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Today I want to share a story from TPG reader Matt, who used a variety of rewards to travel with his wife to Oahu and the Big Island:

My wife and I started planning our babymoon to Hawaii in September, shortly after we found out we’re expecting our first child. Having been to Kauai and Maui for our honeymoon six years ago, we thought it would be nice to visit Oahu and the Big Island this time. We had two requirements: our outbound flight had to be non-stop to the islands, and our return had to be during the day (no red-eyes if we could avoid it). Since we’re based in Denver, that left us searching for United availability on the outbound and relying on a West Coast stopover for the return. We opted to fly DEN-HNL-KOA-SFO-DEN, including a two-day stopover in San Francisco to allow a daytime return flight and see some friends in the Bay Area before heading home.

As we searched through United’s website, we saw additional saver availability thanks to our United credit card, and booked the DEN-HNL-KOA-SFO portion of the trip for 45,000 miles plus $16.80 in taxes and fees each. That itinerary would have cost $1,045 per person, giving us a redemption value of 2.3 cents per point. We took advantage of United’s Excursionist Perk to add a free inter-island flight on Hawaiian Airlines and an open jaw itinerary on the mainland. We then bought inexpensive cash fares for the one-way return from SFO-DEN.

Our United card also got us two free checked bags (except the HNL-KOA leg) and the opportunity to spend some pre-departure time at the United Club in Denver. Lastly, in order to secure the 90,000 miles needed for our booking, we transferred points from our Chase Ultimate Rewards account (earned through a strategic combination of spending on the Chase Freedom, Chase Freedom Unlimited, and Chase Sapphire Reserve cards). The miles appeared instantly while we were holding the itinerary.

For lodging on the Big Island, we booked five nights at the Marriott Mauna Kea Beach Hotel for 200,000 points, taking advantage of Marriott’s fifth night free benefit. We earned over half of those points from the Starwood Preferred Guest Business Credit Card [now the Marriott Bonvoy Business™ American Express® Card] in the fall of 2017 when it had a sign-up bonus of 35,000 Starpoints, which then converted to 105,000 Marriott points after the merger. Thanks to our Marriott Gold status, we were upgraded to a beachfront room during our stay. For our stopover, we redeemed two free night awards from our World of Hyatt Credit Card to book the Hyatt Regency SFO on the way home.

Finally, the week before we departed, we signed up for the American Express® Gold Card (with a targeted 50,000-point bonus) to earn 4 Membership Rewards points per dollar on restaurant expenses during our trip and receive the $100 restaurant credit. In summary, by stringing together sign-up bonuses, strong points earnings, and other miscellaneous card benefits, we experienced well over $5,000 of benefits for our dream Hawaiian babymoon! More importantly, this allowed us to be picky about our itinerary, and to stay at a beach resort that would have been out of our price range otherwise.

Ideally, you could plan your travels far enough in advance to figure out which points you need, earn them, and book awards while there’s still plenty of availability. Realistically, however, your plans won’t always come together that smoothly, and you’ll have to work with what you’ve got. Earning rewards takes time, and in some cases rewards you’ve already earned may not show up in your account right away. To avoid having to wait for points and miles to accrue, it helps to keep some on hand for when you need to book on shorter notice.

Matt’s story is a great example. While he and his wife didn’t book at the last minute, they did have limited time to travel before the baby arrived, and earning that many points and miles beforehand would have been a stretch. Since they already had a plenty of Marriott and Ultimate Rewards points, they could immediately start looking for a suitable itinerary. I don’t advocate holding rewards indefinitely, since expiration policies and devaluations can eat away at their value, but maintaining a stockpile will make it easier to book awards when you want to travel spontaneously.

I love this story and I want to hear more like it! In appreciation for sharing this experience (and for allowing me to post it online), I’m sending Matt a $200 airline gift card to enjoy on future travels, and I’d like to do the same for you. Please email your own award travel success stories to info@thepointsguy.com; be sure to include details about how you earned and redeemed your rewards, and put “Reader Success Story” in the subject line. Feel free to also submit your most woeful travel mistakes, or to contribute to our new award redemption series. If your story is published, we’ll send you a gift to jump-start your next adventure. Due to the volume of submissions, we can’t respond to each story individually, but we’ll be in touch if yours is selected.

Safe and happy travels to all, and I look forward to hearing from you!

Featured photo courtesy of Mauna Kea Beach Hotel, Autograph Collection

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