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My family and I were in Grand Cayman on the Paradise on July 1st. We took the 11 am Nativeways tour to Stingray City and two snorkeling stops. We were late getting there...as we had to wait over an hour to tender off the boat. They waited for us and immediately rushed us over to the boat. We had only about 14 people on the boat. We had two people helping us, and they were awesome. Showed us the sting rays, taught us about them and helped us get tons of great photos. My boys were a bit nervous, and they were very good with them. They taught my sons how to snorkel and took the time to make sure all the snorkeling equipment fit them. We paid $90 for a family of 5 - can't beat that. My youngest (age 3) was free and they're running a promotion now so the older boys are cheaper too. It was worth every penny plus the big tip we gave at the end. It was a great day.
My 3 y.o. was content to sit on the boat and watch. He had a blast....and never even asked to go in the water. They had a small life jacket for him, which he wore the whole time. The sand bar is shallow enough that if your 4 y.o. wants to go in, you could easily hold a child....but, it was nice to have my hands free to touch the stingrays. We left my son on board in Belize, because the tour was longer and we didn't know if he would enjoy it. So, you could do it either way....but Nativeways took very good care of my children.
I have a four year old, that we took out to the Sand Bar and Coral Gardens with Franks Watersports over the weekend. He Loved It. He is quite a good swimmer anyway, but was off the boat as it stopped at the Sand Bar and in with the StingRays. At Coral gardens he donned his fins and mask and was diving down to try and catch the fish!
Most water sports operators are conscious of the younger children and the smaller ones (like Nativeway, Capt Bryans, Soto's, Franks, Capt Marvins etc) will go out of their way to make sure that the little'ns are happy.