First Time traveler - Please review my Itinerary after making previous suggested changes.

8:15am timed entry tickets to La Accademia (arrive 15 min early for
each activity), 9:30am for Uffizi gallery

This is a bit tight. You'll have to move fast. See the David, marvel at The Prisoners, skip rest of museum- allow at least 15 min to get to Uffizi

Not booked, but hoping to plan a horseback ride tour on Viator that
includes a tour of St. Gimigiano

OK I Guess- but horseback riding is not what most people go to Italy to do. I think a day trip to Siena would be fine-- DIY.

Take public transport to my hotel in Venice

Should be easy- let us know exactly where your hotel is and we can share the best way to get there.

Gondola ride @ 11:00am.

No real need to book this is advance- you can just walk up and book with a gondolier you like. This way you are not rushing thru the Doges Palace to make that booked ride.

Visit Saint Mark’s Basilica.

This needs a prebooked timed entry. I would probably put this early in am on same day as Doges- they are right next to each other. Then this am you can do other things- like visit Rialto fish market for example- I guarantee you wil see fish you never knew existed.
Or take vaporetto to one of the islands. On the way back from Burano you can stop at Lido- one of the vaporettos goes there from Burano.
It will be crowded there but OK it is a beach. Realize you wil be surrounded by water while in Venice!

Check out of hotel at 6:30am and take public transport to VCE airport.

If you share hotel location we can tell you best way to get to airport

I have my International Drivers Permit.

ALL drivers need an IDP and be sure to carry your US driving license as well. You will need both to get the car.
Yes you need insurance. It is best to purchase when you book the car. You want NO Deductible. Please search this forum for this info. It's important that you get it right.
We always book our cars with www.AutoEurope.com- stellar service, best rates.
Who are you booking your car with?

Should I waste $100+ on more tickets for the 20th as a backup plan,
and not do the horseback riding tour?

No I would not do that- your flight might be a delayed arrival to Italy but as long as you leave the US you will get to Florence likely on same day as planned. If you are delayed that long- well- just have to roll with it.
As far as horse back riding- as I said above- not something most would do. Your choice. You can ride horses anywhere.

I suppose I can just do a short 3hr wine tour or some sort. The horseback riding is only 1 hour of the trip and it includes a tour of st. Gimignano and a 3 course lunch with wine and gelato. It just sounded fun to me, but I am also looking at pizza & gelato making class

My hotel in Venice is CHC continental; it’s right off the train station Venezia St Lucia.

My gondola is booked with delta because I’m paying for 95% of the trip with a delta gift card.
I suppose i could remove that activity, but will there be a line if I don’t have one reserved ahead of time?

Ok that makes sense. I will book doges palace and basilica closer in the same day. How many hours in between?

Ok I’ll hope for the best on making it to Florence in time! If I should fly into Rome by 8:15am, it would have to be a real serious delay to make me miss the next day. How common is that? Thank you.

There are gondolas all over the place
On main canals on little canals on the Grand canal
I don’t think you need to worry about a line
But if you want to book this one -go ahead
It’s July so weather shouldn’t be an issue

Really bad delays were common in 2021/2022 after COVID as things were just getting going again
There are folks here that had trip delays by a day or. 2

This is what your trip insurance should cover
“Trip Delays and Interruptions “
You would be able to get $$ back if you miss tours that you have paid for due to your trip being delayed
Read all the fine print in your policy so you understand what your policy covers

You might be overthinking this
When we warned against pre booking in case of flight delays we were referring to a couple hours delayed arrival so advice is to not buy train tix in advance just to save a few bucks
I would also not advise booking any major venues or tours on arrival day for a multitude of reasons

Consider a food tour in Florence
Those are always lots of fun and you get to eat a lot of yummy things as well as get some history along the way
Eating Europe.com

This seems like a better plan now!
I have stayed at the CHC Continental Hotel in Venice, way back in 2015.
It used to be the Swiss Embassy , many years in the past.

It was fine then, and having breakfast outside on the deck/dock right at the Grand Canal was really nice.
I was lucky and had a room facing the Grand Canal, so hopefully you will too!

Thank you all so much for the help. I do truely feel like now my itinerary sounds much more smooth and accounted for many things previously, I had a connecting flight from Paris to Florence with only a one hour layover and was told that is horrible. I had a pizza & gelato class booked for 3pm the same day of arrival that I was told is not good because I will be tired and jet lag. I removed cinque terre even though I wanted to see it so bad because I want to swim but it will be packed of day trippers. This gave me more time in Florence. I have made many adjustments and I finally feel like I can sleep at night. I am going to keep the flights / hotel stays for sure.

ok I will look into how I can be reimbursed if I miss those museums in Florence. :)
I’m soo excited!!!!!!!!!!!!!!! Now I’m learning about luggage, TSA, driving in Italy, and looking at visual maps of everything to try and help myself find areas faster like the airport to the train station etc

Also yes if I could go back I’d probably not book that first train from Rome to Florence, however I didn’t know what I do know now. But I do know that I got business class seats and was able to pick my own, and I can change my tickets unlimited times. The next train for Rome termini to Florence is 12:10 instead of 11:10. Should I go ahead and change that now and just be more on the safe side? Thanks!

My other train is booked from Florence to la spezia and I will need to pickup a rental car by 1pm. So I have purchased those tickets in advance allowing myself to get there by 11:23 in case of delays and also catching the bus.

I think you mean your “other train” is booked from Florence to Venice-Mestre?

Oops yea, Florence to Venezia Mestre
My hotel in Florence is right off the train station Florence SMN. And my Venice hotel is right off Venezia St Lucia station.

How often does Italy have train strikes? In any case they happen while I’m there, what would be the best way to get from the airport to my hotel in Florence, and from Florence to Venice?

curious why you are picking up your car at the airport. There are rental car agencies right at Mestre train station which would save you time and money (taxi to airport, possibly an extra charge for pickup at airport). Also if you return the car to Mestre, you can hop on any of the myriad trains that take 10 minutes to get you to Venezia Santa Lucia station.

I'm looking at Autoeurope and they list a large number of car rental agencies at Mestre. Prices seem reasonable. Is there a reason you chose the airport instead?

A few small tips on driving, in addition to studying the signs in the brochure you probably got with your IDP.

• There is no right turn on red in Italy or actually in Europe. Not ever. Just wait for the green.
• At uncontrolled intersections, the car to your right has right of way even if you arrived first. "Order of precedence" is a whole chapter in the Italian driving manual, with many fiendishly difficult variations, but in general, look to your right and if the car there is trying to pull out ahead of you, just let them go and don't argue.
• At roundabouts, anyone coming from the left has precedence. So look left, not right.

In general, though, just drive like at home and you'll be right most of the time. Keep your eyes open, drive defensively and relax

Parking tips: white lines mean free, blue lines mean pay, yellow lines mean don't even think about parking here. You might have to look around a bit to find the pay station for blue lines - there is usually one columnar pay station in a block, several in a lot - but there are never individual parking meters.

Toll roads: avoid the toll plaza lanes with the big yellow rectangle with a black T. Those are for people who have the automatic transponders to open the gate. Pick lanes with the white signs. You take a ticket on entry, pay with cash or credit card on exit. There are other long threads on here with the details, but really just avoid the yellow lanes and you'll be fine.

Hope that helps.

Thank you so much for the info. Yes I may only pick up the rental at the airport, because the entire trip is being paid with a delta gift card. So I had to book my flights, hotel stays, and any rental car or other arrangements through delta vacations.

Ah, a very good reason! I hadn’t seen your other thread. Enjoy your trip! You’ve picked some lovely places.