Dear Fodors friends, we almost have the itinerary pinned down. (14 nights, mid-May,) Here's the plan so far:
5 nights Rome
travel with guide through Umbria, one night in Cortona or Orvieto
3 nights in Tuscan countryside outside of Siena
which leaves us 5 nights to divide between Florence and Venice. We keep going back and forth. I'm not crazy about crowds although I assume both will be crowded. I'm thinking if we avoid the Uffizi during the day - maybe getting 4 pm tickets, we can miss the worst of the crowds there. I'm wondering if we go to less popular spots in Florence do we avoid the crowds. I'm thinking Santa Croce, the Sinagoga, Casa Buonarroti, Giordino Bardini, Cappelle Medice, etc. Am I deluding myself?

I remember Stu suggesting that he wasn't wild about Florence with the crowds and that Venice is so beautiful.

One option is to get to Venice earlier in the day so that even with 2 nights we would still have 1 1/2 days to wander and explore. I think my main desires in Venice would be to go up and down the Grand Canal, and visit the Palazzo Ducal. If we took another day in Venice I was thinking to visit some of the islands in the lagoon. or am I missing something we shouldn't miss?
If this were your only chance to visit Italy how would you divide the time.

We fly out of Venice.

and if we were to drive between Florence and Venice as opposed to taking the train, are there any places for hiking or countryside walks in between or other special places that might make that worthwhile. thanks as always.

Crowds are smaller the earlier you get to a location. You can sleep in at home.

Lose the crowds in Florence by visiting sights on the Oltrarno.

Take a bus or taxi to Piazzale Michelangelo for the view. Visit nearby San Miniato al Monte. Then walk down the hills through green scenery to explore the Oltrarno and eventually get back to the center of town.

I would not rent a car just to find a hike.

Florence is surrounded by hills and it would be easy enough to take a local bus up into the hills for an afternoon stroll to perhaps Fiesole or Settignano or Pian die Giullari. Part of the Renaissance Ring route includes a hike from Galluzzo (accessible by local bus) back into Florence to Piazzale Michelangelo. Learn more here and in other sites about the Renaissance Ring rotes.

https://www.visittuscany.com/en/itin...ound-florence/

I would add that for me a must would be seeing the statue of David at the Accademia gallery in Florence. If you get advance tickets for the earliest opening time, it won't be crowded. The gallery doesn't take long to visit.

>>>Crowds are smaller the earlier you get to a location.<<<

I find the opposite to be true in Florence. It seems many of the tour buses arrive early and leave after lunch. Later afternoon, the crowds at museums are less.

If you don't like crowds, midday Venice is going to be a challenge. The massive cruise ships discharge their hordes about 9 or 10 AM and they throng the city until about 4 or 5. Definitely plan to take in popular sights early in the morning.

I am not sure that the crowds in mid May will be a major problem in Florence. BTW a great place for dinner in Florence is Osteria Pastella - one of our best meals in Italy last summer

RE: flying out of Venice. Be sure to allow sufficient time to get to the airport from your hotel. If you hire a private water taxi it will cost at least €100 but is the fastest way. Your hotel can book it for you.

I'd give it all a Venice! What time does your flight leave Venice?

Thanks everyone, this is wonderfully helpful. Our plane leaves Venice around noon, so just time for breakfast and then to the airport. Whatever we see, it shall be wonderful I'm sure. And I love the Renaissance ring route suggestions. Wishing all beautiful peaceful holidays.

My advice on Venice, some of which confirms others':

To avoid crowds and lines, earlier is better.
Last minute, we signed up for the "Secrets" (skip-the-lines) tour of the Doges Palace. I recommend it.
Going "up and down the Grand Canal" on, I assume, a vaporetto is an overrated experience. Everyone says, "Get a seat at the front." Guess what? That's what everyone else in the world is trying to do. Otherwise, you're shoulder-to-shoulder on a crowded boat. Suggest doing it later at night, when the day-trippers are gone and it's quieter.
With 1 1/2 days in Venice, you're going to miss something. Just decide what your priorities are. Also note that if your plan includes visiting one of the islands like Murano or Burano, that will take a big chunk of time out of your itinerary.

RE: flying out of Venice. Be sure to allow sufficient time to get to the airport from your hotel. If you hire a private water taxi it will cost at least €100 but is the fastest way. Your hotel can book it for you>>

yes they can but it is a great deal less expensive and at least as fast if not faster to get a vaporetto to Piazzale Roma and from there the ATVO bus costing about €8 from there to the airport. They are non-stop, have ample luggage space underneath, and take about 20 mins, leaving P. Roma 3x an hour at 10, 30, and 50 mins past the hour.

Another way to get into the Doge's palace without queuing is to buy your ticket at the Museo Correr in the opposite corner of Piazza San Marco [they are covered by the same ticket] where you are highly unlikely to have to queue. It is a beautiful museum in its own right and has the advantage of a lovely cafe from which you can get what is probably the best view of the Basilica and the Piazza.

As you will be there in May you will have plenty of daylight so a trip to the islands is by no means out of the question. If you want to see a glass foundry you should go to Murano in the morning, otherwise get the boat from Fondamente Nove to Burano first, and then hop straight on the ferry over to Torcello to see the 1000+year old mosaics in the Basilica there. Then hop back to Burano and finally, if you have time, stop off at Murano which is on the way back to Venice proper.

Of course you can decide this on the day; there are lots of other things you might decide to do instead like going to see the Rialto Market, visiting the Frari Church and the nearby Scuola Grande di San Rocco, exploring the little streets and getting lost in the piazzas of Santa Croce and San Polo, etc. etc. As for seeing the Grand Canal I would suggest seeing it in day light and at night; the best thing is to get a No 1 vaproetto which is the slow one and looking for a seat at the back. The No 2 "express" vaporetto has become very popular with tourists who are trying to rush from one place to another instead of just sitting back and enjoying Venice.

To do all this ideally you need 2 whole days i.e. 3 nights.