Exploring Hawaii with Totally Brain Dad

Words and photos by Ben Osborn, creator of Totally Brain Dad.

If you are lucky enough to visit Honolulu, you’ll be awed by the physical beauty, the food and vitality of Honolulu, and the Aloha spirit. Honolulu is Hawaii’s largest city and the #1 tourist destination in the state. It has something for everyone: beautiful beaches, mountain views, city bustle, quiet retreats, restaurants, shopping, nightlife, art, architecture and lots of history. If you’d like to explore paradise on foot, you can sample of all of that in one long run or in a few shorter outings. There is also a great bike share called “Biki” with stations around the city if you’d rather pedal. I’m by no means a local but I created a few easily accessible running routes for Honolulu with the help of the FASTZach app. So now you can see a bit more paradise in your miles!

You may have trouble pronouncing some of the street names or struggle to find street signs on every corner. No worries, friendly locals can get you back where you need to be. I got a bit off track running in Honolulu a few times but maybe I was just where I was supposed to be?

You never know what you’ll find when you “E hele aku a hele” (according to google translate that is “Get out and route”)!

Ben Osborne - Hawaii 1

Route 1: Waikiki

If you want the quintessential Honolulu run with a bit of a local twist, try this 5-mile loop that incorporates Waikiki, Kapiolani Park, and the Ala Wai Canal. You can start anywhere on Waikiki’s main drag, Kalakaua Avenue, and head toward Diamond Head. I started this route near the Waikiki Wall, to highlight a nice snorkeling spot in Waikiki.  You’ll love the shaded sidewalk between the beach and Kapiolani Park. The park hosts a variety of events and festivals throughout the year, including the Honolulu Marathon finish line. As you loop the park there is an opportunity to extend the run another 3-4 miles toward Diamond Head and get some hill work, but this route loops Kapiolani Park and crosses over Kapahulu Avenue. Remember to swing back here to try some local eats. Plate lunches at Rainbow Drive-In, the kiawe grilled chicken at Mike’s Huli Chicken, or warm malasadas from Leonard’s Bakery… Kapahulu Avenue is Ono (delicious)!  

But eat later…..for now keep the run going along the Ala Wai canal. This canal was built in 1928 to drain the swamps, rice paddies, fish ponds, and other wetlands that used to occupy the Waikiki area. You may see locals paddling outrigger canoes in the canal but otherwise the water quality is not suitable for recreational uses…(do not swim here).  Enjoy the great views of the Ko’olau Mountains and the neighborhoods that rise into the foothills. As you come back to Kalakaua Avenue you’ll re-enter the hub of the Waikiki district and become immersed all the shopping, dining, hotels and beachfront ambiance that makes this area famous. There are too many options to really do the area justice but Maui Brewing Co has great beer and is a cool spot for happy hour.        

Route 2: Magic Island and Ala Moana Beach Park

For a different vibe head to Magic Island and Ala Moana Beach Park. This beachside park is less crowded than the famous Waikiki tourist mecca and it has a decidedly more local flavor. I used FASTZach to help create a 9-mile route that will show you a bit of everything Honolulu has to offer. In the park, you’ll see birthday parties, family gatherings, and plenty old men “talking story”.  The outermost paths make a 3-mile loop for runners and walkers. The reef and breakwater protected beaches provide great family swimming. You’ll see lap swimmers and stand up paddleboards here. This is a great starting point to see a different side of Honolulu.  

As you leave the park, you’ll pass Kewalo Basin Harbor and enter the up and coming Kaka’ako neighborhood.  Start by jumping into the quiet serenity of Kaka’ako Waterfront Park. There isn’t a swimming beach here but there is a largely shaded 1-mile loop that gives a totally different ocean view with a steep rocky shoreline that dives into deep indigo blue water.   Head left to make a clockwise loop, if you explore the oceanfront walkway all the way to the left you’ll find the Kewalo Marine Laboratory and an awesome vista of the harbors and beaches you just ran through with Diamond Head in the background.


After this zen excursion, cross Ala Moana Boulevard to explore the livelier part of Kaka’ako. If you are young and hip you’ll feel right at home, if you are like me you’ll feel younger and hipper just passing through. Condo towers are sprouting up in this former industrial area and artists have taken over. A variety of large colorful murals make this area a visual adventure. There are surprises around practically every corner and alley, it is well worth some time to explore beyond the route.


There are several places to quench your thirst in the area, the runner friendly Lanikai Juice hosts a free Thursday night run club. The everyone friendly Honolulu Beerworks has great beers, food and a casual vibe with games for kids and adults. But drink later, for now, cross back to the ocean side of Ala Moana Boulevard and prepare for to see a bit more of the working side of the city and some historical sites. As you head up Ala Moana you may see a giant Cruise Ship docked at the entry to the busy Honolulu Harbor. At piers 8-11 you’ll be able to run harbor side around the Aloha Tower marketplace to get a view of the harbor and the picturesque clocktower. If you’re paying attention you might get an Elvis sighting. There is a public restroom and drinking fountain available in the marketplace.

tower hawaii new

After you’ve snapped a selfie with the tower, crossover Ala Moana Boulevard onto the Fort Street Pedestrian mall to get a small sample of the main business district of Honolulu and with a side of architecture and history. A right on King St will bring you to the Statue of King Kamehameha, Iolani Palace, and probably the most unique State Capital building you’ll ever see. Return to the Palace to learn more about the history of Hawaii before it was a part of the United States.

After you loop around the palace cross back over King Street to run on the ocean side. That will make it easy take the Kapiolani Blvd split back toward the beach. Kapiolani has nice shade, a view of the mountains and a small glimpse of local life. Kapiolani will take you past the Runners Route store if you’d like any Aloha themed running gear. You’ll also pass the massive and luxurious Ala Moana Mall. Stop by Uncle Clay’s House of Pure Aloha for delicious shave ice (think soft tropical snowcone). And finally, you’ll pass the beautiful Hawaii Convention Center before looping through the outskirts of Waikiki crossing the Ala Wai Canal and back to Magic Island.  Take a post run dip in the Magic Island Lagoon and celebrate how lucky you are to be in Hawaii.


If you are interested in getting a true local guide to help you get to know Honolulu, check out City Running Tours of Honolulu. These awesome people combine healthy activity with learning and adventure to explore gorgeous Honolulu. It’s a total “Winnah” (winner)!


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