Do I understand that you are fitting Florence AND Venice into a one night excursion from Rome??

That's crazy.

>>During our day in Florence is it feasible to do the main sites in the city, go to Pisa, AND do a winery tour in the countryside?<<

No, it is not.

You are trying to fit in a week's worth of activities into 36 hours.

Yes -- If you simply must see something else/go somewhere other than Rome . . . Do JUST Rome + Florence or Rome + Venice 4 nights in Rome and 2 nights in the other.

BUT I assume you are flying in/out of Rome - right? That means you have to be back in Rome the night before you fly out.

So -- on arrival travel immediately to either Florence or Venice, stay 2 nights, train back to Rome, stay 4 nights, fly home.

I'd take two pieces of paper one with Venice on and one with Florence on. Throw one away. Go where the piece of paper says. If you are very disappointed, go where the thrown piece of paper says. Do not, repeat not, try to do this crazy trip. Only go to one, do not pass Go, do not collect £200.

Or, please advise me I'm going for a taste of USA and I want to spend one day in Boston, one in New York and one in Philly, can you tll me where to go?

<<Chances are this will be our only trip to Italy. >>

Then don't do it like this.

well it's certainly doable.

Day 1, arrive at Florence 8am (which means depart Rome ~6am train).
Drop off bags at hotel, get to the David by 9am. In the morning, visit the David and that other main museum (Uffizi). Normally it takes about an hr minimum at the David (line, entrance, crowds, etc). You could probably zip through the Uffizi in about 1hr to check it off.

Then you'd have time to see the Duomo & baptistry, pop your head into Santa Croce then run across the Ponte Vecchio. Probably no time for shopping. A quick grab n go lunch will save you time as well.

Day 2. It's only a 2hr train ride to Venice. So get a 6am train and you'd have a full day in Venice before your 4 hr train ride back to Rome that evening.

Howman,
Since you are visiting these cities, to get a "taste" of them, how about this:

Check out visitacity.com. For each city, plug in the number of days, and a list of sights, average times to see, map, etc. I find it useful.
Do walking tours of each city, without visiting the larger museums. Florence is an walking city, so you could easily spend the day visiting the various piazze, the Oltrarno, and perhaps visit the Accademia, and maybe even the Bargello....my fave in Florence. Both are small enough to visit and see some wonders.
In Venice, do the same....if it's just a taste...wander, get lost, perhaps visit the Doge's Palace, if time/interest allows. Sign up for a walking tour, for a bit of history and coherency.

In Rome, you have four days, so check out visitacity.com. Look at the Rome section.

Another thought is to cut a day off of Rome and stay overnight in Venice. One of my favorite memories of Venice is being in San Marco square at night when the orchestras are playing - magic!

IMO -- if you try to squeeze in Venice waking up in Florence and staying that night in Rome -- don't even consider it. You would be there in the middle of the day with every other day tripper and all the thousands of cruise passengers. The city will be VERY crowded and places like San Marco and the Rialto will be a total ZOO.

Do what bilboburgler suggests to pick one -- any means you use, piece of paper, straws, whatever.

I agree with J62 that this can be done and that it's not crazy, I've done similar "quick glimpses" with visiting friends and relatives and no one has ever thought that it wasn't worth the trip.

However, I wouldn't recommend visiting museums on such a short visit to Florence, unless there's a specific thing that you've been dying to see all your life. When I do a flying visit to Florence, which I may be doing next month with another relative, I focus on a stroll through the historic center, including Piazza della Signoria, Piazza del Duomo, along the Rive Arno, and across the Ponte Vecchio. Depending on the interests of the person, I would include one (at most) quick museum visit, and maybe a few churches. Some of the best art in Florence can be appreciated in its churches, where you can see it in its intended space. Often the perspective of a statue or painting is distorted because it was intended to be seen from below, and seeing it in a museum doesn't give the intended impression.

One of my favorite churches to visit on a lightning visit is Santa Maria Novella, which is very near the train station, and which is a treasure box of art by famous Renaisssance artists. Sometimes there are volunteers there who give free tours, and some of them even speak English. (Give an offering to the church maintenance fund to pay for your tour.)

It's not worth visiting the interior of the Duomo on such a short trip. There's always a long queue waiting to get in, and there's not a lot to see inside. Also, if you only have a few hours, I would admire the life-size copy of David on the Piazza della Signoria instead of making a reservation to see the original in the Accademia. If you were to visit the original you'd either have to make a reservation in advance, or wait in a very long queue to get in. Fixed reservations don't go well with lightning visits.

If you really, really want to visit a museum, two other excellent museums that don't require reservations are the Museum of the Duomo and the Bargello. If you get a ticket for the Museum of the Duomo (sold at a ticket office to the left of the Duomo as you face the entrance), it's good also for various other sights associated with the Duomo. One that I recommend highly is the Baptistery, in front of the Duomo, which has beautiful golden mosaics in the cupola.

There is an overnight train Venice to Rome - ultimate daytime time saver. But don't leave Venice until about midnight - gets to Rome just after 8am - private compartments - couchettes - regular seats. Save night expense in a hotel. For lots on overnight trains and trains check www.trenitalia.com; www.italotreno.com - 2 competing rail companies using same stations and tracks - both have nice trains - take whatever is cheaper; www.seat61.com; www.budgeteuropetravel.com; www.ricksteves.com.

As you calculate how much time you actually have in Florence and Venice, keep in mind you'll have luggage. When you arrive in Florence you'll want to leave your luggage at your hotel or the train station (retrieve later that day), and when you get to Venice you'll need to leave your luggage at the train station. Even doing something as simple as this will take a bit of time.

To save time, you could leave your luggage at your Rome hotel and travel super-light, just a backpack with toiletries and a change of clothes. The only downside is that you need to wear/carry the backpack as you sightsee.

Assuming this trip falls between early June and mid-November, I agree with janisj that you'll be seeing both cities under the worst conditions. If the day in Florence falls on a Sunday or Monday, lots of main sights may be closed which will further limit your options.

Your plan is not my style but is possible. I say this as last year when I took a tour to Sorrento and Capri a newly married couple who were honeymooning said this trip was it before they started a family. Since it was the case, they were packing as much as they could in. They based themselves in Rome for a day or two, took our tour of an overnight in Sorrento with Capri back to Rome to catch another tour to Venice for a day then an overnight in Florence then back to Rome to fly home. I guess it worked for them and others with not much time.

As you know, your plan isn't popular but people do it. Given that, cross Pisa off the list. You won't have time if you want to see the main attractions in Florence. Stay in Florence as there is more than enough to do in one day.

I would cross off both Pisa and the wine tour while in Florence. There is just so much to do in Florence and so much to soak in.

Bvlenci gave you great advice. One addition: There might be less of a line at San Marco the monastery where all the Fra Angelicos are. It's also cool to the paintings in situ. That is, as they were intended. In this case, each monk's cell has a painting for the monk to reflect on.

Also, the morning you go to Venice, if you can, set your alarm early and get up and see the Arno before the crowds. I don't know the time for your train ride though.

The Museum of San Marco, mentioned by 5alive, is one of my favorites in Venice. It's a bit of a walk, as I remember, but if you have time, it's worth it.

5alive's idea of getting up very early on your last day in Florence, to get a glimpse of the Arno river before the hordes of day trippers descend, is also a great idea. That way you can skip the Arno and the Ponte Vecchio on your first day and concentrate on the rest. Usually the Ponte Vecchio is so crowded you can't see the river, and can hardly walk.

Why same rules apply to Vatican and Florence secular museums? I think the only way to find out this for sure is to e-mail the museum. I would be shocked if they did not allow such a thing.

The usual policy is that disabled people, and one companion, can skip the line.