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Oahu Hawaii - A Perfect Day on the Windward Side

Updated on April 23, 2015

Somewhere on the Windward side of O’ahu, Hawaii, the ocean is an endless pool of light shades of turquoise and Caribbean blue; the pace of life has slowed down and the towering Koolau mountain range shelters the residents with sharp ridged switchbacks in lush shades of green. Instead of beaches bordered by high-rise hotels, the sandy shoreline blends with the grass lawns of private house rentals where guests can walk 15 yards and be immersed in the warm water.

This is the Windward side of oahu hawaii, and a perfect day here is easy to come by, especially if exploring the natural beauty of Hawaii is on your agenda. The Windward side is only 20 or so minutes away from downtown Honolulu, so even if you are staying in a beachfront hotel in Waikiki, it is readily accessible.

The short, beautiful drive over the Pali highway features waterfall spotted mountains and a tunnel that goes underneath them, ejecting visitors into the arresting view on the other side. Like some bizarre wormhole, the Pali highway tunnel transports visitors from their town experience into an idyllic island paradise. Here is an ideal itinerary during the visit.

Paddleboarding out by Flat Island in Kailua, Hawaii
Paddleboarding out by Flat Island in Kailua, Hawaii | Source

The Mountains

If this day has a second phase it should be spent hiking the trail to Maunawili Falls. Approximately five miles up, this is an easy to moderately difficult hike requiring good river sandals or hiking shoes. The hour and a half trail to the falls is lush and scenic and humid! Bring extra water!

From Kailua Beach, head back up to the Pali highway and turn left at Auloa street. Stay left on Maunawili Road which will take you through a residential area. Take it to Keewina street and find a place to park. This is a good neighborhood, but mind any posted warnings and to be prudent, stay on the trail. At the falls, a nice swimming area sits beneath the cliffs, where people can sometimes be seen jumping off into the water below.

Fitting both of these activities into a single day can be exhausting, so if you are headed back to your beach rental in Kailua, don’t miss the opportunity for a final dip in the ocean to restore your spirits. For those headed back to Waikiki or another part of town, may I suggest cocktails by tiki torch at Dukes on the beach? Do try to make it for the sunset. Ahhhh, what a way to spend a day.

A classic shot of Maunawili Falls, Windward Oahu
A classic shot of Maunawili Falls, Windward Oahu | Source

The Beach

Kailua Beach is and its continuation, Kalama Beach, is long enough to accommodate thousands, but it rarely seems overcrowded. The best place to park is in the beach parking lot, but roadside parking can be found. The Kalama Beach parking lot is also available a couple of minutes down the road. Here the sands are fine and the views are unobstructed.

This is a great place to start for an early morning swim, surf, paddle, run or walk. It is also ideal for a little ocean adventure. The top two choices are kayaking and windsurfing, which Kailua is famous for. The kayak outfitters are close by and rent out sit-on-top kayaks at reasonable rates. Pack a snack from the First Stop convenience store and paddle out to the Mokuleia islands, about a mile off the shore.

The paddle out is typically easy-going, but be prepared for light surf breaks at about the midway point. While not usually large enough to land on your head, they can be enough to turn over the kayak if you run into them sideways! This is a beautiful paddle, and is frequently punctuated by visits from groups of green sea turtles or a rare appearance from the Hawaiian monk seal.

Once you arrive, a small sandy shore offers a place to rest and beach the kayaks before exploring the small bird sanctuary. Pack out what you pack in, especially your trash. Not only does it pollute the environment, but it can be dangerous to birds and sealife. Around one side, a rocky hike rears up against the raw Pacific Ocean, and around the other an enclosed grotto ripe for diving awaits. Sturdy sandals are recommended.

After returning to the shores of Kailua Beach, you may want to get a good lunch in and enjoy the sun before your next activity. But first, if kayaking isn’t for you, Kailua Sailboards and Kayaks offers windsurfing lessons and rentals, and rents a variety of other ocean toys as well. If you need to learn, the lessons are first rate.

Don't worry if you never make it off the beach today. Stay in town and walk over to Buzz’s Original steakhouse where the atmosphere is mellow and the food is delicious. Lunch ends at 3:00 and dinner starts at 4:30.

A beautiful beach day in Kailua.
A beautiful beach day in Kailua. | Source
Shark's Cove, only a mile paddle to the Mok's from the beach.
Shark's Cove, only a mile paddle to the Mok's from the beach. | Source

Fiction and non-fiction I like about Hawaii

Island Boyz
Island Boyz

Listed under juvenile fiction, but you don't have to be a teenager to appreciate this collection of short stories about growing up in Hawaii. Fun, fast read that will transport you to an island far away.



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    • MosLadder profile imageAUTHOR

      Chris Montgomery 

      6 years ago from Irvine, CA

      Thank you! I plan on hopping on a paddle board myself, looks like so much fun.



    • Express10 profile image

      H C Palting 

      6 years ago from East Coast

      This is a useful and beautiful hub. It has reminded me of how much I want to try stand up paddle boarding. Though we have dolphins here in Virginia, the surroundings are not as beautiful as Hawaii.

    • MosLadder profile imageAUTHOR

      Chris Montgomery 

      6 years ago from Irvine, CA

      Thanks stellakeira!

    • MosLadder profile imageAUTHOR

      Chris Montgomery 

      7 years ago from Irvine, CA

      Ian, I'm going straight to your profile after this to find your surfing hubs, that sounds awesome. I appreciate your comments, thanks!

    • MosLadder profile imageAUTHOR

      Chris Montgomery 

      7 years ago from Irvine, CA

      Thanks Tammy! Ironically, half of that vacation was dreary and rainy. Not that I really cared :-) Thank you for your comments.

    • MosLadder profile imageAUTHOR

      Chris Montgomery 

      7 years ago from Irvine, CA

      Perspycacious, my pleasure! With one or two exceptions a year, all my vacations come by mouse these days, and the occasional turn of the page. Thanks for your comments!

    • MosLadder profile imageAUTHOR

      Chris Montgomery 

      7 years ago from Irvine, CA

      PracticalMommy, it really is. I mean, sure you have the hustle of Honolulu, but once you get past that, it's all paradise! Thanks so much for your votes and comments. Cheers!

    • Ian Dabasori Hetr profile image

      Ian D Hetri 

      7 years ago from Papua New Guinea

      I only wish and fantasize that one day I will have a holiday in Hawaii. Such a dream place for me...Great hub. Voted up..Hope you enjoy mu hubs on Surfing in Papua New Guinea (Pacific)

    • tammyswallow profile image


      7 years ago from North Carolina

      Beautiful sights on a cold, dreary, winter day. I am sold! Nice work.

    • Perspycacious profile image

      Demas W Jasper 

      7 years ago from Today's America and The World Beyond

      A Hawaiian vacation whose only cost was clicking a mouse!

      Thanks for the great photos and presentation.

    • ThePracticalMommy profile image


      7 years ago from United States

      When my husband and I were in Hawaii on our honeymoon, we were on Maui and the Big Island, but we didn't get to see Oahu. It seems just as beautiful if not more beautiful than where we were! This is a great travel guide for anyone who plans to visit Oahu in the future. Voted up and useful!

    • MosLadder profile imageAUTHOR

      Chris Montgomery 

      7 years ago from Irvine, CA

      Thanks for reading this hub Danette. I especially love the windward side. Every time I go back it feels like home. If you go to Kaua'i, be sure to do part of the Koolau trail; but I don't think you can go wrong there if you're looking for natural beauty. By the way, if you liked this hub, there are two similar ones you might enjoy:


    • Danette Watt profile image

      Danette Watt 

      7 years ago from Illinois

      My son is stationed in HI, due to transfer out in March. We went out to visit him in Oct 2009 (?) and I absolutely loved it out there. (wrote a hub on what to do on Oahu) He's on Oahu, Kailua in fact, so I could relate to what you wrote about. I'd love to go back and this time to Kauai (don't think that's spelled right)and do some hiking.


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