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A Private Boat Charter is a must in Grand Cayman

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Hands down the highlight of our eight days in Grand Cayman was the day we chartered a boat. We knew it was a splurge but through past experiences we all knew it was worth it.  We were a group of 10 – so for all of us to pay $75++ to for an overcrowded snorkeling boat just didn’t make sense. For roughly the same price, we liked the idea of chartering a boat for 5+ hours, being leisurely about the day, being able to stop where we wanted to, stay in a spot as long as we wanted to and enjoy lunch without dozens of other people crowding the boat. We couldn’t have made a better choice.

We were picked up by Native Way Water Sports at our condo complex right on time by a large van that held all of us comfortably. Off we went. Sunscreen, towels, lots of local cold Cayman beer and most importantly everyone eagerly looking forward to the day.

The captain and his mate were super accommodating, immediately asking what we wanted to do/see. Of course, the stingrays were on everyone’s radar. Other than that, we had no expectations except a great day on the water. The kids took turns sitting at the front of the boat, the back of the boat or up with the captain. (side note: the boat had so much shade. thank goodness!!!)

The stop at Stingray City was just incredible. The 3 foot deep water was as clear as a swimming pool. You could see the stingrays perfectly. The first mate jumped in and demonstrated what to do and not do with these beautiful creatures. We all had the option of touching or feeding the ray. The captain was dicing up some squid on the side of the boat for us to do a little feeding. The feeding swiftly brought a bunch more stingrays swimming against our legs and through our arms. It was a little strange at first, but they are so gentle and deliberate. Easy to warm up to.

Stopping at Stingray City further confirmed that we had made the right move by hiring a charter for the day. See that crowd of people in the photo above? That group was only part of one boat that pulled up, over flowing snorkelers, screeching anxiously about getting in the water. We had our own little area to ourselves. Oh so perfect.


As we left Stingray City we decided to stop in a spot with some really nice snorkeling. As we were pulling into our spot, the captain pointed out a really large sea turtle. We never did see him once in the water but it was awesome to see the turtle quickly passing our boat. When the boat stopped, the mate dove right in and came back up with a couple of star fish. The kids (and the adults) loved being able to safely hold these cuties. Once we had all had our turn, the mate dove back in and placed the star fish back where he found them. 

We all agreed it was time for some lunch. The captain had passed around a menu earlier and called in our order – genius. We were headed to Rum Point. We docked and walked towards the restaurant, as we approached from the dock, the waitresses met us at bright colored picnic tables with our food. Blackened fish sandwiches, jerk chicken (which made me wish I wasn’t a vegetarian), veggie burgers, kids grilled cheese + french fries, you get the idea, something for everyone. Such a perfectly Caribbean spot with really good food and a great atmosphere. A must visit.

I think we were all in agreement that this restaurant at Rum Point was the perfect island setting. I could just imagine a wedding reception or rehearsal dinner in this spot. Maybe a family reunion? The island vibe, the breeze, sand between your toes, the gorgeous crystal clear blue water, I could have stayed longer swaying in one of the shady hammocks. But off we went, walking down this long dock back to the boat. (PS. If you look really, really close, I am wearing my black/white sarong that you will see reappear year after year, trip after trip. I just love that sarong!!! A $10 pick up on the side of the road on the North Shore of Oahu)

After lunch we found a new snorkeling spot. It started out as a snorkeling spot but it turned into the perfect spot to jump off the top deck of the boat. Over and over and over. So. much. fun.

Then it was time to head back. The day passed so quickly. 

These two guys were outstanding. Dave and Thomas were personable, knowledgeable about the Caymans, the water and all the sea life, great conversationalists, easy going and able to have a good time. We couldn’t have asked for a better way to spend the day together!

Private Charter: Native Way Water Sports

(It turns out the owner of the outfit that we did our charter went to the same college as we did. What a nice coincidence. Also why it’s always nice to strike up a conversation!)

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