Cayman Islands

Pirates Point Resort, Little Cayman

Tip #1:  If Gladys is there, talk to her and pay attention to her stories.

Tip #2: Go diving! They have awesome dive masters!

One of the best things about my trip to Little Cayman was staying at Pirates Point Resort.  It’s not what I was expecting, and I’m grateful for that fact.  When I think resort, I think crowds, umbrella lined beaches, fruity cocktails served poolside, next to another resort (or 3),somewhere you can get a massage on the beach and a pedicure in the spa.  I relate resorts to my experience in Mexico.  Those types of places can be fun, but as someone who doesn’t like crowds, resorts aren’t generally my preferred place to stay.


Pirates Point Resort, like Little Cayman itself, is very relaxed, with a down-to-earth feel. It has 10 cottages, which wonderfully limits the amount of people who can be there and has nothing but a few houses and a protected reserve nearby.  A bell that’s actually an old scuba tank is rung every meal time, breakfast and lunch are eaten outside, happy hour and dinner are inside, followed by coffee at the small bar, and the food is AMAZING.  The policy of the resort is to make you feel at home.  There’s a bar, but no bartender.  Guests can go behind the bar, make their drinks, and are trusted to keep track and be honest about what they had.


The owner, Gladys, is one of the most interesting women I’ve had the pleasure to meet. She’s 82, dives to the depth of her age, from Texas, and opened the resort in 1986 after getting divorced. She studied cooking with Julia Child and to combine her love of cooking with her love for diving, which is how Pirates Point came to be. She’s a dynamo. If you go and are lucky enough to meet her while you’re there, spend time talking to her.  She has some interesting stories.

Pirates Point is primarily a dive resort and if you’re not a diver, you can expect to have the place pretty much to yourself during the day while most everyone else is out on the boat. It’s a great time to lounge by the pool and work on your tan (or hide in the shade in an effort to not burn) while enjoying the breeze and beautiful ocean view. Should you decide to try diving or want to go out on the boat for some snorkeling, you won’t be disappointed.


If you snorkel, it’s pretty awesome.  If you try diving, the resort has some great instructors who made me feel very comfortable with what I was doing and pointed out some underwater creatures I certainly would have missed on my own. The resort staff is an eclectic and interesting group, as are the other guests. When I was there, the large majority of the other guests were friendly and fun to talk to and everyone was social.

If you’re looking to stay somewhere that offers an endless amount of activities, this isn’t the place fro you.  There are bikes, snorkeling gear, a pool, and hammocks for your enjoyment.  There’s internet, but only in the main building and outside by the pool area. It’s great. It’s not a fancy place, the only night you might want something a little dressier is Friday night, when there is a champagne and sushi happy hour.  All other nights, casual dress is the norm.  Aside from my stays at hostels, this is probably the most laidback place I’ve ever stayed. I loved it.  If you’re looking for your next vacation spot (and aren’t on too much of a budget), this is definitely a great place to relax.



Shell/pebble maze on the beach at the resort




  • kutukamus

    Pirate-wise, this is treasure! 🙂

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