Rome to Sorrento to Siena/Orvieto to Florence

Sounds like a good trip to me! Since your flights are set let's get right to the itinerary. Rome is worth 5 nights. See the big sites during the day and then go back at night for a completely new viewing. I prefer renting an apartment when I'm in Rome. I love cooking with the fresh vegetables.
Getting to Sorrento isn't difficult at all. Take the Freccia line from Roma Termini to Napoli Centrale. If the weather is nice, I like to take the ferry from Naples over to Sorrento. It makes that part of the trip a part of the vacation. Bad weather? There is always the Circumvesuviana train that takes you directly to the center of Sorrento. My favorite (10 years?) hotel is il Nido which is actually above the city. They have excellent shuttle bus service to/from the city. They also have my absolute favorite restaurant in Sorrento. Dinner is spectacular and breakfast (free with your room) is excellent. I don't think you could do both archeological sites in one day. My favorite is Herculaneum, which is also less crowded. Capri takes planning because the boats get very crowded which means getting back to Sorrento can be especially challenging - like not getting on the last boat! I usually take the boat from Sorrento to Positano and then on to Amalfi. The views are spectacular. I take the bus back (it originates in Amalfi town so it's easy to get a good seat). The bus will drop you off right in front of il Nido - just keep your eyes open, they won't stop unless you ring the buzzer.
Getting to Siena is not that difficult - the Freccia train will take you from Naples to Rome and then on to Florence. A couple of hours travel time. Bus to Siena is 90 minutes but the scenery is very good. Siena is a wonderful place to be. There's plenty to see while you just wander around. I'm not big on museums but the museum at the Duomo is well worthwhile. Orvieto is nice but that's about it for me. Had a wonderful rabbit dinner there one year!
Florence for 5 nights? You could day trip to Lucca and even Siena from there quite easily. The recently re-opened Duomo museum is a must see. 5 nights? Plan your daily schedule - you might want to add some time to Sorrento. Can you tell that Florence is not my favorite place in Italy.
Food? Hey, it's Italy. It's very hard to go wrong (just keep away from the touristy places - the ones with menus in a dozen different languages).

You're right, this is a great group and it's fun to read/write here!
What? No Venice!?!

Siena is much bigger and busier than Orvieto and probably requires a change in Florence whereas Orvieto not as far and on the main train line
For that reason I’d choose Orvieto
We loved our 2 nights in Orvieto this past spring
My sister just returned from a month long trip to Italy and they stayed for a week in Orvieto-it was her favorite place.
Siena can easily be visited as a day trip from Florence.

Sorrento is a perfect place for what you have planned.
A day trip from Rome to Pompeii is brutal.

Robert: Thanks so much for the detailed and helpful reply!
Hotel Il Nido looks very nice. I appreciate the suggestion. I just have to decide if I should get a room with a view... or if the alfresco dining area's views might suffice. What would you suggest? Inflation is making me think twice :(

I love the idea of taking the ferry! It sounds like a fun way to see the area.

How might you organize seeing Herc., Pompeii, and the Arch. Museum in Naples? Pompeii for a full day, then combine the other two? Thinking it might be best to see the museum artifacts last.

I'm delving into the Siena/Orvieto options now.

You have me re-rethinking the timing in Florence, maybe 4 nights. The last time I was there it seemed the Uffizi was half closed off due to renovations. It will be nice to enjoy it thoroughly this time. Also want to see the Boboli Gardens (it started to rain heavily when I was there) and Piazzale Michelangelo.

No Venice this time - that was a few years ago - and great!
Your suggestions are really helpful!
Happy travels.

ChristineH: I appreciate your reply.

Knowing Orvieto is a more direct commute is very helpful. I'm researching it and Siena further now. You're right, I can always do a bus trip to Siena if I don't make it home base.

Thanks!

It partly depends on your interests. The Renaissance came much later to Siena than to Orvieto or Florence, so the main art museum's collection (and the town's architecture) are very different. Also, Siena is much bigger than Orvieto. However, Orvieto is very easy to like, and certainly worth one night. Some people find the history of the Palio race, or the neighborhoods of Siena to be very interesting. You might also check if the Siena cathedral floor is uncovered for viewing the week you plan to travel. Siena is busy enough to have timed bookings and long lines at some attractions. But that's true of Florence as well, so you can't snub Siena just for that.

The distance from Sorrento to Tuscany is important. Also note that Sorrento books up six to twelve months in advance. You need a list of preferred hotels before you start booking. I personally would not stay in a hotel with a shuttle to town, because it adds a "seat" to every excursion from a town that has very good transport connections. But clearly budget is important to you. Do NOT consider a daytrip to Pompeii from Rome. Sorrento is not a "beautiful" place like Orvieto, but it has the best transit connections in the area. Read about Frecciarossa train service, here (search box top left) or elsewhere.

I am not deliberately recommending it, but many people have posted positive reviews of the luggage storage at Pompeii and at Herculaneum. (Note that Herc is a 15-minute steep walk from the Circumvesuviana station, however.) The Naples museum has lockers, and there is commercial luggage storage as well. I personally prefer to make daytrips without luggage. You should take account of very serious crowding on the Circumvesuviana train. It's intimidating. There's a special tourist train service for a little more, but it's very few trains per day.

Even in May, the sun and heat exposure at the ancient sites can be serious. Pompeii is almost more than you can see in a day, so you need to make a plan; One plan is our host's walking tour in his Italy books.

Hey Veryspecialquilts! Glad my thoughts gave you something to think about. About Sorrento (which I really love), and especially the Hotel il Nido, it is a wonderful place especially in the evening. The sunsets are, for me, the most beautiful. On more than one occasion the people along the cliff watching the sun go down were quiet but at the last sight of the sun, they broke out in applause. Right - I couldn't believe it either. The evening is the time to meander around the streets. It's a great way to end a busy day.
The hotel can get crowded, so book asap. Room with a view? OK, but not necessary. The veranda late at night, or in the afternoon, is quiet. Dinner there cannot be beat! Say hi to Dino for me! He and his brother have run this family business for a few decades now.

I don't know if there is luggage storage at the train station in Naples but if there is, then maybe drop the bags off there and head to the museum before heading north. Bags at Pompeii? Don't know about that but after hours in the heat and humidity that is hard to escape in Pompeii, you might not feel too comfortable starting a long train ride. :)

The RS guidebooks will give you good ideas for each city you mention. But when it comes to restaurants he recommends, remember that thousands of other tourists have read the same reviews! I've never been disappointed but I've always had great fun finding great food in a great setting - that is crowded, yes, but with locals and a few adventurous tourists. My rule: turn left (or right) away from the tourist traffic. Each one of those cities can be a whole new experience!

Hi again Robert.
We seem to travel - or eat - the same way. I want a place where I hardly speak the language! No photos of food, thank you. In Italy, it is tough to go wrong that way. Funny, I devour RS books for the how-to's, where-to's, hotels, and to know the top spots for food but really enjoy finding restaurants on the go. I do like to try the must-try dishes. My goal in Rome this time is the artichokes. Silly?

So, how many hours for the Arch. Mus. in Naples? His book says 2 hours, but being an art history nerd, I usually double his suggestions. This is one reason why I travel. Perhaps I'll make it a day trip from Sorento.

Thanks again very much!

Hi Tim.

So many good points in your reply. Thank you.

Orvieto is near many good photo spots and a new city for me, so it holds some appeal. I'd enjoy diving deep into Siena and her 17 neighborhoods.

Long lines are no fun but do signal worthy places. Tickets are my solution for them. I appreciate the heads-up about the lines in Siena.

Yes, a hotel shuttle to take another bus is a bit redundant. Thanks for pointing that out. Do you have any hotel recommendations? I've got to make some firm plans ASAP if the area requires 6+ months advance bookings. Yikes!

I'd rather do luggage-free day trips also. Lugging bags is no fun. Neither is baking in the sun while sight-seeing. I'll prepare for that - another good point.

I was just reading about the beauty of Ravello/Capri/Positano. So much to see in Italy!

Thanks again.