Jeff and his family enjoying another Hawaiian sunset on Polo Beach in Wailea.
The Travel Miles 101 family is rich with tales of travel adventures from across the globe. If you’re not yet part of our private Facebook group, join our free email course here to gain access and learn how to take these life-changing trips yourself!
Today we’re sharing one of those amazing success stories. Jeff H. has been collecting travel points and miles for three years, after reading about the concept on a travel blog. Coming from a finance and accounting background, Jeff had always been very conservative with credit cards, usually paying with his bank debit card.
“Then one day it just clicked with me that I could be earning cash and points instead of earning nothing,” Jeff said with a laugh. “And just using my regular spending, I could start paying for our vacations.”
This traveling family is a great example of folks who take the time to understand their local market and customize their points and miles strategy based on the availability of airlines and seats at their regional airport.
Jeff’s home airport of Denver is a hub for behemoth United Airlines, so UA’s MileagePlus program provides the foundation for the family’s travel rewards strategy.
Traditional Hawaiian shaved ice at Ululani’s in Lahina.
“Before Chase’s 5/24 rule, my wife and I acquired two or three Chase United cards each, so over those first few years, we accumulated hundreds of thousands of airline points.”
In November of 2016, Jeff, his wife, and their 12-year-old son took their third trip to Hawaii in the last 2 years. There’s a lot to love about Hawaii as a destination for this family. It’s a 7-hour nonstop flight from their home airport of Denver, and it’s hard to beat this tropical paradise that doesn’t require knowledge of a foreign language.
The Flights to Paradise
Round trip tickets clocked in at 45,000 United miles round trip, per ticket. The only out-of-pocket cost for the airline tickets was the tax of $11.20 per ticket.
The Fairmont Kea Lani in Wailea as seen from beautiful Polo Beach.
Hotels in Hawaii
The hotel accommodations were equally impressive, with two free nights at the Fairmont Kea Lani in Wailea, courtesy of the 2 free night bonus on the Chase Fairmont card (which unfortunately no longer exists!).
When the family moved the party to Kaanapali, they parked at one of their favorite hotel brands, the Westin, taking advantage of SPG’s stay-4-nights-get-the-5th-free on category 4 or higher properties. Five nights at the Westin ran the family only 48,000 Starwood points.
In addition, Jeff earned 1,500 Starwood points during this stay from his Gold level welcome gift and opting in to the hotel’s Make a Green Choice Program for the week.
“Free flights and free hotel? It’s hard to beat a nearly free trip,” Jeff said.
As our TM 101 resident experts on Hawaii, we asked Jeff to share some of the highlights from his most recent trip.
Ziplining in Kapalua
Calling it the highlight of their excursions, Jeff reported that the scenery was remarkable. “We had just bought a go pro camera so we shot a video of that day – my son loved it and we all had a blast.”
Parasailing in Lahina
“My wife and I went parasailing on our honeymoon in Hawaii fifteen years ago, so it was great for both of us to do it again with our son – all three up together. The view of the mountains of Maui when you’re 1,200 feet up in the air is incredible.”
Napili Bay in Kapalua.
Kapalua Coastal Trail
This free adventure made the family’s must-do list. “This was a new part of the island for us and the views and scenery were so beautiful. We would highly recommend it.”
Breakfast with a View
Sea House Restaurant in the Napili Bay area offered reasonable prices for breakfast, with some of the most gorgeous views on the island.
Jeff said he and his family will be back to Hawaii, as it’s become their go-to family vacation spot.
But he has his eye on another dream adventure for the future – Machu Picchu.
“I love the idea of making the 4-5 day hike down into the site. What an experience that would be,” Jeff said. “And to think we can make that dream trip happen for free or very little money makes it even more incredible.”
For newbies to the travel rewards game, Jeff has a few words of wisdom.
Buddy System!
Get your spouse or significant other on board with the plan, and watch those points grow. “When you can tag team with your spouse, you’re essentially doubling your earnings. Before you know it you have half a million points.”
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A diver jumping at sunset – photo taken during the sunset torch lighting ceremony near Black Rock.
Baby Steps
The concept of rewards travel is simple, but can be a stretch for those with a more conservative approach to finances and life. “I’ve always been more cautious and didn’t want to do anything crazy. So we started slowly and I would recommend that to everyone.”
But after that first trip?
“You’re sold,” he said with a laugh. “We’re more hooked now than ever. Every time we take a free trip, we can’t wait to plan the next one.”