Goal: End up in UII Monday morning, to meet a boat to a different island.
Yellow: Option 1
Red: Option 2
Pink: Shared
Option 1, Yellow:Sun.: LGA-ATL, DL904 6:30a - 8:45a
--- 0:51 connection ---Sun.: ATL-SAP, DL575 9:45a - 11:06a
--- 3:54 connection ---Sun.: SAP-LCE, NSO65 3:00p - 3:30p
--- 0:30 connection ---Sun.: LCE-UII Private Charter 4:00p - 4:20p
Thu,: LCE-UII NSO41 6:00a - 6:20a
--- 1:10 connection ---Thu,: LCE-TGU NSO72 7:30a - 8:10a
--- 4:34 connection ---Thu,: TGU-ATL DL552 12:46p - 6:24p
--- 2:06 connection ---Thu,: ATL-LGA DL8:30 - 10:53
Option 2, Red:Sun.: JFK-SAL, AV671 4:40a - 7:40a
--- 0:45 connection ---Sun.: SAL-RTB, AV482 8:25a - 9:55a
--- Flexible connection ---Sun. or Mon: RTB-UII Private Charter, Whenever
Thu,: LCE-UII NSO41 6:00a - 6:20a
--- 1:10 connection ---Thu,: LCE-TGU NSO72 7:30a - 8:10a
--- 10:20 connection ---Thu,: TGU-SAP AV723 6:30p - 7:18p
--- 2:27 connection ---Thu,: SAL-JFK AV574 9:45p - 3:55a +1
Option 1 Pros: As a DL Diamond, I'd get free E+ and most likely upgraded to J (based on typical loads). Leave NY later and arrive earlier, without much of a penalty on vacation time.
Option 1 Cons: Comes out around $300 more in total. 4pm arrival in UII means I can't do anything that day. Supermarket (mandatory stop for us) in UII is small and has a weak selection. Go through customs in SAP, which is supposedly more strict and will likely confiscate our meat. 4:30 layovers in LCE and TGU with nothing to do.
Option 1 "Meh"s: J is basic recliners, so nothing very special. Relatively boring from a travel collector's perspective: Only one new airline and one new country.
Option 2 Pros: $300 cheaper. Arrive RTB before noon, and can take the charter to UII whenever; this means I could choose to spend the night on either island and do an activity or two on either island. RTB has a proper supermarket. Customs happens in RTB, which is rumored to be more laid back; better chance of keeping my food. No boring layover in LCE.
Option 2 Cons: Coach flying all the way, not even an exit row or E+ - and on longer legs (5h). Leaves NY crazy early in the morning, and arrives back crazy late, pretty much killing two nights. Seriously brutal 10 hour layover in TGU; leaving the airport is not an option.
Option 2 "Meh"s: TGU layover could be cut to 0:30 or 3:00 for an extra $100-200, but that negates a big chunk of this option's financial edge (this would also get me back to NY around the same time as Option 1). I could try to match to my DL status, but AV's J upgrades are notoriously stingy, so I need to assume Y throughout. "Cooler" route, having one additional new airline, new aircraft, new country, and new airport over Option 1.
In summary: More comfortable flights (timing and classes), at the expense of more cash, possible big food problems (customs and available shopping), and half a day's vacation? Or more tiring and less comfortable flights with a nasty connection, but a better food situation and another day of vacationing?
HEEEELP! WWYD?