How We Did It: 6 days and 5 nights in Hawaii

This is part of a series explaining how Travel Freely members can 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.

Our destination was Kauai, the Garden Island of Hawaii. The trip was a combination of fun and relaxing. 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 direct flights. 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. For the return flight, United did not have great options on the way back. We ended up flying 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.

Important tip: Many people never think about booking award flights as one-way tickets. Often you can find better award tickets, especially in business and first class, if you search for one-ways. The reason this works out is because one-way award tickets are normally half the price of roundtrip. So, you don’t pay a premium for one-ways with miles the way you do when paying cash. That can be especially handy when looking for business or first class tickets one way and then economy on the way back. There’s no requirement that you fly the same airlines on both flights! You can have a totally different airlines for your departing and returning flights.

 

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

 

 

 

 

Free Hotel Nights at Sheraton Kauai

 

The Sheraton Kauai (under Marriott Bonvoy) did not disappoint. We used points from welcome offers on a personal and business card to cover the stay. 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.

 

 

Marriott award stays of 4 nights get the 5th night free. So we booked 4 nights with points and got the 5th night free. It’s essentially like getting a nice discount on your average points per night. 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. They have some great deals for Costco members. We paid for the car rental and helicopter tours ourselves, but if you have a Capital One Venture card, you can have the option of erasing travel expenses using Venture miles once the card statement comes out.  You can redeem Venture miles to reimburse yourself for any expenses that code as “travel” on your credit card bill. 

 

 

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.

 

 

 

Overview of Awards Used

• Nonstop Flights from Denver to Lihue, Kauai (22.5k miles each on United Airlines. Return flights – we flew back separately via Hawaiian Airlines and American Airlines (30k Hawaiian miles and 25k Advantage miles)
• 4 award nights + 5th night free at the Sheraton Kauai at Poipu Beach
• Car Rental from Costco Travel ($250, option to get reimbursed using Capital One Venture miles)
• Helicopter Tour ($370 total, option to get reimbursed using Capital One Venture miles)

 

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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