Yay! I am feeling so accomplished on Mother’s Day! Finally decided on our plan for HI at Christmas! 12/18- Fly to CA, 12/19-24- Grand Wailea, Maui, 12/24-28- Grand Hyatt Kauai, 12/28-1/2-Kona (Hilton timeshare thing), 1/2- Fly to CA, 1/3- Fly to BWI. Maui and Kauai hotels are booked! Need to call tomorrow to book the timeshare but I need to decide which one still. Then I’ll just have flights to book and overnights in CA. I am feeling excited again! Let’s hope this vacation actually happens!
Hurray, that sounds like a fantastic trip! We did Big Island/Maui over the holidays last year, but the opposite of you...Christmas on the BI and New Year's on Maui. We stayed at the Grand Wailea and it was AMAZING!
Question for those with Hawaii experience- We’re looking to possibly go sometime after Christmas but need to be home by Jan 8. I’ve read that it’s very busy that time of year. What does busy look like in Hawaii? I mean I know wdw is wall to wall crazy through New Year’s. Are we talking that kind of crowded in Hawaii at that time- like at the resorts and beaches? We are looking to stay at Grand Wailea and visiting the popular sites on Maui. Now with 2 kids in college timing is tough. For DS it would be ok for us to go in May right after finals but DD will be playing college softball and their season runs several weeks after classes are out. By that time DS will be into his internship and not able to get off. We could possible go early August before they go back to class but I’m not sure when his internship will end. So I think we’re stuck with last week of Dec/first week of January. Anyone who has visited at that time have some thoughts?
So much talk of Hawaii, I love it! We stayed at the Grand Wailea this past year, Dec 28-Jan 3. The resort is so beautiful, even more so decorated for the holidays. I was so nervous that it would be super busy and crowded too, but it wasn't bad at all. The resort is huge, so it does a good job of absorbing people, We never had a hard time finding chairs by the pool, unlike at Aulani where it feels almost impossible. We sometimes had to wait for beach chairs, but it wasn't too bad. It was a little busy in the mornings for breakfast, but I don't think we ever waited more than 15min for a table. I would suggest making any dinner reservations you want as far in advance as possible, that includes the resort restaurants, popular ones in Wailea and restaurants around Maui in general. I didn't think that through very well so we sometimes were scrambling to find places to eat. We attended their luau, which we enjoyed, but it was our very first luau so we had nothing to compare it too. Pro tip: you can get
discount tickets through Costco. If you are there for NYE, they do fireworks on the beach which were fantastic! Wailea Beach is the most perfect beach! Even though GW is known for their amazing pool complex, we honestly preferred the beach. The waves were perfect for playing in and the surroundings are stunning.
If you are booking with Hilton points, I would do it as soon as you can. I booked as soon as our dates opened up and later wanted to apply a free night award, but couldn't because they would not allow a one-night booking and, despite calling Hilton numerous times, their agents could not figure out how to combine it with a 5-night booking, plus by that time the other dates were not bookable on points, so we just kept the 6 nights booked on points, with one night free. Great deal, especially since rooms were going for $1,200/nt that time of year.
Feel free to ask any questions you may have! It really was an amazing trip. Now I'm thinking we should go back for Labor Day weekend...if Hawaii is back open then.