Need some help with the last details of a 30th anniversary trip to Italy

I also wanted to say that I have always planned our trips, doing lots of research for the best experiences at the best price. I once planned a 10 day Disney trip for the 5 of us, with airfare, that came in under $3000 total. That being said, I do want good experiences with minimal time wasted in lines, I won't be cooking but we are fine with picnic lunches, and most of our hotels provide a decent breakfast, saving us money. I'm okay with the occasional splurge but I want it to be well worth it. thanks!

Venice: car rental offices are at PIAZZALE ROMA, inside the City Parking structure.
Sorrento: I would drive all the way to Sorrento. Too many train changes otherwise, which are not fun with luggage.
Florence stop: kind of difficult city to drive into. Parking is limited too and I wouldn’t leave the car parked with luggage inside. You might be better off visiting Florence from San Gimignano once you are settled in the Agriturismo. At least you can leave luggage at home. Also, by the time you arrive from Venice, half day is already gone, and not much is left to see Florence.

Gardens? I have added a few gardens to my April 2020 trip based on gardens shown on Monty Don's Gardens of Italy show. This is by BBC, but I think you can get it on YouTube. Currently it is on Netflix for we Canadian folk. You might also get be able to get the book from your local library. The challenge is that not all are open to the public. With a car it will be easier for others. Of course, there is the Boboli Gardens in Florence, there are some possible gardens near Fisole (in the book) as well as gardens at the Palladian villas along the Brenta Canal from Venice to Padua. Padua has one of the first medicinal gardens. Tivoli (near Rome) has Hadrian's Villa as well as Villa d'Este. Why not do it last day? I think it is really just a quick bus trip from Rome. Why not use local transport then you can see the gardens at your own pace?
If you plan to see St. Mark's in Venice, you can check whether there is advance reservations available for April - or go right at start of day or late in day. Worst case, you can get a combo tour ticket with the Doge's Palace (which I enjoyed, and for whatever reason remember better than the cathedral).

Didn't think about luggage in the car at Florence. Wish there was a way to hide or check it. We are traveling light with backpack suitcases and day bags. Driving to Sorrento? From what I've read getting anywhere close to Rome will be very busy with traffic. Any other thoughts? Yes, we would do Tivoli by train or bus. The only place we are using a car is in Tuscany between Venice and Sorrento. Thanks everyone. Keep the ideas coming!

Could we take the train to Florence, store our luggage at the station, do some sightseeing, and then pick up our car in Florence? Is it easy to leave the rental car area to head southwest without racking up any fines? Thanks!

Yes, you could definitely take a fast ("Freccia") train from Venice ("Venezia Santa Lucia") to Florence ("Firenze SMN") and store your luggage in the train station. There is a direct train 7:25 - 9:30 am; another with a quick change 8:20 - 10:40. There is a large rental car facility (multiple agencies there) on Borgo Ognissanti, about a half mile (or less) south of the train station. Could be easily walked, but with luggage you might want to spring for a cab from the train station. When I rented a car from (Hertz?) at that location several years ago, they gave me excellent directions on how to drive south out of town (heading for Montepulciano) without going through any ZTL zones.

hey cindyblye
couple of things you may be interested in. look up discoverytuscany.com search garzoni garden and butterfly house or pinocchio.it. it is in the town of collodi, the home of pinocchio. you could do a day trip from san gimignano, check rome2rio for directions and time to drive.
while in rome look at withlocals.com rome "beautiful countryside day trip: castelli romani" ride thru small villages, lakes, hills, the town of nemi is home to wild strawberries (italymagazine.com search lake nemi and it's wild berry), wine country of frascati, stop at ceralli.it for the "best porchetta", family bakery and pizza maker, walk around the small village. wanderingitaly.com search castel romani travel guide.
oldfrascatiwinetour.com also has a tour. get out of the hustle and bustle of rome for the day, the area is the summer home for the popes.
hope this helps you with a couple ideas for relaxing and enjoying.
aloha

If you plan on touring St. Marks and the Doges Palace, DO purchase your tickets in advance!! We failed to do so for touring the Doges Palace, and we stood in line for an hour (even before it opened) and watched as they let the line of prepurchased tickets move ahead of us over and over. It was so exasperating to be held back to favor the line with prepaid tickets. Learn from our mistake!

So...I'm rethinking the stop in Sorrento due to the long day it will take to get there from San Gimignano, no matter what mode of transportation we use. My original plan was to go to the Cinque Terre, but I nixed that thinking that if it rains there wouldn't be any good hiking. But now I'm thinking it might save some time to head there after the agriturismo, spend two nights so that we can explore, and then heading to Rome, giving us an extra day in Rome where we can take a day trip to Pompeii. The Amalfi coast is something I don't have to do (the Cinque Terre would replace that), and Capri will just have to wait.
Thoughts?

Thank you for all the tips and advice. After looking at which trains go where, I think I've decided that we will spend that last night in Tuscany in Florence, so that we will check out of our agriturismo on Friday, head to Florence, turn in the car, explore, spend the night and then catch an afternoon fast train to Sorrento after more exploring. It seems to make the most sense with the least amount of travel time and frustration. Our other two days in Tuscany will be spent traveling to the hill towns. Thanks so much for the information!

We just returned from Italy a couple days ago. We have traveled to all of the places you have mentioned. Here are a few thoughts when we arrived in Florence we checked our luggage at the train station it cost us €30 for four pieces of luggage for 5 hours but that saved us from lugging them around the city. We took a taxi to the car rentals at the airport to avoid city driving the taxi cost €27 and rented from Hertz. There is about 5 to 10 minutes of driving in the city before getting on the freeway. The car had a great system to let you know when you were approaching speed cameras so I think we avoided tickets. We chose a lovely town halfway between Florence and Siana called Colle Di Val D’elsa . It allowed us to visit small towns (Siena, San Giamagno, Volterra , Poggi and do a winery tour one day and a cheese farm but to simply drive seeing all the beautiful sites of Tuscany. We have avoided staying in Naples. We’ve been to the train station and you have to walk around underneath to a lower station to take the train to Sorrento. It’s a regional train and I believe there are 25 to 30 stops on the way to Sorrento. Sorrento was good for three days and one of those days we went to Pompeii. From there we headed To Positano for three days to see the Amalfi coast. It makes sense for you to go to the CT and skip the Amalfi coast - logistically the Cinque Terre is a lot easier to get around believe it or not

cm.jennings - Thank you for that. I know I'm probably making this way harder than it needs to be, but I'm just trying to maximize our time. How did you get to Sorrento from Tuscany? I was going to change our plans slightly and just drive to Florence the morning of our last full day in Tuscany, stay the night, and then take the fast train to Sorrento the next afternoon, essentially saving us an additional changeover or two. We will go straight to Naples and then onto the subway to Sorrento. We are not staying on Amalfi Coast but just day tripping there and then one day to Capri, and then to Rome.
Do you think CT would be okay weatherwise in early April? If we did that, we would probably only stay two nights and then take the train to Rome for an extra day there. .I'm also considering only staying in Venice 2 nights so that we could rent the car there in the early afternoon on day 2 and go straight to the agriturismo for an extra night since my plan was to skip Florence until the end of our time in Tuscany (loping off a night in Tuscany in order to only drive to Florence once - overnight in Florence and then off to Sorrento on the fast train). Hopefully that makes sense. How many days did you have in Italy? Did you feel that Amalfi was not worth it? I am getting the sense that logistically it is out of the way and more difficult to get to. I'd also thought about Salerno since it is easier to access and we could still get to the coast and also to Paestum, but not to Capri.
Thanks!

We did Sorrento and the Amalfi on a Separate trip where we focused on the south of Rome. The trip we just came back from was Rome and Tuscany. I just have been having a similar conversation helping a friend plan a trip about going to the CT versus Amalfi-I think the CT would work well for you in April and give you a similar experience and also free up some of your time . Sorrento is not too far from Naples but on the regional train I think it’s the 25th or 26 stop so for you to get unless you drove your rental car as close to Sorrento as you could I think that would be a very very long day . Our first trip to Italy , we stayed in 4 or 5 cities and wasted a lot of time on trains getting from one destination to the next, now we stay in 2 places with lots of day trips .