Every year, Hawaii’s pristine beaches and natural beauty beckon to our Travel Freely members. This makes it the top tropical travel destination for our community. What’s incredible is that with some patience and the right strategy, most of our members can make their dream trip to Hawaii a reality even sooner than they might have imagined. Travel Freely member Lora is one of those people!
A nurse and mom of 3 from St. Augustine, FL, Lora followed the “Always Be Earning” points and miles strategy even when life (i.e. COVID and raising a family) made travel plans seem like a far-off goal. Lora’s patience (and intelligent, strategic thinking!) paid off, and she seized the opportunity to travel with close friends on an epic Hawaiian adventure to celebrate her milestone birthday.
Tell us about yourself. How long have you been using points and miles towards free travel?
Driven to make travel affordable and accessible for my family, I began my journey with points and miles 6 years ago. The pivotal moment came when I was able to fly my family to my childhood best friend’s wedding in upstate NY. Armed with a Southwest card, I secured flights for my family solely using points, and after that, I was hooked! 😁
Since then, I’ve been able to take my family on other points trips in the US. With every trip booked using points, I felt a sense of pride in providing enriching experiences for my family without straining our budget.
Hawaii has always been a bucket list trip of mine, but with a family to support and competing priorities, traveling there seemed out of reach. That is, until I found myself thinking about my quickly approaching 40th birthday!
Like everyone else, travel had taken a backseat during COVID-19, but my desire to travel reignited as things opened back up. Before long, I opened a Chase Sapphire Preferred® Card because I had read that it was a great beginner card. No matter what I decided to do for my milestone birthday, this card was definitely a great place to start!
Then, things started falling into place.
A close friend told me her daughter was planning to visit her boyfriend, who was stationed at Camp Smith in Honolulu, for the annual Marine Ball. She didn’t want her to travel alone, so she came along. I had always tried to convince them about earning points to assist with travel costs, and a lightbulb went off. I told them I’d join, and I PROMISED I would figure out a way to get all of our flights AND hotels covered.
Which kinds of points did you use for this trip?
My friends and I opened the AAdvantage® Aviator® Red World Elite Mastercard® (the elevated bonus at the time was 70,000 miles; currently 50,000 miles), which paid for our airfare (45K miles each roundtrip on American Airlines), plus island hopper flights from Kauai to Honolulu (7.5K miles one-way) and Honolulu to Hilo on the Big Island (7.5K points one-way) on partner Hawaiian Airlines.
For accommodation we used Chase Ultimate Reward points from opening Chase Sapphire Preferred cards (one for me and one for my husband). We booked 2 nights at the Grand Hyatt Kauai (60K points total), 3 nights at the Hyatt Regency Waikiki (60K points total), and used my free hotel night certificate from Hilton for a stay at the Waikoloa Village.
Tell us about your trip. Where did you go and what did you do?
Without my family in tow, I was able to accomplish a great deal on this trip. I’m very active, and hiking was at the top of the list. Along with many epic hikes on each island, highlights included:
- Celebrating my birthday with an epic sunset paddle on Waikiki Beach.
- Watching sea turtles and Friday night fireworks from the water.
- Eating the best pork of our lives at the Waiahole Poi Factory on Oahu. It looks like a shack on the side of the road – but if you stop there, I promise you won’t regret it!
- Sunrise from ABOVE the clouds at Mauna Kea – the highest point in Hawaii. This was honestly the most amazing experience of our trip.
What advice would you give to someone interested in booking a trip like yours?
Following the advice of other points and miles enthusiasts, before my arrival, I emailed the general manager at each resort to let them know I was so excited to be visiting Hawaii for the first time while celebrating my 40th birthday.
Upon arrival, the Kauai Hyatt gifted me champagne and decorated my room for my birthday.
Then we received a complimentary ocean view upgrade in Waikiki along with a bottle of wine, a fruit plate, and a hand-written birthday card after check-in.
At our third location, Waikoloa Village, we received an upgrade to the Makai Tower – an ocean view room just in front of the dolphin sanctuary. We could watch the dolphins swim from our lanai!
This trip was already going to be so unique, and these upgrades just topped it off!
How much money did you save by using points and miles for your trip?
While this trip was not entirely free, my calculations estimate that we received 90% off the regular price for a trip like this, saving us over $6,500!
What advice do you have for someone just starting out with points and miles?
Covering a trip exclusively with points and miles feels like a lot of pressure, so I approach it more as a supplemental part of my total budget for a trip. I recommend starting with a specific goal. For this trip, that meant getting me, my friend, and her daughter all on free roundtrip flights to Hawaii. Then go from there.
How has Travel Freely helped you and what do you like best about the site and app?
I actually only used the Travel Freely app once I accumulated cards and prepped for my Hawaii trip. I use the app to track renewal dates and recommend which cards I should get next. I also love the advice and tips included for each card and what to do when an annual fee renewal comes up. It’s very helpful to stay organized.
In Summary
Thank you to Lora for sharing her story! By skillfully navigating the world of points and miles, Lora transformed her dream of exploring Hawaii into a tangible reality. Through the meticulous accumulation and savvy redemption of rewards, Lora not only secured substantial savings, but also indulged in luxurious upgrades and unforgettable experiences throughout her adventure.
Here at Travel Freely the goal is clear: Help people achieve more travel than they ever thought possible. There’s no better time than now to get started and no better way than signing up for Travel Freely!
Cards used for this trip:
Our #1 personal card we recommend most often. Hands down the single best "starter card" for beginners and the MVP card for free travel.
This is a great card for American Airlines flyers. A very low spending requirement for the bonus. Keep in mind that sometimes Barclays can be difficult to obtain approval.
