Oahu, Hawaii in 72 Hours

What to see and do in Oahu, Hawaii.
Aliʻiōlani Hale with King Kamehameha V Statue out front.

When booking long-haul flights, do you ever think about spending a few extra days in your connecting city to break up the trip? Or maybe you just want to get away for a quick trip but don’t have a lot of time to give up. Sometimes, a short trip can be just as fulfilling as a week or two away.

While researching our flights from New Zealand back to Toronto, Tristan and I weren’t exactly excited about the prospect of spending 24+ total hours up in the air. As we looked over our route (Christchurch to Sydney, Sydney to Honolulu, Honolulu to Vancouver, Vancouver to Toronto) we couldn’t help but feel a little excited that we’d be flying through Hawaii. So we did what any sane person would do (right?). We decided to break up the trip and spend 2 nights in Honolulu, Oahu. I know, toughest decision of our lives! Our flights also worked out in such a way that we would arrive at 8am and depart in the evening, so it meant we had 3 days to spend on the island.

We viewed our stopover in Hawaii as a final bonus to our backpacking trip, a little “mini-vacation” from 8-months of travel. But even though we were tempted to just relax on the beach for 3 days, we couldn’t just sit there and not experience a little bit of Hawaiian culture. Clearly, our travel style wasn’t going away any time soon.

We had less than 72 hours on the island of Oahu, so we decided it would be best to stay in tourist-central Waikiki. Below is a guide to help you maximize your short vacation time on the island.

Day 1

You’ve arrived bright-eyed and bushy tailed from an overnight flight. Make your way to your accommodation either by public transportation or taxi. We opted for the public bus, which got us right into central Waikiki for $2.50/person. It’s likely that you won’t be able to check into your room until 2 or 3pm, so ask to leave your luggage in their storage room and go grab a bite to eat.

Hike Diamond Head

Diamond Head, Oahu, Hawaii
Looking out onto Waikiki from the top of Diamond Head.

After you’ve dropped off your luggage in your room, head out to Diamond Head, one of Hawaii’s most famous natural landmarks. Located just east of Waikiki, Diamond Head is an extinct volcano crater that got its name after 19th century British sailors thought they had discovered diamonds in its slopes (they turned out to just be shiny crystals). The moderate intensity hike takes less than an hour and provides amazing panoramic views of Waikiki and the South Shore. A public bus from central Waikiki takes about 30 minutes, and entrance to the park is a meager $1/person.

After the hike, make your way back to Waikiki Beach, give your feet a rest and enjoy the sun set.

Day 2

It’s your one and only full day on the island. So make the most of it!

Go Surfing

Surfing in Hawaii
Everybody’s gone surfing…surfing USA.

Hawaii and surfing are practically synonymous.  The best surfers in the world have all surfed the shores of Hawaii, so why not give it a try yourself. If you’ve never done it before, you should consider signing up for a lesson. It’s a lot harder than it looks. If you’re confident enough in your skills, surfboards are available for rent right on Waikiki Beach. We paid $20 for 2 hours. Waikiki is ideal for beginners as the waves don’t get particularly big (be sure to be on the water by 9am so you’re not fighting the tide), but for those looking for a challenge, consider making the trip up to the North Shore where the pros go. Keep in mind, it takes about an hour to drive there from Waikiki. If surfing doesn’t tickle your fancy, you can also try stand-up paddling, a new sport quickly gaining popularity.

Waikiki Trolley

What to do in Hawaii.
All aboard the Waikiki Trolley!

You’ll see a lot of the “hop-on-hop-off” buses driving around Waikiki, but none of them are as charming as the Waikiki Trolley. Modeled after the classic San Francisco Cable Car, there are 3 different routes to choose from (Scenic, Historic, or Shopping Tour). A single day ticket costs $25 and allows you to ride all 3 of the routes, getting on and off as many times as you like. After yesterday’s hike and today’s surfing, you’ve earned the right to sit back and let someone else do all the work.

Attend a Luau

Luau in Hawaii
Hawaiian dancers entertain us at the Paradise Cove Luau.

One of the best ways to learn about Hawaiian culture is to attend a luau. We decided to check out Paradise Cove Luau, one of the largest in Hawaii. Located about an hours drive west of Waikiki, we were picked up and transported to the site, welcomed with mai tais and leis, tried our hand at traditional games and lei making, watched the traditional Hukilau Ceremony, and learned about the process of Hawaiian underground cooking. Of course no luau would be complete without a buffet meal and live performance. The basic package tickets are $88 a person and include transportation, food, entertainment, and 2 drink tickets.

Day 3

Before you head out for the day, pack your bags and ask to lock up your luggage in the storage room so you can maximize the time you have left.

Honolulu Central Business District

What to see and do in Oahu, Hawaii.
‘Iolani Palace

Take the public bus to Honolulu’s Central Business District and explore the historic buildings on your own. In a small, two-block radius (with Richards St. to the west, Punchbowl St. to the east, S. Beretania St. to the north, and S. King St. to the south) you can visit the ʻIolani Palace, Kamehameha Post Office, Aliʻiōlani Hale (currently used as Hawaii’s Supreme Court), King Kamahamaha V statue, the Hawaii State Library, and Kawaiahaʻo Church.

Go Shopping

Waikiki, Hawaii
Pick up some souvenirs at the International Market Place.

There’s no shortage of shops in Hawaii, especially in Waikiki. Kalakaua Ave is lined with name brand stores like Chanel, Forever 21 and even Apple. If you’re looking for some last minute souvenirs to bring back, check out the International Market Place, located on Kalakaua Ave between the Holiday Inn and the Sheraton Hotel.

Although Waikiki is the tourist-hub of Hawaii, there was still something very authentic about the area. Hawaiians are beautiful, both inside and out. Their warm hospitality, laid-back mannerisms, and desire to share their culture really came through, even in the short amount of time we were there. It’s totally possible to have a completely fulfilling holiday, even if it lasts less than 72 hours.  Research your destination in advance and just dive right in!


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