First trip. 10 nights. How to divide time?

This is an option:
5/23 - fly
5/24 - land in Rome, train to Florence
5/25 - Florence
5/26 - Florence
5/27 - train to Venice
5/28 - Venice
5/29 - Venice
5/30 - train to Rome
5/31 - Rome
6/1 - Rome
6/2 - Rome
6/3 - fly home

You could also take a day from Venice and add it to Florence, otherwise I'd skip the wine tour. If you do that, I'd take an early train to Venice to make the most of your 1.5 days there. It would have saved backtracking time if you could have flown into Venice and out of Rome but since you already bought your tickets, I'd go directly to Florence on arrival day.

Depending what time your flight arrives, you could go directly to Venice, and do Florence as you work back to Rome.

Doing Venice as a day trip from Florence would not be a satisfying experience. As Kathy suggests, spend 2 nights in Venice or save it for a trip when you can spend more time.

Flying into Venice and home from Roma will be a more effective time management strategy. Plus, Venice deserves more than just a day trip. This type of airline ticketing is called multi- city or open jaw and it is very time efficient.

Buon viaggio,

You may find that flying into one geographic end and out the other (Into Venice and out of Rome) is basically the same price and it will save you a lot of travel time better spend sightseeing. With only 10 days, I would tailor the flying maximize free time on the ground.

You should be able into Venice by noon on arrival day via one of the larger European hubs. The seasonal direct flights into Venice and Rome usually carry a pretty stiff price premium for the convenience but don't buy you a whole lot of extra time...

Also, with only 10 nights on the ground, you're only going to hit the major sites in each city. To get a better appreciation, you might consider cutting back to just two cities.

I would also consider apartment rentals in each city. I have found they are a much better value than multiple hotel rooms and afford you a lot more space. Plus, you can usually find them with laundry machines.

As for the wine tour, I took the Walkabout Florence Chianti wine tour a couple years ago and loved it.

As previously posted, I'd agree 100% with flying into Venice and out of Rome BUT their airline tickets have already been purchased. Making changes at this point would depend on how much $$$ they're willing to spend to do that and what sort of tickets they purchased.

I second Kathy's suggested itinerary, with this possible change: switch your nights in Venice and Florence. When you arrive, take a freccia (fast) train directly to Venice. From Roma Termini train station it should take approx. 3 - 3 1/2 hours. That way, you are doing the longer train stretch while you are exhausted, already. Get some sandwiches and beverages in Termini (or other) train station to take with you on the train. Spend the 3 nights in Venice, and take an EARLY train to Florence on the 27th. That way, you will have almost two full days for sight-seeing in Florence and can take your wine tour on your third Florence day. Continue on to Rome on the 30th, as Kathy suggests. (You could go to Rome late in the day, so that you have one more sight-seeing day in Florence. The fast train Florence-Rome is only about 2 hours.) The general consensus on this Forum is to end your trip in your departure city, thus not needing to do a one-night "repositioning" hotel stay before departure. Once you've decided your cities and nights, I would PREBOOK your train tickets, probably using trenitalia.com (the official website for the main Italian train company). You will save oodles of money (adding up those six tickets!) and can choose seats together. Usually the train reservations open up somewhere in the neighborhood of 2-3 months ahead of travel time.

First, If you are set on those 3 locations then I would agree to start with Venice and end in Rome. If you are willing to forgo Venice then I would start in Florence and possibly hit the beach areas and maybe Pompeii or Amalfi before going back up to Rome.

Second, I would also suggest trying to fit Siena into the mix. It's a good day trip from Florence. It's a way to see the tuscan countryside without trekking all around the area. You could take a car down in the daytime and stop at wineries in Chianti and then get to Siena in the afternoon and stay for dinner - it's beautiful at night.

If you need a recommendation for a driver for any of your Florence trips, I would highly recommend Paolo Cesaroni Driving Guide
+39 347 3803408. You should use the railway system for all other traveling though - it's very convenient and easy to book from your phone.

Have fun!

We did Venice 3 nights, Florence 3, Rome 4 and it worked out well

There's no point in flying directly to Venice unless it actually saves you time or gets you there earlier than flying to Rome and training to Venice (or Florence). Some people can get direct flights to Rome but not to Venice. Flying direct to Rome may mean you can arrive at 7am there instead of connecting in Europe somewhere and arrive in Venice at 11am. I'd much rather fly directly to Rome and take the train to Florence to start myself than doing the connection into Venice - or just train directly to Venice to start. I'd rather be on a train to Venice than be at an airport and a connecting flight, even if it gets me into Venice at exactly the same time. Personal preference.

I would first decide what you want to see/do in each city, and then allocate days accordingly. You could consider making an overnight trip to Cinque Terre with a stop in Pisa, with Florence as the base. For us the trip to CT was a good change from the overload of museums, churches and other historical sites that one encounters in Italy.