6 Best Oahu Hawaii Hikes | Easy to Intermediate, Family-Friendly Oahu Hikes

6 Best Oahu Hawaii Hikes | Easy to Intermediate, Family-Friendly Oahu Hikes

Make room in your Hawaii itinerary for these Oahu hikes. They are not the hardest, but these Oahu hikes will make you happy you got out of Waikiki.

Here are our 6 favorite easy-to-intermediate Oahu hikes. With our toddler in tow, we show you how to climb Diamond, conquer Koko Crater (almost), traverse Makapu’u Point Lighthouse Trail, and climb to the best Oahu pillboxes on the island. These are family-friendly, kid-friendly, senior-friendly type hikes for you to enjoy.

Listed in no order, find the best Oahu hike for your trip to Hawaii!

11 Best Oahu Hiking Trails: https://thehawaiivacationguide.com/best-hawaiian-island-for-hiking/

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Best Oahu, Hawaii Hikes | Our 6 favorite Oahu hikes
00:00 Intro
01:14 How to hike safely on Oahu
02:00 Judd Trail to Jackass Ginger Pool hike
03:42 Koko Head Crater Tramway Hike
05:36 Diamond Head Hike (Le’ahi)
08:12 Makapu’u Point Lighthouse Trail
10:05 Ehukai Pillbox Hike (Sunset Pillbox Hike)
11:41 Lanikai Pillbox Hike (Kaiwa Ridge Trail)

Google Maps Directions to Each Oahu, Hawaii HIke:
Judd Trailhead: https://goo.gl/maps/wToxheF15yBbqdW1A
Koko Crater Trailhead: https://goo.gl/maps/6Pf7VLCZFMy6h1ECA
Diamond Head Trailhead: https://goo.gl/maps/MHit9N7NkYEsb6QT7
Makapu’u Point Lighthouse Trailhead: https://goo.gl/maps/WcbsKL6rKiMJfGNx7
Ehukai (Sunset) Pillbox Hike: https://goo.gl/maps/Z1hg4U31fdCMBaMm9
Lanikai Pillbox Hike (Kaiwa Ridge Trail): https://goo.gl/maps/jRwhtTJRGUpuyjvM9

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50 Comments

  1. @ColleenDelaney918 on January 18, 2025 at 9:17 pm

    Have you done the stairway to heaven?

  2. @philvie on January 18, 2025 at 9:17 pm

    Ive always called it "hana a oou ma" bay, plus I would have added the Manoa falls hike

  3. @TolKOZAK on January 18, 2025 at 9:21 pm

    I’m so happy to find your site. We missed Oahu this December. My wife and I have spent about 20 weeks in Hawaii over the last 5 years, mostly in Oahu. We have only been to 3 of your 6 with Diamond Head the most times. In my 70s but still can do Diamond head in about 30 minutes. Thanks for the very informative and well done video. Hope to come back soon. Aloha.

  4. @ramangill5193 on January 18, 2025 at 9:22 pm

    If only 1 hike can be done, which one do you recommend?

  5. @mysticada on January 18, 2025 at 9:26 pm

    I love you guys planning on my first trip to Hawaii hopefully this spring. Your videos are so helpful and congratulations!

  6. @TV-md7vx on January 18, 2025 at 9:28 pm

    아기랑 산에 올라가니 멋져요.
    자주 올게요 어메이징

  7. @angelabeniaminov6550 on January 18, 2025 at 9:29 pm

    Hi guys, first I want to thank you!! All your info has been relevant and has helped us a lot to plan our vacation on April. I have a question which one of this is accessible to get in and specially OUT in uber? thanks

  8. @magdalena5565 on January 18, 2025 at 9:32 pm

    Beautiful Family ❤

  9. @DaddyBLUE90S on January 18, 2025 at 9:32 pm

    Wearing a mask outdoors with no one around.. 🤦🤦🤦

  10. @birdman5223 on January 18, 2025 at 9:35 pm

    😍

  11. @Soulman6969 on January 18, 2025 at 9:36 pm

    Sponsored by Tevas!!! 🤣🤣🤣

  12. @vanillall1 on January 18, 2025 at 9:37 pm

    Was this a hiking video or a tavas commercial 😅 great video! (Going to get me some tavas now lol)

  13. @redcoatphilip on January 18, 2025 at 9:37 pm

    Hi All I have seen online and some of your hikes are on private land and there’s fines. Can you please confirm?

  14. @Webbfamilyforyou on January 18, 2025 at 9:37 pm

    As a person that works out on a regular basis; Kiki head should not be on this list… it’s definitely hard and not “family friendly”

  15. @XioArleen on January 18, 2025 at 9:39 pm

    thanks so much!! I was looking for easy hikes to do and the fact that your toddler can do it gives me confidence. lol

  16. @billhobartclairvoyantmedium on January 18, 2025 at 9:40 pm

    Another great video but I’ll probably be staying on Maui and Jordan does need TEVAS! No one can wear flip flops to hike…can they ?😉

  17. @megalomaniac7972 on January 18, 2025 at 9:40 pm

    on Judd trail do you go left or right?

  18. @ThrivingAfterThirty on January 18, 2025 at 9:41 pm

    We did Koko Crater yesterday and it is the most challenging hike we have ever done.

  19. @KimofCoventry on January 18, 2025 at 9:41 pm

    Have been enjoying your videos, even though our kids are grown. We have our 30th anniversary trip planned/paid, Feb 2022. Hoping we can still make it! Can you tell me what sunglasses you are wearing in this video? We live in New England so already have much loved Tevas 🙂 My husband lived on Oahu as a child. I can never live away from snow! Thanks for all of your useful content!

  20. @AlohaGirlwithAkitas on January 18, 2025 at 9:42 pm

    so i’m from switzerland and i’m doing some hikes here. I find Koko head hard

  21. @minzyminz9987 on January 18, 2025 at 9:42 pm

    if henry can do the koko head stairs I should be able too :<

  22. @dioniubales on January 18, 2025 at 9:43 pm

    Hello, quick question what are the drone rules in hawaii? I have a mavic mini 2 can i fly it there?.

  23. @mydogisbailey on January 18, 2025 at 9:44 pm

    sis ur husban is foin!!!!!

  24. @debby7822 on January 18, 2025 at 9:44 pm

    Erica-Which Tevas do you recommend? Light hiking/rocky water activity wise..

  25. @bertbrecht7540 on January 18, 2025 at 9:47 pm

    Well done review. Thanks! I don’t think ill need to buy a guide book ever again.

  26. @tipsontravels2218 on January 18, 2025 at 9:47 pm

    From Waikiki beach hostel to Koko Crater is there a bus ???
    Great vid thankU👍

  27. @TheLynchbro on January 18, 2025 at 9:47 pm

    I’m going next month! Planning koko crater and diamond head same day. Possible to park and one and walk other? Or park one and Uber?

  28. @kathleenvera3395 on January 18, 2025 at 9:49 pm

    i won’t be driving when i get there will uber or lyft take you to those parks?

  29. @ShopBanksTees on January 18, 2025 at 9:52 pm

    Is there a second Diamond Head trail? I hiked it (or so I think now lol) but definitely didn’t go through a tunnel.

  30. @qtnuisance on January 18, 2025 at 9:55 pm

    koko head is a hard hike & not family friendly. If anyone does do it & youre not physically prepared , please go early in the am. Koko head is not an easy hike!!! So many people get rescued there!!

  31. @kapellekonig6512 on January 18, 2025 at 9:56 pm

    Hey guys, I’ve been doing some research on ridge hikes on Oahu. It has come down to Wiliwilinui and Kuli’ouou. I will just be able to make time for one. Any opinions?

  32. @unfightersjuve77 on January 18, 2025 at 9:57 pm

    Thanks for this perfect video ! Really helpful to organize my trip next year. Aloha ! 🌴

  33. @deborahharrington5379 on January 18, 2025 at 9:58 pm

    Maybe I missed this but it looks like there are two separate pillbox hikes? The second one being the Lanikai pillbox hike, what is the first called? Or was it all the same hike? Planning a trip to Oahu with our will be 10 month old in March and loving your videos and itineraries!

  34. @kristenabbate9446 on January 18, 2025 at 9:59 pm

    Thank you for another wonderful video. For all intermediate hiking on Oahu would you say that teva/ Chaco type shoes work or should we pack our actual hiking boots like we wear for national park hiking?

  35. @wdwnutjm on January 18, 2025 at 9:59 pm

    very cool!!! I agree the Tevas are excellent but I’ll go one step further and say we bought hiking sandals for our last trip – they were a game changer!!!

  36. @hremaddox on January 18, 2025 at 9:59 pm

    Koko Head is not intermediate! 😂 i cursed and crawled the last half of it. I thought i would die.

  37. @grisseldasoto on January 18, 2025 at 10:00 pm

    Thank you for this! I’m planing a trip to Oahu towards the middle of April & hoping to hike some of the trails you recommended!

  38. @emyabara3371 on January 18, 2025 at 10:01 pm

    Try Aiea Loop Trail. You’ll see H3 freeway .

  39. @jaisonlives on January 18, 2025 at 10:02 pm

    My trip is going to be the bomb! Thanks for your videos.

  40. @Ash_Avvy on January 18, 2025 at 10:04 pm

    Thanks ❤

  41. @megalomaniac7972 on January 18, 2025 at 10:04 pm

    Do you have any suggestions for easy hikes for older people? Like >65 or just places to walk around that look nice. I was thinking Manoa Falls, Byodo, maybe the lighthouse

  42. @kaleoy7584 on January 18, 2025 at 10:04 pm

    I live in Hawaii Kai. The ONLY way I would climb Koko Head, if there was a huge slide to go down after reaching the very top of the hike.

  43. @JordanHeller1 on January 18, 2025 at 10:07 pm

    Kind people and a favorite channel

  44. @MokuNui808 on January 18, 2025 at 10:08 pm

    The questions is can people pop off the judd trail and do any wild camping?

  45. @jopayskicapulong9036 on January 18, 2025 at 10:08 pm

    Did you take Henry to Lanikai Pillbox? Thanks.

  46. @lizdancer1023 on January 18, 2025 at 10:09 pm

    Do you think that all of these hikes would be doable in chacos? Similar to tevas but wanted to see if you (or anyone else) had any ideas about chacos!

  47. @mistermerita341 on January 18, 2025 at 10:11 pm

    New subscriber here. Thank you for all the trails..

  48. @annaherrera-cdhs327 on January 18, 2025 at 10:13 pm

    Are Masks still required?

  49. @LivingTheDreaminHawaii on January 18, 2025 at 10:14 pm

    Such a nice video. Mahalo for posting.

  50. @dc-13258 on January 18, 2025 at 10:15 pm

    Lanikai Pillbox Hike was surprising difficult for me, but I think it was mostly due to a combination of recovering from a cold, eating a heavy breakfast, and wearing bad shoes not good for the steep sandy rocks. I even specifically bought a pair of Chacos but didn’t use them for the hike because it didn’t match my outfit. Lesson learned!

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