Itinerary Help!

I'd prefer to be in Croatia earlier, so I'd be more inclined for option A. The end of September is sort of the end of the season (you don't say where in Croatia, but I'll assume you mean Dalmatian Coast e.g. Dubrovnik area), and when October rolls around you find fewer excursions, shorter hours, reduced ferry schedules, etc. Not necessarily a terrible time to be there, just something to keep in mind if you choose that.

I'd also suggest doing all your time in London at the end, so you don't have to split up your time in London or stress over getting back for the final night out. That would mean either flying out the same day you arrive for your first destination or taking the train. Some people find the idea of this kind of first day connection too stressful, but I've done it numerous times without a problem. There is some risk involved, especially the shorter your layover in London (what if your flight into London is late?), but you can reduce the risk with a longer layover. And sometimes, trip delay insurance will cover extra costs (say you arrive in London five hours late and must spend the night there and miss your first day and flight back out - the insurance might cover the cost of a last-minute hotel and a new flight).

Of course, you could also fly an open jaw ticket - into say Amsterdam or Dubrovnik or whatever, home out of London, and not start in London at all, just end there. That's probably how I would do it unless you've already locked in a London round-trip ticket.

Also do you experts think is a bad idea to fly or take the train back to London on the same day I have to fly back to US?

I agree that it is a bad idea.

I am locked in on my round trip in and out of London and my first 4 nights of accommodation there. I could shorten my 4 nights to 3 or 2 nights. What do you think?

I think you meant to say you prefer option B.

I appreciate your suggestion of starting in Croatia. I probably will shoot for option B and spend the last night in London.

Yes I am spending 5 nights in Dubrovnik

Yes, - option B. Sorry. Start in Croatia.

Dubrovnik is lovely but also not very big - and extremely touristy during the day (cruise ship tour groups). Five nights is a really long time to spend there, unless you have specific day trips planned to get away from the crowds during the day. You might consider heading up to Split for the last few nights and flying to Prague from there - or perhaps heading to an island like Korcula for the first few days the day you fly into Dubrovnik, then back to Dubrovnik for the last few nights and fly out of there.

Thank you. Yes! I was planning to visit Korcula but as a day trip. So you think I should consider maybe 1 night in Korcula, 3 in DB and the last one in Split. Is it cheaper to fly to Prague from Split?

How should I do London:
2 or 3 nights upon arrival and 1 before departure? Or 4 nights upon arrival and 1 before departure?

I was considering taking Amsterdam out of the equation and adding those 3 nights elsewhere. Any suggestions?

I second Andrews' idea to put all of your London days at the end. Traveling the day before to your departing destination is a little bit risky. Every now and then there are strikes in Europe or you could get sick. Have fun.

Next time go for open jaw but since your already locked in I would save London for last. Start the furthest away and end in London.

Next time I will do open jaw but for now since my Airbnb requires a two day minimum stay and they will only refund me 50% of total cost I’ve already paid, I will have to do the first 2 and the last 2 nights in London. Live and learn huh. :(

Thank you so much guys :)

I don't know if it's cheaper to fly to Prague from Split or Dubrovnik - depends on time of year, day, etc. Some airlines don't fly every day or don't have a direct flight. If Split was not a direct flight or expensive, maybe I'd stick with Dubrovnik. Check it out on Google Flights.

You might have trouble booking just a single night in Korcula Town (where you'd probably stay in Korcula). Sometimes the lodgings there have minimum stay requirements. You might find it impractical to spend just a single night in Korcula Town, anyway, when you look at the transportation options. When I visited Korcula years ago, I had to take the bus from Dubrovnik (no catamaran option at that time) which got me in late in the day, and the catamaran to Split departed at 6am - so with two nights, I really had only one full day. With just one night, I would have a single evening - clearly not worth the hassle.

Also do you experts think is a bad idea to fly or take the train back to London on the same day I have to fly back to US?

Yes! Even amateurs think its a bad idea

Going to London from Amsterdam on departure day back to the US is a potentially expen$ive idea.