At the heels of The Issues Man’s first-ever “Issues Struggle,” we are again with any other version — and this time we are venturing each north and south of the equator.
Brian Kelly, founding father of The Issues Man, challenged two TPG teammates to duke it out and spot how they might every maximize shuttle advantages from their Chase Sapphire Most well-liked® Card (see charges and costs) to plot without equal, Instagram-worthy, awe-inspiring time out.
This problem was once made sweeter with Issues Spice up, a to hand perk that makes your Chase Final Rewards issues value extra and stretch additional while you e-book choose accommodations and flights during the Chase Shuttle℠ portal.
Upload in longtime favourite advantages like incomes bonus issues on eating and shuttle, the facility to switch issues to airline and lodge companions, and a $50 annual lodge credit score for reserving thru Chase Shuttle, and we had an epic festival on our palms.
The Issues Man’s senior lodge reporter, Tanner Saunders, authorised the problem along Lyndsey Matthews, senior shuttle editor at TPG.
Here is the way it all went down.
Issues Struggle: Chase Sapphire Most well-liked version
Like maximum competitions, this Issues Struggle had some regulations, together with choosing subject matters for the time out through spinning a wheel of shuttle parameters, discovering the easiest Instagram footage and placing in combination a in reality memorable adventure whilst additionally leveraging issues and card advantages successfully.
Lyndsey takes a spin
Whilst running at TPG’s New York place of work, I gained a cryptic textual content message from Brian telling me to visit his place of work — a extraordinary request making an allowance for I knew he was once off jet-setting. Strolling towards his place of work, I realized my favourite colleague, Tanner Saunders, heading in the similar course. He’d gotten the textual content, too.
Within the place of work, we discovered a magic wheel of time out subject matters and directions to spin it thrice every to decide the place we might shuttle and what we might revel in alongside the best way. I landed on visiting someplace with a rainforest local weather, seeing a marvel of the arena and consuming a meals I had by no means attempted ahead of. Whilst Tanner took his flip, I began making plans.
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Tanner learns his destiny
Tanner right here! I used to be excited for the danger to spin the wheel 3 times over to plot my journey. Because it became out, I’d be heading to a desolate tract local weather and staying in a bucket-list lodge, an ideal are compatible for this lodge reporter. It additionally gave me a possibility to position my Chase Sapphire Most well-liked card’s $50 lodge credit score to paintings.
With journey calling, Brian knowledgeable us we might every have as much as 150,000 Chase Final Rewards issues to show our journeys into fact, and that the winner would take house any other 150,000 issues to make use of for a time out that didn’t require trouncing a co-worker.
With the principles in position, our issues balances loaded and a few pleasant festival within the air, we set out on our adventures.
Issues are a battlefield: Making plans 2 epic journeys
Prior to any time out, Issues Struggle or now not, there is numerous making plans to be achieved. Our two TPGers set to work seeing how a ways their issues may take them and hammering out each element alongside the best way.
The struggle was once simply starting.
Lyndsey: Wasteland and wine in New Zealand
Armed with 150,000 Final Rewards issues, I had a choice to make: In finding business-class flights someplace with reference to house or stretch my issues so far as imaginable to get to the opposite aspect of the arena.
Whilst I may simply discover a dish I have never attempted ahead of in any nation, the opposite parameters of my time out — a rainforest local weather and a marvel of the arena — lent themselves to locales a bit of further from my house base in the USA.
A number of of the brand new Seven Wonders of the International are in rainforest climates, however I had already been to Machu Picchu in Peru and the statue of Christ the Redeemer in Brazil. I sought after to look one thing new, which led me to Milford Sound on New Zealand’s South Island. Thought to be through some to be the 8th marvel of the arena, this epic fjord sits inside the Te Wahipounamu UNESCO International Heritage Website online, which in order that occurs to be a temperate rainforest.

Discovering flights to New Zealand with out burning thru my complete funds took some paintings. However fortunately, after evaluating a couple of routes and airways, I secured a round-trip Fiji Airlines price ticket from Los Angeles Global Airport (LAX) to Auckland Airport (AKL) with a layover at Nadi Global Airport (NAN) in Fiji for 63,083 issues by means of Chase Shuttle.
Tickets in hand, it was once time to go to the airport. I earned 5 issues in keeping with greenback spent on my Lyft journey through paying with my Chase Sapphire Most well-liked card.*
After touchdown in Auckland, I made my option to the Park Hyatt Auckland. I booked one evening in a king room at this luxury Class 8 Hyatt belongings through shifting 25,000 Chase Final Rewards issues to International of Hyatt.

The Park Hyatt Auckland has 195 visitor rooms and suites with floor-to-ceiling home windows overlooking Waitemata Harbour and the town skyline. My room featured Maori-inspired decor, like the standard tukutuku wall panels woven from pink, black and white New Zealand wool, hung throughout from the soft king-size mattress.

The spacious marble toilet featured a free-standing bath overlooking the harbor. I feel my favourite element was once the walk-in closet that allow me unpack with out cluttering the gap. I used to be touring solo, however households can e-book adjacent rooms, giving themselves much more area to unfold out.
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LYNDSEY MATTHEWS/THE POINTS GUY
Regardless of the jet lag, there was once no time for leisure since Brian shocked me with an advantage issues problem on the Park Hyatt to “are living like a neighborhood.” Since New Zealand is mainly Heart-earth, I determined to partake in a hobbit’s favourite actions: consuming and consuming. For that, I boarded a 40-minute ferry from Auckland to Waiheke Island for a food-and-wine excursion.
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LYNDSEY MATTHEWS/THE POINTS GUY
I tasted a vibrant and flavorful chardonnay and a peppery syrah at Mudbrick Winery, sampled 4 native olive oil sorts at Allpress Olive Groves, and slurped contemporary Te Matuku oysters harvested simply down the street from the Ki Maha eating place proper on Onetangi Seaside. I earned 3 issues in keeping with greenback spent on eating with my Chase Sapphire Most well-liked card and was once additionally in a position to test off the “meals I have by no means attempted” a part of my problem right here since I have by no means had oysters from New Zealand.

Completely at ease and revived, it was once time for some thrills at the South Island. To get to Queenstown — New Zealand’s journey capital — I booked round-trip flights from Auckland on Air New Zealand the usage of an extra 19,440 issues by means of Chase Shuttle.

For my house base in Queenstown, I booked two nights on the Sofitel Queenstown Lodge & Spa. Since this French-inspired luxurious lodge with a complicated spa within the middle of the town is bookable thru Chase Shuttle with Issues Spice up, I redeemed 37,838 issues as an alternative of paying $454, for a worth of one.2 cents in keeping with level.
Alternatively, since my problem was once to look a marvel of the arena in a rainforest, I wasn’t going to spend a lot time on the lodge spa. To profit from my time, I booked a scenic flight excursion to Milford Sound, bypassing the four-hour force through hovering over Fiordland Nationwide Park’s glacier-covered peaks ahead of descending a number of the dramatic inexperienced slopes of the fjord.
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LYNDSEY MATTHEWS/THE POINTS GUY
The knowledgeable guides at Rosco’s Milford Kayaks whisked me out onto the water, the place we paddled to the 500-foot-tall Stirling Falls and noticed a seal pop up within the spray close to our kayak. A pod of dolphins additionally gave the impression, leaping out of the water to my joyous marvel.

The journey did not finish there. I could have handed on bungee leaping at its birthplace simply outdoor Queenstown, however I used to be up for the technical demanding situations of canyoning, which concerned rappelling down waterfalls, sliding thru slender canyons and wading thru transparent alpine streams for an adrenaline rush as an alternative.

For my ultimate bonus issues alternative, Brian challenged me to “do one thing that makes you are feeling totally loose.” Problem authorised: I booked a high-speed all-terrain-vehicle excursion, racing thru a pine woodland and splashing thru streams to the highest of the hills overlooking Lake Wakatipu, the place I bogged down lengthy sufficient to absorb the view and respect simply how a lot I had packed in throughout my time in Aotearoa, or the Land of the Lengthy White Cloud, because the Maori name it.

And because I used to be in a position to earn 2 issues in keeping with greenback spent on most of these shuttle actions with my Chase Sapphire Most well-liked card, I knew I used to be heading house with a lot of issues to spend on my subsequent time out — win or lose.
Tanner: Morocco on my thoughts
With a whopping 150,000 Chase Final Rewards issues in my pocket and the parameter of visiting a desolate tract local weather, my thoughts in an instant went to at least one position: Morocco.
Well-known for its sweeping desolate tract landscapes and jewel-box riads, I set my points of interest on Marrakech and the within reach Agafay Barren region. However the best way to get there?
Looking out Chase Shuttle, I noticed there have been numerous inexpensive flight choices for my adventure to North Africa, however the easiest way to stretch my issues concerned an sudden in a single day keep in Madrid after which a handy guide a rough jaunt over to Marrakech.
That is when it hit me: I may use that in a single day with the intention to spend the evening at The Madrid Version, a lodge I might dreamed about visiting for years after seeing footage of its moody foyer bar and dramatic white spiral staircase on social media.

For 37,618 issues, I used to be in a position to e-book a round-trip Iberia price ticket between New York and Marrakech with a prevent in Madrid every manner. Some vacationers hate a stopover, however I noticed the in a single day as a possibility to revel in two locations in a single time out, or even revel in an evening out in town in Madrid alongside the best way.

Extra importantly, I might test off the bucket-list-hotel portion of the problem through reserving The Madrid Version thru Chase Shuttle. After incomes my Chase Sapphire Most well-liked card’s $50 annual lodge observation credit score at the reserving, the lodge got here in at 31,585 issues, a worth of one.25 cents in keeping with level.

I earned 5 issues in keeping with greenback spent on a Lyft journey to John F. Kennedy Global Airport (JFK) with my Chase Sapphire Most well-liked card* and stuck up on motion pictures at the lengthy flight ahead of checking in to The Madrid Version. The lodge’s iconic Don Pedro de Ribera-designed baroque door was once the easiest position for a Brian-worthy selfie.

On the lodge, I in the end were given to revel in cocktails with the cool crowd and performed a sport of pool in what I will say is now my favourite lodge foyer on this planet.

Outdoor the relief of my stunning, just about all-white room, I had time to roam the streets of Spain’s capital town with a prevent for vermouth and tapas at Taberna L. a. Descubierta, the place I earned 3 issues in keeping with greenback spent on eating with my card. I had time to wait a flamenco display or even took a excursion of the Royal Palace of Madrid.

Feeling refreshed, I hopped on a brief flight to Marrakech and became my consideration to these stunning riads and checked in to the dreamy Lodge Izza for 2 nights for 41,300 issues, saving me $521.
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TANNER SAUNDERS/THE POINTS GUY
Within the middle of the walled Marrakech medina, the oldest a part of the town and a UNESCO International Heritage web site, Lodge Izza was once precisely what I sought after: fashionable, design-forward and stuffed with personality with tiled courtyards, postcard-worthy photograph backdrops and a rooftop eating place stuffed with greenery. It was once the easiest house in Marrakech, and any other lodge that ended up being bucket list-worthy to me.
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TANNER SAUNDERS/THE POINTS GUY
As soon as settled in, I headed directly to the town’s well-known souks to benefit from buying groceries, or even had the danger to make my very own footwear with a Moroccan leather-based employee (a tanner, if you’re going to, similar to me!). And within the buzzy, packed middle of the medina, I watched snake charmers play tune for swaying cobras similar to you spot within the motion pictures.

Prior to I left Marrakech, Brian shocked me with an advantage problem to benefit from some self-care. For me, that was once simple, as a result of no one must depart Marrakech with out spending a couple of hours getting a scrub in a conventional Moroccan hammam — and I did simply that (within the spirit of festival, after all!).

Marrakech was once the entirety I had was hoping it might be — like stepping again in time within the souks and medina, a visible banquet of swish palm bushes and the snowcapped Atlas Mountains, and one of the crucial friendliest folks I have ever encountered in my travels.
Again throughout the making plans procedure, I had idea to myself, “What if I in truth head into the desolate tract as an alternative of simply staying within the town?” With about 40,000 issues left in my funds, it made sense to e-book an evening on the castle-like Kasbah Agafay Lodge & Spa on the fringe of the Agafay Barren region, the place I may traverse dunes on an all-terrain automobile, which was once an process I had by no means achieved ahead of, assembly that situation of the problem.
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TANNER SAUNDERS/THE POINTS GUY
A boutique, in the neighborhood owned lodge, Kasbah Agafay was once like staying at a chum’s space … if that space was once a conventional desolate tract riad so picture-perfect, it appeared adore it was once proper out of a film. The hotel was once captivating, with stunning courtyards, a large swimming pool, and a lot of plush, colourful seating spaces.
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TANNER SAUNDERS/THE POINTS GUY
It was once additionally with reference to the actions across the Agafay Barren region, like taking an ATV out around the dunes with the wonderful Atlas Mountains looming better and bigger in entrance of me as I cruised around the sand. Rising up in West Texas, I’ve at all times felt hooked up to the desolate tract, and this adrenaline-filled revel in left my blood pumping and my garments muddy (however simplest as a result of I assumed it might be a laugh to force thru some giant puddles).
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TANNER SAUNDERS/THE POINTS GUY
In this leg of the time out, Brian hit me with any other bonus problem to be informed in regards to the native tradition. I visited the Saida Berber Space on the foot of the mountains to revel in how the Indigenous communities lived and ate thru a a laugh and informative cooking category that left me each full-hearted and stuffed with conventional tagine, which I made myself.

After a couple of days of touring throughout Spain and Morocco, it was once time to go back house to New York. Taking a look again on the entirety I might skilled over the previous couple of days, it felt just about unimaginable that I had booked this whole time out with issues … virtually as unimaginable as packing a Berber-made rug, Moroccan pottery, native olive oil and a brand new pair of home made footwear in my suitcase. (Observe to self: Take a look at the Chase app for any Chase Provides to in the end purchase a larger suitcase at a cut price.)
The overall tally
So how did Tanner and Lyndsey fare on this epic Issues Struggle? Let us take a look at their ultimate tallies.
Lyndsey’s ultimate tally

Here is how I took benefit of my 150,000 Chase issues, plus a couple of different card advantages I used:
- Spherical-trip flights from Los Angeles to Auckland on Fiji Airlines and from Auckland to Queenstown on Air New Zealand: 82,523 issues
- Park Hyatt Auckland: 25,000 issues
- Sofitel Queenstown Lodge & Spa: 37,838 issues
- Different card advantages: Benefiting from Chase switch companions (International of Hyatt), the usage of Chase Issues Spice up at the Queenstown lodge, incomes 3 issues in keeping with greenback spent on eating and incomes 5 issues in keeping with greenback spent on Lyft rides to the airport
Overall: 145,361 issues
Tanner’s ultimate tally

And now for my ultimate issues roundup, in addition to different card advantages I used:
- Spherical-trip flight from New York to Marrakech with Madrid stopover: 37,618 issues
- The Madrid Version: 31,585 issues
- Lodge Izza: 41,300 issues
- Kasbah Agafay Lodge & Spa: 35,440 issues
- Different card advantages: $50 annual lodge credit score, incomes 3 issues in keeping with greenback spent on eating and incomes 5 issues in keeping with greenback spent on Lyft rides
Overall: 145,943 issues
And the winner is …
Lyndsey and Tanner each maxed out their stash of issues and Chase Sapphire Most well-liked card advantages to head on two significantly epic journeys that made Brian jealous as he adopted alongside on Instagram.
Whether or not it was once the mix of stress-free spa moments and desolate tract thrills or immersive cultural moments with locals in Morocco, Brian’s select for the winner of this TPG Issues Struggle was once Tanner.
He creatively put his $50 annual lodge credit score to paintings for a bucket-list lodge keep throughout a stopover in Madrid and likewise immersed himself in native tradition with leatherworking and cooking categories, all whilst incomes 3 issues in keeping with greenback spent on scrumptious Moroccan foods.
The posts from Lyndsey’s time out indubitably had Brian hankering for some New Zealand wines and out of doors adventures, although.
Congratulations to each contestants, and keep tuned to look how Tanner makes use of the issues he received!
*Legitimate thru Sept. 30, 2027; does now not follow to Wait & Save, motorbike or scooter rides; activation required.




