O’ahu Travel Tips: Walkable Waikiki and Honolulu

This winter, we spent 33 days in Hawaii, and most of it was spent with Waikiki as our home base. I’ve had a lot of time to think about our experience there (this post is about 4 months late…) and I am super happy that O’ahu and Waikiki were our home base.

Waikiki is known as the super-touristy part of Honolulu. People call it the Vegas of Hawaii (wait, I just made that up) but I am/was surprised to say that Waikiki was my jam. Yes, many people deride the area as one of the main drags is nicknamed Luxury Row, but who says you have to go inside?! We biked down Kalakaua Ave many times and it makes for decent sightseeing, even as someone who has no desire to go inside.

Anyway, my point is, I highly recommend staying in Waikiki if you’re considering a trip to O’ahu. It all comes down to one thing: ACCESSIBILITY!!

From Waikiki, we drove alllll over the island. To the North Shore, to the westernmost tip of the island, allllll up and down the eastern coast and through the center. Nothing outside of Honolulu is more than an hour’s drive, and most destinations are 30-45 minutes away. (And please note, there are gorgeous drives!)

Ride a bike…and rent a car!

A car is hands down necessary on O’ahu. You really can’t get around it, but if you reserve it ahead of time, the prices are decent. There are so many different parts of the island to explore, and little places you’ll want to stop, it’s worth it.

When in Honolulu, I recommend riding bikes around the city to explore! Depending on the length of your stay it could be worth it to buy cheap bikes on Craigslist or Facebook, which is what we did. We rented bikes from Biki the first day for $3.50 for 30 minutes which would quickly add up! If you will only be renting bikes, I’d plan a specific “biking day” or know you’re going to do lots of city exploring and commit to buying a cheapo!

Now, any old travel blog or book will list restaurants and popular attractions to visit in Honolulu. But below I’ve listed what I think of as “scenarios.” And when I say scenarios, I mean that anyone can tell you to visit Diamond Head when you’re on Oahu. Duh! But a scenario is how to get there and where to stop on the way.

Walk around Waikiki and greater Honolulu…

  • Pack a picnic lunch and ride bikes to Diamond Head. The ride from Waikiki takes you through a cute neighborhood with great views of the city, and takes about 30 minutes. Once inside, pay the small fee, lock up your bike and hike to the top with hundreds of your new best friends! Spend some time taking in all the different aerial views of Honolulu. Once you hike down, plop down and eat your lunch INSIDE A VOLCANIC CRATER! Once you’ve ridden back down into Waikiki, return your bikes if you rented them and stop at the beach for people watching or take a dip.
  • Grab a Mai Tai from the Hale Koa Hotel’s Barefoot Bar and wander the Waikiki beaches for sunset. If it’s a Friday, grab a spot on the sand for the weekly Friday night fireworks in front of the Hawaiian Hilton Village. The Hale Koa is the beachfront spot we frequented the most due to price and accessibility. Every other beachfront hotel bar involves entering their restaurant, but this bar is sand-level if that makes sense.
  • Park at Ala Moana Park a couple of hours before sunset (it will fill up close to sunset) and walk across the street to Ala Moana Center to wander around, maybe grab a bite from the extensive (and high quality) food court and finish by grabbing the best shave ice on Oahu at Island Vintage Shave Ice. Make sure you get a bowl – big enough to share – that includes ice cream, boba and fresh fruit! Then hop back across the street and enjoy the show on Magic Island. This particular piece of beach has a great view of Diamond Head and is frequented by locals so you know it’s good!hawaii shave ice
  • This particular activity is only entertaining to folks who are nosey AF like me, so take that into account. On a rainy day, we explored all the swanky beach-front hotels and found it highly entertaining. Grab the island’s only purple taro malasadas for $1 each at the Prince Hotel and make your way to the Hawaii 5-0 famous Ilikai for some 70s awesomeness.

Bike around greater Honolulu…

  • Bike down Kalakaua Avenue and take in the sights. Park your bike outside of the Yard House and enjoy one of the extensive beers on tap.
  • If you have time and love the idea of seeing an inclusive view of Honolulu, devote some time to exploring Chinatown. Chinatown is bikeable from Waikiki and has tons of cool markets, shops, bars and is a cool look into the city’s history. It’s considered the happy hour destination for all the trendy folk, although we never ended up there at night.
  • On Saturday or Sunday, walk or bike to the Honolulu Zoo’s art exhibit. Art on the Zoo Fence takes place from 9-4 and features lots of local artists. Then walk across the street to the beach, take in the huge old banyans and watch the surfers at The Walls.
  • Catch old-school lounge singers and hula dancers at The Chart House in the Ilikai Marina. We didn’t eat out very often (Hawaii is famously pricey) but we loved the retro sunken bar and you can tell the clientele is local. In our month on O’auh, we probably ate here three times, including my birthday! They have great happy hour specials, a beautiful view of the marina and the BEST POKE I had on the island!

I hope some of these tips are helpful, feel free to shoot me an email or message if you have any specific questions – I am happy to help!



  1. Mom
    May 30, 2019 / 9:58 pm

    Miss you bunches!!!!! <3

  2. Heidi
    May 30, 2019 / 10:41 pm

    Thanks for the memories! I second everything you said. Xoxo

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