Three Week Trip to Italy - Itinerary

You'll lose a little time by going from Rome to Florence to the CT to Venice because of backtracking. It's somewhat easier to take a direct train from Rome to the CT. You'll go through Florence from the CT to Venice. I also wonder if the CT is the best place to "slow down and relax" in high season, when the towns are usually swamped with day-trippers, especially from huge cruise ships.

Not a bad itinerary, but I would add another day to Rome. You don't need a full day to do San Gimignano. We did Siena and SG in one day. Also, for visiting Siena, SG, and Lucca, why not ret a car and spend the night in Siena or Lucca and take in Pisa as well?

Warning, the regatta in Venice is a zoo. It is interesting, but the crowds are huge. I have seen it twice and it is worse now than 25 years ago.

Thank you. I am not too worried about the time lost, as I don't feel it would be that much. You make an interesting point about Cinque being very busy during peak season. Is there an alternate place you would suggest to recuperate? I would be looking for something in the north, next to water.

We went to Via Reggio for a beach day. Took train from Florence. it was lovely. Very relaxing. I think we stayed in a hotel named San Francisco.
looking at your iternary others might recommend Lake Meggio or lake Como in the north of italy.
Can I suggest adding the Borghese Gallery to your Rome iternary. It was a highlight of our trip. You need advanced tickets , which are timed entry for 2 hrs total in the museum. Amazing art in uncrowded setting. The museum is in the park, so we then rented bikes and enjoyed that setting for another hour or so. Just a lovely day.

It is rare a posted itinerary actually has sufficient time per location.
I am usually telling me folks they need more nights in a location, if anything I would say your plan has too many nights in Florence.
If it were me I would work in a 5th location, taking some time from your Florence portion to make it work.
I assume you may be getting a good deal on a full week lodging for Florence. Florence logistically is the best base for Tuscany so not implying at all any issues with your plan. I think if you stick with your plan, working in more places on your planned day trips makes sense, for example you could see Volterra and San Gim on the same day and Pisa along with Lucca or work in some time for the Tuscany southern countryside (Val D'Orcia area).

For me 3 weeks in August's heat I would probably tire of such a city intensive plan (Rome, Florence and Venice all likely will be very hot and humid) with CT really being your only break from the heat.

Agree with others suggesting using Florence night for another locale. You had concerns about museums closing Monday, so why not arrive in Siena on the 20th and stay 1-2 nights? Siena is a magical introduction to Italy!

Also, we can help you with "Explore Rome" day. What sort of exploration? Borghese and the park is a great suggestion. If you can take more museums and/or would enjoy a charming side of Rome, you could go to the Capitoline Museum, get a bird's eye view from the lookout at the top of Vittorio Emanuele Sky Elevetor and jump across the river to Trastevere.

For relaxation, Lake Como is tops. But Cinque Terre is close 2nd. Although I hear cruise crowds are bad there recently, if you find a nice place with a good view, you could wait out the cruise crowds during the day and enjoy the Mediterranean evenings. I stayed in Manarola at La Torretta. A wealth of views and a nice place to unwind. If you really want to disconnect, follow the Germans, and go to Elba Island!

Just returned from a 2 1/2 week trip to Italy. A M A Z I N G.

I would not spend an entire day in Lucca. We left Florence on a 9am train to Lucca, rode our bikes around the city (not nearly as thrilling or picturesque as we imagined) walked through the city, found lunch and boarded a train for Pisa. Made it to Pisa, climbed the tower with our prepurchased tickets and hit the 5pm fast train back to Florence. Lucca didn't hold a candle to the beautiful hill towns in Umbria.

Looks good. Firenze is one of a few cities that has some museum closures on Monday and some on Tuesday, so check individual websites.

Lots of people enjoy the lakes and there are several not so far from Florence/Venice. In summer they are usually full of tourists, but not the floods of day-trippers that the CT gets. I haven't been to any . . . yet.

Another thought - not sure if it would work out, is to go to Ravenna. There are some wonderful 5-6th century buildings with original amazing Byzantine mosaics. This site describes some beaches in the area. The closest seems to be 8 km from Ravenna. Ravenna is connected by train to Ferrara and Bologna, so it's simple, if a little time-consuming (not more than to the CT), to go between Florence and Venice.
If you are willing to give up the water element, Bologna is a pretty low-key city that doesn't attract nearly as many tourists as others, has a few "second-tier" sights, and is famous for its cuisine. It's a rail hub, so you have the option of day trips to several towns that are well worth seeing. If you choose Bologna, consider dropping one or two of your Florence day trips and choose from Bologna's options, like Ravenna, Ferrara, Modena, and Padua.

I want to thank all of you for your well thought out and helpful replies. I have been so busy with work I have been unable to review my post until today. I love the lively conversation and strong opinions you all have shared!

I have the weekend off, so I will be taking all of your suggestions and coming up with my final plans, which I will be sure to post for your further review and expert options.

Thank you all!