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It’s all about people and connections at Pirate’s Point Resort on Little Cayman. What do I mean by that? Keep reading and the salty story will reveal itself.

Castaway Crystal and myself recently packed our bags and hopped a fast plane south to Pirate’s Point Resort so that we could discover the joys of Little Cayman. Little did we know, we would be discovering new ways to step outside our comfort zone. And I’m glad we did.

The Resort

First, a little about the resort. Pirate’s Point Resort is a small boutique style resort with 10 rooms. The rooms are spread out across the property’s sandy grounds. Some rooms/cabins sit right on the beach, while others are tucked behind lush Sea Grape trees and dancing Coconut Palms.

Little Cayman Pirates Point Resort

Little Cayman Pirates Point Resort

resort rooms

cottages on Little Cayman

In the middle of the grounds sits a relaxing pool and spa that over look the blue Caribbean waves. While a pool usually draws the attention of relaxers, this castaway was super fond of the shaded hammocks that where placed around the property. Oh, Ryan’s late for dinner? Just look in one of the hammocks!

Pirates Point Resort Little Cayman Pool

Hammocks at Pirates Point Resort


Pirates Point Hammocks

Also in the center of the property is the dining room, bar & lounge, shop, and front desk. This is where all meals are served and where people gather after dinner to talk about what sea creatures they saw on the day’s dive. You can grab a drink from the honor bar and settle into a good book or an exciting game of dominos.

Pirates Point Resort Dining

Dining room

Pirates Point bar

Dominos at Pirates Point

If you’re looking for a lively nightlife, drunken shenanigans, or a sports bar type atmosphere–Pirate’s Point Resort is not for you.

If you’re looking for a relaxing, quiet, and intimate experience where you really get to know the other guests and staff, then this is the place for you. There is no bartender, just grab what you need from behind the bar and mark it down, it’s a true honor bar. On a dive package, don’t worry about marking your drinks down, they are included!

Worried about what to have for dinner? Don’t. All meals are served buffet style at the same time every day. Just listen for the sound of the bell (dive tank), and you’ll know a fantastic feast is waiting for you–breakfast, lunch and dinner.

Dinner bell

During these meals, you dine with other guests, six to a table. This is what I meant when I said this resort is about people and the connections you make. It’s also what I meant when I said Crystal and I had to step outside our comfort zone a bit. What started out as a slightly uncomfortable surprise, quickly turned into something truly special.

We dined with people from Canada, the BVI, London, Germany, South Africa, Portugal and other states. Each person had a unique story to tell and I’m glad we were put in the situation where those stories could be told. Those experiences, those stories, are reasons why travel is one of the best tools to see life from different perspectives. Just like Mr. Marley said, One Love…one love all the way.

The Island – Little Cayman

Ahhhh Little Cayman, how I do I describe you? Little Cayman sits about 60 miles to the east of Grand Cayman. Where Grand Cayman is busy with traffic, cruise ships and huge resorts….Little Cayman is the exact opposite.

You get to the island via a Cayman Airways twin propeller plane which lands on a single short runway. You arrive to the smallest airport terminal I’ve yet to see in the Caribbean. The plane literally has to taxi across the street you take to get to Pirate’s Point Resort. It’s so cool!

Little Cayman Sign

Cayman Airways

Little Cayman Airport

The island has 170 permanent residents. This means the island’s iguana population out numbers the human population.

Little Cayman Iguanas

Little Cayman Iguanas

Speaking of animals, Little Cayman is serious about conservation. There’s a large booby pond next to Blossom Village, the main town on the island. Wait, did he just say booby pond?! I did!

The Booby Pond National Reserve is a protected tropical wetland that is home to many bird species, one of those being the Red-footed Booby. Each day the Boobies head out to sea to catch fish. Each day around sunset or late afternoon they return, only to face the harassment of the Frigate birds. Apparently the Frigate birds don’t fish or can’t land on water, so what they do is wait for the Boobies to return and they scare them into throwing up their catch, then the acrobatic Frigate will steal it right out of the air. It’s really something to see when you’re not getting pooped on! Yes, that almost happened too, but we saw it coming! Crystal has a great photo (is a poop picture great?) of the near miss!

Little Cayman Below The Waves

You can’t talk about animals and Little Cayman without mentioning probably the biggest reason why people travel to this quiet rock…the world class diving.

I’m going to save most of this part for a separate blog post, but let’s just say, I was blown away by what I saw under the waves. It was a true diving paradise where you could observe abundant wildlife acting completely natural with a human presence there. I believe that most of the island’s waters are a National Marine Park, completely free from fishing and touching.

Little Cayman Diving

Little Cayman Dive Resort

The island has over 60 dive sites and has dramatic wall dives like the famous Bloody Bay Wall. Crystal and I took the Scuba Discovery Experience with Tiago at Pirate’s Point Resort and I’m sooooo glad we did! We did two dives on the Bloody Bay Wall and I can’t describe the feeling you get when you’re slowly swimming a few feet above the reef in 30 feet of water and then suddenly the reef stops and you’re floating over the edge of a 1200 ft. cliff. It was truly amazing, Crystal and I are definitely getting certified soon.

More to come on the diving!

The Food

Pirate’s Point Resort is known for its amazing food. Sure sure sure, lots of places have good food right? But this place is different. There’s a good story and history to go with the food of Pirate’s Point Resort as well.

The name Gladys Howard is well known all over Little Cayman. The late owner of Pirate’s Point Resort moved to the island in 1986 and quickly made a name for herself with conservation and cooking. Originally from Texas, Gladys was a Cordon Bleu-trained chef, having studied with the likes of Julia Child and Jacques Pepin. This focus on food at the resort did not go away after Gladys passed in 2015. She left the resort in great hands, passing it to her daughter Susan, who keeps up the tradition of making Pirate’s Point Resort the best spot on the island to eat.

Pirates Point Resort Dining

Pirates Point Resort Dining

Pirates Point Resort Dining

Pirates Point Resort Dining

Pirates Point food

The minute we arrived to Pirate’s Point Resort, we were whisked away to a special champagne and sushi happy hour at Susan’s home on the property. The spread was amazing! This is something she does each week for guests as a thank you send off. Typically guest arrive and leave on Saturdays, so she likes to treat them to something special on their last day.

Pirates Point Sushi Night

Pirates Point Sushi Night

The People

For me, it always come down to the people. There are millions of resorts that sit on beautiful beaches around the world, but it’s the people that make a place special. It’s the people that give a property its personality. It’s the people that create the experiences guests will cherish for a lifetime. It’s the people at Pirate’s Point Resort that are the reason why guest usually end up booking their stay for next year before they even leave.

I can tell that Pirate’s Point takes great care when they hire a new person. Each team member has to wear many hats. Don’t be surprised if you see your dive instructor pour wine for you at dinner the next night and then captain the dive boat the day after. It’s a small team, but because of that, you really get to know them and their unique lives. Remember when I said people and connections, this is what I was talking about.

Susan Howard Pirates Point Resort

If you need a lunch to take with you for a beach day, just ask, they’ll pack one up for you. Want to go night snorkeling off the beach to catch lobsters, they will go with you and cook up the lobsters afterwards. There’s nothing they won’t do to make your stay perfect.

Thank you to Susan, Tiago, Gay, Ed, Michelle, Dianne, Winston, Dania, Cameron, Steven and anyone else if I missed you. You guys made our salty stay one to remember. We will be back.



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About the Author: RumShopRyan

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty. To learn more, visit our About Us Page.