Been to Italy 4 times in the last 4 years (1 vacation, 3 for work).
In general: there 4 good apps for Europe
For Tours: Viator and GetYourGuide
Taxi (their Uber): FreeNow
So many places take ApplePay, but good to have cash to tip a tour guide
Italy (and most of Europe) is very easy to move around in trains (you can book first class for not much more $$$)
In general, its safe, just use common sense
If you have a small backpack, carry it in front of you (vs. in back)
Lock your passport in your hotel safe
Have a picture of passport/driver’s license in your phone just in case.
Our Itinerary:
Rome (2-3 days)
The Coliseum
Trevi Fountain
The Pantheon
Several more
Florence (2-3 days)
Florence Duomo
Florence Accademia Gallery
Gallerie Degli Uffizi
About an hour south is a factory outlet mall (Prada, Gucci, etc)
About an hour west is Lucca (this is a cool town surrounded by a wall)
Earlier, Siena was mentioned – did not visit
Pisa (1/2 to 1 day)
~1 Hour train from Florence
Leaning Tower of Pisa
Venice (2-3 days)
1 hour train back to Florence, 3-4 hours to Venice)
Doge's Palace
Gondola ride
Boat tour for Murano (tour a glass factory) and Burano
So many bridges and amazing scenery (sunset pictures)
Milan (1 day)
About 1-2(?) hour train from Venice
Milan Duomo
Naples (2-3 days)
Naples (2-3 days)
1 hour flight from Milan)
Amalfi Coast
Positano
Sorrento
Pompei (we did not visit, but sounds cool)
Take a ferry to the Isle of Capri
Bus to AnaCapri, “ski-lifts” to top for an amazing view
Train back to Rome (1-2 hours)
Hope this helps! Go Sabres and Go Bills!