Clearing customs in Rome and making it to Sorrento the same day? Cowboy boots?

Yes, you will be a walking target in your cowboy boots, no doubt about it. Your look will scream "tourist". But maybe you can handle that attention ... That's your call.

Thank you. Probably won't wear them then. What's your input into making it to Sorrento on the day we land? Go for it?

You will probably have the most insanely painful feet in all of Italy! The walking is that hardest I have had to do any where in the world. Get some nice shoes with thinking soles and padding.

Are flying USA to UK to Rome all in one day?

I would go to Sorrento the first day and leave Rome for last. You have plenty of time to get there. As long as you can catch the Leonardo Express train at the airport station by 6:53 pm, you can make it to Sorrento.

This is your last chance:
LEONARDO EXPRESS 3331
Depart FCO Aeroporto: 18:53
Arrive ROMA Termini: 19:25
FRECCIAROSSA 2645
Depart ROMA Termini: 19:40
Arrive NAPOLI CENTRALE: 20:55
CIRCUMVESUVIANA 71
Depart NAPOLI PG: 21:11
Arrive SORRENTO: 22:17
or also:
CIRCUMVESUVIANA 72
Depart NAPOLI PG: 21:41
Arrive SORRENTO: 22:47

Timetables:
www.trenitalia.com
and
http://www.eavsrl.it/web/sites/default/files/allegati/Orario%20Napoli%20Sorrento%20con%20Pozzano%20e%20Scraio%20e%20viceversa.pdf

Thank you Roberto. Will spend time tonight checking out the timetables you provided.

I love wearing my cowboy boots all round but will I just be a walking pickpocket target in Italy if I choose to wear them?

Yep. The pickpockets will get everything you have, including your clothes.
Look at what happened to this guy in Naples.

I will just add that while the heels on cowboy (or Idaho logger lol) boots may give you some advantage in dirt and on a slope in backcountry, they will be a huge disadvantage on the aforementioned cobblestones and very uneven pavement especially if they are slick from rain or fog.

You are going to be e.x.h.a.u.s.t.e.d. You will need to take the train to Roma Termini, switch to one for Naples and then get on a different train for Sorrento. You don't say exactly when you are going. Even if it is not close to the summer solstice, it should still be daylight when you get to Sorrento. Daylight or dark, unless your lodgings are very close to the station, to get to them I would take a taxi or a shuttle if possible.

Rome2Rio -- http://www.rome2rio.com/s/Rome-Airport-FCO-Italy/Sorrento gives you all kinds of transportation options to Sorrento from FCO. I think train option number 2 is the best one mostly because it is the quickest. But you will be so tired that you will be more vulnerable to pickpockets, especially in the train stations and on the Circumvesuviana. The EAV Campania one from Naples to Sorrento is the Circumvesuviana that so many people talk about.

I would spend the night in the town of Fiumicino, and make the trip the next day. We stayed at the Hotel Tiber Fiumicino -- http://www.hoteltiberfiumicino.it/en/. The rooms are small but modern and many have balconies with a view of the water. I did not like their restaurant, but there are many along the quay that are good. Their breakfast is great. They have a shuttle service, €6 per person each way, that I thought was very reasonable. This is the link to the info about the shuttle -- http://www.hoteltiberfiumicino.it/en/position-hotel-tiber-fiumicino-roma.html. Scroll down the page to see the schedules from the airport to the hotel. If you arrive early, call Umberto (at the very bottom of the page) or the hotel for an early pick up. There is no extra charge. The shuttle picks you up at bus parking place number 26. You turn right after exiting through customs and walk all the way down the sidewalk (or inside the public side of the airport to the last exit) to the right to the area where the tour buses and other shuttles are and wait under 26.

I tout the Hotel Tiber because we were stuck there for 5 nights in early November. They treated us great. We'd check out each morning and come back a few hours later each day when we (flying standby) couldn't get on a Delta flight from Rome back to Atlanta. We stayed in the Best Western for 2 nights when we arrived at FCO (got on ATL-FCO flight earlier than expected). There was a very good restaurant very close, but the rooms weren't nearly so nice, there was no view and the price was higher. The Hotel Tiber is much, much better and cheaper. The same shuttle serves them both.

If you don't go through passport control in the UK, you will have to do it in Rome. That's what can take the longest. Customs with nothing to declare is a quick walk past a bunch of guys who pay absolutely no attention to you.

The train station is across the street from the public part of FCO. You get to it by walking to your right when you come through the doors past customs and following the signs. If you haven't already purchased your tickets, there is a ticket booth just inside the station on the left. They speak English. They were able to sell us tickets to Roma Termini, Milano Centrale and on to the Milan airport right there. I'd guess they could do the same for you heading south if you need them.

You would be a walking target with cowboy boots on. I know they are very comfortable for many people, but most don't wear them 8+ hours walking and standing which you will most likely be doing on this trip.

And download the free App
Rome2rio
really easy to use for departure/destination information showing travel options and frequency, how much time the trip takes and costs.
Still have to search train timetables for the schedule.

Roberto, you brighten my day. (^_^)

Thank you everybody for the great info. Sadly, I will forgo wearing my cowboy boots in Italy. Have really appreciated the advice and hints I've received. Am checking out all options. Funny pick Roberto. My boots look better than his.

bcrowe50,

You'll be fine. Clearing customs took us 5 seconds. But make sure they stamp your passport! They didn't stamp ours and by the time we flew out of Europe (Amsterdam) three weeks later we had to sit in passport "timeout" for the authorities to get it all worked out. We almost lost our flight.

At the airport you go across the street and up the stairs to the train terminal to Rome. Takes about half an hour once the train departs to Termini.

Have fun! Oh, and listen to Roberto.