Off-time Adventures: Waikiki, Hawaii

It’s no secret that one of the chief benefits touted in the airline industry is the flight benefits. That is, if you can use them. Though you may never get to visit Rome in the summer on non-rev benefits, with some planning [and backup planning], you might just luck out.

With luck in tow and hopes high, we headed out to Hawaii this fall. Though the flight out itself was rather uneventful, part of that was because we flew out a night before and did an overnight in DFW to increase our odds of making it out on the first try, which we were able to do. Several hours of “Making a Murderer” later, we landed in Honolulu!

Knowing that we had more limited time, we mapped out our itinerary in advance, some of which was scaffolded out with the content of my blogger friend, Kait. [If Hawaii is your jawn, her content will inspire you and give you actionable ideas on how to maximize your time on the ground.]

With that in mind, here’s what we did over the course of our 6 day trip:

  • Morning hike of Diamond Head and crater

  • Drove around the island and to the North Shore [with stops to snorkel and ogle at the waves and water]

  • Ate our body weight in shave ice

  • Brewery hopped to two local places plus one tap room

  • Floated and people watched at Waikiki Beach

  • Went to a luau

  • Ate some amazing food: Udon, plate lunches, sushi, poke

  • Tried [and failed] to go to Pearl Harbor. We arrived and the entire site was closed [with no admittance or notice] due to a sidewalk safety concern and medical emergency.

Key Takeaways In Making This Happen:

  • We chose an Airbnb with a flexible 24 hour cancellation policy. That way, if for whatever reason we got stranded in Dallas, we wouldn’t be out the total cost of our accommodations. Hotels generally have more flexible policies, but doing the trip on the cheap required that we find more affordable places to stay. Even so, we ended up with a condo in central Waikiki two blocks off the beach.

  • Have backup flights both ways and for every leg of the journey. Consider arriving in a layover airport the night before to max out flight options.

  • Go on the shoulder/off season if you can swing it. We had more flight availability for departures and returns. However, going on the off season also meant that if the flight for the day filled or was cancelled, another one wouldn’t be available until the next day [which happened on our return from Honolulu]. Which takes us to…

  • Leave a buffer day coming back. Crew knows better than anyone the impact of delays and cancellations. Don’t make your timeline any tighter than it needs to be.

  • We had a buffer day mid-trip to do something that we wouldn’t know about before we arrived [we ended up using it to drive back to a secluded beach we fell in love with]. While planning was essential in actually being able to see and do everything we wanted in a fairly limited amount of time, a buffer day mid-trip allowed us to do something that we really wanted to do without sacrificing other plans.