The challenge was set: a head-to-head battle of travel expertise, fueled by the power of the Chase Sapphire Reserve card. Founder Brian Kelly wanted to see who on The Points Guy team could unlock the most value from their benefits – and he armed them with a generous stash of points to make their dream trips a reality.
The Chase Sapphire Reserve had recently leveled up its perks, offering enhanced earning rates and new credits for hotel bookings. This was the perfect opportunity to put those advantages to the test, pitting two seasoned travelers against each other in a quest for ultimate reward redemption.
The contestants? Medha Imam, a dynamic travel host and producer, and Eric Rosen, TPG’s director of travel content. Both were eager to prove their mastery of points and miles, and claim the grand prize: another 250,000 Chase points for a future adventure.
Before the planning began, a playful twist was introduced. Eric and Medha each spun a wheel of trip ideas, adding an element of chance and creativity to their missions. The stipulations were simple, yet intriguing, promising unique and memorable journeys.
Eric’s spins dictated a road trip through a Spanish-speaking country, maximizing Chase’s Points Boost feature when booking through Chase Travel. He’d long held a fondness for Spain, stemming from a study abroad experience decades prior, and a desire to experience Iberia’s cutting-edge Airbus A321XLR.
Medha’s spins led her toward a Spanish-speaking destination she’d never explored, with a focus on incorporating water activities into her itinerary. Escaping the New York winter, she envisioned sunshine and vibrant culture, ultimately setting her sights on Cartagena, Colombia.
Armed with 250,000 Chase Ultimate Rewards points each, the game was officially on. The race to craft the perfect trip, and unlock the full potential of the Chase Sapphire Reserve, had begun.
For Eric, the points unlocked a remarkable opportunity: a round-trip business class ticket on Iberia’s A321XLR from Boston to Madrid, redeemed for just 82,000 points and $300 in taxes and fees – a flight that would normally cost nearly $6,000. He even enjoyed access to the Chase Sapphire Lounge before departure.
He strategically used his $300 annual travel credit for a connecting flight to Bilbao, and another portion for a car rental, benefiting from the card’s primary rental car insurance. His journey began with seamless security thanks to Global Entry, a perk previously funded with a Chase Sapphire Reserve statement credit.
In Bilbao, Eric discovered the Radisson Collection Hotel, Gran Via, a stunning property within The Edit by Chase Travel. Points Boost allowed him to redeem just 14,000 points per night, further enhanced by a $250 statement credit towards The Edit bookings. The hotel’s rooftop bar and included breakfast added to the luxurious experience.
He explored the city’s medieval center and the iconic Guggenheim Museum, indulging in local pintxos and savoring the Basque culinary scene. His adventure continued to San Sebastian, where he booked the Nobu Hotel, again leveraging Points Boost and The Edit perks for an incredible value.
Even in the off-season, the Nobu Hotel commanded a high nightly rate, but Eric secured it for just 22,000 points. He relished the hotel’s prime location overlooking the bay, and enjoyed included breakfast and a $100 on-property credit.
His final destination was the Rioja wine region, where he booked the Marques de Riscal, a Luxury Collection Hotel, designed by Frank Gehry, for 46,000 points per night. A private wine tasting and a horseback ride through the vineyards completed his immersive Spanish experience.
Meanwhile, Medha’s journey to Cartagena unfolded with equal excitement. She secured a round-trip flight for just 42,182 points, saving $633 on airfare. She also utilized her card’s monthly statement credit for a ride to the airport, maximizing every benefit.
The Sofitel Legend Santa Clara Cartagena, a former 17th-century convent, captivated her from the moment she arrived. Booking through The Edit unlocked an upgrade, free daily breakfast, a $100 on-property credit, and an unforgettable experience in a historic setting.
Medha immersed herself in the city’s vibrant culture, booking snorkeling trips to the Rosario Islands, salsa lessons, and private walking tours – all with Chase points. She savored local delicacies, from arepas de huevos to fresh zapote juice, and embraced the warmth of Colombian hospitality.
She even leveraged a new Chase Sapphire Reserve perk – a biannual $150 StubHub credit – to attend a local concert, adding another layer of enjoyment to her trip. A sunset horseback ride along the Isla Tierra Bomba provided a perfect ending to her Colombian adventure.
In the end, both Eric and Medha demonstrated exceptional skill in maximizing their points and utilizing the Chase Sapphire Reserve’s benefits. But it was Medha who ultimately claimed victory, impressing Brian Kelly with her innovative use of points and her immersive exploration of Cartagena.
Her ability to seamlessly integrate points into every aspect of her trip, from flights and hotels to activities and dining, showcased a true mastery of travel rewards. While Eric’s Spanish road trip inspired future adventures, Medha’s Colombian escape proved to be the winning formula.
