a day on the same tracks; it has a/c, nicer rail cars and is more expensive.

I assume there are also bus tours from Sorrento to Pompeii, and maybe even public buses. However, from what people say about the traffic on the Amalfi Peninsula, the Circumvesuviana (or the Campania Express) is the way to go.

Thank you for everyone's input. I have added visiting many of the churches to my Roman itinerary. I have also moved our stay in Sorrento to Positano. My next steps is to research how to and from these places efficiently.

would it be easier to visit Ravello and Amalfi from Postino if I dont have a car?

Don’t need a car. You can take the bus or ferry from Positano to Amalfi. They both run frequently. To get from Positano to Ravello, you take the bus or ferry to Amalfi and then another bus from Amalfi to Ravello.

All great suggestions. Mine is to add the Domus Aurea (Nero's Golden Palace) on the afternoon of your Day 2. It is right by the Coliseum. We found it fascinating and very different. Part of the tour uses virtual reality to show you what it would have looked like in its heyday.

If I had an extra day in Rome I would take the train (about an hour) to Orvieto/Civita da Bagnoregio. You could also consider the catacombs and the Appian Way and then spend some time in the late afternoon in Trastevere.