I love credit cards so much! v4.0 - 2021 (see first page for add'l details)

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I am planning for Hawaii September 2022 (3-17) and have questions. I've tried to search the forum for the answers since I know we discuss Hawaii trip planning using cards/points, so forgive me if these are repeats or just point me in the right direction! Thank you in advance!

I'd like to visit Kauai, Oahu, and Maui. We are coming from the East Coast (NC). We could travel anywhere from 10-14 days for this trip and wondering if a stop in CA on our return would be beneficial. I'm thinking yes, but not sure. How many nights on each island? Should we only focus on 2 islands (for us I would likely choose Kauai and Oahu)?
  • What can/should I book now? Everything will need to be refundable and changeable for us since DH work is not as predictable this far out. Is that possible if I use points? I'd like to book Grand Hyatt (Kauai); have the WOH card and Globalist status. When making the reservations, I need to go ahead and have/use all of the points to make the reservation now, correct? I've priced it out and it's 25K per night, so those 100K points would sit there for that reservation for a year? Or will they only hold the reservation with a CC and then I use the points when we confirm/check in next fall?

  • I'd like Marriott Ko'Olina and we have points but looking both in the Chase travel portal and direct on Marriott there are no points bookings available. Is that accurate? Have I already missed the window to book that room on points a year out or have they not been released yet?

  • Will we miss out completely if we choose not to stay at Aulani while we are there? I know people do a split stay but my people are already going to struggle I'm afraid with so much change doing island hopping. If I throw in a hotel change on the same island, I'm not sure they'll be pleasant. Should we choose to stay at Aulani only and not Ko'Olina? Not DVC so I don't have points for Aulani so that would be a cash stay.

  • Wailea Beach Resort is available with points on Maui as is the Hyatt Regency. They appear to be on different sides of the island so I'm not sure if one is better than the other. Something I should consider here? I know Grand Wailea is often referenced but we don't have points or cards w/ Hilton. Should that be my next card to start earning those or will the other two I've listed work just as well? I'm 4/24 (CSP/CSR, Amex Plat, Hyatt)

    Thank you again for offering advice! I feel like I've worked hard in the last year to earn the points, but now I'm not as confident on how to actually use them most efficiently.

We just did Hawaii this summer, also coming from NC! We flew SW (yay points and companion pass), so we had to stop in CA both ways because of SW’s flight schedules. Having also flown all the way to Hawaii and back in one slog a few years ago, we all (me,DH and two teen boys) all GREATLY preferred stopping in CA. Not having to take a red eye on the way home was particularly lovely. I did a bunch of pretty detailed reviews/trip reports from our trip - if you search my username in this thread you should find them (they are from July of this year).
Two general comments - I concur with what someone else said about doing maui and kauai and skipping Oahu. We’ve now down all of the main islands and Oahu was by far our least favorite. If you really want to see Pearl Harbor, that’s worth a visit, but tack on one night at the beginning or end (and fly into or home from HNL) and otherwise skip Oahu. Kauai was hands down the favorite island for all 4 of us, and the one we would all most likely return to. We stayed at the Marriott villas resort in Poipu and absolutely loved it.

Second, book anything and everything that you can ASAP. We found almost everything (excursion/activity-wise) to be fully refundable. Car rentals especially, although hopefully the car rental insanity will have passed by next fall. Autoslash is a great tool for finding good car rental rates if you haven’t used it before. Otherwise, Costco Travel is my favorite place to book car rentals.

I’m a spreadsheet freak and have spreadsheets for both of our trips - feel free to PM me if you want to check them out!
 
So ds doesn’t want to go on our Disney cruise next summer which is fine. He’s a pain to travel with. Now I’m wondering if we should stick with Greek isles or switch to a late May Mediterranean cruise. Dd finishes school early may. She needs a summer job and I also think she’d like to take physics 2 over the summer (for some reason they often recommend to don’t take it at gt). I just don’t know if late may or late June works better given these constraints. I am a terrible decision maker!
 

So ds doesn’t want to go on our Disney cruise next summer which is fine. He’s a pain to travel with. Now I’m wondering if we should stick with Greek isles or switch to a late May Mediterranean cruise. Dd finishes school early may. She needs a summer job and I also think she’d like to take physics 2 over the summer (for some reason they often recommend to don’t take it at gt). I just don’t know if late may or late June works better given these constraints. I am a terrible decision maker!
We did a late May Med cruise with DCL in 2010. It was a great time to travel, as weather was not so incredibly hot as it can be later in the summer. DD was almost 15 at the time, DS was turning 13 and moody. While we did most excursions with DH, some of my best times were with just DD (my mini me) and I, shopping on our own in Mediterranean ports while DH and DS went back to the ship after we did sightseeing. DD and I have done several trips together (NYC multiple times, carribean cruise on DCL, and a trip to Ireland) throughout her teen years. Enjoy your trip with you and your DD!
 
Are we just giving up on our amex dining credits from the beginning of the month? Mine from sept 3 still hasn't posted to my surpass.

Still need to pay cell phone, have those started working?
 
We did a late May Med cruise with DCL in 2010. It was a great time to travel, as weather was not so incredibly hot as it can be later in the summer. DD was almost 15 at the time, DS was turning 13 and moody. While we did most excursions with DH, some of my best times were with just DD (my mini me) and I, shopping on our own in Mediterranean ports while DH and DS went back to the ship after we did sightseeing. DD and I have done several trips together (NYC multiple times, carribean cruise on DCL, and a trip to Ireland) throughout her teen years. Enjoy your trip with you and your DD!
I’m really looking forward to either cruise with just her. After visiting her in Atlanta last weekend, we had a great time and I wasn’t constantly worried about keeping ds happy.

And the May cruise is so much cheaper (I’m paid in full but the refund would pay for one or two other week long cruises).
 
Are we just giving up on our amex dining credits from the beginning of the month? Mine from sept 3 still hasn't posted to my surpass.

Still need to pay cell phone, have those started working?
I SMed with Amex yesterday on my 3 wireless credits that are still outstanding. Said they are a known issue, my charges were eligible and should credit. Screen shot the convo so I can remind them if they don’t show up. My wireless from a 9/12 charge credited normally. So I think you should be good. Seems to be a beginning of the month glitch.
 
I did a bunch of pretty detailed reviews/trip reports from our trip - if you search my username in this thread you should find them (they are from July of this year).

Thank you!! I tried to search and got lost in the 500's looking for a trip report from this summer! I knew someone had recently gone this summer. Adding your experiences to my Hawaii notes and will PM for more info! :)
 
So ds doesn’t want to go on our Disney cruise next summer which is fine. He’s a pain to travel with. Now I’m wondering if we should stick with Greek isles or switch to a late May Mediterranean cruise. Dd finishes school early may. She needs a summer job and I also think she’d like to take physics 2 over the summer (for some reason they often recommend to don’t take it at gt). I just don’t know if late may or late June works better given these constraints. I am a terrible decision maker!

It sounds like May is the better choice, as it would leave more of the rest of the summer open.
 
Are we just giving up on our amex dining credits from the beginning of the month? Mine from sept 3 still hasn't posted to my surpass.

Still need to pay cell phone, have those started working?
still waiting on two of mine, but they are only $5 each and we were eating regardless, so I guess if they don't show up, it's not the end of the world.
 
I don't need a new suitcase but am interested in finding out if there are decent hard sided that weigh closer to 5 lb than 10 lb. I don't want to spend a ton, but also don't always want my suitcase taking up 1/5 of my weight.

Any ideas on where to look? I normally shop at tj max or marshalls for my suitcases.
 
Thank you!! I tried to search and got lost in the 500's looking for a trip report from this summer! I knew someone had recently gone this summer. Adding your experiences to my Hawaii notes and will PM for more info! :)

I have a trip report here too from this summer and hotel reviews for GH Kauai and the Grand Wailea over on the hotel thread.

To add to the car rental recs, I also check here, sometimes they're cheaper. Have used them a few times over the years with no issues.
https://www.discounthawaiicarrental.com
 
Have very big bills coming up. Looking for a good card(s) with a big SUB?

Sadly I'm 5/24 and pretty sure wife is too (so looks like a CIP & Hyatt are out)
Already have the Amex Gold and 2 Plats

Thanks!

Do the big bills take Amex? There's a 150k for $15k spend offer out there on the business plat. $595 AF, which can be somewhat mitigated by the $200 airline credit and $200 Dell credit.
 
Are we just giving up on our amex dining credits from the beginning of the month? Mine from sept 3 still hasn't posted to my surpass.

Still need to pay cell phone, have those started working?

Surpass1 - used 9/15, shows credited today (with 9/15 date, but it was not showing credited yesterday)
Surpass2 - used 9/15, shows credited today (with 9/15 date, but it was not showing credited yesterday. Statement balance readjusted as well since it closed on 9/17, that doesn't usually happen.)
BonvoyBiz - used 9/8, no credit yet
 
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