7/17/26 - This was our funnest day, hands down. The operator that runs the Lady Lynsey, Cruz Bay Watersports, also runs private charter boats that you can reserve. I wanted to make the most out of my son seeing the islands so I arranged a 37' Boston whaler for us on the first Friday we were there. The boat was super nice, about 1.5M with three 350 outboards, a cabin with bed, sink, and toilet as well as plenty of seating and a very advanced helm.
That Friday morning, Corey came to the Ritz Carlton to pick us up. He anchored right out in the cove and we took a dinghy out to him and boarded. The first stop was over to Caneel bay on the north shore of St. John, we were headed here for prime snorkeling and it paid off. As soon as we pulled up, a hawksbill turtle was right in front of us getting air at the surface, this was Zylar's first time ever seeing one so it was really special. The weather was beautiful and the sun fully out so the water was perfectly clear. We geared up and jumped right in the Caribbean Sea right off the boat. As soon as we got in the water, there were 2 more sea turtles and a massive stingray gently gliding around on the sea floor, it was only about 10' deep. Zylar got to see all of that and more as we swam further over to the actual reef. We wrapped that up and then set course for Jost Van Dyke where we would clear customs for the British Virgin Islands.
Once at Jost, Corey started all of the paperwork and we were allowed to leave the boat and walk over to Foxy's while he worked on that. Foxy's is a famous bar on Jost, right on the water, it's a short walk from the customs building. We got a couple of drinks here and chilled until Corey brought the boat over to get us so we could head to White Bay.
Once we were cleared through customs and back on the boat, we went east along the coast of Jost about 5 minutes if that, to White Bay. White Bay is a very famous beach and hosts the Soggy Dollar which is the bar that invented the original Painkiller drink. The name comes from people swimming up to the beach to go to the bar with soggy dollars in their pockets hence the name, there's no dock. Corey took the boat right up to the beach where we anchored and swam up to the beach and had lunch at Soggy and of course two painkillers, one virgin obviously.
After a little bit of swimming in White Bay, we got back on the boat and departed west along the shore to Sandy Spit. A small atoll that changes shape every week from the wind and waves. It's very tiny with only 3 palm trees in the middle, you can walk the whole thing in like 2 minutes. Zylar and I swam up to the atoll and checked it out, we swam on the shores and threw a ball around while we looked out at the surrounding islands and beautiful water.
Once we were done at Sandy Spit, we set course south through Drake's Passage named after Sir Francis Drake, it's where winds converge and make for excellent sailing which is why they host a sailing regatta there. Working our way through the passage, we were on our way to Norman Island to go to the cliffside caves and Willy T's. We got to the spot and jumped right into the sea and swam to all three caves, we saw fish and jellyfish in them and had a really cool time just exploring. Once we finished that up, we went right around the corner to Willy T's.
Willy T's is super cool, it's a barge anchored out in the cove at Norman Island and has been turned into a bar and restaurant. You dock on the side of the barge and climb on where you can eat/drink, and at the top, you can actually jump off into the clear emerald green water. Zylar really loved it, he was nervous at first but after the first. jump, he wouldn't stop. I was so happy to see him doing something new and loving it.
After all of this, we cruised along the south shore of St. John back to the hotel, this was a day him and I will never forget.






Jellyfish in one of the caves
Sea turtle
Stingray
Inside one of the caves
At Caneel Bay

















Painkiller at Soggy Dollar
Leaving customs and headed to White Bay
Headed to Jost










Zylar jumping off the boat
On Sandy Spit
Swimming
Zylar and I throwing ball
Pulling up to Sandy Spit













Pulling up to the caves
Pulling up to the caves
Jumping at Willy T's
More Jumping
More jumping