How to book virtually free flights and hotels for an epic Hawaiian vacation with just 2 rewards credit cards

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Hawaiian Airlines Flight

Hawaiian Airlines

Even though Hawaii is part of the United States, traveling there feels like a journey to a different world. Each Hawaiian island is as diverse as it is beautiful, but they all feature stunning beaches and dynamic landscapes that will take your breath away.

Lush greenery, volcanoes, waterfalls, and crystal-clear waters perfect for surfing and scuba are the norm in this tropical paradise, making any vacation there a dream come true for both nature lovers and lovers of water and sea life. The only problem? Hawaii is notoriously expensive to visit, both due to the exorbitant costs of airfare and the high prices of hotels.

Fortunately, many travel credit cards make it possible to rack up rewards perfect for an epic Hawaii trip. If two spouses were to pick up two cards and earn the sign-up bonuses on both, they could even get both their hotels and their airfare fully covered for the Hawaiian vacation of a lifetime.

Read more: Most people think paying $450 a year for a hotel credit card is insane - here's why I signed up for the Hilton Aspire anyway

Hawaiian Airlines World Elite Mastercard

Like any trip, the first detail you'll need to handle for your journey to Hawaii is airfare. For this component of your trip, you should consider picking up the Hawaiian Airlines World Elite Mastercard.

Not only does the Hawaiian Airlines World Elite Mastercard offer 50,000 bonus miles after you spend $3,000 within 90 days of account opening, but you also earn 3x points on Hawaiian Airlines purchases, 2x points on gas, dining, and grocery store purchases, and 1x points on all other purchases. You also get a free checked bag on Hawaiian Airlines flights, along with a $100 annual companion discount and no foreign transaction fees.

Currently, Coach SuperSaver flights from the US mainland to Hawaii are just 20,000 miles one-way or 40,000 miles round-trip. You can also fly within the Hawaiian Islands for just 7,500 miles one-way with a Coach SuperSaver fare.

As a result, each person who signs up for the card and earns the sign-up bonus would have enough miles for a round-trip open-jaw fare into Hawaii and one intra-island flight at the very least. This makes this card perfect for a couple who both get the card and want to visit two islands during their trip. For example, a couple could use 20,000 miles each to fly into Oahu, 7,500 miles each to fly from Oahu to Kauai, then 20,000 miles to fly home to the US from Kauai.

On top of their airline miles redeemed, however, each person would need to pay government-mandated airline taxes and fees of $5.60 per leg.

The Hawaiian Airlines World Elite Mastercard also charges a $99 annual fee.

Hilton Honors American Express Ascend Card

When it comes to covering your Hawaiian hotels, focusing on the Hilton Honors hotel loyalty program is an absolute no-brainer. This is mainly due to the fact that there are so many Hilton hotels all over Hawaii, but it's also due to the fact the Hilton Honors American Express Ascend Card makes it so easy to rack up points.

Currently, the Hilton Honors American Express Ascend Card is offering 125,000 bonus Hilton Honors points after you spend $2,000 on your card within three months of account opening. You also earn 12x points on all your Hilton Honors purchases, 6x points at restaurants, supermarkets, and gas stations in the US, and 3x points on all other purchases.

Finally, this card comes with no foreign transaction fees, automatic Hilton Gold status, and a free weekend night award from Hilton Honors after you spend $15,000 on purchases on your card within a calendar year. This card does charge a $95 annual fee.

While the points you need for a free night can vary at Hilton properties depending on dates and demand, some of your hotel options include:

  • Grand Naniloa Hotel Hilo - a DoubleTree by Hilton: 40,000 Hilton Honors points and up
  • Hilton Garden Inn Waikiki Beach: 49,000 Hilton Honors points and up
  • Hilton Hawaiian Village Waikiki Beach Resort: 58,000 Hilton Honors points and up
  • Hilton Garden Inn Kauai Wailua Bay: 45,000 Hilton Honors points and up
  • Grand Wailea, a Waldorf Astoria Resort: 95,000 Hilton Honors points and up

These are just some of the Hilton properties you could choose from, but there are plenty of others. Also note that Hilton Silver members and those with higher status receive a 5th night free when they book certain five-night stays with Hilton Honors points. The Hilton Honors programs also lets you pool your points with up to 10 people within the program, which makes it a winner for couples who want to combine their points together for optimal travel redemptions.

As an example of how this could work, let's say that two partners both signed up for the Hilton Honors American Express Ascend Card and earned the 125,000 bonus Hilton Honors points. This would leave the couple with 250,000 bonus points total not counting points they earned on their regular spending.

If they wanted to spend five nights at the Hilton Garden Inn Waikiki Beach at 49,000 Hilton Honors points per night, they could combine and cash in 196,000 of their points for four free nights and get their fifth night free provided standard award nights were available during their entire reservation period. They could also break their stay up across a few of Hawaii's famous islands, redeeming points for a few free nights at each.

The bottom line

If you're angling for a trip to Hawaii this year, a handful of rewards cards can make travel an especially cheap proposition. You'll still have to pay for food and fun, but having your airfare and hotels covered can help you stretch your travel budget much farther than most people realize.

Click here to learn more about the Hilton Honors Ascend from Insider Picks' partner: The Points Guy.

Click here to learn more about the Hawaiian Airlines World Elite Mastercard.

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