As the Spring Semester concluded for our eldest in college and our younger daughter wrapped up high school in mid-May, the anticipation for a memorable family trip began. Having previously taken advantage of a 30% transfer bonus from Chase Ultimate Rewards to Air Canada’s Aeroplan mileage plan, my curiosity led me to explore the possibilities these points could unlock. After careful consideration and research, Munich emerged as the ideal destination, with an enticing 8-day stopover in Rome to explore the wonders of multiple Italian cities.
The intricacies of our travel plans intensified as we delved into accommodation options. Most major hotel chains proved limiting, accommodating only two to three individuals per room. This prompted a shift towards platforms like Vrbo and Airbnb to find lodging that suited our family’s needs. However, with costs averaging around $200 per night and factoring in expenses for food, tours, and a rental van in Munich, the overall expenditure, even with flights covered by points, would have approached nearly $6000. This realization prompted a strategic decision to postpone this European adventure to the following May.
This turn of events led us to recalibrate our plans, resulting in the exciting prospect of an affordable family adventure in Hawaii for the last two weeks of May.
Affordable Airfare
In my initial quest for affordable flights to Hawaii, I naturally turned to Air Canada, given their partnership with Star Alliance. Our previous Hawaiian adventure involved United flights, booked through Air Canada, so it seemed like a logical starting point. Disappointingly, the Air Canada search yielded no results, leaving me to explore alternative options.
Next on my list was Delta, as I already possessed 20,000 Delta miles. Considering Delta’s connection with American Express, I anticipated leveraging my 350,000 Amex Membership Rewards points. However, my enthusiasm dwindled when I discovered that the Delta flights came with a staggering cost of 85,000 points!
Undeterred, I continued my search and found myself revisiting United, thanks to its affiliation with Chase’s Ultimate Rewards. While both United and Delta may not typically yield optimal point values, a little-known secret came to light during this exploration. The key to unlocking excellent value with United miles lies in holding a Chase United card with an annual fee. As a cardholder, you gain exclusive access to Saver Award flight prices visible within your United account. Fortunately for us, my wife holds the United Explorer Card, which comes with a reasonable $95 annual fee. This unexpected perk significantly enhanced the value of our United miles.
Upon accessing her United account, I navigated through the available dates and discovered Saver Award flights that perfectly aligned with our preferred travel dates, all at a remarkable cost of only 50,000 points for a roundtrip! This presented an outstanding 35,000-point saving compared to Delta’s offerings. Additionally, when contrasting the point redemption against the cash rate on United, it translated to an impressive 2 cents per point, underscoring the unparalleled value we gained from our United Explorer Credit Card.
Unlocking the full potential of Ultimate Rewards, one standout benefit is the ability to seamlessly transfer points between household members. Leveraging this perk, my wife and I, both proud holders of the Chase Sapphire Preferred, combined our points to address a travel goal. Specifically, my wife possessed 70k United miles, while we aimed for a total of 300k United miles.
With 250k Ultimate Rewards at my disposal, I initiated the process by contacting Chase’s Customer Service through the number on the back of my card. The knowledgeable agent verified my identity and subsequently confirmed my wife’s account details, facilitating a smooth transfer of my points into her account. Once her account reflected the updated balance, she effortlessly transferred the essential 230k Ultimate Rewards to her United account.
Equipped with the now-complete 300k United miles in my wife’s account, I navigated back to the booking portal and secured our outbound flight from Newark (EWR) to Oahu (HLN). As I delved into planning the return journey, I noticed an intriguing detail—our Oahu departure featured layovers at KOA and LAX. This prompted a curiosity about KOA, leading to the discovery that it represented Kona International Airport on the Big Island. seizing the opportunity, we decided to extend our adventure to the Big Island.
Armed with this newfound plan, I entered the return date and successfully booked a 25k Saver Award flight from Hawaii (KOA) to Newark (EWR), turning a routine booking into a strategic win for our travel itinerary.
Opting for United award flights not only grants you the freedom to explore but also comes with the perk of minimal fees. Unlike other carriers, United imposes a mere $5.60 fee per ticket. Picture this: a roundtrip journey from New Jersey to Hawaii for our family of six, and the out-of-pocket cost was a mere $67.20. Even factoring in the $95 annual fee for the United Explorer card, our total expense of $162.20 pales in comparison to the staggering cash rate of $6420. The savings are nothing short of remarkable.
As I planned the final leg of our journey from Oahu to the Big Island, the choice between Hawaiian Airlines and Southwest became pivotal. Both offered multiple daily flights at competitive rates, but the distinction lay in the baggage fees. Hawaiian Airlines charged $25 per bag, while Southwest generously included 2 free bags per passenger. With this insight, the decision was clear—I opted for Southwest, paying the cash rate of $54.40 per ticket or a total of $326.40. The strategic choice not only saved us money but added a layer of convenience, making our travel experience all the more rewarding.
Hotels
When delving into hotel options for our initially planned trip to Italy and Munich, the challenges and high costs prompted us to defer the journey for another year. However, the prospect of exploring Hawaii presented a more favorable scenario, thanks to several benefits that effectively reduced the overall trip expenses. Notably, the larger room capacities in U.S. hotels—accommodating up to nine people in a two-bedroom setup with a sleeper sofa—proved advantageous. Additionally, the flexibility to utilize points across various hotel brands further enhanced our cost-saving efforts.
Commencing our Hawaiian adventure on the vibrant island of Oahu, renowned for its plethora of hotels and resorts, we decided to leverage our Disney Vacation Club timeshare points at Disney’s Aulani beachfront resort. Fortuitously, we secured a five-night stay in a two-bedroom accommodation that aligned seamlessly with our arrival plans. While not all nights were in the lowest-point Standard View, necessitating a booking mix of Standard View for two nights, Garden View for one night, and Ocean View for two nights, we strategically employed Disney’s “Waitlist” feature. This hopeful measure aimed to secure a Standard View for our Ocean View nights, eliminating the need to switch rooms during our stay. It’s worth noting that Aulani, being Disney’s most luxurious property, commands steep rates, starting at over $1500 per night for a Standard View two-bedroom suite.
Transitioning to the Big Island, where our exploration included a visit to Volcano National Park on the east side, we faced a different set of accommodation challenges. As hotels and resorts predominantly occupy the opposite side of the island, we turned to alternative lodging options, specifically platforms like Airbnb where points aren’t applicable. Fortunately, a valuable revelation came from research—Wyndham points could be used with Vacasa, a property management company. Armed with over 92k Wyndham points from my Wyndham Business Earner credit card, I successfully booked a three-night stay in a two-bedroom house located just five minutes from the park’s entrance, saving us a substantial $1100 after factoring in taxes. This strategic use of points through Vacasa and Wyndham proved to be a significant win in optimizing our accommodation budget for this leg of the journey.
In partnership with Vacasa, Wyndham enables travelers to utilize Wyndham points for bookings at a rate of 15,000 points per night per bedroom. Our chosen two-bedroom property, under this arrangement, cost us 30,000 points per night. While some Vacasa properties can accommodate six people in a one-bedroom setting for 15,000 points per night, none were situated on the east side of the island.
With our nights near Volcano National Park secured, the next task was to arrange accommodations on the resort-heavy west side of the island for the remaining nights before our return flight. Already aware of my preference for future stays, I had earmarked Hilton’s Waikoloa Village due to its extensive amenities, as attested by reviews.
Hilton’s Waikoloa Village boasts four distinct hotels, and after inputting our dates, party size, and carefully weighing prices and amenities, we opted for the most economical choice: Hilton Grand Vacations Club Kings’ Land Waikoloa. The only dilemma remaining was whether to pay the cash rate or utilize our substantial Hilton points balance, which currently exceeded 1 million points.
In May, signaling the onset of the high season, the standard nightly rate for a two-bedroom suite at our selected Hilton property was $489 when utilizing our Hilton Honors discount. Despite the relatively high cash rate, the alternative option presented itself in the form of redeemable points. Each night required 216,000 points, potentially translating into substantial savings. However, after careful consideration, I opted to secure these three nights at the cash rate. This decision was influenced by the valuable 5th-night-free benefit extended to Hilton Honors members when booking with points. Since our stay was limited to three nights, I deemed it more prudent to retain those valuable points for a future trip, where we could maximize a 20 percent savings on a more extended stay.
Car Rental
During our previous visit to Hawaii, I stumbled upon remarkable cost savings in Maui by utilizing Turo for a minivan rental during our scenic drive along the Road to Hana. Naturally, when planning our upcoming trip that involves a two-hour drive to explore Volcano National Park, my instinct led me back to Turo for our rental needs. Despite a plethora of van options available, the cumulative cost hovered around $400 for a three-day rental. This prompted me to explore alternatives, leveraging my American Express Platinum card’s elite status and discounted rates with National and Hertz.
After diligent searches with both rental companies, Hertz emerged as the frontrunner, offering exceptional value. I secured a minivan for a mere $220 over the course of the three days, showcasing the practical advantages of exploring various rental options beyond the initial go-to platform.
Conclusion
Despite having to postpone our Italy and Munich trip to next year, we’re excited about revisiting Hawaii as a family. The world of credit card rewards has been a game-changer for us, opening up travel possibilities we once deemed financially out of reach. Remarkably, just two years after our initial visit, we’re Hawaii-bound again, all thanks to savvy credit card points utilization!
Our meticulous use of credit card rewards has translated into substantial savings for this trip—well over $15,000 encompassing airfare, hotels, and car rental. This impressive sum stems from the combined benefits of Chase Ultimate Rewards points, Wyndham points, and Disney Vacation Club points. Despite allocating roughly $2500 for our two-week stay, we’re strategically accumulating even more points. Whether it’s paying for our Hilton stay on the Hilton Surpass card, booking our Southwest flight with the Amex Platinum, or securing our Hertz rental with the Chase Sapphire Preferred, every expense contributes to building points for our future adventures. If you’d like assistance in planning a similar adventure, follow this link and fill out the form, and we’ll be delighted to help you make your dream vacation a reality.
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