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This is part of a series explaining how Travel Freely members travel for free.
You might also want to check out our other series How We Did Costa Rica For Free! and Zero Expenses: How We Did Our Free Mexico Trip with Points.

We just got back from a super fun and relaxing trip to Kauai, the Garden Island of Hawaii. This was a babymoon for my wife and I, but it was also the first time back since our honeymoon in 2011. Needless to say, Hawaii is one of our favorite spots on the planet. Thanks to big welcome bonuses from top cards, we were able to use rewards to get free flights and free hotel nights during our stay. Because we saved so much money, we splurged on a helicopter tour and made shaved ice a mandatory, daily treat. =)

Free Flights to/from Hawaii


We flew on United Airlines to get to Hawaii because they had a great deal on a direct flight. It’s pretty amazing to fly nonstop to Hawaii. We transferred Chase Ultimate Rewards points to United MileagePlus and booked these flights for 22,500 miles + $5.60 in taxes. On the return flight, we flew back separately on Hawaiian Airlines (30,000 miles) and American Airlines (25,000 miles). The total for return flights was 55,000 miles + $13.20 in taxes. Grand total was 100,000 miles and $26.40 in taxes.


Total = $26.40 Spent vs. $1,650 Retail Price.



Direct flight from Denver to Lihue, Kauai for 22,500 United miles and $5.60 in taxes.



Free Hotel Nights at Sheraton Kauai


The Sheraton Kauai is a resort hotel that did not disappoint. Last year, Starwood merged with Marriott, which owns Sheraton. So, we were able to use Starwood Preferred Guest (SPG) points to stay here. We used points from our welcome offers we got from the personal American Express SPG and business SPG card. (Note: Now there is a new Amex SPG Luxury personal card). The resort included a pool overlooking the beach, which was just a few steps away. There were also plenty of other quiet spaces to view the sunrise and sunset each day.


Sheraton Kauai, beachside with the pool and palapas in the background

The open air resort feel is amazing, especially heading towards the beach.

At the Sheraton, the pool overlooks the beach. A pretty nice combo.

Sunrise at the Sheraton Kauai

Contemplating life while looking at a sunset on Poipu beach at our hotel


My wife and I combined our SPG points and used a total of 48,000 points to stay for 5 nights. The room was 12,000 points per night, and SPG had a promotion (as they often do) for getting a 5th night free when you book 4 nights. So, we still had to pay state taxes ($1.25/night) and a resort fee $30/night), which came out to $156.25 for the whole stay. This resort averages $260 to $420 per night. Putting this room at $300/night would come out to $1,656.25 with taxes and fees.


Total = $156.25 Spent vs. $1,656.25 Retail Price.


(Free) Car Rental and Helicopter Tour


We also rented a car to get around to local restaurants and to use on our day trips. When paying for rental cards, I like to use Costco Travel. They have some great deals for Costco members. We paid for the car rental and helicopter tours, but we have the option of erasing these expenses using points once the card statement comes out. Because we got good deals, we may save the points and use them for higher valued redemptions like future airfare or hotels. For purchases like rental cars or heli tours, you can use a Capital One Venture Rewards Credit CardCapital One Venture or Barclay Arrival Plus card to pay. Then, you can redeem miles to reimburse yourself for any expenses that code as “travel” on your credit card bill. 


Since I was a kid and saw Jurassic Park, I’ve always wanted to take a helicopter tour in Hawaii. Thanks to points and miles, we were able to achieve that dream.

Waimea Falls in Waimea Canyon seen from the helicopter

The famous Napali Coast. 90% of the coast can only be seen by helicopter or boat.


Seafood and Treats


Part of traveling for free with Travel Freely is getting to spend some of the extra money you save. Some people choose to stay longer or do excursions they would not have otherwise done. For us, it allows more room in the budget for food. We went to one fancy dinner at the #1 Yelp ranked restaurant in our area, Keoki’s Paradise. Then we checked out local food trucks and tried to find the best shaved ice on the island. Food can be a sneaky travel expense, but there’s much less financial stress when you get free flights and hotels.


Eating at Keoki’s Paradise, an incredible open air restaurant with delicious seafood.

Get some authentic Hawaiian food at Trucking Delicious in Hanelei – a great cheap, tasty meal

Wishing Well Shaved Ice doesn’t mess around. Pictured here: passion fruit and guava with coconut shavings.



Overview of Awards Used


How we earned the points:


Over the last two years, we earned the following bonuses for this trip…

  • Chase Sapphire Preferred: 50,000 points sign-up bonus

  • Citi Advantage Platinum Select World Elite MasterCard: 60,000 miles for sign-up bonus 

  • American Express SPG Card: 25,000 points for welcome bonus

  • Hawaiian Airlines Business card: 35,000 miles for sign-up


In Summary


Going to Hawaii on points can be a tough task because it’s such a popular destination. Spring Break and Summer are the hottest times, but people travel there year-round. Fortunately, we were flexible and able to get some great deals on flights. The hotel was a great steal as well.

There are plenty of other airlines and hotel programs you can use to stay for free in Hawaii. We chose our flights and hotels based on wanting to stay in Kauai and what worked best from Denver.

Overall, we used points from spending bonuses that we received from our average monthly spending. Each bonus takes roughly 60-90 days of normal spending to earn. We didn’t go out of our way to earn these points, and we were able to log them over time and convert them into an incredibly relaxing and memorable vacation.


Total Retail Cost of Flights and Hotels: $3,306.25


Actual Cost of Trip: $182.65


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