We went for the first time in 2024 and took the kids. I wrote about that trip here.
While we’ve traveled to many amazing places, my wife thinks the beaches at the Caymans are the best she’s seen, so she was eager to return.
I want to spend the next two newsletters explaining how we booked this trip with points & how you could do the same.
The cost of this trip, if you were paying cash, is likely more than you would be comfortable paying. It certainly would’ve been for us. But points allows you to splurge in ways you likely wouldn’t do otherwise.
Let’s start with flights.
Flying to the Caribbean can be expensive. One of our flight attendants told us that they get paid for an 8 hour trip on only a 3 hour flight because of where we’re going. That’s why they like to fly this route.
American Airlines has a direct flight to the Caymans from our home airport. The direct flights can be a bit more expensive, but we find it worth it rather than having to fly to Florida, stop, change planes, and then head to the Caymans (we get a bit spoiled with travel hacking, we know).
The way we booked this flight was with Alaska miles that we earned from the Amex transfer to Hawaiian Airlines that I wrote about a while back here. You could also use AA miles or even use Chase/Amex/Capital One points & book in their portal.
Figure out which airline is best from your destination to the Caymans & consider getting a co-branded credit card from that airline with a big welcome bonus. That welcome bonus alone could cover your flights. If not, perhaps you’ll be able to transfer some of your unbranded points to your favorite airline.
Ok, let’s assume you’ve got your flights figured out.
Let’s talk about the hotel.
We’ve done quite a bit of research about hotels on the island, including talking to locals, and the one we keep going back to is the IHG Kimpton Seafire Resort. Highly recommended!
We’ve considered staying in the Ritz Carlton down the beach but after researching, we’ve continued to choose the Kimpton. Even our taxi driver who has lived in the Caymans for 40+ years said that the Kimpton is the best in his opinion for location, vibe, service, etc.
This is where it gets expensive. If you go outside of hurricane season (which we’d recommend) during the winter months & early spring, the room rate can be between $1,500-$3,000 per night (that’s when everyone else is trying to go too).
If you’re like me, I just can’t see myself ever paying that amount in cash for a room per night.
But, I’m happy to stay there if points pays for it - ha!
We’ve typically stayed in a room that costs 70,000 points per night.
Here’s what I would suggest for earning IHG points:
- Get either the personal or business co-branded IHG card (we’ve done this both times we’ve gone) - you’ll likely get a big welcome bonus of 140-200k IHG points
- For the extra points, transferring Chase points to IHG is usually not a good redemption. Instead, I recommend waiting for IHG points to go on sale & buy them at half a cent per point. You can redeem Chase points for cash to pay for these points. E.g. If you bought 70,000 points (one night) when they’re running the discount, it would cost you $350 (or 35,000 Chase points redeemed for cash). This is a great deal!
- Also, if you have the co-branded card, if you stay 3 nights, you get the 4th night free — jackpot! So, for a 4 night trip, you’d just need 210,000 IHG points. You can get most of those from the welcome bonus + buying some points at half off.
This is the way we’ve booked the hotel in the past using points.
I’ll share in next week’s newsletter how to cover other costs you’ll incur on your trip.
Can’t wait to hear how much you enjoy the Kimpton if you decide to go!
