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Definitely gotta take a captain Andy’s Catamaran tour of the Napali coast in kauai
Highly recommend staying at Kohanaiki on the big island if you can snag an invite.
I would recommend sticking with 1 or maybe 2 islands--3 is definitely overkill
Oahu/Waikiki is going to be most touristy but for good reason and you could make a whole vacation out of staying there
Places to live:
If you stay in Waikiki would HIGHLY recommend the Royal Hawaiian Hotel or Sheraton. They're right next to each other and they're effectively the best ones located On the beach. Avoid the Ritz and Trump International--the views and location are inferior to RH and Sheraton and they're overpriced
Things to do:
Learn to surf--Oahu is the best all-round surfing venue in the world, so you should def allocate some time to trying it out. Super easy in waikiki and would highly recommend paying ~$100/hour for a private instructor--they can basically guarantee you catch some waves
Walk along North Shore--if you want to see the turtles then North Shore is the best place to do it--start from Haleiwa beach park and walk along the coast and you'll see a lot of turtles basking
Hiking--Lot of great trails that were originally established for military purposes. Would highly recommend Koko Crater Trail, Manoa Falls, Kaiwi Shoreline Trail, but Diamond Head is overrated
Kaneohe Sandbar: Accessible by boat/tour, and it's the place where they filmed parts of Pirates of the Caribbean and Jurassic Park because the scenery is incredible
Places to Eat:
Mostly japanese/fusion cuisine so lots of sushi and katsu places--Ritz has a famous sushi restaurant but you have to book far in advance for it
Lots of fish: Paia in Waikiki's pretty good and Nico's Pier 38--it's locate right next to the harbor
Also if you're on Oahu Don't rent a car unless you're travelling with a family:
It costs like $300/day + like $50/night for parking so it's far and away cheaper to Uber everywhere
Also if you're mildly competent with maps then the bus is a great alternative
Only would add Turo is a good rental option (rental by owner). Found a great tiny, literally mini, red hatchback that could park anywhere, crushed gas mileage and was super cheap. Otherwise stop at a shrimp truck in North Shore and don’t be hesitant of poke from grocery stores, it’s truly great. Try out Maguro Brothers if you’d rather pickup from a “counter”.
Appreciate the advice so far. We will narrow it down to two islands, that makes sense that we don't want to waste so much time/effort traveling. I'm thinking about eliminating Kauii because I've already been there long ago.
Good to see that you will narrow it down to hopefully one island because this will be the most relaxing.
Each island will be a bit different but Oahu is going to be the busiest, but would have the most nightlife. Kauai is probably the quietest and most natural.
I will recommend Maui. It has great golf, beaches, snorkeling, whale watching (if you are there in season), good surf spots (not a surfer myself so can’t say how it compares to other islands) and the food is good. You would want a car for Maui, most places that you would want to stay are away from the airport and require a bit of driving. We like the Wailea area (best weather, nice beaches and accommodation) but lots of options on the west side of the island (from Wailea in the south to Kapalua up north). I think the play is to rent a condo so you can bbq or cook when you want and go out for some meals.
I'll add another vote here for the Royal Hawaiian in Honolulu. I was there in December and loved it. Not only does it have great beach access but it's also right in the center of everything with shopping and dinner and nightlife all around you. I was there for a week and never needed a car or uber, you just walk to wherever you want to go, it's all so close and really nice. Plus, if you like Dean & Deluca, they have one of the last ones left in the country, right within the hotel grounds. I really can't say enough about this place and location, I had a great time.
Have also stayed in Royal Hawaiian and it's pretty hard to beat. Ocean view room with a balcony is a must though. I will say that if you like really sleek/modern/generic hotel vibes then the Sheraton (which is right nextdoor to the Royal Hawaiian) might be better but Royal Hawaiian has a nice cozy/homey vibe
I can DM u nude beaches if ur into that type of thing (and the best ones, they’re not all the same)
Definitely interested...just so I know where to stay away from of course.
Can u dm me too?
DMed you
I have my running list (Oahu centric) - since I’m the “Hawaii guy” in the office - that I just add to and forward as a long email. The suggestions made so far are good and not in my list.
Enjoy your time. Turo is / was a good option (although I’m going to bet the rental car scarcity has alleviated a bit post-pandemic) - especially in the small market Neighbor Islands.
Oahu is still my jam, mainly for me because I have a lot of friends there. But I like nature and nightlife - and eating out.
I’ve never been to Kauai. I feel like if you are a nature traveler purist, you have to go there (if you like Patagonia for example). My wife likes the comforts of a big city so quite the opposite of that.
Maui - love the snorkeling in West Maui. Going up Haleakala is always an event. Maui is slower than Oahu, so might be more relaxing.
Big Island / Island of Hawaii - the island is big compared to Oahu or Maui. There is so much to explore and drive, you’ll have to go back to see it all. I always wanted to see the volcano. I did Kona a couple times already.
Two islands is good if you only have a week. Or stay in Oahu for the week, and get comfortable.
If you don’t know how to surf but can swim pretty well, buy a body board and fins and body board at Makapu’u. My favorite beach for that. It is safer than Sandy’s which has a dangerous shore break (ie broken necks). I grew up near Makapu’u and a few hours body boarding there is an awesome workout and it’s a consistent break. Living in San Francisco, I sometimes dream of being able to body board Makapu’u.
Local Pro Tip: Buy a plate lunch (to-go) before heading for the airport to leave Hawaii, and carry it on the flight. You’ll get to enjoy your Hawaii vacation on the plane ride, and sure beats the airplane food/snack. Your neighbor sitting next to you might be J, but you’ll eat well and then take a nice nap 30,000 feet in the air.
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