East coast to Italy strategy

[u/knights014]

Looking for some advise / perspective for a trip I’m planning.

Looking to take 3 ppl business from either PHL; EWR; JFK; or LGA into Italy (ideally). Trip is flexible, ideally leaving last 2-2.5 weeks of sept 2027 and returning ~2 weeks after.

Trip would be Naples -> Rome -> Florence. Open to flying into surrounding cities (e.g., MXP) or even CDG or other close by cities to then fly into Italy.

I booked 2 business class on Air France 3 years ago for like 50-60k pts per person per way but I’ve heard it’s gotten more tricky of recent.

The routes ive been thinking of monitoring:
1. Aeroplan to book united EWR to Rome or surrounding
2. Emirates fifth freedom JFK to MXP. Either direct with them or using JAL if availability exists
3. American from PHL to FCO - though no clue how hard to get 3 tickets at a reasonable rate
4. Flying blue JFK to CDG then another flight from CDG to Naples.

I was using a few sites to track and monitor but open to suggestions / what has worked for you.

Points wise:
-350k chase
-700k Amex
-200k BILT
-200k American Airlines
-70k JAL

Anyone plan something similar recently? I know 3 is going to be hard but trying to ensure I’m doing everything right or if I’m missing something.

[u/emberlanes1]

one thing people overlook is that flying into naples direct narrows your options a ton. might be worth flying into rome and taking the train down to naples first, then working your way back up. way more J availability into FCO

[u/knights014 → u/emberlanes1]

I’m super open to non direct to Naples. Was thinking CDG, Amsterdam, or looking at Emirates. Open to others as well!

[u/Edvardelis]

There are only 3 flights from the U.S. direct to Naples:
United from EWR
Delta from JFK
American from PHL

There are plenty of flights with a single European connection. FRA/MUC/CDG/DUB/AMS are the big ones. LHR connections exist BUT they compete with EasyJet out of LGW so they're not common. Air Canada can also route you through YYZ or YUL.

Direct to Italy is either to FCO or MXP. Rome is an hour train ride from Naples.

Florence/Pisa is the same as Naples, no direct connection.

Edit:
ITA Airways? They exist, but Alitalia's route network was terrible before they collapsed, and ITA isn't much better.

[u/knights014 → u/Edvardelis]

Super open to non direct to Naples. Was thinking of looking for 60k AF to CDG (or if they have a connecting to Naples). I was also monitoring emirates jfk to mxp and then fly down from there. Also monitoring KLM. It seems like it’s just far enough out where most of the award availability is priced on the higher end. May have to wait a bit.

[u/Edvardelis → u/knights014]

Air France has quite a few CDG -> NAP flights. I've done that connection a number of times. (Not fond of CDG itself, though.)
KLM (technically Air France) does AMS -> NAP also. I've flown that route as well.

All the main European airports are very used to travelers going through hubs like this. Just expect to get hit with passport control and occasionally security when switching between non-Schengen and Schengen flights. Air France will happily sell you a 90 minute transfer, and I'm like nope.