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Music recs for deck building please
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Pro
Start at Oahu for the first half and do all of the touristy things there, then fly/boat to a less touristy place for the second half
We just went to Maui and stayed at the Westin resort fully on points. It was great!
The Hilton Hawaiian Village on Oahu is nice and should fit that budget. That's in Waikiki.
The Marriott Waikiki is awesome as a base to explore Honolulu. The Hilton Hawaiian Village is also great for Honolulu. The Marriott on Kauai is also fantastic if you want to peace of Kauai!
Chief
Hilton Waikoloa on the Big Island is a great resort. Check the prices at individual towers: some towers have hotel rooms, some towers are all suites (and more expensive).
Haven’t stayed anywhere else in Hawai’i so I can’t compare.
Rising Star
Maui/ Big Island of Hawaii combined trip. Avoid Honolulu, Oahu (city with tourists/crowded) but Pearl Harbor is definitely the thing worth seeing there. We also did Kauai as a separate trip and that is lovely. Ps: we never would pay $400 on vacation so you can find good lodging on all of these islands.