Combining everything here because our main mode of transportation in Florence was our feet. We varied more in Rome because it was bigger and the options easier to figure out.
Best place I found for researching transportation options in Rome and navigating the train system to get to Florence was Ron in Rome. Worth checking out to get detailed information about tickets and so forth.
Rome – Metro
True, it doesn’t cover the city well, but it’ll get you out to Vatican City quickly and there was a stop just a block or so from our hotel. I ended up getting the seven-day passes for us the first night we were there mostly for the convenience factor. We didn’t come close to using that amount in transit (lots of walking off dinner!) but to not have to stop to worry about a pass every time – priceless. (Note: the ticket machines only took Euros, no credit cards. Boo.)
The B line trains – run north-south – look like you’ve been dropped into 1980’s New York. Every car completely graffitied, some in an “artistic, on purpose” kind of way. The A line trains – running sort of east-west – look like what New York might get to in 2020. Brightly lit, open from car to car, comprehendible sound system, TV screens and signs telling you not only the stop, but which side to exit on. Thank you!
Rome – Taxi
We had a car coordinated by the hotel get us at the airport. Cost more, but I didn’t have to find it after arriving bleary at 8 am. And it was plenty big enough for our luggage and much more comfy than a regular taxi.
Other than that, we took cabs a few times. I was only sure once that I was paying a fair fare, but not sure enough to challenge anyone. (Wuss!) Just wasn’t worth the couple of euros hassle for me. They’re clean, drive reasonably safely, easy to find. Didn’t always have to find a taxi stand to get a taxi, either. Several times had the restaurant or hotel call to make arrangements for a taxi to come get us, which was nice.
Rome – Bus
OK, this would have been my transit mode of choice. You’re above ground, so you can see the city, and it goes places the subway doesn’t get to. But dang it, you have to buy a map to get the bus system and we often waited for long periods without a promised bus showing up. Just proved faster/easier to walk or hit the subway most of the time. Sigh. The few times we did get the bus, it was clean, plenty of places to hold on and it stopped a lot. It helps to know the stop before yours and watch the signs when it does stop so you can push the button to ask to get off at the next stop. There are no announcements made on the bus or signage to let you know what the stop is.
Rome to Florence to Pisa to Florence to Rome – Trains
US to Rome – Plane
Apparently, I got truly spoiled on the British Airways flight I took to Kenya a few years ago. Because flying American Airlines overseas was nothing like that. Dang. BA gives you a little bag with your own blanket and eye mask and toothbrush and headphones. Sweet. AA … not so much. And it was a much smaller plane and just felt it in every way, including the space back by the bathroom. Sigh. Neither of us slept much, so thank goodness it was just an eight-hour flight from NY. Walk in the morning, nap in the afternoon and good night’s sleep and we (well, I) was back to normal.
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Tarot Card Deck Mockup 
Pizza Truck 
Bus Bench Ad