where do you stay? Any tips? what time of year is best for weather and price? Planning a trip there in 2021.
I stay on my boat in Ko Olina ...its west about 20 minutes from Oahu...its a secure area of houses, golf course, restaurants & a Disney resort/4 Seasons etc. The resorts are pretty pricey, but I like it as there's 4 nice protected beaches, snorkeling is close at Electric Beach, Costco etc is 4 miles away. You would need a car.
Its never cheap in Hawaii, groceries and wine is expensive compared to the mainland, any edible restaurant will cost. Lots of crummy restaurants that would never be in business on the mainland.
The best weather is during hurricane season...end of May to end of August...less trade wind action , best for golf but surfing is not as good as winter. Winter is the time for surfing/kite boarding and wind surfing though if thats your passion. It seemed to me to be more crowded in summer than winter...being Canadian I would have thought this is backwards.
After this virus thing I think prices will become very competitive once things open up there...they are suffering deeply thru lack of tourism.
If I was to go and stay in rental accommodation I would stay in a BnB or a cooking suite in Lahina on Maui. Best food in Hawaii is in the grocery store.Great town, lots of fun, snorkeling & beginner surf right in walking distance. We have stayed in the Pioneer Inn there...old hotel but huge lānai and great location.
Car rentals are pretty expensive, tourist taxes on rooms & cars is extreme....$50/day is a cheap price there for a rental car. I rented from a rent a wreck type joint...was about $20/day but the car was well...a wreck lol.
Anyway I would bring only about 1/3 the clothes but 3x the spending money than normal. I think the best things about Hawaii for me is that everything (boat parts,sports equipment,good steaks)is readily available, there's no language barrier and flights are cheap & direct.
Having said all that I still put the Gold Coast of Mexico ahead of anywhere else I have been long enough to form an opinion.