Italian Virgin

From my experience of traveling Italy last May it was warm sunny in the day and cooler at night.

But here Rick also lists what to expect weather wise (according to RS 9 day Heart of Italy) and some tips what during your free time: https://www.ricksteves.com/tours/italy/heart-italy

You can search for flights using Google Flights and then when you see a price you like book it directly with the airline.
Or try Expedia; I've never had a problem with it and sometimes the flight was cheaper
You can take the train from Florence (where the tour ends) to Venice using the Trenitalia website http://www.trenitalia.com to book it. I think the earliest is 90 days in advance.

Thank you so much!

1. May is generally warm (70s/low 80s F). Rain is possible. However check weather forecast just before you go.
2. Search flights on Kayak.com starting this fall.
3. Train to Venice. Websites: www.trenitalia.com or www.italotreno.it No need to purchase ahead, but if you do there is a chance to get discounted tickets (economy or super economy). These are restricted. Once booked a specific train no refunds or changes are possible.
4. Plenty of opportunities for fun activities in Venice: ride boats, visit museums, go to cafes and restaurants, just walk around.

Don't be afraid about "going it alone" after the tour. By the time you finish the tour with the RS guide, you will be very comfortable traveling in Italy. The guide will show you how to travel on the metro and even help you with train tickets to get to Venice if you ask.

I haven't checked the Heart of Italy tour, but if it doesn't include the Borghese Museum in Rome, book that on a free afternoon ahead of time. You get a specific entry time and have to check in 1/2 hour ahead of time. The entry is for 2 hours, then the museum is cleared out and the next entry group goes in. One of the best experiences in Rome. Many sculptures, paintings, and the the inside of the building itself is
worth spending time to look at. Relax and have a Great Time!

Thanks for all the advice!!!

Something unique and very fun to do in Venice is to book a rowing lesson through Row Venice. You will row a historical boat on side canals and even the Grand Canal. Lessons are a little spendy but so worth it. It was one of our favorite Venice experiences. You can find them on google for more info.

Great idea, love activities like this. Thanks!

Taking the train will be easier....from the heart of Florence to the edge of the Grand Canal in Venice. In this case taking the train is easier and should take less time than flying..And since you are already in Italy and know when the tour ends you can purchase a very cheap train ticket far in advance.

Also if you are returning to the USA after Venice try and book a flight that flies directly to the US from Venice. The direct flights leave around mid day. A mid day flight avoids you having to travel to the Venice airport in the early morning which is a bit of a problem and is a much discussed problem on this forum.

Here's one. While in Venice buy a vaporetto ticket for two days (or however long you will be there). That allows you unlimited travel for that period and saves a ton of money if you are moving around the city a lot. You can even ride the entire length of the Grand Canal on a vap.

Taking the train from Florence to Venice (2h journey) is the fastest option and also the cheapest (45euro, full fare)
You can also fly from FLR to VCE if you want, but there are no direct flights, so you will need to connect via Paris or Frankfurt or some other European and instead of just 2 hours it will take you all day.