Because we are pirates and people of the sea, one of our favorite grounds for plundering is the Caribbean. There are so many great destinations with beautiful beaches, crystal clear waters and gorgeous reef full of tropical fish for a pirate to swim with. The first mate and I recently made a short sojourn down to Grand Cayman for 5 nights at surprisingly little cost. A magician may never share his secrets, but we Pirates like to stick together and help each other out, so here’s how we did it!

For starters, we usually plan our voyages well in advance, normally almost a year out. Successful pillaging requires proper prior planning! Airlines let you book 330 days in advance, so let’s start with how we got free airfare to Grand Cayman on points. Sure, we’d love to have sailed our pirate ship down there, but nothing goes to windward like a 737. Living in South Florida was a help for us, as the distance to Grand Cayman is not that far and American Airlines uses reward points based on the distance flown. In our case we used Chase Ultimate Rewards points that can be earned with the Chase Sapphire Preferred or Reserve card. (Click link to sign up)  We found reward redemption from British Airways of a round trip ticket between Miami and Grand Cayman for 15,000 British Airways Avios points. So using 30,000 Chase Ultimate Rewards points, easily attained with the signup bonus, we made the instant transfer from Chase UR rewards to BA Avios points, then booked with BA to get 2 round trip airline tickets. Even though we were actually flying on an American Airlines plane, we got the better redemption rate from British Airways through their rewards portal. Often when looking out close to the bookable 330 day window you can often get the same round trip flight straight from American Airlines for the 15,000 points. Round trip airfare for 2 can be attained with the signup bonus from the Citi American Airlines card.

Our lodging in Grand Cayman was another great score. Like most other things, the life of a Point Pirate is far more rewarding as a 2 player game, so the First Mate and I both signed  up for the Chase IHG Credit Card from Intercontinental Hotel Group which offers 80,000 IHG point bonus after meeting the $2000 minimum spend. The card comes with an $89 annual fee, but like most of the Chase cobranded hotel cards you also get a free night every year at an IHG hotel for that annual fee. Well worth it in my opinion. IHG offers a 4th night free benefit when redeeming reward stays, so at 25,000 points a night for the Holiday Inn Grand Cayman one persons sign up bonus will get you 4 nights at this beautiful property. Another perk of having a cobranded credit card is that it gives the lowest level hotel status by owning the card, so we managed to get upgraded to a slightly better room that far exceeded our expectations with a full kitchen, separate bedroom, ocean view and steps away from dining at the Blue Iguana restaurant on premises.

The property is a little off the beaten path and a car is almost a requirement unless you want to pay a lot of cab fare. Rest easy though, car rental prices are surprisingly affordable in Grand Cayman. Our 5 night rental from Avis at the airport was only $135 booked in advance, and as long as you have a Chase Sapphire Card that comes with excellent rental car insurance you will be earning extra reward points on that rental car while knowing that you can safely decline all the extra insurance charges that rental car companies always love to try and scare you into accepting.

At the moment there aren’t a whole lot of great point hotel choices on Grand Cayman, although there is another IHG property, the luxury Kimpton Seafire Resort. The good news however, Hyatt is planning to open a new resort on 7 mile beach in 2021 so it’s worth saving up those Chase Ultimate Reward points because they offer tremendous value when transferring to Hyatt hotels.

One of the best things to do in Grand Cayman besides laying around the beautiful 7 mile beach is scuba diving, and we highly recommend Ambassador Divers for some under the water fun. They will even teach you a course and let you hunt the invasive lionfish that have been plaguing the Caribbean.

Scuba diving in Grand Cayman