I am just starting to look into these.

I have come up with what I think will be a legal route and just wanted to run it by some of the experts.

I would like to make more mileage but my admit the gf will not be wanting to do a lot of that. But I always listen to ideas.

1: JFK-LAX: 1st of 1 (North America Transcon)
*1: JFK-LAX: 1st of 6 (North America)
2: LAX-LHR: intercontinental. Possible 1 day stop here
3: LHR-FCO: 1st of 4 (Europe) 5 day stop here traveling by train. Doesnt matter to airline as we will arrive and leave from Rome so no overland to them.
4: FCO-LHR: 2nd of 4 (Europe)
5: LHR-DXB: 3rd of 4 (Europe) stay here. also seperate ticket to maldives and back.
6: DXB-HKG: intercontinental. one night here
7: HKG-SYD: intercontinental. one night.
8: SYD-CHC: 1st of 4 (Southwest Pacific). near a week. same as rome.
9: CHC-SYD: 2nd of 4 (Southwest Pacific)
10: SYD-HNL: 1st of 1 (intercontinental entry to North America without immediate transit & departure). Spending a few days.
11: HNL-LAX: 2nd of 6 (North America)
12: LAX-ORD: 3rd of 6 (North America)
13: ORD-NYC: 4th of 6 (North America) Start of several month stopover.
14: NYC-MCO: 5th of 6 (North America). Later in year going to MCO on same ticket. Is this possible?
15: MCO-NYC: 6th of 6 (North America)

Specific question would be the 1 transcon limit. I assume that is only a limit on actual non stop transcons and not a limit on touching the coasts.

Also I am wondering how stopping in NYC will effect things as I would assume a stop over at home would not be allowed but dont know. I can sub in swf or hpn or can i force the issue that aa says ewr is no co-terminal with lga/jfk.

I am not an expert, but as far as i know you can touch the coasts multiple times, but no more than one transcon.
So JFK-LAX-ORD-JFK would be ok, JFK-LAX-JFK would not.

Not sure about the NYC/EWR issue.

Suggestions for additional miles:
Instead of DXB-HKG i suggest DXB-LHR-HKG. Not much additional time and lots of miles (and F in case you do a AONE)

Check if SYD-HNL has F (in case of an AONE).

Since you have some segments left: A day trip HKG-NRT-HKG in real F is not too bad.

It appears to be a valid route, and correct, only one transcon between the designated city pairs allowed, but you can certainly touch both coasts as often as you like within the rules.

Speaking of which, don't forget the 2 stopover rule in continent of origin. It sounds like you have 3 (at least - HNL, NYC, MCO.) Transiting the city of origin (NYC, including co-terminals) is permitted, but the 2 stopover rule still applies.

Given the price of D/AONEs in N. America, and given your route, I'm inclined to think you'd be better off starting and ending the trip in Europe. You'd save significant money on the ticket price, and you'd be allowed the full six stopovers in N. America (including Central America and the Caribbean). You'd easily earn enough miles to replace any award miles used to get there in the first place, or if traveling off-season you could buy a cheap hop over the pond, and start someplace cheaper than N. America (particularly if traveling in J.) For instance a DONE4 starting in N. America is currently $8300 while it's around $6600 in Sweden.

Devour the sticky threads - lots of answers there.

I've been using the mileage monkey which warns of more than 16 segments.

Just found that AA allows 20. So I can pad this up a little as suggested by maybe going to japan for a day?

Looking at AONE4. Sweden looks to be about 1000 cheaper than NYC. Italy which would be ideal is actually more. Maybe some way to get it to start in DXB

That 2 stopover thing is something I need to relook at. Would I be able to end it in MCO. And do my own thing back to NY? To avoid a stop over in mco in their eyes?

BTW. Season of travel is April.

If contemplating an AONEx, then also you should pay attention to which sectors actually offer F (remember DONEx books into A on 2-class N. American flights.)

For example on your initial itinerary, you'd only have international F between LAX and LHR, LHR and DXB, and and HKG-SYD. All other segments would be with J as the top cabin (except the AA flights within N. America.)

Yes, you can end anywhere in N. America. Note as of a couple of days ago, the 20-segment rule includes surface segments.

... and, if that is not bad enough, AA is well known for considering that a surface segment is TWO stopovers, not one, so there goes your full allowance in just one open-jaw.

Please post your decision regarding starting in JFK v. Sweden, etc. I'm also contemplating an xONE4 and trying to decide where to start. At the moment I'm leaning towards JFK for simplicity.

To be absolutely precise, if you start in the USA you can end anywhere in the USA or Canada. (You couldn't start in the USA and end in Mexico, the Caribbean, etc).

Note also that DXB-HKG is an aircraft configured for regional flights (cradle seats, no AVOD) which IMO is really really not a good way to do one of your intercontinental flights on a A/DONEx ticket.

correct me if im wrong, but surely North America, Europe and Southwest is 3 continents and therefore a DONE4 is not neccessary??

Plus Asia, makes it four.

Nope. Is a DONE4 as all flights Eu to SWP (SYD) land in Asia to pick up / drop off pax and take on fuel. Even though its the same flight number and you are not stopping its a DONE4, as the aircaft lands in Asia. That's the rules

The OneWorld site says “Your journey must include at least three oneworld continents, or four from the Southern Hemisphere and Africa where three-continent itineraries are not possible.”

For me, Sweden is definitely out as I need more segments in specific places in europe for this trip. So of the two options I will start with jfk.

Ideally I would like CMB because I need to go through there anyway to get to the Maldives. But it seems a thing of the past from what I can tell.

Number 1 would be.... 49813 with 2 non NA or Europe segments possible.

1: JNB-HKG: 1st of 1 (intercontinental entry to Asia without immediate transit & departure)
2: HKG-NRT: 1st of 4 (Asia)
3: NRT-SIN: 2nd of 4 (Asia)
4: SIN-SYD: intercontinental
5: SYD-NRT: intercontinental
6: NRT-HNL: 1st of 1 (intercontinental entry to North America without immediate transit & departure)
7: HNL-ORD: 1st of 6 (North America)
8: ORD-HPN: 2nd of 6 (North America)
9: HPN-ORD: 3rd of 6 (North America)
10: ORD-MCO: 4th of 6 (North America)
11: MCO-LGA: 5th of 6 (North America)
12: LGA-JFK: surface
13: JFK-LHR: intercontinental ..... Start of actual trip continuing to NYC before MCO in second part.
14: LHR-FCO: 1st of 4 (Europe)
15: FCO-LHR: 2nd of 4 (Europe)
16: LHR-DXB: 3rd of 4 (Europe)
17: DXB-LHR: 4th of 4 (Europe)
18: LHR-JNB: intercontinental

Number 2 would be.... 42229

1: JNB-HKG: intercontinental
2: HKG-PER: intercontinental
3: PER-SYD: 1st of 4 (Southwest Pacific)
4: SYD-CHC: 2nd of 4 (Southwest Pacific)
5: CHC-SYD: 3rd of 4 (Southwest Pacific)
6: SYD-HNL: 1st of 1 (intercontinental entry to North America without immediate transit & departure)
7: HNL-ORD: 1st of 6 (North America)
8: ORD-HPN: 2nd of 6 (North America) End of main RTW trip.
9: HPN-ORD: 3rd of 6 (North America)
10: ORD-MCO: 4th of 6 (North America)
11: MCO-LGA: 5th of 6 (North America)
12: LGA-JFK: surface: Layover from end april until new calendar year.
13: JFK-MAD: intercontinental
14: MAD-LHR: 1st of 4 (Europe)
15: LHR-CAI: 2nd of 4 (Europe)
16: CAI-LHR: 3rd of 4 (Europe)
17: LHR-JNB: intercontinental

This does require DONE5 instead of Done4 which means 2*6300 vs 1*8300. But I think it is a decent value to pay basically 4300 for a second trip and be allowed the NA stopovers I wanted.

There are tweaks possible and I'd love to bump up miles. But so far its looking like this.

I assume it is physically impossible to start in JNB and get australia without a ONE5.

You can do JNB and australia on a xone4, for example: JNB-SYD-LAX-LHR-JNB is valid. You could also route that through south america instead of north america, but that is probably not what you want.

Europe is the only continent you cannot skip.