When wanderlust calls, sometimes you have to answer quickly. Just last week, I realized I had five days off in a row and knew I couldn’t stay stateside, even to celebrate my bestie’s birthday. I craved something tropical, luxurious, and easy to reach. That’s when the Kimpton Seafire Resort in the Cayman Islands popped up on my radar. Using my American Express points, IHG Premier Card benefits, and smart travel rewards strategies, I planned a five-day Caribbean escape — and spent less than $500 on flights and a luxury accomodation.
Why I Picked the Cayman Islands for My Getaway
When I have time off, my priority is maximizing leisure, not spending precious hours in airports. With only five days off in a row and no need to burn additional PTO, I wanted a destination that offered direct flights from my home airport. The Cayman Islands fit that need perfectly. A nonstop flight meant more time with my toes in the sand and less time worrying about connections, delays, or long customs lines. Grand Cayman is well-known for its safe environment, stunning beaches, and luxurious accommodations, making it the ideal spot to unwind without the hassle of complicated travel logistics. Once I saw the ease of getting there, paired with the possibility of redeeming points for an incredible stay, the decision was simple.
Finding the Flight with American Express and Travel Rewards
My journey to the Cayman Islands started with a quick check of flight options. Cash prices for a nonstop flight were $1,100 per person — yikes! But thanks to my American Express Business Platinum Card and its travel portal, I found the same flight for 115,000 Membership Rewards points. After my 35% rebate, I paid only 74,750 points.
At the same time, I used my American Airlines AAdvantage miles to book my bestie’s ticket for just 24,000 miles plus $114 in taxes. Her cash ticket would have been over $1,100 as well, but by using my miles, I gifted her a memorable birthday experience without either of us stressing about the cost.
Pro tip: you can use your miles to book travel for friends!
Why I Booked my Flight using AMEX MR points over American Airlines Miles
While it might seem tempting to book both tickets with AAdvantage miles, I made a strategic decision to book my own flight through the American Express Travel portal instead. Here’s why: when you book a flight with miles, you don’t earn Loyalty Points or Elite Qualifying Dollars toward airline status. Since I am currently requalifying for AAdvantage Executive Platinum status, every mile, point, and dollar matters.
By booking my flight with AMEX Membership Rewards points through the portal, it counted as a paid ticket. That meant I would still earn Loyalty Points with American Airlines, helping me maintain my top-tier status. Elite status unlocks incredible travel benefits like upgrades, free checked bags, priority boarding, and bonus miles — all of which make future travel even more rewarding.
Choosing to use American Express points allowed me to leverage my rewards today while still investing in better travel experiences for the future.
Booking Kimpton Seafire Resort with IHG Premier Card Benefits
The heart of this trip was staying at the stunning Kimpton Seafire Resort in Grand Cayman. Standard rooms cost 70,000 IHG points per night, which would typically total 280,000 points for four nights. However, because I used my IHG Premier Card, I unlocked the Fourth Night Free benefit. I booked my stay for only 210,000 points total, saving 70,000 points instantly. Compared to the $1,000+ nightly cash rates, using my travel rewards felt like a massive win.
Enjoying My Stay at Kimpton Seafire Resort
Upon arrival at Kimpton Seafire, the experience lived up to every expectation. The property blends laid-back Caribbean luxury with stylish, modern design. One of my favorite discoveries was the Library Bar, tucked quietly off the lobby, offering curated cocktails and a cozy, elegant atmosphere perfect for a pre-dinner drink.
Dining at Avecita was an unforgettable experience. As the hotel’s upscale dining concept, Avecita offers a chef’s counter experience where you watch the chefs create magic before your eyes. We celebrated my bestie’s birthday here, and the multi-course dinner was worth every bite and every point earned.
Cocoloba, the beachfront casual dining spot, was a daily treat. They served the best piña coladas I’ve ever had, and my bestie raved about the fresh ceviche she ordered every single day. Whether we were relaxing by the beach, exploring the culinary scene, or sipping cocktails by sunset, Kimpton Seafire Resort offered the perfect home base.
Things to Do in the Cayman Islands While Earning Travel Rewards
One of the best parts of a Cayman Islands getaway is the variety of excursions that allow you to see the island’s beauty. I used Viator to book two memorable experiences: a rum and distillery tasting and a Stingray City tour, where we got to swim with stingrays in the wild.
Booking excursions through Rakuten, paired with my American Express cards, allowed me to stack rewards easily. Many tours, activities, and even spa treatments across Grand Cayman are available through portals that offer bonus points or cash back. Travelers using travel rewards can stretch their experiences even further, making luxury excursions affordable and rewarding.
If you love snorkeling, diving, or simply relaxing on the beach, the Cayman Islands deliver. Every part of my trip was enhanced by knowing I had earned valuable points for my next adventure.
How I Stacked and Earned Travel Rewards During My Cayman Islands Stay
Traveling smart isn’t just about saving points upfront — it’s also about earning them strategically while you’re on the ground. During my stay at the Kimpton Seafire Resort, I made sure that nearly every dollar spent came back to me in the form of future travel rewards.
Dining with American Express Gold Card
Meals were a major part of our experience. For dining, I used my American Express Gold Card, which earns 4x Membership Rewards points at restaurants. From our $400 birthday dinner at Avecita to casual breakfasts by the beach, I charged every meal I could. In total, I earned more than 2500 Membership Rewards points just from dining — all while treating my bestie to unforgettable culinary moments.
Excursions with AMEX Blue Business Plus and Rakuten
Adventure was on the agenda too. I booked excursions through Viator, including a Stingray City tour and a distillery tasting. To maximize rewards, I used my American Express Blue Business Plus Card (earning 2x MR points per dollar) and clicked through Rakuten, which was offering a 12x MR points promotion at the time. Between both excursions totaling about $215, I earned around 429 MR points from my card and 2,575 MR points from Rakuten. Double-dipping like this made each activity even more rewarding.
Hotel Spend with IHG Premier Card
Back at the resort, I leveraged my IHG Premier Card for all hotel expenses, including the daily amenity fees and incidental charges totaling about $990. Thanks to my Platinum Elite status, I earned 26x points per dollar: 10x from using the card, 10x from being an IHG member, and 6x bonus from elite status.
That resulted in 25,740 IHG Points from my resort spend. Additionally, after a minor issue with the in-room TV, the property graciously awarded me another 25,000 IHG Points as a goodwill gesture. Altogether, I earned 50,740 IHG Points from my hotel spend.
Every choice — from swiping the right card to booking through the right portals — turned everyday spending into fuel for future travel dreams.
The IHG Premier Credit Card offers up to 26x on IHG hotel property stays, automatic Platinum Elite Status, a complimentary anniversary night, Global Entry/TSA Precheck, and More… with a small $99 annual fee. Currently, you can earn 140,000 IHG points when you hit their minimum spend requirement. That is enough for two nights in the Cayman Islands! To learn more about this card, click here.
How Much I Spent and How Much I Saved
Here’s the breakdown:
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Bestie’s flight taxes: $114
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Resort amenity fees: $340
Total cash spent: $454
Compared to paying over $6,200 for flights and the hotel in cash, the savings were incredible.
In addition to saving big, I also earned valuable rewards. I walked away with over 50,000 IHG points from hotel spend and another 4,800 Membership Rewards points from my dining and excursion charges. Strategic use of my IHG Premier Card, American Express products, and travel portals made this an easy win.
How Much I Earned During my Stay
One of the best parts about this trip wasn’t just how little I spent — it was how much I earned back in rewards for future travels. Every dollar strategically spent at the Kimpton Seafire Resort, during excursions, and at local dining spots translated into valuable points across my loyalty programs.
Here’s what I earned during my five-day stay:
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Over 50,000 IHG One Rewards Points
Thanks to using my IHG Premier Card for hotel charges — and a 25,000-point goodwill bonus for a minor inconvenience — I walked away with enough points for another future hotel stay.
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More than 4,800 Membership Rewards Points
By leveraging my American Express Gold Card for dining and my AMEX Blue Business Plus Card (plus Rakuten) for excursions, I kept building my Membership Rewards balance while celebrating and adventuring.
These points are not just numbers — they represent the ability to offset costs on my next hotel booking, book flights, or redeem for upgrades. By intentionally using the right cards for the right expenses, I was able to stretch my trip’s value even further beyond the memories we made.
Why Travel Rewards Are Worth It
This trip reinforced why I keep healthy points balances across my favorite airline and hotel programs. Having points ready to go gave me the flexibility to book an international getaway on just two days’ notice. I also remembered why it’s important to consider elite status goals. Booking through American Express Travel instead of using miles meant I still earned loyalty points toward my next tier with American Airlines. Strategic planning made all the difference.
Travel rewards are not just about saving money — they are about creating opportunities. From staying in world-class resorts to enjoying gourmet dining, it’s about living well without draining your bank account.
Would I Do It Again? (Spoiler: Yes, and It Involves Scuba)
Absolutely. I’m already planning my next trip.
During this trip to the Cayman Islands, I finally realized how much I want to get scuba certified. After experiencing the beauty of Grand Cayman’s beaches and reefs, it’s time to take the plunge—literally. Smart travel planning, leveraging points, and maximizing rewards made this trip possible, and it’s only the beginning.
If you’re sitting on points and miles, now’s the time to use them. The world — and maybe even your next scuba adventure — is waiting.
Travel Smarter, not harder. The world is waiting.
