Welcome back to another trip report post! In this post, I will recap my recent trip to Oahu, Hawaii! Its been over a year since my last trip report, so this one is way overdue.
Posting my trip reports are one of my favorite parts of having my blog as I get to recap how anyone can travel for cheap if they want to, even if they are in debt. I see all too often that people make excuses why they can’t travel. I hear: “I wish I could, but I have no free time” or “I can’t afford it right now, but maybe in the future.”
For me, I want to prioritize travel now because I am not guaranteed anything, so I want to explore the world as much as possible now.
To travel cheaply, I utilize Travel Hacking to get flights, hotels, and rental cars for free or reduced costs. I put my everyday spending on travel credit cards and strategically open up new travel cards when I know I have high future expenses that will meet the minimum spend requirements. I always pay off my credit cards in full every month and never accrue any debt.
Related posts: Introduction to Travel Hacking & How Much I Saved This Year by Travel Hacking
If you’re interested in getting a customized Travel hacking plan check out my Travel Hacking Consult page for more details
Check out some of my previous trip reports below:
Hawaii
This year I have been focusing on paying off my upcoming wedding (in January 2020) and planning my honeymoon, so my personal travel schedule has taken a brief hiatus. However, that didn’t stop me from booking a trip to Hawaii 2 months before my wedding. Most people wouldn’t go on a Hawaii vacation so close to their wedding date; however, because of the power of travel hacking, I was able to make it happen. I spent a small percentage of what the trip would have cost if we paid full price.
Below is how I accomplished my first ever Hawaii trip with my fiancee.
Flight
We have the Southwest Companion Pass so I can get my fiancée to fly free with me when I book with points through Southwest. The Companion Pass has been a crucial part of us being able to accomplish so many trips in the last few years.
We obtained Companion Pass by signing up for 2 Southwest Credit cards while they were offering their 60k bonus on each card. I had signed up in October 2017 and met minimum spend requirements for both cards on Jan 1st, 2018.
Note: Southwest changed the rules where you can’t get two personal SW cards at one time. However, you can still get one business and one personal card to obtain Companion Pass quickly.
Our Companion Pass is good until the end of 2019, so we wanted to take advantage since Southwest opened up flights to Hawaii last year.
If you are in the position to get the companion pass, I recommend it. It’s the best value for domestic flying in the travel rewards market. If I didn’t have Companion Pass, I would be transferring my Chase Ultimate Rewards points to Southwest or United to book single flights with points.
Hawaii Bookings on Southwest
To find good Hawaii deals on Southwest, you have to act quick because the flights get booked very quickly. After following Go To Travel Gal and subscribing to her email list, I found out the times when Southwest released their new flights. In May, they released all the flights up until the end of 2019.
I set my alarm for 6 am on the release date, and I found a round trip flight from Austin to Honolulu for 37k southwest miles. I quickly transferred 37k Chase Ultimate Rewards points to Southwest and booked the flight. Since I had the Companion Pass already, I was able to add my fiancee to the same flight for free.
Total Costs: 37k points + $22.40 (mandatory taxes)
Hotel/lodging
Whenever I am picking a place to stay, I always compare Hyatt (my favorite hotel reward program), Chase Ultimate Rewards portal, and Airbnb to see what the best value is for my trip. Booking a place to stay in Hawaii is expensive. Most (nicer) hotels are over $300 per night in the Waikiki area. So I wasn’t looking to pay cash for a hotel stay here. That also meant there weren’t many deals on the Chase Ultimate Rewards portal since the points rates are based on the cash value of the hotel.
Airbnb was an option, but the downside was we only had two people, and I couldn’t use points for our stay with Airbnb. If I went the Airbnb route, I would be spending at least $500 + for four nights.
That leaves looking for options on Hyatt. I ended up finding a pretty sweet deal with Hyatt by using points. There was a Hyatt Place 2 streets off the beach in Waikiki that was only 12k points per night. It was a great deal because the room was usually $250 – $350 per night (2-3 cents per point redemption). Most other Hyatts or Marriotts in the area were going for 25k points or more per night. The hotel also had cool perks like free rentals for beach equipment (beach towels, beach chairs, snorkel gear, etc). They also provided complimentary breakfast, which is always vital to keeping food costs lower.
I transferred 48k(12k per night * 4) Chase Ultimate Rewards points to Hyatt and booked my stay.
Total Costs: 48k points – $0 out of pocket for four nights
Rental Car, Food, Souvenirs & Miscellaneous Costs
Rental Car
Unlike my flight and hotel, I paid for my rental car in Hawaii. I found out about this rental car site called AutoSlash earlier this year and now use it all the time to find the best deals on rental cars.
The cool thing about Autoslash is it finds you the best deals on car rentals, even if you have already booked elsewhere. That was what happened in my case. I had booked a car in the Cash Ultimate Rewards portal for $212 using Dollar car rental (for an SUV). I typed in the same details into Autoslash, and it returned a deal for $149 for the same SUV option with Hertz. They took care of canceling the first rental for me and booked my SUV with Hertz. They also email you if they find you a better rate before your trip dates.
Total Rental Car Cost – $149
Total Rental Car Gas – $33.99
One bummer of the trip was there was minimal parking in the area we were staying in. Most people don’t rent a car when they go to Hawaii, but for us, it was a necessity for all the places we wanted to go to. There was a public parking garage that was a few streets away for $20 per day. However, it was on a busy intersection and would have been a hassle to cross traffic every day (especially checking in and out of the hotel with our luggage).
We ended up doing valet parking at the hotel for $39 per night. Usually, I would say valet is a waste of money and not do it, but in this situation, I was pretty glad we did. We saved so much time and eliminated any worries about the car (the hotel would cover any damages to the vehicle under their watch). The convenience was worth the cost for us.
My fiancee and I split the cost for four nights – $156 ($78 per person)
Total Transportation Costs – $338.99
Food
Finding new places to eat is one of our favorite things to do when we travel. For Hawaii, getting authentic Hawaiin food was a must for this trip. We ended up eating a lot of Poke, Hawaiin BBQ, and seafood on the trip. Hyatt provided free breakfast every morning, so that was important for keeping costs low.
We also made a stop to the local Costco in Oahu to pick up snacks and some quick lunch foods while we were on the go.
Our favorite spots to eat where:
Coco Cove for Poke (Waikiki Beach)
Big Wave Shrimp Truck (north shore of Oahu).
Total Food Costs – $128.45
Souvenirs & Miscellaneous Costs
Nothing too crazy here for Souvenirs. We picked up some fridge magnets at a local shop and some t-shirts for my parents and ourselves.
Total Costs – $62.99
Entertainment
If you have read any of our other trip reports, you would see we love enjoying the outdoors. In Hawaii, there were so many cool spots to see. Since we had the rental car, we were able to explore all over the island of Oahu.
The first day, we arrived in the afternoon and decided to relax and check out the beach in Waikiki.
The 2nd day, we drove to North Shore of Oahu (surfing capital of the world) and went to Waimea Bay. It was a great beach with some massive waves. It was my first time to see 20-25ft waves. The beach was clean, and the water was crystal clear.
After the beach, we talked with some locals and went on a hike at a local state park that overlooked Waimea Bay (we had the place to ourselves). Meeting locals always enhance our travel experiences.
After North Shore, we drove the west side of Oahu and checked out Mermaid Caves – a cool spot where you can swim inside the caves.
We capped off our 2nd day at Chiefs Luau – a traditional Hawaiin Luau that provided dinner and one heck of a show.
Our third day was pretty special. We woke up early and hiked up Diamond Head. Diamond head is a massive crater on the south point of the island. The hike wasn’t too bad and gave us some pretty cool views.
Later in the afternoon, we went to Hanauma Bay Nature Preserve. Hanauma Bay was created by a volcanic explosion and created a protected bay (shown below). It is known for having calm/shallow water and a high population of exotic fish and coral reefs. Here, we had a fantastic time snorkeling in Hanauma Bay.
Our 4th day was dedicated to Kualoa Ranch. Kualoa is located in the northeast part of Oahu. Many movies were filmed there, such as Jurrasic Park/World, 50 first dates, Pearl Harbor, King Kong, Godzilla, The Last Frontier, and TV shows like Lost and more. We had a great time going on a movie set tour, riding ATVs, and exploring the area.
Total Entertainment Costs – $292.74
Total Costs for the Trip: $845.57
Review
Hawaii was one of my all-time favorite trips. It was indeed like something I haven’t seen before. The beaches were amazing; the water was crystal clear everywhere we went, the hikes were great, the weather was 75-82 and sunny, essentially the whole time we were there, the food was excellent. I really can’t believe I didn’t come here sooner.
$845 for the trip might not sound like a budget trip, but considering that we got 2 round trip plane tickets from Tx to Hawaii for basically free and had no cost for the hotel, this trip could have easily cost $2500-$3k. I was glad I decided to “splurge” a little on the Luau, Kualoa Ranch tours, and I don’t regret the valet parking due to the parking situation.
By travel hacking the flight and hotel on each of our trips, we are cutting out the most substantial travel expenses. Due to our highest costs getting cut on this trip we were able to do better activities. For me, it was worth it.
I can’t wait to revisit Hawaii. Next time I would like to stay longer and visit some of the other islands.
My Automatic Travel Savings Plan
To pay for my trips throughout the year, I put money away automatically 2x a month in my Capital One Performance savings account*. I have separate savings account just for travel, so it makes my budget trips very doable because I already have the money in my account. So I never really have to adjust my monthly cash flow for travel. I withdraw from my travel account to pay for the trip.
Question for You!
What’s holding you back from traveling more?
How do you get the most value when you travel?
What are your favorite things to do in Hawaii?
Gary is the author behind Debt Free Climb, a blog that shows how to live intentionally, pay off their debt, build a side income, and travel the world
Gary's favorite free financial tool he’s been using since 2017 to manage his net worth is Personal Capital. Each month he uses their free Investment Checkup tool and Retirement Planner to track his investments.
His favorite way to save automatically is Capital One Performance Saving, a bank that allows him to create multiple high-interest savings accounts and create an automatic savings plans for each account. He uses these features to meet short and long term savings goals.
His favorite way to save money on car insurance is by using Root, an app-based car insurance service. He saved $240 this year after switching from Geico to Root
- Debtfreeclimb 2020 Update - October 23, 2020
- DebtFreeClimb v2- Our Debt Freedom Progress Report - June 17, 2020
- Trip Report: Our Honeymoon (not on a budget) - February 7, 2020
What a great breakdown, Gary! Your trip looks amazing—and coming from Texas, $845 is definitely a steal for four nights. (I gotta see how flights are from Houston now.) Also seems like this trip was a nice preview of your upcoming honeymoon 🙂
Joyce @ Financial Impulse recently posted…Making Money from YouTube Videos: Interview with Ryan Scribner
Thanks a lot, Joyce! There are certainly ways we could have been “more frugal”, but I don’t mind spending more on experiences and increasing convenience at times. By covering the largest travel expenses with points it reduces the cost by ~80% right off the bat.
Really awesome information. Thank you for sharing excellent post. Keep it up.
As a Hyatt status member, Nicole and Stacey (VIP Services) made me feel very welcomed, amazing first impression! Additionally, had dinner at The Buffet and the service from the staff and my waitress Pam was exceptional. Their recommendations were on-point, and Pam didn’t overly check-on me to disturb my peaceful eating. Awesome Hyatt experience at this location! Thank you!
Yolanda recently posted…Best Budget Cross Trainers of 2020
Wow, this was such a steal of a trip for you guys! Thanks for all the tips, I bookmarked your site for when I book some travel in the near future hopefully!
Jemme recently posted…Sidney Spit Landscape Photography Planning
I love that Southwest has flights available to Hawaii – so cheap and economical! I’ve also had good luck on Oahu with an Airbnb, especially if you book with multiple days to spread out any cleaning fees. Thank you for sharing your tips!
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