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Maui. Enough there to get a feel of pacific life, yet enough there to keep you and your brother entertained. Given the timetable, you are going to be up early so squeeze in the Haleakala at sunrise. Moving experience you would not soon forget, nor regret if you bring a camera
Maui is gorgeous, great food and very chilled - and some great outdoor options around Haleakala (think it’s possible to bike down from the summit). That said think the only night-life is on Oahu - only place we saw any was around Honolulu, so if that’s what you’re looking for then would go there. Enjoy!
Oahu has the most diverse activity set and the only night life.
How many days are you going? Oahu is the most populated and commercialized but gives a good range of experiences. Maui is more clean/resort like and Kauai is more isolated. Big Island also worth a visit
Maui
If you’re under 30 you need to do Honolulu / Oahu. The other islands are mostly families and retirees albeit beautiful paradise. It’s just that everything is shut down by 10pm, Honolulu is a city vibe
Oahu<Maui<Hawaii<Kauai. That being said, all are worth visiting at least once and have great things to offer, so you can’t go wrong.
Thanks A1. Still TBD on how many days. It will be either 5 days or 10 days. If we were to go for 10 days, I’d probably visit two places.
Thanks everyone! Have a great weekend!