Rome for 3 days; Tuscany for 3 Days; Cinque Terre for 2 Days; Venice for 1 Day. Help!

So much of this is subjective, but I tend to avoid one-day stops in general (unless it's a needed stop the first or last night). Just a few random thoughts:
Your Rome parts looks good, and I am all for driving in Tuscany, but I would choose just one place to overnight, and just see places close to that base.
I would keep in mind that August will likely be very very hot, so a slower pace might be warranted. You could not pay me to go to Cinque Terre in August, but if I were going, I would stay in a village and not in La Spezia.
Anytime I have heard anything negative about Venice, it is usually from someone who spent only a day there. But if you are flying out from there, it does make sense if you just want a peek.
Could you tell us what is booked (flights) and what is set in stone? I think it is safe to say that most people would make only three stops with nine days, so reordering your priorities might be in order. Also, how many are in your party? A young couple might like this pace, but for a family with young kids, it would be madness for example.

I have done a very similar trip and it took nearly four weeks.
To explore the Tuscany area I rented a car and we stayed at an Agre Turismo for 5 days.
You are shorting your time in Rome, Florence, Venice and trying to fill in too many stops in between. This trip will not be fun.
Try to plan so that you have at least two nights at every stop else your trip will be like the business trips I used to do, one night in every place, no chance to ever settle and relax. You can say you were there, just not what you did.

Sit down with Google Maps and trace your trip, noticing the time it takes to get from one destination to the next.

Here's my advice, based on our trips to Italy. Instead of renting a car in Rome Monday morning, take the train to Orvieto and rent a car there. We've driven from Rome to Tuscany and the first part of the trip is on the Autostrada and while you do see some nice areas, with your time constraint it will be better to skip it.

I think overall your Tuscany plan is unrealistic. You are trying to see way too much in two days. It will take half a day without stopping to drive from Pienza to San Gimignano. Plan on an hour minimum to drive from San Gimignano Volterra. That leaves you with maybe an hour or so at each.

By the time you check out, drive, return the car and check in it will be past lunch time in Florence. That gives you a couple of hours in the afternoon and that evening in Florence.

Cinque Terre will be a nightmare in August. It will be hot and overrun by tourists from cruise ships. It's become a tourist trap and there's really not a lot to see and do other than the pretty vistas.

I think your trip will be hurried and frustrating. In an attempt to see everything, you'll end up seeing nothing. Chunk seeing CT. Plan to see Pienza/Montepulciano or San Gimignano/Volterra but not both. Add time to Florence and Venice.

Keep in mind that August is the most popular time for Europeans to go on holiday. You'll not only be vying with fellow Americans for accommodations, but also with the Germans, French and English. It is really late to be making reservations for August. Your choices will more than likely be limited and expensive.

I think you are deceiving yourself on how much time you will have. For example, you say drive from Volterra to Florence, ditch the car and spend all day and night in Florence. By the time you drive to Florence, turn in the car, and check into your hotel, you will have not have "all day". You basically are talking about having afternoon and evening in Florence. You will have the same in Venice.

At the very least I would eliminate Cinque Terre. It takes a lot of time to get there and it is opposite direction from Venice. Add one night to Florence and to Venice. That would give you 3-1-1-2-2 which is still moving a lot. Right now you have 3-1-1-2-1-1.

Pienza/Montepulciano/Montalcino: The plan right now is rent a car in Rome Monday morning and drive up to Pienza and spend the day in Pienza and Montepulciano. Time permitting, we may try and hit Montalcino as well. Any thoughts on renting a car and driving from Rome? Good idea or bad idea? We would stay Monday night in Pienza and leave for San Gimignano early Tuesday morning.

Reading your itinerary it sounds like you’re comfortable with this being a bit of a whirlwind trip. That being said I don’t think you’d be able to realistically visit all three of Pienza, Montalcino, and Montepulciano while also driving up from Rome that morning.

Given you’re staying in Pienza I would drop Montalcino from the plan - it’s 30 minutes driving each way from Pienza. You can visit Montepulciano on the way off the A1 and then head to Pienza in the afternoon. Montepulciano is the biggest of these towns and you may want to spend a little more time there - Pienza is cute but quite small, does have a great gelato place for a late afternoon treat!

I am all for the 'see all you can' method of travel. Since you need a car for Tuscany, that part seems like a good idea, but you asked for advice, and mine is: keep your driving in the city (Rome) to a minimum. It is not like driving anywhere else and it is crazy, and I've done it.

Arriving on Aug 16 means you are arriving the day after the biggest holiday of the year in Rome, Assumption Day is Aug. 15. Don't be surprised if you find some restaurants and shops closed.
I would say that Cinque Terre is worth a visit, but don't try to see it all. The views are similar at all the towns there. I highly recommend you look at Rick's advice on this, he loves CT.
I would leave Florence Thursday morning and go to Cinque Terre, then go to Lake Como, then go to Venice (train does go to Milan then Venice). All doable by train with no back tracking, and Lake Como is the best of the lakes region. Depending on how you want to spend your time, you could stay where it suits you.
Have a wonderful trip.

Have to agree with some of the others. I'd eliminate one or 2 of your Tuscan towns; as it is you will spend more time driving from place to place than actually being IN those towns. It will just be a hurried blur. And I'd definitely ditch the CT for all the reasons given. It will be just as hot as everywhere else in Italy, but you really can't understand how jam packed crowded the villages will be unless you've seen it for yourself. And good luck with the trains between the villages- they are just as jam packed (SRO) as the towns. Instead, give those days and nights to Florence and Venice. Especially Venice.

hey hey jakegtaylor
congrats on first trip. is trip this august 2023 and how many people are traveling?
we all want to see it all with go go go. you are traveling during high season, crowds, lines, waiting, HOT
my feelings you are traveling too much, one day/night here. no time to really enjoy and wander around, some of the times may be longer than you think. many people wanting to see the same places you are planning. have a map and italian traffic signs for driving, get an IDP at AAA/CAA (read up about this permit), where the parking areas are for your car, will you have luggage in car while roaming around.
my own thoughts, we were on a tour (4 of us in a car) got to san gimignano & was a nightmare. had about 8 big tour buses, 5 tour vans, plus people who drove. couldn't even walk down the shop area or look in shops so packed, gelato shop outside had a line going around whole building OMG, told driver get us outta here.
if venice is only an overnight, i would not even waste time going there. most flights leave early (6am ish) find a way to airport for check in to gate/airport at that hour. fly out of florence since you're there already
remember that check in times to hotels is usually 3-4pm and check out 10-11am, do they have luggage store until check in, ask for early check in if possible, so you won't be waiting/pushing/pulling luggage over uneven pavement/cobblestones/bridges/steps/stairs.
hate being deloris downer but just forewarn you what you can expect. we sit down at cafe outside, have a glass of wine with cheese/salami and people watch. enjoy it, fun place to be
aloha

This has been very, very helpful. I really appreciate everyone's help in answering my questions and giving their input and advice on the proposed itinerary that I offered up. It will be just my wife and I traveling (celebrating a 40th birthday and our 20 year anniversary). The only plans we have set in stone / booked are our flights (arriving in Rome on the 17th and departing out of Venice on the 27th), hotel in Rome, and a few guided tours there as well.

After reading everyone's replies, I think we do as suggested and skip several of the Tuscany stops and train directly from Rome straight to Florence and stay there for several days before traveling to Venice for a few days and then back home. Maybe if we're feeling like we have time while in Florence to venture over to CT or to SG, for a day, we can make that call. We don't mind being on the go but we definitely don't want it to be a whirlwind and we don't want to spend all day driving in a car only to be frustrated that we can't find a place to park once we get to our destination town. That would be terrible! I sincerely appreciate the advice everyone has offered! I guess the bottom line is we will need to go back again when we can spend more time in some of these other towns and do it right and not be rushed. I wouldn't mind that at all!

Jake

I think we do as suggested and skip several of the Tuscany stops and
train directly from Rome straight to Florence and stay there for
several days before traveling to Venice for a few days and then back
home. Maybe if we're feeling like we have time while in Florence to
venture over to CT or to SG, for a day, we can make that call.

Very glad to read this! I think you will both be happier with this decision.
A few thoughts- you have 9 nights- since you arrive in Rome late in day you should probably give Rome 4 nights- that is 3 full days and a bare minimum for Rome.
You might consider skipping Florence/Tuscany entirely.
From Rome take the train to Orvieto-about an hour- a beautiful Umbrian hilltown with an amazing duomo and several other interesting activities. It will be a bit quieter than Rome, Florence and Venice and possibly a bit cooler
Spend 2 nights there as your "hill town visit"

From Orvieto head to Venice for your final 3 nights- that is also the bare minimum needed there to really enjoy Venice and time to get away from the crowds- head out to Burano, etc.

SG is a bit of a pain to get to without a car- if you stick with Florence you could look into a guided bus tour that takes you to a few hill towns- there are many to choose from.

Leaving from Venice can be a hassle- make sure you've got your transportation to the airport figured out- plenty of help here for that.

Lastly- Happy Anniversary and Happy Birthday!
Start planning your 25th anniversary trip to Tuscany.

Thank you Christine! Yes, we have a full three days in Rome, checking into our hotel Thursday night and checking out Monday morning. I am not familiar with Orvieto.... I will certainly get on right now and check it out. Sounds like that could be a good option as well. And thank you for the heads up on the transportation to the Venice airport. It's an early a.m. flight out on the morning of the 27th so I would hate to miss it! I will do some digging on the forum to find out the best tips for that. Thank you once again. Can't say enough how much I appreciate everyone's advice to help make this a successful trip for us. Many thanks!

Jake

Some info right here

https://www.ricksteves.com/europe/italy/orvieto

https://www.ricksteves.com/watch-read-listen/read/articles/orvieto-what-an-italian-hill-town-should-be