Two trips went head-to-head using Chase Sapphire Preferred benefits, Points Boost, and airline/hotel transfers to build unforgettable itineraries.
A travel showdown is playing out in the points world, and it’s less about speed and more about whether a single card can turn two very different itineraries into experiences that look tailor-made for Instagram.
In a new edition of The Points Guy’s “Points Battle. ” Brian Kelly challenged two colleagues to plan trips—north and south of the equator—by squeezing the maximum value out of a Chase Sapphire Preferred® Card.. The competition leaned on Chase Ultimate Rewards® flexibility. including Points Boost. a perk that increases the value of points when booking select hotels and flights through the Chase Travel℠ portal.
The card’s long-standing perks were central to the challenge: bonus points on dining and travel. the ability to transfer points to airline and hotel partners. and a $50 annual hotel credit when booking through Chase Travel.. Each contestant also worked within a framework designed to keep planning grounded in real travel choices rather than guesswork.
Rules set the tone from the start.. The competitors spun a wheel of travel parameters to determine themes for their journeys. then focused on assembling memorable days paired with standout photo moments—while still using card benefits efficiently.. A final twist added stakes: each competitor was given up to 150. 000 Chase Ultimate Rewards points for their trip. with the winner also taking home another 150. 000 points for a separate future trip.
Lyndsey Matthews drew the theme of a rainforest climate, a “wonder of the world,” and a new food experience.. That combination pointed her toward New Zealand’s South Island, landing on Milford Sound as the awe-inspiring centerpiece.. She also made her flight routing work without draining her balance: after comparing options. she booked round-trip Fiji Airways service from Los Angeles (LAX) to Auckland (AKL). with a layover in Fiji. using points via Chase Travel.
For lodging. Matthews transferred points to World of Hyatt to book the Park Hyatt Auckland for one night. using 25. 000 Chase Ultimate Rewards points.. The hotel stay became part of the story itself. with details ranging from harbor and skyline views to Maori-inspired design elements.. Even after jet lag. the itinerary pushed forward immediately with a bonus challenge to “live like a local. ” which led to a ferry ride to Waiheke Island and a food-and-wine tour.
Dining and local experiences were woven into the points strategy.. Matthews sampled wines and other local flavors during her tour. and she also used her Chase Sapphire Preferred card on dining to earn additional points.. From there. the trip shifted from the “rainforest” theme into adventure: she flew to Queenstown—framed as an adventure hub—and based herself at Sofitel Queenstown Hotel & Spa for two nights.. That booking used Points Boost through Chase Travel. and she redeemed points instead of paying the cash rate shown in her plan.
To keep the “wonder” requirement front and center. she added a scenic flight to Milford Sound. then followed it with water time via kayaking.. From the fjord to adrenaline. the itinerary didn’t stop at views: she also chose canyoning. using the trip’s momentum to trade rest time for technical. waterfall-focused thrills.
Another bonus challenge pushed her toward something that made her feel “completely free. ” and she responded with a high-speed all-terrain-vehicle tour through pine forests and streams to viewpoints over Lake Wakatipu.. With travel activities still tied to her card’s earning structure. the New Zealand itinerary positioned itself as both outdoorsy and points-smart. leaving her with points for the next trip even after spending most of her allotment.
Tanner Saunders. meanwhile. was drawn to a desert-climate challenge and immediately set his sights on Morocco—specifically Marrakech and the nearby Agafay Desert.. Instead of relying on a straight shot, he found that stretching points meant planning around an overnight stop.. That led him to book a round trip from New York to Marrakech via Madrid using points through Chase Travel. turning the stopover into a destination in its own right.
The bucket-list-hotel requirement became the highlight of his Spain segment.. Saunders booked The Madrid Edition through Chase Travel and applied his Chase Sapphire Preferred card’s $50 annual hotel credit during that booking process.. The rest of his plan around Madrid focused on enjoying the city beyond a layover. with meals and a mix of experiences that kept the itinerary moving rather than simply “passing through.”
From Madrid. he flew to Marrakech and checked into Hotel Izza for two nights. described as a design-forward retreat inside the walled medina.. His time there leaned into the city’s culture and atmosphere—visiting souks. exploring the medina. and even joining in activities connected to local crafts and traditional experiences.. A bonus challenge centered on self-care, which he met by booking a traditional Moroccan hammam.
The desert question didn’t stay theoretical.. Saunders reflected on why not just remain in the city. then used remaining points to book a night at Kasbah Agafay Hotel & Spa at the edge of the Agafay Desert.. The plan focused on movement and scenery, including an ATV ride across dunes with views framed by the Atlas Mountains.. A further bonus challenge encouraged cultural learning. and he completed it with a cooking class at Saida Berber House. where traditional tagine was a key part of the experience.
After both trips. the competition returned to its original purpose: showing how a points balance and card benefits translate into real itineraries.. Lyndsey’s total relied on her 150. 000-point starting stash plus other benefits. including transferring points to World of Hyatt for the Park Hyatt Auckland and using Points Boost for a Sofitel booking in Queenstown.. The plan also counted on dining and Lyft earning mechanics tied to her card use.
Tanner’s total similarly combined flight bookings with hotel stays. again using his $50 annual hotel credit for The Madrid Edition and connecting Morocco experiences to points-backed reservations.. His itinerary’s earning approach also included dining and rides to airports using the Chase Sapphire Preferred card.
With both competitors maxing out their point budgets, the “winner” was ultimately decided on the way Tanner used the annual hotel credit and how deeply he leaned into immersive local culture—particularly the leatherworking and cooking-class components—alongside the desert-adjacent thrill of Agafay.
For travelers watching the subtext. the broader lesson is straightforward: points strategies aren’t just about where you go. but how you build the route. align credits and boosts with eligible bookings. and make sure the itinerary’s defining moments match the theme you’re chasing.. In this case. one competitor leaned into fjords and wildlife-adjacent adventure in New Zealand. while the other built a Morocco run that blended riads. medina culture. and time at the desert’s edge.
Chase Sapphire Preferred points Chase Ultimate Rewards Points Boost New Zealand travel Morocco itinerary luxury hotels