First timers, need itinerary help

I would leave Tuscany for another trip. Since this is your first trip to Europe, slow down and enjoy Venice, Rome, and Florence. Once you go you will get hooked and want to go everywhere. Figure that you won’t return to these cities because of so many others to visit that you don’t want to rush them. Also, it will erase the need for a car, a headache in Italy.

You really don't need to rent a car for what you propose to do. After Florence my suggestion would be to take the train or bus down to Siena and base yourselves there for a few nights, taking advantage of local day trips to explore some of the countryside when you're not enjoying the relaxed ambience of the beautiful city ... once the day trippers depart in the afternoon that is.
Save the car for your next trip when you can devote more time to exploring the countryside where a car is necessary.

For me, it's easier to think in terms of nights in a location, versus days. If you arrive on the 24 Sept and depart on 8 Oct, you have 14 nights.

3 nights Venice
3 nights Florence
4 nights Tuscany
4 nights Rome

That would be too much moving for me personally and the way we like to travel (myself & husband, mid 30s, and our 5 year old). You'll lose at least a half-day checking in and out of hotels, traveling to your next destination, and orienting yourself with a new city. I'm not sure if it's worth staying in two separate places for both Florence and Tuscany. I'd pick one location to use as your base, and do day trips. I'm a city girl at heart, so I'd base in Florence and do day trips to smaller Tuscan cities, or set up a wine tasting tour that would pick up at my hotel and avoid the hassle of renting a car. But it sounds like the countryside might be a priority for you, so you might want to base in a smaller town (Lucca or Arezzo would be my pick) and then train into Florence to see the sights.

Of course, you know your energy level and travel style best, but for a first time to Europe, there will be a bit of a learning curve, and I find it less stressful to slow down and try to "do" less.

I would suggest adding another day to Florence and another day to Rome. That would mean sacrificing the Tuscan countryside though. If you do decide to do more in Tuscany than Florence I suggest Siena. I did not rent a car in my trip so I don’t have any suggestions there.

In Florence, we picked up our rental car on Via Borgo Ognossanti and there was a direct way to the Autostrada, quite easy,
We have stayed all over Tuscany but prefer the Chianti region where we have stayed many times. Look at Castellina, Radda and Panzano . You will be near Siena which is a gem. You can see a lot of this part of Chianti in four days.

A bit rushed.

Give some consideration to overnighting in Milan and pre arranging a tour to view the Last Supper.

For Florence I was pleasantly surprised by the views of Florence from Cimitero delle Porte Sante. ( Delle Porte Sante Cemetary). I always tour cemetaries when in Europe. Located it when I chose to walk up from Piazzale Michaelangelo which is known for its views of Florence. Good exercise getting up there.

Florence is about meandering. Discovered the tiny Cafe degli Artigiani coffee spot by wandering. Great coffee and pastry. Its in the neighborhood between Ponte Vecchio and Ponte Santa Tarinita bridges.

If Tuscany is a must see you could train from Florence to Chiusi and rent a car there. Friends have a lovely Vrbo rental property in the olive groves near San Casiano dei Bagni. I rented a car in Chiusi Drove to Orvieto one day, meandered, had lunch.
Returned rental at Chiusi and trained back to Rome.

Couple of hidden gems I discovered on 2 separate visits:

First off be prepared for graffiti through out Italy.

Florence:
1.) A flea market on Piazza dei Ciompi. This was a decade ago so you’ll need to research if still there or in business after Covid.
2.) Fabulous meal at Trattoria 4 Leoni
3.) Torigianni Gardens which are fairly close to the Pitti Palace. Its a private garden. Can’t recall how I got in.

Venice:
1.) The park of Remembrance. Quiet. People watched.
2.) Church of Madonna dell Orto houses art by Tinoretto. Loved the solitude on a December visit. Loved the architecture. Found it because I was lost. Getting lost in Venice is an exact way to find intriguing off the beaten track sites.
3.) My 3 course meal at Osteria Al Bacco

Rome
1.) A guided tour of the Antica Farmacia S Maria in the Travestere neighborhood. Its so unique. Have to research how to arrange a tour.
2.) The stained glass at Casina delle Civette and the entire Villa delle Torlonia Museum grounds.

Its a lovely country. So much history. Fantastic food. If wine drinkers pretty sure you’ll be happy. The Italian beer is good as well.

Wear comfortable shoes. Scarf to cover head and bare shoulders in the churches.

When shopping for fresh fruit ask the vendor to choose for you.

Prego is thank you and I found it an easy way to show respect to shop owners, restaurant staff, cafe owners, museum staff, and bus drivers.

Sadly pick pockets abound in Italy so hide your money in money belts to help alleviate any anxiousness.

Ciao

Thanks to you all
Barbara pretty much hit the nail on the head, long with Erin and Julie.
I am not one to visit a new place and not take in more than any sane person would. I can't get enough of a new place and need to explore every inch. But something tells me to slow it down just a tad. Italy IS a big place and I plan to return to see more, hopefully.
So, we will do 4 nights in Venice, 5 in Florence and 5 in Rome with a day trip or two to Tuscany towns. But I hear Robert loud and clear and a night in Siena sounds wonderful. Thanks Suki for the car rental info and Chianti ideas and Claudia for all those really cool inside tips, they will come in handy.

Now I'm on to hotels. I think it best to ask for recommendations on another post if need help after a little digging first. I do know I'm a little late getting started and some of my choices have been booked up already.

My understanding is that Florence has very strict ZTL zone laws when it comes to car rental. Since you want to explore the Tuscan countryside why not take a direct bus from Florence to Siena (1h 15m) and sleep there. The following day rent a car in Siena and get on the very scenic Sienese Crest Road that features many different landscapes to Pienza and then on to Montepulciano and spend a night there. The next day return the car in Chiusi and take a direct train from the Chiusi-Chianciano Terme station to Rome.

You're going to have a great trip! I could be in museums and churches pretty much all day, every day, but my husband is not a "museum person", and obviously my kiddo doesn't have the attention span for a never-ending rotation of museums. We aim for one museum visit a day, usually in the morning, and leave our afternoons free for a lot of outdoor time in parks, piazzas, or cafes. I think your revised itinerary will really allow you to balance the sights with the true culture of the cities. And you'll have lots of time for enjoying gelato!

In Florence, I'm going to go ahead and throw out my vote for neighborhood - the Oltrarno. I'm completely biased because that's where I lived when I studied in Florence in 2008, but it's a great neighborhood, across the river Arno, with a local feel. It's removed from the tourist crush but still only a 15 minute walk from the main sights, with lots of great restaurants (especially in Santo Spirito area) nearby. Gelateria La Carraia is my pick for best in Florence :)

Dan - regarding hotels, I have come to the personal conclusion that AirBnB's are often a better and more affordable choice. Don't get me wrong - I still have favorite hotels in Italy, but finding an apartment that has separate bedrooms, balcony, kitchen, etc. and at a rate that is less expensive has become my go-to. That being said, if you choose that route then do research on what part of the city you want to be in. I use Google Maps and Street View extensively. Best of luck!

I fondly remember my first trip! I rushed around like a crazy person with limited time...a bit of a blur. These days, as a retied person, I can take my time. No matter what you decide it will be magical. In any case, with all the time I have spent in Italy, i have never rented a car. The train and bus system is highly efficient. Yes, you might miss a tiny town in the hills wihout train access but with 14 days/nights there is plenty to see via train or bus (Bologna, Lucca, Parma, Greve, Cortona, Siena on and on). You can do so many day trips from Florence or if you stay in a small town nearby. Someone mentioned Arezzo which is close to Florence so you can get there quickly to see the sights. Even just sitting in a pizzza (Santa Croce is a favorite of mine) people watching and having a gelato...pure joy!

I saw a mention that "prego" means thank you...actually, it means "you are welcome"....grazie is thank you....grazie mille is "thank you very much".

You folks are awesome!
So many insights, good information and willing to help.
I have to admit, I'm having trouble staying put in Florence. The open road keeps calling me, I've read so many posts of scenic drives in Tuscany and small villages to wander in. But I think Barbara is right, slow down and enjoy the cities. Darn, I wish it was so easy for me! Do I stay in Florence and be content with a day trip to the country or vice versa? Such problems I have, lol.
Erin, thanks for Oltrano and June with Santa Croce, all these tidbits are invaluable, also Marc for the Airbnb, which we are quite familiar with but my wife might like the hotel experience for this trip.

I would do 3 nights Venice and add the extra day to Florence so you can do a couple Tuscany tours.

I'd advise against renting a car. Driving in Italy is full of pitfalls. Italian drivers tend to be aggressive. Those charming towns with historic centers have ZTL's - limited traffic zones. There are little signs with excellent cameras. If you miss the sign and accidentally drive in (the road keeps going but you're supposed to turn off it) you'll get his with a triple-digit fine. So you have to be doubly alert and find parking outside the historic center. Parking is often hard to find and expensive. And even outside the historic center the streets may be hundreds of years old, so they're narrow and sometimes tricky to drive through.

If you do decide to rent a car, take the tram from the Florence train station to the airport and pick up and return the car there.

As others have said, you can get around Tuscany by bus and train, much more relaxing and you can drink wine with your meals too.

So, we will do 4 nights in Venice, 5 in Florence and 5 in Rome with a
day trip or two to Tuscany towns

Dan, this is a terrific plan for a maiden voyage to The Boot! When it comes to exploring at a pace that allows you to really absorb the details, less is definitely more! This first adventure will help to prepare you for tooling about on 4 rented wheels next time; you'll be able to observe a bit of what might involve. :O)

Yes,, you can easily day-trip to several Tuscan towns from Florence....and the city itself is CRAZY with glorious Renaissance art and architecture. Additional wisdom from Chani?

... by bus and train, much more relaxing and you can drink wine with
your meals too.

Amen to that!!! :O)

I think you'll be glad you're saving driving in Italy for another trip.

We have driven in Italy on many trips and my husband is a great driver and is fluent in Italian so he can read the road sign AND he actually enjoys the hair-raising challenge of driving (briefly) in places like Rome and Palermo and Naples. The only ticket we've ever gotten was a parking ticket for parking in a spot we knew was dumb to park in overnight.

I just double-checked with him about how much scenery he actually gets to see while he's driving and he said "Not much." I also miss a lot of it because I am navigating. It should be easy for you to find someone local to drive you either to smaller towns or to see scenery, for instance Tours By Locals. Also use Google Maps to find buses that will take you places.

And, really, the three "biggies" that you will be staying in will astound you with their urban scenery --- there is nothing like it in America.

Thanks Kathy and Chani, I needed that, I think I'll hang in Florence. I am trying to get my footing on this trip and plan well so it flows. I do see four rented wheels under me at some point in Tuscany.
Lulu I have been back and forth on that last night in Venice. I think I will stay with the plan of 4 nights and savor Venice as the experts here have said. A day trip or two to Tuscany, or not, can suffice for now.
Being a country boy, public transportation is more daunting than driving! I will need to learn how to negotiate buses and trains.

I'd like some thoughts on something that is a no no. Taking a tour the day you arrive. Let me state my case.
We live on the east coast - 6hrs time diff - and we are early risers, waking at 3:30 daily. My wife will sleep on the plane, I won't. I can power through pretty much anything, standing on a Venice street for the first time - I probably won't even be touching the ground! I see Venice Free Walking Tour has their Legends and Curiosities tour on Sat. & Wed. which touts getting the "backdoor" tour of Venice and will help you get acquainted with the city. We arrive (hopefully) Saturday at 10:35am on a non-stop from JFK. Tour kicks off at 1:30. Hotel Flora looks to be the winner for us and the tour kicks off at Campo S. Geremia. Am I crazy? (ok don't answer that). I'm thinking it will keep us occupied and outside keeping us awake and acclimating to our surroundings. Ok, so, is this a dumb idea?
I read VCE immigration is about 1/2 hr, baggage can take as much as an hour.!! (we are planning on just carry-ons, for the ease of travel) Customs, walk right through. The ride from the airport is a little less than a 1/2 hr and then I have to figure what kind of boat to take from where the driver drops us off. If you give me the green light, will 2 hours cover it from jetway to Campo? 21/2? Or should I get a spritz at a sidewalk cafe and just enjoy?

I love Italy. So happy your first experience in Europe will be in Italy. The people are so charming, the sights so fabulous, the history and the arts are…magnificent!It feels luxurious to me when I am there. All suggestions I have read are spot on. No need to rent a car, especially since this is your first trip. I have been many times and have never rented a car. I would suggest you may wish to consult with one of the RS travel consultants. For $45 for a half hour you will get all the help and advice you need. Enjoy your trip! Ciao

Neither crazy nor dumb. The timing might be a little tight, but it looks like you can leave your bags at the hotel and either walk 20 minutes (including a super-short vaporetto ride just to cross the Grand Canal at one point) OR (what I would do), drop your bags at the hotel and get back on the vaporetto #1 that you took to get to your hotel and go all the way back to the train station and walk to the meeting place from there. You can't ride up and down the Grand Canal too many times --- it just never gets old. The tour you are talking about doesn't sound like the tours people say not to do --- they mean like a tour of the Vatican or an expensive tour you cannot escape from or an indoor art tour that requires a lot of brain power.

I am also an early riser (4:00am) and retired, so I adjust my sleep and eating schedule while at home to partly match up with Italy time --- I can now gradually get myself 4 or 5 hours onto Italy time, and thus completely eliminate what used to be horrendous jet lag, but even 2 or 3 hours will help you and your wife with jet lag. I can't sleep on planes, either, so I don't even bother to try. The excitement of being in Italy easily keeps me going the first day after a night of no sleep.

People on this forum love to answer questions, so ask all you want. Like, you'll want to know exactly how to buy tickets or passes for the vaporetto and how to actually take one somewhere.

I suppose you have read all the information about the three cities on this site and you have received a lot of good advice here, so I will just add my favorite Venice information site: https://europeforvisitors.com/venice/

Also: if you are early risers, you may need to prepare for late dinners. At least I think 8pm is late and I am a late riser :-)

Think about getting a vaporetto pass in Venice, so you don't need to think about the cost of sailing - at least when you have paid the price for the pass. In the past I have often caught myself spending too much time walking to save the price of a ticket. And though walking the streets a Venice is one of my favorite pass times - I sometimes need to be somewhere at a specific time.

Whatever else you do, remember to visit San Marco at least one evening to enjoy the music - and maybe even a (terribly expensive) cup of coffe or glass of wine.