Planning a trip in Italy for me is “taking a breath” from my regular work pace Sure, you can take a breath too as long as you will not need a respirator when landing in hot and crowded Italy in 18 days without all final arrengments. Would you like me to call you bank and politely inform them that “this is just a beginning”? . By the end of your trip, you’ll spend close to $ 7,000 (min $ 5,000) usd, not counting the airline tickets. 20 nights @ hotels @ $ 150 - $ 200 USD (+ local taxes).. ~ $ 4,000.00 5 segments on trains/boats @ $ 100 per segment …………..~ $ 500.00 5 organized group tours/day trips/Vatican ( $45 to $ 150) ~ $ 500.00 Tickets to museums, local transport, miscl ………………..….. ~ $ 500.00 20 days meals/water/juice @ min $ 50 USD/day…………... ~ $ 1,000.00 If you are concerned about the cost, and rightfully so, I can rework hotel choices and find accommodations between $ 100 to $ 150 USD. Let me know if you want different hotel choices. That’s perfectly OK by me, it will not take much time. Frugal is good even if one has money. You have a VERY valid point about “lugging your luggage too much”. You have many segments, and will be lugging luggage a lot. Cutting out at least one such necessity is a good idea. Then plan to stay all 4 nights in Sorrento, and take a day-trip to Capri. I’ll gladly make my suggestions about “best of Capri” you can see in one visit. In that case, when you arrive Naples Central Train Station, you will simply walk over to the section where Circumvisuviana trains depart, and take one directly to Sorrento. Then on the day trip to Capri you can enjoy the boat or hydrofoil ride. However, on the subject of how much time to spend in Capri when times allow, I strongly disagree with IceAlica about a day trip being enough, but I’ll address her directly. Let me work with TrenItalia site, and I’ll let you tomorrow morning if I can find answers to all your train questions. I noticed the TrenItalia site has changed (at least since the last 6 months) and became more customer friendly (compared to before). I see there is an option to “buy as visiting customer” without having to register.