Which places are best seen with guided tours and which best seen without

I don't find it head-spinning at all, I think it sounds very reasonable.

The question above is not, "here's a supposed itinerary, give your opinion or evaluation or whether it is doable or reasonable". I already asked that in another posting. The question is, which major places in my list above would I get more out of by seeing with a small group non-private tour versus just buying a ticket and seeing it alone? Or which places would you find guided tours for and which places would you see unguided?

Pompeii is the destination that jumps out at me as a place where it would be good to have a guide. Herculaneum is much smaller. If I'm remembering correctly, you can get an audio-guide to help make sense of what you're seeing. I don't see any need for a guide in Pisa. Be sure to visit the duomo and baptistery, not just the tower.

Honestly, it depends on what your particular interests are, and what you want to get out of the various places that you'll be visiting, and your personal style. For example, for the most part, I would rather experience a place on my own (with my family group), referring to various (very detailed) guidebooks. That way, I / we can spend as much time as we want at various places. That being said, we have taken several tours with Context Tours, including of the Roman Forum and Palatine Hill, because the Palatine Hill is so ruinous that I thought it would be better to learn about it with a guide.

Places like Piazza della Republicca in Florence are a great location to sit at a cafe and people-watch, rather than a place to make sure that you walk through.

I usually prefer to go at my own pace at sights (usually with the sight's audio guide), so I haven't used human guides very much. I have taken group walking tours and have enjoyed them, seeing bits that I would have missed, sometimes learning a great deal about various aspects of a city. I've also done all Rick's audio tours of Italy and most were very good (be sure to download the maps, sometimes the directions can be a little fuzzy). Of the places you mention, here are my experiences:

Florence: A 2-3 hour city walking tour is a good idea. Rick's audio tour for the Academia was helpful.

Naples: After just having been there, I recommend a guided walking tour if you find one. I used the RS book's guided walk and it was okay. In summer in "crazy" Naples, I think a group walk would probably be better. For Pompeii, Rick's audio walk was enough for me. I also picked up a little booklet at the entrance that had a brief description of all the numbered places (I am pretty sure it corresponds to the audio guide and had all the same info). If you have the time, take a longish walk to the Casa dei Misteri, it's one of the very best bits of Pompeii; and skip the longish walk to the amphitheatre. At Herculaneum I used the audio guide. At the end of my visit, I saw the little booklets like at Pompeii. My visit was several years ago. Many places in Italy now use tablets for the audio guides, so there may no longer be booklets, which may have been meant to accompany the audio guides.

Rome: National Museum sites are spread out. My faves are the Massimo (wonderful mosaics and Livia's Room - frescoes not to be missed) which is a couple minutes' walk from the Baths of Diocletian (which underwhelmed me) and the Altemps (near the Pantheon and the San Luigi church with its Caravaggios). You can (and will) see Trajan's Column when you're in the area. Trajan's Market is not very interesting. I went to Ara Pacis last week - the audio guide was good. The Victor Emanuel is worth climbing up, if you have the time, for some nice views and also to see the monument up close. The Trevi Fountain is best around 7-8 am, when there are few people there. (At least this week, there were only a handful of people at 8 am.) I believe the Great Synagogue is only with a tour. Don't expect too much from the museum.

I paid an extra €6.50 for the guided tour of the Borghese. The audio guide is about the same price. The Borghese visit is not quite 2 hours. Get there 45-60 minutes before your entrance time. You have to line up (not necessarily in this order) for [1] your entry ticket; [2] to check your bag; [3] optional - to rent the audio guide or pick up the audio thingy for the guided tour; and [4] to get in line for entry to the galleries (unless you take the tour). It takes about 15 minutes for everyone to enter the galleries. If you are among the first in line, you'll have more time in them. If you are with the guided tour, you'll be the last to enter the galleries. The tour lasted about an hour and was good and covered the highlights and some of the history of the building and the family. That left me about 1/2 hour to look at some of the pieces the tour hadn't covered. So I recommend that you skip the tour and take the audio guide. Be near the beginning of the line. Lastly, the galleries are on 2 floors. The audio guide, the tours and most visitors begin with the first floor. If you start at the second floor, it will be nearly empty. By the time you've gone through it, the first floor will be nearly empty. Then you can wander back to re-see anything you want. The collections are wonderful, so pace yourself. You won't be able to look at every work in every room in one visit.

I did take the pricey Roman Foodie tour (The Roman Guy website) and it was excellent.

Walks of Italy has a tour called "NEW! Welcome to Florence: Evening City Stroll & Gelato". I just wouldn't eat the Gelato. It starts at 5pm. Would I be able to do it on the same day I arrive in Rome?

The two main places for me are colosseum underground and Pompeii. We did Pompeii independently and had a great time but in hindsight I may have been good to do a tour and then wander on our own if desired

Does anybody know if the following tour is worth it?

http://www.italy.artviva.com

I screwed up and made reservations in Florence on Tuesday and Wednesday each at 9:30, now if I want an outdoor walking tour in Florence, I may have to make it on the Monday, the day after I arrive, and then after the tour, everything will be closed...

The tour itinerary sounds good. I wouldn't fret over having "everything closed" afterward. There are so many churches and other sights that are open. According to this website, the Great Synagogue is open on Monday till 6.30. The Medici Chapel is open till 2.00. The Boboli Gardens are open on Monday.

Would any of you go on this tour? I would give them 20-30 Euros.

http://www.freewalkingtournapoli.com/

I agree with a guide for Pompeii. When we were there it gave us more insight.

I just wouldn't eat the Gelato

Why not? Good gelato is Food From The Gods!!!!! I

I would definitely try one of the free tours in Naples. I think €10 per person is the norm for a 3-hour tour. In low-priced Naples, it may even be generous.

Tours generally stop at one of the best gelaterias around. They should be "artigenale" (home-made) and with all-natural products. Feel free to ask your guide about what goes into it. (see my post how-to-choose-a-roman-restaurant which also includes advice about gelato.)

I am on a radically restrictive diet high consisting mostly of fruit; I swore off all junk foods - ice cream, pop, pizza, baked goods, typical foods and so on. When you swear something off, it means you never eat it again.