Member Success Story: $15,000 Saved on an Unforgettable Family Trip to Maui
When Travel Freely member and physical therapist Clay set out to plan a special trip for his family, he had 2 goals in mind — take his family somewhere amazing, and honor his mother-in-law on her 60th birthday. With his wife, 2 kids (ages 5 and 3), his in-laws, and his mom in tow, Clay used points and miles he’d been carefully accumulating to pull off a dream vacation to Maui, Hawaii.
Here’s how he did it and what made the trip so unforgettable.
Where do you live, and how long have you been using points and miles to get free travel?
We live in Lexington, South Carolina, and our journey with points and miles started years ago, even before my wife and I got married. Listening to the ChooseFI podcast inspired us to explore the world of travel rewards, and we were hooked from the beginning. We even covered most of our honeymoon at Sandals South Coast in Jamaica using points!
Fast forward to today, and points and miles have become a part of our lifestyle, enabling us to create incredible experiences for our family.
Where did you go and what did you do?
This trip was a special one — we wanted to celebrate my mother-in-law’s 60th birthday in style. Thanks to months of planning and saving points, we got all 7 family members (me, my wife, our 2 children, my mother-in-law, my father-in-law, and my mother) to Maui for a 10-night stay at the Hyatt Regency Maui. The resort was beautiful and the pools and waterslides were a hit with our kids. And we had access to the neighboring Hyatt Vacation Club pool, giving us a 3rd pool option.
Lucky for us, we received a Guest of Honor award on each of the 2 rooms we booked, giving us Globalist status so we could partake in free perks (free breakfast, snacks, and parking) which made the stay even more enjoyable.
The itinerary was packed with unforgettable experiences:
- Snorkeling cruise: We explored vibrant reefs, spotted sea turtles, a spotted eagle ray, and even saw a whale crest — an amazing sight in October, just before whale season.
- Hyatt’s Drums of the Pacific Lu’au: This cultural experience was a highlight, especially for my mother-in-law and our kids, and was located right on the grounds of our hotel. It was a great way to learn about Hawaiian traditions while enjoying the show.
- Hike to Twin Falls Maui: Our guide led us through the rainforest to stunning waterfalls, where we enjoyed wild fruits and learned about local flora and culture.
- Road to Hana: Despite the long drive, on this tour we saw lots of waterfalls and movie set locations and we made it to Wai’ānapanapa State Park’s Black Sand Beach. The lava rock formations and stunning coastline were breathtaking, probably my favorite part of the trip.
- Teralani Sunset Sail: A magical evening on a catamaran with a sunset over the water and incredible family photos.
- Haleakalā National Park: Driving from sea level to over 10,000 feet in 2 hours was an incredible experience. Although we missed the sunrise, the views at the summit were unforgettable. (Tip from Clay: Book a sunrise tour here for your first morning on Maui. With the time change, you’ll be up early anyway!)
What kind of points did you use for this trip?
For this trip, we primarily relied on the following cards. My wife and I doubled up on each of these cards, and the combination of these programs allowed us to maximize our savings and create an unforgettable vacation.
Card that earn Capital One Miles:
For a limited time, new cardholders get a $250 Capital One Travel credit to use in their first year! Best "easy to use" starter card (or complement to the Chase Sapphire Preferred® Credit Card) for those who don't want to think when it comes to earning and redeeming miles.
Great "ultra-premium" card. Despite the big annual fee, the overall first year value is worth it for most people. This is due to the large signup bonus, extra benefits like Priority Pass, up to $300 annual travel credit and Global Entry/TSA PreCheck credit.
Cards that earn Chase Ultimate Rewards® points:
Our #1 personal card we recommend most often. Hands down the single best "starter card" for beginners and the MVP card for free travel.
A no-brainer, great business card. Your choice to receive 1.5% cash back or 1.5x points.
Great signup bonus for a business card with no annual fee, now with an extended timeline for hitting the spend requirement. Great for carrying a balance. 5x earning categories, and if paired with a premier Chase credit card (one that carries an annual fee), your points are worth even more.
How much money did you save using points and miles for your trip?
We saved over $15,000 in total on this trip:
- Flights: Using Capital One Miles accrued by both my wife and I from the combination of cards listed above, we transferred points to British Airways and booked 7 roundtrip plane tickets for just $77 in taxes per person ($539 total). This saved us approximately $4,000, as each ticket would have cost approximately $600.
- Hotels: We used Chase Ultimate Rewards accrued by doubling up on the Chase cards listed above to book 2 rooms at the Hyatt Regency Maui for 10 nights. With a cash rate of $500 per night per room, we saved $10,000.
- Guest of Honor Pass Perks: A Guest of Honor pass for each room added another $1,000 in savings with free breakfast, snacks, and parking.
What advice would you give someone interested in booking a trip like yours, and what advice do you have for someone just starting with points and miles?
Anyone can do it! The biggest hurdle for us was getting used to applying for multiple credit cards throughout the year. With our lifestyle, we spend enough to hit most signup bonuses ranging from $2,000-$4,000 of spend in 3 months. It might seem like a lot to circulate bills to different credit cards, but it really only takes about 5 minutes to change which card you pay your water and electricity bill with. The digital wallet, Apple Pay, makes it easy for both me and my wife to use whatever designated card we need to hit the bonus on at the same time.
I, personally, like to target cards with no annual fee or waived annual fee for the first year. 2 of the Chase Ink business cards offer the best signup bonuses with no annual fees.
In order to be successful in this hobby, you must pay off the cards each month. Our credit scores are both >740 with applying for lots of cards.
Just like the market, time in the points hobby is better than timing the points hobby. Just get started!
How has Travel Freely helped you achieve your free travel goals, and what do you like best about the app?
We are always in Player 1 and Player 2 mode, and Travel Freely makes it so easy to track how many cards you have, as well as the 5/24 rule, annual fees, when to call and cancel versus downgrade a card, and best of all, they notify you (via email newsletter, special alert email, and/or on social media) when the best signup bonuses come out.
In addition, I really like the countdown for when I should apply for another card. The emails with success stories and tips are also incredibly motivating and I really enjoy them.
This trip to Maui was an absolute dream come true, and it wouldn’t have been possible without points and miles. Seeing our 3-year-old daughter run around and proclaim her love for Maui was priceless, and everyone in our group is already talking about how we can return.
Final Thoughts
Reflecting on the trip, Clay’s family agreed it was a 10/10 experience. From snorkeling and sunsets to cultural immersion and stunning natural beauty, the trip exceeded everyone’s expectations.
Clay expressed heartfelt gratitude to Zac and the Travel Freely team, saying, “Y’all definitely helped make this happen!” He hopes his story inspires others (like you!) to use points and miles to create unforgettable family adventures.
