• Menu
  • Menu

Last Minute 3 Day Trip To Oahu

Last minute trips are the best – especially when you’re escaping your cold local climate to the beautiful Hawaii

There’s just something about this place that is magical. The climate, the scenery, the people being so chill – literally everyone is smiling all the time. In my opinion the 5+ hour flight from mainland USA is worth it, even if only for a few days.

Search Last Minute Deals:

WestJet– Canada and US Flights

Southwest-You know them…line up.

Skiplagged– One of my favorite go to search sites.

Momondo– An all encompassing travel site.

Google Flights– A good starting point but always check the airlines directly as well, sometimes the prices are cheaper directly.

3-Days in O’ahu

Day 1 (unofficial)

Layover in some dreary airport due to the snow storm that you almost missed, but it got you anyway. True story, I was literally sitting on the next plane in line after the last plane that took off just before the storm hit… We waited 2 hours on the tarmac just in case there was a sliver of a window to get the hell out, but no dice.

ToeB was lucky enough to layover in Dallas where the airport allowed for warmer and quieter ambiance. They also provided cots and blankets! What the heck?

De-Icer and airport cots…winter travel at it’s best.

I on the hand had to layover in Chicago O’Hare – the world’s worst airport to “sleep” through the night. It is so large and there are windows everywhere, which makes for a very cold and loud setting. And forget about finding a comfortable place to lay your head – every bench has those pesky armrests. Bah!

Day 1A (official) – Arrive in Paradise

Most flights tend to go to Honolulu, the capital and largest city of the state of Hawaii. This city is actually on the island of O’ahu, one of eight islands on the Hawaii archipelago. Honolulu, meaning sheltered harbour, is located on the south shore of the island, and is the most populated Oceanian city outside of Australasia with roughly 1 million residents as of 2012. But that’s nothing compared to the estimated 7.6 million tourists that visit the island annually.

Landing in Honolulu-look at that density
HNL-Daniel K. Inouye International Airport-Honolulu Airport
Rolling into Oahu with my one bag strapped to my back like…

Higher population obviously means some level of congestion and more mainstream amenities that take away from the “vibe” of Hawaii, such as the many mega malls, retail enclaves and stretches of fancy boutiques and upscales stores. Honolulu is definitely a shopper’s paradise – be prepared to drop some coin.

PRO TIP: Buy Hawaiian products and whatever else you need at the ABC Store, Hawaii’s convenience store, and earn a free souvenir such as a T-shirt, mug or key chain.

To Stay in Waikiki :

There are plenty of hotel or hostel options, restaurants, bars and where most touristy things are based. Ironically, we chose to stay in Stay Hotel Waikiki (https://www.stayhotelwaikiki.com/), attached to the Wang Chung Karaoke Bar (http://wangchungs.com/), and conveniently located two blocks from the beach and the famous Duke Paoa Kahanamoku’s statue.

Stay Hotel Location
Stay Hotel Room-Waikiki Beach

FUN FACT: Somehow moisture got inside of my camera lens causing these really great O.G. Instagram filter style photos.

Popular Meet-up Location: The famous Duke Paoa Kahanamoku Statue – a bronze sculpture honouring the Hawaiian Olympic swimming champion and “father of surfing”, who popularized the ancient Hawaiian sport and brought it to the world. Duke is usually adorned with lei’s – presented by the Hawaiian people upon arriving or leaving as a symbol for affection.

Duke is a legend – worth the read of his wiki page (https://en.wikipedia.org/wiki/Duke_Kahanamoku).

Duke Paoa Kahanamoku’s Statue-Waikiki Beach

Places to Eat in Waikiki:

  • Anywhere they serve fresh tuna, sushi or poke, such as:
  • Marukame Udon: Known for their long line (which moves quickly) and their killer house-made udon noodles; nothing is over $10.
  • Duke’s Waikiki: Beach front restaurant with the staples
  • Rainbow Drive-in: Cheap Hawaiian classics
  • Hawaii Shave Ice:
    • Matsumoto Shave Ice: Located on the North Shore is always number on most Top Lists.
    • Waiola Shave Ice: Always a line at their two Honolulu locations and a local favorite since 1940.
    • Shimazu Shave Ice: Next door to Rainbow Drive-In they are known for their mountainous servings. 3111 Castle St, Honolulu, HI 96815
    • Monsarrat Shave Ice Natural Organic Fruit: They are not as sweet as the other shops, but if your into healthy fresh fruit this is the ice for you.3046 Monsarrat Ave, Honolulu, HI 96815
Hawaii Shave Ice and Guava Juice

Check out the Top 9 dining options recommended by Eater at: https://www.eater.com/maps/the-9-top-dining-destinations-in-waikiki

Places to Drink in Waikiki:

  1. Barefoot Bar at Duke’s Waikiki: Beach front bar where you can catch the sunset and a mai tai https://www.dukeswaikiki.com/
  2. Honolulu Tavern: Small dive bar excellent to start your evening
  3. Bacchus Waikiki: Gay bar that hosts numerous events throughout the year
  4. Arnold’s Beach Bar: A true tiki bar feel. Strong drinks and low prices.
  5. Kelley O’Neils: Irish pub best for late night drinks (one of the few bars open till 4am)
Honolulu Tavern
Arnold’s Beach Bar
Grab some Mai Tai’s-We never knew that pigeon was under us…

Day 2 – Tour the Island

Book an Island Tour – there are a lot of options, but most are about $100CAD pp by minibus and last the entire day. Pick up is usually in the morning near your hotel, and the tour includes multiple stops around the island.

We chose the Oahu Circle Island and Snorkeling Tour through Tripadvisor.

Oahu Circle Island and Snorkeling Tour Map

Tour Highlights:

  1. Visit the many pristine beaches along the east coast.
  2. Chinaman’s Hat-photo-op.
  3. Macadamias Nut Farm (great place to buy nuts and coffee).
  4. Halona Beach Cove-The From Here to Eternity beach.
  5. La’ia Point – this is the famous cliff where the characters from Forgetting Sarah Marshall jump off into the ocean (our tour guide and one of tourists actually jumped!).
  6. A secret beach near Sunset Beach.
  7. Keneke’s Grill at Punaluu-Hawaiian Style BBQ shack.
  8. Haleiwa Alii Beach Park-Snorkeling with the turtles at North Shore.
  9. Dole Plantation (get the pineapple ice cream!!).
  10. King Kamehameha Statue-Our awesome tour guide stopped here for a minute to talk about the history of the Iolani Palace including Princess Liliuokalani’s imprisonment and eventual overthrow. 
Halona Beach Cove-From Here To Eternity Beach
Chinaman’s Hat
Laie Point Cliff Jump-From “Forgetting Sarah Marshal”
Dole Pineapple Plantation – GET THE ICE CREAM!!

Hawaii is a dominant producer of pineapples, all of the pineapples grown on the island stay on the island. Although pineapples were introduced to Hawaii in the 18th century, the most famous investor was James Dole who started the famous 60 acres Dole Plantation in 1900. Pineapple production in Hawaii declined in the 1970s due to competition and a shift to refrigeration. Despite the decline, O’ahu produces 0.1% of the world’s supply of pineapples, and the pineapple fruit continues to be the symbol for Hawaii.

Pineapple Growing on the Dole Farm
King Kamehameha Statue

The tour ends early evening back in Waikiki, where you can have a short R&R before hitting up the bars, restaurants and nightlife.

Day 3 – Explore Honolulu

It’s choose-your-own-adventure day.

Pick from one or all of the following:

  1. Visit Pearl Harbour National Memorial – grab an Uber or take the bus west of the city. The bus is inexpensive and easy to navigate.
  2. Hike Diamond Head State Monument (walking distance from Waikiki beach). We took a bus to Diamond Head and walked back (down hill).
  3. Visit King Kamehameha I’s famous gold statue on South King Street, in front of the Hawaii Supreme Court Justice, and across the street from the Iolani Palace, the former home of Hawaii’s monarchs – an hour walk from Waikiki beach but several buses drive past this statue (https://www.gohawaii.com/islands/oahu/regions/honolulu/king-kamehameha-statue)
  4. Learn to surf at Waikiki Beach-one of the easiest places to surf in the world.
  5. Eat and drink your way through the various beachfront watering holes.
  6. Go shopping (real or window)
  7. Walk the beach and enjoy the sunset
  8. Go to the Honolulu Zoo-Pricing is as follows: Adults (13+) $19.00Children (3-12) $11.00Infants (Under 2) Free. They also have military discounts.
Diamond Head Entrance
View of Honolulu from the top of Diamond Head
Waikiki Beach Surfboard Rental
Traditional Hawaiian Hula
Waikiki Beach Sunset
Waikiki Beach Magic Hour
Waikiki Beach Sunset

Leave a Reply