After over 2 years of planning (I have emails from Mrs. FIby35 to prove it), we finally made the much-anticipated trek to Hawaii in May of this year. Our 15 day, 14 night tropical extravaganza spanned 7 flights, 6 hotels, and 2 islands, making this my most laborious Travel Hack Recap to date. So much so that I decided to break it up into multiple posts to separate the activities and associated costs by region, with a cumulative total at the end. Without further ado, here’s the first post – a Travel Hack Recap of Hawaii: the Backstory.
Where we went (in excruciating detail)
This requires a fairly lengthy explanation before getting into our arrival in Hawaii itself. As I noted, planning for this trip began over 2 years ago with several iterations before it came to fruition. We learned a while back that Southwest Airlines was planning on opening routes to Hawaii starting in 2020 – perfect for our initial plan of traversing the Pacific in May 2020 with our newly-minted Companion Pass. Then, of course, COVID struck.
Once Hawaii reopened for tourism, we booked our flights from Minneapolis to Oakland, CA and Oakland to Honolulu, Oahu. As an aside (which will become important later on), the state of Hawaii required all travelers to take a COVID test by one of the state’s approved testing partners (Vault Health, if you’re interested) within 72 hours of their flight leaving their previous destination. The negative test results then had to be uploaded to a travel profile along with a detailed itinerary prior to even boarding the plane.
We thought we had things finally lined up, until Maui decided to require negative COVID tests for inter-island travel in addition to the test within 72 hours of departing the mainland. Our original trip called for 3 nights on Oahu before a short hop to Maui for another 8 nights, so this was not ideal. Fly all that way just to risk getting quarantined mid-trip? I don’t think so.
So we pivoted (thanks to Mrs. FIby35) and flipped our itinerary – starting on Maui before heading to Oahu. Southwest proceeded to rearrange our flights once, twice, and maybe once more after that, as they scrambled to piece together their flight schedule amidst the ever-changing local and federal restrictions. It was exhausting.
Just weeks before we were supposed to take off, our itinerary was finally set: an early morning flight on Thursday, May 6 from Minneapolis, long layover in Oakland, finally arriving in Kahului, Maui later that night. Eight nights later, we would fly to Honolulu, Oahu and spend 3 days before flying back to Oakland and on to Denver. The following morning (Sunday, May 16) we would return to Minneapolis.
For the obsessive planner I am, this whole ordeal was torture. I don’t care for surprises or plan changes. At this point, if you’re following along at home, you may be doing the math and wondering how 8 nights on Maui plus 3 nights on Oahu adds up to the 14 nights I mentioned up in the intro.
Well. Just 2 weeks before our trip, Hawaii announced it would be COVID-testing travelers upon arrival in addition to the required test 72 hours before departure, effective May 4. Rather than risking spending our entire trip in quarantine on our own dime, we pivoted again. Luckily, we had the work flexibility and stockpile of Hyatt and Southwest points to change our flights yet again and tack 3 more days onto the front end of our trip, leaving Minneapolis on Sunday, May 2, spending that night in San Jose, CA, and heading to Maui at long last on Monday, May 3.
Minneapolis -> Oakland -> Oahu -> Maui -> Oakland -> Denver -> Minneapolis
Minneapolis -> Oakland -> Maui -> Oahu -> Oakland -> Denver -> Minneapolis
Minneapolis -> Denver -> Oakland -> Maui -> Oahu -> Oakland -> Denver -> Minneapolis
Minneapolis -> Denver -> San Jose-> Maui -> Oahu -> Oakland -> Denver -> Minneapolis
After all that booking and re-booking, we were finally on our way on Sunday, May 2. Itinerary finalized, negative COVID test results uploaded to our travel profiles, we embarked on our longest vacation to date. I should have known that the adventure was just beginning…
