Hello travel brain trust! I am trying to make Hawaii happen in July or August 2027 and would love some advice from this group before I get my next card in early August. Will need to use points for some lodging and all flights. LOTS of Info:
2 adults 2 kids. Plan to do 4 nights at Grand Hyatt Maui on points and 4 nights Aulani cash. Will rent car likely for cash
Within 2 hours of both PHL and BWI; 2.5 hours from IAD; 3.5 hours to JFK. Willing to fly in/out of different airports for a good deal
If possible, would love to make United work, but also realize the utility of a SW companion pass for this
Also need flights for 3 to MCO in March 2026 and need flights for 4 to FLL in August 2026
Relevant Cards:
CSP: since 2021, bonus post 6/15/21
CFU: since 2022
Biz Unlimited since 2023 (will be closing)
Biz Cash since 2024
Chase United Explorers bonus post 2/19/24
Chase United Mileage Biz bonus post 4/7/25
Have 124k URs and a paltry 506 United miles (lots of trips recently!)
Also hold Bonvoy, IHG, Barclays AA, and Diz and
Amazon cards. Used Bonvoy SUB to book 4 free nights for WDW in March 2026; will use annual free night to book pre cruise room for August 2026
Ave spend : $5800 on cards a month
Do NOT have a P2 (or he is VERY unwilling - it would have to be the SUB of the decade to get him to sign up and even then he might not transfer any rewards to me. Love, am I right?)
At 5/24 thru 7/31/25
I have not yet dabbled in Amex - was thinking of Amex Gold and transferring points to delta and flying out of our small regional airport (MDT) to MCO for March trip, but point values have looked pretty bad.
Am planning on getting SW personal and SW Business in late 2025/early 2026 for companion pass and points - that would get us points we need for FLL trip in August plus companion pass for 2027. Then would look for Hyatt card in spring 2026 to have SUB wrapped up and ready to book a year out in advance.
Holes in those plans? Would you do something differently?