When Travel Freely member Robert started using points and miles 20 years ago, little did he know that his knowledge and expertise would lead to such an epic and rewarding trip. Fast forward to today, and thanks to Travel Freely, Robert has mastered the art of traveling on points and miles — saving thousands of dollars while exploring new places and supporting meaningful causes.
His most recent adventure? A journey with his wife that not only took them on a scenic road trip through the Pacific Northwest, but also helped raise over $20,000 for an important cause. Here’s how he turned a dream vacation into an unforgettable experience while maximizing his rewards.
Tell Us About Yourself
My name is Robert, and I live in Tennessee. I’ve been using points and miles for travel for the past 20 years, although I really began focusing on maximizing them about 10-15 years ago. Travel Freely has been an immense help during this journey, helping me unlock amazing experiences without breaking the bank. Over the past decade or so, I’ve really honed my strategy, particularly with the help of Travel Freely, which has made managing my points a breeze.
Tell Us About Your Trip
Recently, I took an amazing trip to the Pacific Northwest with my wife. The highlight of the trip was climbing Mount Hood in Oregon as part of an adventure philanthropy trip to raise funds for Atlas Free, an organization that fights human trafficking worldwide. Thanks to the support of friends and family, I was able to raise over $20,000 for the cause and summit Mount Hood. The trip was centered around this climb, but we also spent time exploring Seattle and Portland.
How Much Money Did You Save Using Points and Miles for Your Trip?
We saved thousands of dollars on flights, a rental car, and hotel stays on this trip.
What Kind of Points Did You Use for This Trip?
We used Chase Ultimate Rewards® points, mostly accumulated through Chase business cards, and transferred them into my Chase Sapphire Reserve® Credit Card account. We used these points for everything — our first-class flights, car rental, and hotel accommodations.
Flights
We flew first class on Alaska Airlines from Nashville to Seattle. These tickets on Alaska Airlines would have cost several thousand dollars each, but we booked them using Chase points through the Chase Travel™ Portal with the 50% boost thanks to the Sapphire Reserve. Flying first class was a fantastic experience — comfortable seats, great service, and the ease of booking through the portal made it a seamless part of our journey.
Hotels
In Portland, we stayed at the Kimpton Riverplace Hotel, part of the IHG chain. I booked this hotel through the Chase Travel portal, which came with unexpected perks like a room upgrade, a complimentary bottle of wine, a $100 credit, and free breakfast. The experience was far beyond what I anticipated, and it added a luxurious touch to our trip.
Highlights of Your Trip: Any Special Experiences or Memorable Moments?
The standout memory from this trip was definitely summiting Mount Hood. It wasn’t just about the climb itself, but also knowing that I had raised $20,000 for Atlas Free, a meaningful cause, which made it a meaningful adventure. It was an unforgettable and deeply personal experience.
Another surprise was the fantastic upgrade and perks at the Kimpton Riverplace Hotel — an unexpected treat that added to the joy of the trip.
What Advice Would You Give Someone Interested in Booking a Trip Like Yours?
My biggest tip is to use points strategically. Look for value in premium experiences like first-class flights and high-end hotels where you can get the most out of your points. Also, always be ready to pivot! For example, when our return plans changed, I quickly used Chase points to rent a convertible and book a great hotel instead of settling for a mediocre airport stay.
How Has Travel Freely Helped You Achieve Your Free Travel Goals, and What Do You Like Best About the App?
Travel Freely has been instrumental in teaching me how to maximize my points and miles. It’s helped me stay organized, especially with business cards, and reminds me when to downgrade cards to avoid annual fees if I’m not getting value out of the perks of the card any longer. Without it, I’d struggle to keep track of everything. Travel Freely makes points and miles accessible and manageable, and it’s been a key tool in my free travel success.
Robert’s story is an excellent reminder that with the proper knowledge and tools, you can make your travel dreams a reality — all while supporting causes that matter to you!
Cards Mentioned in this article:
Great choice for a frequent traveler, but note the large annual fee. If you're starting out or not going to travel frequently in the coming year, you might want to instead consider the Chase Sapphire Preferred.
