World Travel – Grand Cayman – “Revisiting my youth with my Youth”

Caribbean, Grand Cayman – What We Did

Into the ocean we went, met some really nice Stingrays, had a cold one where pirates used to tred and about killed myself on my jet ski!  All is a week’s work trying to keep up with my kids!

The Billy Bones Hat

Well, I didn’t go to Hell.

In fact we didn’t stray too far from our condo. Typically, if I were on this trip solo, which is how I usually travel, there were several places on Grand Cayman that I would have ventured out to see.  One of those places is a little town called Hell.  From what I understand, it is a tourist trap.  There is a man dressed as the devil and visitors buy postcards or bring letters to get them stamped, thus being able to send something to someone from Hell.  But since this trip was really about a vacation with my kids, I let them steer the ship and needless to say I did not make it to some of the places I wanted to go, such as George Town (we avoided that because of the many cruise ships in port,) the museums, the Botanic Park or the Turtle Farm.

Meet Georgina...

What we did do, however, brought out the 20-year-old in me again!  Our first outing, after the trip to Beer Pong heaven that I talked about in my post about Time Together, was to Stingray City.  Yes, I was a little nervous given memories of the loss of the Crocodile Hunter to one of these animals but off we went.  I’m not sure why they call it “city” because we motored out on a catamaran for about 50 minutes to the middle of the ocean.  It must be because the Stingrays in the Cayman Islands have all learned where the food is, and they congregate on a sandbar just off a reef in the ocean.  There are dozens of Stingrays in the water, and dozens of boats with dozens of tourists as well.  I was glad we took the recommendation of the condo manager and booked with Dexter.  He and his sidekick, whose name I tried to pronounce all day but couldn’t, have obviously been doing this their whole lives.  I will just call his partner Old Seadog, because he was the epitome of one!  Rather than being on a big boat, our catamaran held about 15 people so it was a much more personal and enjoyable experience I think, based on what others in the water were saying about their big boats.  And getting to the Stingrays was easy.  Well, sort of…

Ahh, lucky Georgina...a kiss from Stephen

Getting off the catamaran in snorkel and fins proved to be a challenge and a hilarious opportunity to watch each other try to do just that!  Add in that my waterproof camera that was about to die so I was rushing to jump in and get what pictures I could as quickly as my battery would last and I think we looked like circus clowns trying to jump into a barrel of water.  But once we were in the water, the real fun began as one after another, the big Stingrays brushed up against our legs and we were literally surrounded by them just under the water.  It was shallow on the sandbar, so you could stand.  We really didn’t need the fins, but they were handy to help us when we needed to get back to the cat.   We each took turns “meeting” and feeding the Stingrays.  Old Seadog calls them by name – I got to meet Georgina.  Georgina is huge, and with Old Seadog’s help I held her in my arms, gave her a kiss and she massaged my back.  The underside of a Stingray is soft and velvety, and when they undulate their wings on your back it does feel like a gentle massage.  I’m a massage regular – and I never thought I would be able to say a Stingray massaged my back!  That was a first! The kids went through the same meet-and-greet with Georgina, we exhausted my camera with underwater shots of our new cartilaginous fish friends, who happen to be related to sharks.  I think I’m glad I didn’t know that going in! Especially when I was feeding her!

A Stingray massage for Jess

After leaving Stingray City, we had the chance to snorkel a nearby reef – beautiful, but, for the record, not nearly as beautiful as the snorkeling in the Pacific.  The highlight of our snorkeling trip was when Jessie spotted the reef shark and, well, I didn’t know you could haul ass in fins back to a boat so fast!  It was a leisurely trip back, as Dexter let down the sails and the wind took us home as we enjoyed music of the Islands.  I’m glad we got pictures, because it’s hard to describe these mysterious animals.  It was a long day in the sun and a must do if you find yourself in the Cayman Islands.

When I was in Tahiti a year ago, I spent a morning jet skiing around Bora Bora, and it was truly one of the best times in my life.  So suffice it to say, I was pumped about jet skiing in Grand Cayman!  And so was Stephen, as you can imagine.  I booked a private jet ski tour with EBanks Watersports and I will tell you, in a word, they were fantastic!  They picked us up at the condo and provided two guides.  We each had our own jet ski, and the rules here were looser than anywhere else I’ve ever jet skied.  Essentially, it was one rule.  Don’t get too close to each other so you don’t crash or run over someone if they fall off their jet ski.  Other than that, the ocean was the limit!

With my starfish

Our first stop was at a sandbar, which was home to hundreds of starfish.  Our guides dove down and grabbed one for Jessica and me, Stephen got his own – it’s a macho guy thing.  After taking proud pictures with our beautiful starfish we dropped them back into the sea and I never realized just how fast those little buggers were in the water!  Damn!  They can move!

Yeah, I think he liked this day..

Then we set out across North Sound to Rum Point.  It needs to be noted here that this was my first time on a jet ski in the open ocean…a much different experience than on a calm lagoon!  It’s very choppy, and you are hitting the chop hard – over, and over and over again.  There’s lots of spray, you and the entire jet ski get soaked.   I would recommend women wear board shorts.  Bikini bottoms go all over the place when the ski gets wet….just use your imagination here and trust me about the board shorts!  But I was having so much fun, watching my kids have fun, riding a jet ski in the ocean on a beautiful, sunny day in the Caribbean…and I confess to getting all up in my Cheerios thinking I could keep up with the youngsters.  So I full-throttled my jet ski, inspired by seeing my two kids ahead of me streak across the water like bats out of Hell.  Well, the next thing I know I just barely turned my handlebars and BAM! I hit chop so hard it threw me 20 feet off my jet ski!  I’ve never been thrown off a jet ski before so the shock to my system was huge!  Thankfully the jet ski key is attached to your life vest and goes with you, stopping the jet ski on a dime.  When I found my wits again, I realized I had lost a shoe, my new Melting Hearts sunglasses and was sporting a new bruise on my leg from hitting the handlebar mid flight off the ski!  But I was alive, and so happy that no one was behind me to see that spectacle!  Immediately the kids and the guides came back to help me once they spotted the rider-less jet ski.  Somehow they found my sunglasses floating in the ocean – this was the second time I dropped them in the ocean and they came back to me!  I now consider them my lucky sunglasses and plan on wearing them for all future water activities!

Relaxing at Rum Point

Back on the jet ski, quite embarrassed and humbled, we made our way to Rum Point –one of the most picturesque places I saw on Grand Cayman.  The story goes that this was the place where pirates of old would stash their treasure and prized rum.  The modern day story is the weekend parties at Rum Point, where everyone who has a boat sails out on Sundays and basically hop from boat to boat to socialize, eat and drink.  It’s quite a drive to Rum Point from Seven Mile Beach – we considered doing that to experience the Sunday fun – but were told that the party in on the water, not on the land.  So we settled for a jet ski break at Rum Point, complete with food, cold beers and fun conversation getting to know our guides and the history of this beautiful little site.  I wish we could have stayed longer, but we did have to cross the North Sound again on our jet skis to return home.  My ride back was a lot saner and slower and I stayed firmly glued to my jet ski.  I think this will be one of those memories of a special day playing on the ocean, in the sun together that neither my kids nor I will ever forget!

It was quite a week revisiting my youth with my youth.  Nightclubs, beer pong, hangovers, jet skiing, kissing Stingrays, shopping, swim-up bars, French fries every day (I know I’m gonna pay for that one later!), shots, late night heart-to-heart talks, laughter, one argument, new friends, dancing….

Maybe I didn’t go to Hell, but I would definitely call this vacation a little slice of Heaven.



  1. You and your starfish both seem to be happy with each other. Great post! I think Cayman has a lot to offer; one needs to visit here and should have more and more time to spend there. I want to know whether food, wine and beach hotels are all affordable or expensive. Could you please suggest an online Cayman Guide?

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