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Hawaii Island Hopping – The Quad Squad +
- By Michael Lakus
- 2 Comments
- Read Time: 6 min
The Squad in Hawaii
The Quad Squad strikes again in Hawaii, but this time bringing friends. We spent an extended weekend on the islands of Oahu and Kauai hiking through jungle, eating all the foods, avoiding Smirnoff Ices and more! We even had time to drive all the way around each island to really get a feel for each.
Here is a summary of what went down – thanks Mark for the edit!
How to do Hawaii for less
Anyone who knows me, knows I’m a big time points guys. I won’t go into too much detail here, but felt it was necessary to mention how anyone can score cheap airfare to Hawaii. And to prove it, here is a picture of my total. I paid for two round trip flights from Orlando for just over 50k points. That’s the equivalent of roughly $500 total or $250 per flight. Not bad! So how does it work? Here are some pointers:
- I get notified about potential flight deals (there are several subscription services out there)
- I verify on Google flights, and then verify the prices match on the card issuers portal (think Chase Rewards, AMEX Rewards, etc)
- Using certain cards, redeeming points for flights nets me an additional 50% off an already cheap flight
- Book and pat yourself on the back
With that said, there are some things to be aware of:
- These are normally basic economy flights (understand restrictions)
- Flexibility is key
Nevertheless, 25k points round trip to Hawaii from the east coast is a steal. Not to mention unlimited complimentary drinks when a flight is considered “international.” I’m a huge fan of stretching points as much as possible for many trips rather than a few luxurious ones, so I’ll take an offer like this all day. Ok, now on to Hawaii!
The points game
In general practice, points are more valuable when redeemed with transfer partners for business and first class. However, it really comes down to travel preferences and frequency.
Hawaii - Kauai - Logistics
Even though we flew into Honolulu (HNL) the first day, our trip actually started on the island of Kauai. This is where the dinos are! Jurassic Park lovers rejoice. Anyways, we took an early flight from HNL to Lihue (LIH) where we would get exactly one full day to be on the island.
At first, this time stretch may seem ridiculous. But in the course of those hours, we were able to:
- Get an amazing breakfast
- Take a jungle hike on Kuilau Trail
- Grab drinks on the coast
- Look out over Waimea Canyon
- Stop at a brewery
Kalalau Trail Update!
This is the well known trail from many pictures of the rugged coastline on Kauai's north end. Very recently (Aug 2019), visitors must book and pay in advance to hike the trail. Trust me, we tried to just enter.
Kauai - One Day
Breakfast was at Kalaheo Cafe & Coffee Co and the food set the tone for the day. My sweet tooth got the best of me and I ordered some carrot cake complimented by a morning madness – 4 espresso shots added to a mega mug cappuccino. It was absurd and amazing.
After breakfast, our first mission was a 2 hour hike on the Kuilau Trail for some jungle vibes. It wasn’t our first choice, but I don’t think anyone regrets the views. At this point we did a pit-stop at Kalypso for drinks and to regroup. We decided to take the trek immediately to the other side of the island to see Waimea Canyon while light was still good before sunset. Once we reached the top, we could witness Kauai’s finest with a coffee chug Friday while other people around us looked very confused.
As the sun set, we made our way back around Lihue with time to spare. We were in desperate need of clean clothes after spending a full day hiking around. In the spirit of efficiency, we simply walked into a Walmart, purchased new wardrobes and then immediately went to a brewery to celebrate our success. Nice.
Hawaii - Oahu - Logistics
With the dino island checked off the list, the remainder of our time in Hawaii was spent on Oahu. Once again, we were able to fit in quite a bit of activity and drive the entire island!
- Snorkel and Diving
- Diamond Head Trail
- Manoa Falls
- Stairway to Heaven
- Restaurants
- Waikiki Nightlife
- Pearl Harbor
Oahu - Hiking
Two trails were done while on Oahu. The first being Diamond Head, and the second being Manoa Falls. Diamond Head is one of those “can’t miss” hikes. It’s easily accessible, relatively painless, and gives you great views of the island from the top of on old volcano.
Manoa Falls was a little more inland and took us on a 30 minute hike with the end being the falls. The hike itself was definitely on the easy side, and after everything we did on Kauai, this was a little underwhelming. I think I can give this one the skip.
The final hike, which I didn’t get to do, was Stairway to Heaven. The reason I am still mentioning it is because of the controversy around it. First, the hike is technically illegal if taking the quick Haiku Stairs to reach the top radio tower, but legal if you access it through a grueling 9 mile hike. Obviously, I wanted to take the stairs not only because it was quicker, but because stairs are a lot easier to climb than rugged terrain. Anyways, after much research one night, I finally decided to forgo it. I’m glad I did, too, because the next morning the rest of the squad heard from the locals that security has been increased quite a bit now in 2019. It’s really a shame, since the hike holds the best views on the island and probably one of the best in Hawaii.
Oahu - Nightlife
Unless there is some extravagant luau, the Sheraton Rumfire at Waikiki is the place to be. It’s a hotel in the day and full on club by night. Looking for the cheapest beer? Don’t worry. The Quad Squad discovered Beer and Be Merry in the shopping district in Waikiki. You’re welcome. Having a hangover in Hawaii is inevitable at some point! If that’s the case, check out Cinnamon’s for the brunch and the bloody Mary selection.
Naturally, there are not a lot of decent pictures for this section. Sorry.
Oahu - Boating and Food
Woah – a lot to cover in this section. First, we took a boat out not far from the island to dive down to a shipwreck 120 feet below the surface. I can’t speak from experience since I do not have a licence, but I heard second hand it was pretty cool. What I can speak on is Scuba Steve. Steve was a character, of the niche variety. This dude was quirky and relentless, but definitely provided us with unlimited inside joke material. What made it even better was his constant harassment of our squad mate, Kolbe, aka Professor S.
Alright, let’s talk food. We covered a lot on Oahu, but I’ll list the three:
- Ono Seafood
- Nico’s
- Shimazu Shave Ice
Ono is for the poke. It was the best I’ve had to date, even if I was sweating bullets from the spice. Nico’s on Pier 38 is an more upscale restaurant with just delicious dishes. Period. They have an expansive menu with all locally sourced seafood. No regrets here. Lastly is Shimazu Shave Ice for dessert. The kid-sized cone is basically an extra large. They have plenty of flavors, with the option of adding mochi and condensed milk. Sugar overload incoming.
Oahu - Pearl Harbor
Our last stop before heading back to the airport was Pearl Harbor. We spent a few hours going though the exhibits and getting a guided boat tour out to the battleships. It’s still crazy to think how those events transpired, starting the Pacific theater some decades ago.
Well that wraps up the Quad Squad + adventures in Hawaii. As always, the icing was plentiful, but we regret nothing. Until next time!
Recap of Places
- Kalaheo Cafe & Coffee Co
- Kuilau Trail
- Kalypso
- Waimea Canyon
- Diamond Head Trail
- Manoa Falls
- Nico’s Pier 38
- Ono Seafood
- Sheraton Rumfire
- Pearl Harbor
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Michael Lakus
IT professional, athlete, musician, ponderer of many things... Born and raised in Florida, I began traveling internationally after college. I created this site primarily to remind myself of where I've been and to share my experiences on traveling with a quirky, stress-free, travel attitude.
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This Post Has 2 Comments
I enjoyed reading your trip commentaries. You’re one lucky dude!
Thanks, Terra!