Planning a trip to Hawai'i in June of 2019, so I have plenty of time to accumulate miles and points and all that jazz. Will probably stay 7-9 days. If anyone else enjoys planning out credit card strategy, feel free to join the fun.
Stats:
-Need to buy five tickets, hoping to go to Kauai since I've already been to Oahu for a great great KSU 'Cats fan's wedding. Would consider Maui, but know less about it.
-Have SW companion pass, SW will be announcing flights to Hawai'i as early as next month, prices are expected to be competitive
-Wife is churn-friendly, though we're both pretty much maxed out on Chase
-I've hit all of the big Amexes, MrsWonderMeal hasn't had any
-Have ~50,000 URs and will be eligible for a Chase Ink 80k here in a few weeks
-160k Membership Rewards
-~50k SPG
-Like 50k Hilton, but could crush the Hilton 125k business for MrsWonderMeal if it's still available
Strategies:
-Should I just bang some Alaska cards? Churn those 65k AA cards I get a mailer about every two days? Wait for SW?
-Do both Hilton and SPG have free-fifth-night-if-you-book-four-nights things? Up until this point I've been a Hyatt guy and only used Hiltons in non-Hyatt cities, but I doubt I'll have enough URs for Grand Hyatt Kauai for that length of time. (Wife wants a hotel with beach access on the property, which seems like it might be difficult on Kauai. Any thoughts?)