With its pristine beaches, lush landscape, and abundance of beautiful waterfalls, Maui is a dream destination. There is only one problem. Lodging is incredibly pricy on this particular Hawaiian island. Even camping or renting camper vans can cost over $100 a night! And while one might be able to rough it and get through a trip camping under the stars, my partner insists on a bed and a fully functioning bathroom.
I had almost given up on the thought of a trip to this island, until my favorite airline Southwest finally decided to fly from our home airport to Maui, and the deal was just too great to pass up. After quite a bit of time spent planning, I was able to book an amazing 6 nights trip to the beautiful island, including three nights in luxury resorts, for a grand total of $507.
In this post, I will breakdown how much everything cost and how we earned the points used.
By the time Southwest finally decided to put tickets to Hawaii on sale, I had already been waiting and following the news for months. As soon as they announced that the first wave of flights will be out of the airport 10 minutes away from us, I knew that we will have to make trip to Hawaii happen. On top of the perfect flight route, I also hold what I consider to be the best travel perk there is: Southwest Airline’s Companion Pass. The companion pass will allow my partner to fly with me for just taxes and fees (usually $5.60 one way). To get the companion pass, we also accumulated a ton of points that we could still use towards the flight.
On the day that the tickets went on sale, I was able to snag tickets at 7407 Rapid Rewards points + $5.60 each way. According TPG, these points are worth about $111 dollars. However, because I hold the companion pass, I was able to fly an additional person by only paying an additional $5.60. All in on flights for two, we spent $22.40 and 14,814 southwest points.
Most of these points were earned from the last time I was shooting for the Companion Pass. I did so by leveraging a 40K point signup bonus from a Chase Southwest Card and booking hotels on SouthwestHotels.com.
Maui Seaside Hotel: $128.69
Hyatt Regency Maui Resort And Spa: 25,000 World of Hyatt points
Courtyard by Marriott Maui Kahului Airport: 35,000 Marriott Bonvoy points
Airbnb in Hana: $129.84
Grand Wailea Maui, A Waldorf Astoria Resort (2 nights): Hilton Aspire Card Free Night Certificate + 95k Hilton Honors points
I had originally wanted to book the entire stay on points, but we really wanted to explore the entire island, maximizing time spent at each stop and minimizing driving time. And since points hotels in Maui are mostly luxury resorts, it didn’t make sense to stay at one every single night given our plans.
For example, our flight to OGG lands at night on the first day, so I decided to go for the nearest most reasonable option at Maui Seaside Hotel. The hotel is nothing fancy, but we were just there for a bed. It is also conveniently located by the ocean and a cluster of shops where we did some grocery shopping for the rest of the trip to keep our food budget in check.
I also figured that it would be a great idea (and it was!) to spend the night in Hana to extend our Road to Hana drive. There was only one luxury property in the area that is not bookable with points as far as I know. However, I was very lucky to find a fantastic Airbnb that was sparkling clean and cost just about the same as camping in the area.
For all of the points hotels, I used points we have earned through signup bonuses of various cards. I dipped into the 60k points I got from a special promotion World of Hyatt Card signup bonus. I also earned an elevated 75k bonus from the now discontinued Bonvoy AMEX Card. For the Grand Wailea stay, I used a free weekend night certificate from the Aspire card as well as 95k points from my Hilton Honors account. Partly earned from the Aspire signup bonus, and partly earned from some stays last year in Europe.
Having now completed the stays, I can say that the mix of locations and levels of luxury were just perfect. The lower tier accommodations (Maui Seaside, Airbnb, Courtyard) were all clean and comfortable, while the luxury resort properties were worthwhile splurges. Since we stayed all over the island instead of a single place, we were able to drive very little and spend more time at the resorts and points of interests. One thing to note is that we travel very light (one backpack each plus a bag of food, more on that in another post), so packing takes less than 10 minutes, so checking in and out was never a problem. If you tend to bring a lot of luggage with you, switching accommodations like this might not be a great idea.
Car Rental: $225.84
Renting a car to see Maui is one of the best decisions we made. Not only did it allow us a lot of flexibility and convenience, it also helped us save a lot of money on cab rides and tours. With a car, we were able to visit almost the entire island on our own time without booking a single tour. Most notably, we were able to do the famous Road to Hana drive ourselves.
Just for fun, I calculated how much we would have spent without any travel hacking here, and the total came out to be $3,158.26!
With a little bit of planning and saving on points, a comfortable and affordable trip to Maui can absolutely be done. We had a blast, and I hope my experience here can help you do the same.