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A $4,000 Five Day Trip to Grand Cayman Island for $290.75

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Grand Cayman Island is a supreme destination for those looking to take a basic break from the work grind back home and stock up on some vitamin D! Our recent trip down to the Cayman Islands was everything that we hoped for and so much more. Fresh Seafood, Scuba Diving Adventures, Beautiful Beaches, and even Kissing Stingrays ended up on the agenda. Our favorite part is that the $4,000 Five Day Trip to Grand Cayman Island for $290.75 is one of our best award redemptions yet!

Flights to Grand Cayman Island

The Cayman Islands are located in the Caribbean and about a 90-minute direct flight from South Florida. From Buffalo NY, a round-trip flight to Grand Cayman Island will cost on average $500 and take about 8 hours to travel to with one stop. Popular carriers include Southwest, JetBlue, American, and Delta Airlines. We ended up going with Southwest thanks to the buy-one-get-one free Companion Pass deal! 

Southwest Airlines 

Flights to Grand Cayman Island (GCM) were going for 13,104 Rapid Rewards Points each way. A total of 26,208 Rapid Rewards points was needed to cover my roundtrip flight from BUF to GCM. Since this is an international flight, there is a higher tax & fee that cannot be waived for the flight back which ended up costing $90.18. The flight down only costs the standard $5.60! My flight total cost me 26,208 Rapid Rewards Points Plus $95.78! 

Adding Companion for FREE

I added Lisa to the reservation using our Southwest Companion Pass for FREE. The only costs that were not waived are the taxes & fees. Her total roundtrip flight from BUF to GCM costs ZERO Points and $95.78. 

Two Roundtrip Flights from BUF to GCM for $191.56

Bonus Round 

One great Southwest Airlines Strategyy is that you can use Southwest Credit to pay for those pesky Taxes and Fees. Luckily for us, we had a ton of credit banked up which we were able to unload for these flights. Alternatively, we could have used 19,156 Capital One Venture Miles to “erase” the travel Credit! 

Total Cost for 2 Flights from BUF to GCM = $0 

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Other options to Fly from BUF to GCM

  • JetBlue Roundtrip flights using TrueBlue Points –  25,000 Per Person
  • American Roundtrip flights using AA Miles – 20,000 Per Person (WebSpecials) 
  • Delta Roundtrip Flights using SkyMiles – 17,000 Per Person
  • United Roundtrip Flights using UA Miles – 35,000 Per Person 

Hotel – Staying at the Kimpton Seafire 

The Kimpton Seafire is a premier hotel and resort located on the famous Seven Mile Beach in Grand Cayman Island. We love the experience that Kimpton Hotels offer which always includes top-notch customer service and an overall fun vibe. Picture being in grade school on a Friday night and everyone is heading to the cool kid’s house for a party. Back in grade school, the place people were heading to was often a secret or you had to know someone to get invited. 

Secrets out, Kimpton’s are the place to be if you’re looking for a fantastic experience that consistently seems to come off as exclusive! The staff are fun and down-to-earth, while at the same time providing top-notch customer service. There are always fun social events taking place around the hotel and everyone is excited to be a part of the experience. With all of that said, you can probably guess that a night at the Kimpton Seafire will cost more than a pretty penny. Luckily, the IHG Rewards Program offers a great option for using Points! 

How we booked 3 Nights at the Kimpton Seafire For FREE

Award nights at the Kimpton Seafire go for 70,000 IHG points per night. This is a whole lot better then paying $1,044 per night! The best part about booking nights at the Kimpton Seafire is that up until recently, the property was accessible with the Annual Free Night Certificates that come with the IHG Credit Card. For $49, the cost of my Annual Fee, we were able to book one night at the Kimpton Seafire. The additional two nights were covered with 140,000 IHG points! 

IHG points are pretty easy to earn with the regular promotions that they run to earn bonus points. The IHG Credit Card also offers a large signup bonus for opening and additional opportunities to earn bonus points from spending. 

Kimpton Seafire Resort Fee

There is a mandatory $75 Resort Fee per night that is tacked on to the final bill. At the Seafire, the Resort Fee includes:

  • Free food for kids under 5 
  • High-speed wifi
  • Morning coffee in the lobby
  • Evening social with complimentary Drinks/Snacks 
  • Daily Fitness Classes
  • Watersports Access – kayaks, paddleboards, rafts, water tricycles
  • GoPro Underwater Cameras to use
  • Snorkeling Gear and Lessons
  • Beach and Mountain Bikes to Ride (We took these into town for a fun adventure!) 
  • Valet Parking

Since I am an IHG Credit Card Holder, I already receive free high-speed Wifi and was able to get $5 credited back to my account per day. The Resort Fees totaled $210 for the three nights. We could have used 21,000 Capital One Venture Miles to “Erase” the credit but instead, I used my IHG credit card for 5X IHG Points! 

Three Nights at the IHG Kimpton Seafire – $210

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AirBnb – One Night for a Different Experience 

I wish we could have spent the entire 5 Day Trip to Grand Cayman Island at the Seafire 🙁 but our basic adventure had to move forward. We ended up booking one night at the Tranquil Hideaway AirBnb for $65. It was a private room in a house that included a pool and our own bathroom. Not as luxurious as the Seafire but we always like to try and stay places that give us a feel for the local community. Our host, Rockella was great and very accomodating! The final costs of a night at the Tranquil Hideaway with taxes and fees worked out to be $85. I booked the night with my Chase Sapphire Reserve to take advantage of a 5% discount that I found in the Chase Offers of the month. Plus the 3X Ultimate Rewards Points on Travel always helps with my favorite award currency. 

One night at the Tranquil Hideaway – $80.75 with the 5% Chase Offer Discount

One night at the Tranquil Hideaway – $80.75 with the 5% Chase Offer Discount

Basic Recap

There you have it! We were able to go on a 5 day Trip to Grand Cayman Island for only $290.75. Of course, this price only includes our flights and hotels which should have cost us over $4,000! With the money that we saved on travel, we were able to book some awesome excursions with Red Sail Sports Cayman Islands, Enjoy a fantastic Dinner at Agua in Camana Bay, and take Cayman Ferries up to Rum & Starfish Point! 

Have you used Points and Miles to visit Grand Cayman Island? I’d love to hear about how you did below in the comments or in our 3,000 + Member Basic Travel Facebook Group!

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An easy-going, fun-loving couple who have a passion for adventure and exploring the world! Our strategies have saved us over $100,000 in travel over the last four years, and our goal is to help you do the same.

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