Trip Introduction: Luxury for Cheap(ish) in the Cayman Islands Using IHG’s Best Points Redemption

Ah, the Cayman Islands. Land of idyllic blue waters, seven mile beach, and tax evasion (should I move here for 183 days per year?). Kidding. I think?

More importantly to this trip series, it’s home to one of IHG’s best points redemptions in the Kimpton Seafire, which I was lucky enough to snag for a mid-November trip. In the upcoming posts, I’ll be reviewing the Air France lounge at JFK, the flights to and from Grand Cayman, and most importantly, the Kimpton Seafire, which was overall an incredible resort and probably the best use of IHG points outside of Europe / Asia.

In this post, you’ll find:

1. Upcoming Posts
2. Flying Into a Hurricane & Weather Considerations for Trip Planning
3. Itinerary & How I booked

Upcoming Posts

In the coming series, you’ll find:

• Air France Lounge JFK New York Terminal 1 Review (Priority Pass)
• Cayman Airways Review: New York JFK to Grand Cayman (Economy) 737-Max 8
• Honest Review of The Kimpton Seafire: What To Expect from IHG’s Flagship Caribbean Resort
• Jetblue Economy Review: Grand Cayman to New York JFK on their A320

Flying Into a Hurricane & Weather Considerations for Trip Planning

There was only one slight problem I ran into on this trip, see below:

More on this in the hotel review, but I actually lucked out and managed to have decent weather for most of the trip, and was still able to swim in the ocean everyday. I was definitely sweating a bit flying into this, if I’m being honest. This is something to take into consideration if ever booking a trip to the Caribbean that I overlooked, even though I was towards the tail end of hurricane season.

For those planning a potential trip to the Cayman Islands, it’s important to note that Hurricane season in the Caribbean officially starts June 1 and runs until November 30. I was expecting smooth sailing in November, but with oceans staying hotter longer, there was actually one hurricane and one tropical storm within a 2 week period in November. If you’re planning to travel in this window, just know the tradeoff for lower hotel rates and cheaper flights is a gamble you might get washed out by a hurricane.

For those traveling to the Cayman Islands, I’d highly recommend using the government’s weather forecasting website HERE.

The weather app on my iphone showed rain every single day, which did happen, but only for relatively short spurts followed by clear skies. So don’t be discouraged if you have a trip planned and you see the same: it’s highly unlikely you’ll get completely rained out every day (unless, of course, you’re in the direct path of a hurricane).

In terms of seasonal weather, see below for average rainfall in the Cayman Islands:

Itinerary & How I booked

I flew out for a long 4 night weekend as follows:

11/14 Cayman Airways 793 JFK-GCM, arriving at 1pm

11/18 Jetblue 766 GCM-JFK, arriving at 5pm

The Cayman Islands are great for any US Mid / East Coasters because it’s super close – even NYC to the Cayman Islands is just over a 3 hour flight with no time change.

West Coast is a bit harder and Hawaii can start to make more sense for a tropical getaway, although Cayman Airways does currently operate flights from LAX.

In terms of how I booked, I used cash for the Cayman Airways flight, and booked with my Amex Platinum for the 5x multiplier (Apply HERE to support the blog).

I used Cash + a few remaining Jetblue points in my account for the JetBlue flight. In general, expect to spend $300-$500 for nonstop roundtrip economy flights from NYC to Grand Cayman and back if booked in advance, and more if book close to travel or if flying during peak season (the winter / spring).

In terms of booking the Kimpton Seafire, I used points and the fourth night free benefit from the IHG One Rewards Premier Credit Card. At its lowest points rates, the Kimpton Seafire can be booked for around 70k points per night, which is a relative steal given cash rates can be exorbitant, but more on this in the upcoming hotel review.