Itinerary questions from a first timer!

What about saving the Amalfi Coast and add it to a trip including Rome? There are lots of great options between Florence and Venice- Bologna, Parma, Modene for food, culture. Also great sights in Lucca, Padova, Verona. Or visit the Dolomites or Lake Garda or Bellagio. There is so much to see in this area, save the Amalfi coast for another trip.

I would save the AC for when you have more time. I would then go directly to Venice and end in Tuscany so that you're near the airport. This will save you a change of hotels at the end of your trip. A week or so in Tuscany will be wonderful.

Donna

If you are not going to Rome then the Amalfi is still farther away and very similar to the Cinque Terre. If that is your thing then go for it! If you want to mix it up a little you can stay for 2-3 days in a Tuscan Hill town like Siena and then rent a car and do the agriturismo thing. (I have to admit that I am only a public transportation tourist and have never been to one)
As far as Venice is concerned any 2 days you can manage in Venice are good enough unless you intend to spend all your time inside museums. The thing we enjoyed in Venice was just walking around the canals and bridges and just getting lost.
Have a great trip!!

Thanks for the input! My original thought was to save the AC for a return visit (along with Rome and Sicily), but it is nice to see the confirmation. There is just so much to do and see, I have really been trying to limit regions to get the most out of what we see!

If you are dropping the Amalfi Coast, I would highly recommend at least one more day in Venice, maybe two. With more time, you can visit the outlying islands of Murano, Burano and Torcello. Venice can be crowded but once you get away from the main areas the crowds disappear and it is a great place to "meander the town" as you mentioned.

You are correct that a rail pass does not make much sense and you will need to rent a car at some point to stay at an agriturismo. If you are committed to the train trips you would like to take, you can save money on the high speed trips by prepurchasing tickets. If you would end up taking regional trains, those prices don't change and they never sell out so there is no need to buy ahead of your trip. I think there is a schedule change in June and not all dates are currently available, so if you don't find your dates of travel, that is why.

A wise decision, I think, to save the Amalfi for another trip, Leanne. You can combine it with Rome and Naples for a nice combo of city/seaside activities.

You probably will need a car if staying in an Agriturismo, and you don't need a rail pass for the traveling you'll be doing the rest of the time. Even if you do a little getting-about Tuscany by train, they're most likely to be regionales, which are very inexpensive: just purchase your tickets the days of your journeys. You'll be using regionales to get about the CT if not taking a ferry now and again. Exactly how "near" to the CT are you going to be located? On a train line?

The only tickets I might consider purchasing in advance would be for high-speed trains between Venice and Florence, and only to snag any advance-purchase price breaks which may be available. Both Trenitalia and Italotreno serve that route (Firenze S. M. Novella and Venezia S. Lucia stations) so I'd check both for best $$? I'd add one or two of your extra days to Venice as well.

Venice is one of the truly unique cities of the world. Others may disagree, but your original two nights there, in my opinion, really short changes yourself in a super place. Since you now plan to save the Amalfi Coast for another trip, consider using those three nights for Venice. Five nights in one place may seem like a lot, but we've been there several times and still find new things to see and do. If you do want a diversion from Venice there are several days trips you can take from that location. Also, it always takes more time than one places to get from place to place and that is simply time lost.

I agree with those who say to add days to Venice. Venice is unlike any other city in the world.

I agree with those who say to add days to Venice. Venice is unlike any other city in the world.

Ok, I am sold on the idea of extending Venice several days, but that leads to a question of lodging. I was thinking in the vicinity of the Rialto Bridge, for no other reasons than it is rather central and there is a vaporetto stop close. We would very much like to keep the expense below 150EUR/night, but we would be willing to go higher if a particular location makes the most sense. Any suggestions? The things we would like to do are pretty typical - St Marks, the Bridge of Sighs, the Doge's palace, wandering the city, perhaps one of the museums and with the extra time, Murano and Burano. I would like to stay far, far away from the cruise port.

The Rialto bridge is right in the middle of the most jam-packed area of Venice. I would recommend to stay somewhere east of Piazza San Marco. Since you will be arriving by train you can walk right out of the station and on to a vaporetto. You don't need to be in the middle of everything; Venezia is small enough you can easily walk everywhere.

I like the Cannaregio area. A couple of years ago, I stayed at Locanda Ca' San Marcuolo, with a vaporetto stop (San Marcuolo) fifty meters from the hotel. Quirky but reliable elevator.

I would use VRBO to rent an apartment. Venice is easy to walk around, and most areas away from St. Mark's are only about a 20 minute walk at the farthest. I stayed in Cannaregio area last time I went, not far from the train station, and it was lovely. This time we are staying in San Polo, but on the north side. Since half the fun of Venice is just wandering, you can pretty much stay anywhere and be just fine. I prefer to be away from the hordes in St. Mark's. I always choose apartments with a large number of reviews.

An apartment gives you the added benefit of a kitchen and sometimes laundry facilities as well.

Any suggestions instead of an Agriturismo in the countryside.

You might take a look at Borgo Argenina. It is more or less between Chianti and Sienna. We stayed there several years ago and were very pleased. The accommodation is fairly simple but the view from the terrace of Chianti's vineyards is very relaxing after a day's touring.

I prefer to stay in the Dorsoduro, cheaper, less touristy, and reasonably priced eateries (it's a student area). Vaporetto stops, walking distance to San Marco (well, just about everything in Venice is walking distance from everywhere). The best dinner I had last month in Italy was in Cannareggio, and far from expensive.

We've stayed at Pensione Guerrato that is near Rialto Bridge and love it. While the bridge itself and one or two small plaza at either end are crowded, we've never felt the crowds were overwhelming. Just one or two blocks from the bridge and things are calm and peaceful. If you decide to stay there, we know a back door way to get to the hotel and avoid the crowds around the bridge itself.

After looking at many, many options, we have reserved a flat thru AirBNB, located between San Marco and Castello, for 4 nights.
Thanks to all for the suggestions!