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Endless Playtime in the Caribbean

Updated: Jul 7, 2021

February 2019

February 2019 – The Caribbean with Casey & Erin on their Catana 47 Performance Catamaran

Further Cruising Preparation: We head to the Caribbean!

We have a wonderful and sweet family in our lives. We met Casey and Erin from our Marina del Rey sailing community. When they aren’t traveling, they live near us in Southern California. They have an interesting story. They itched to explore the world, so they sold everything they own, quit their successful careers of over ten years at SpaceX, bought a Catamaran, and set off to sail the world with their two small children ages 3 and 5. Steve helped them find their boat which they named Endless Playtime.

In early November of last year, we met up with them at the Annapolis Boat Show before they joined the Salty Dawg Rally headed for the Caribbean. While visiting, we joined them on a short sail on the Chesapeake Bay. Coincidentally, we ordered our own boat the very same week.

They invited us to visit them in the Caribbean, and since we are fond of them and missed them, we decided to go. The purpose of our trip was two-fold. One, they appreciated seeing friends from home who brought them lots of goodies and gear that they needed. Two, it was an opportunity for us to get additional experience on a Catamaran before our boat arrived.

We arrived in St. Lucia in mid-February. After a welcoming tour of the island, we enjoyed a nice dinner ashore in Marigot Bay where they were moored.

Casey asked me what my goals were for this trip – a very good question I thought to ask a guest. I requested a white sand beach and a night crossing. So, the next morning we set off for Wallilabou Bay, Saint Vincent & Grenadines, famous for the filming location of Pirates of the Caribbean. You might recognize this arch and some of the town scenes from the movie.

Upon our arrival, we learned our first lesson of the trip. When you pull into an anchorage there, the boat boys immediately come up in their skiffs looking to sell local produce and baked goods. They’ll even help you find a spot to anchor, for a price of course. Casey and Erin were keen to send them away most of the time unless they wanted to buy what they had to offer.

After a fun visit to the Pirates of the Caribbean Museum with the kids, we enjoyed a delicious dinner ashore complete with rum drinks for the adults.

The following morning, we set off for Tobago Cays to fulfill my first request — white sand beaches. Along the way, we enjoyed 30 knots of trade winds and about 10-foot seas. Sargassum weed, a type of floating algae or seaweed, was everywhere which was a new experience for us. Tobago Cays is a beautiful place and popular with tourists. The anchorage is usually crowded this time of year, but Casey skillfully found us a spot just leeward of the reef in very shallow, warm, and clear water. The area is protected and known for being a haven for sea turtles.

Steve took some time to clean Casey’s hulls while we were there just to see how long it would take. This was part of his research of course for our own boat. The task took him a little over an hour to clean one hull (in case you were wondering).

There is nothing better than feeling the trade winds blowing steadily and warm, clear water. We could certainly get used to the Caribbean cruising life. It was just perfect!

Next on the itinerary was Union Island where Casey had the opportunity to do some windsurfing. Erin and I headed to shore to pick up some colorful produce and enjoy girl talk over some island drinks.

Maintaining a boat with children in tow is a lot of work. Erin and Casey had gone from full-time working mom and dad to full-time cruising parents in a very short time. We were happy to help with the kids and take care of chores around the boat to give them a little break. I enjoyed cooking for them while we were aboard Endless Playtime. One afternoon when they went ashore with the kids, Steve and I surprised them by completely washing their cockpit area, cushions and all. It was just a little thing we thought we could do to show our appreciation for letting us join their sweet family on their adventure. The last thing we wanted to do was be a burden.

As we were departing Union Island, we spotted the Royal Clipper, one of the largest sailing passenger ships in service. She’s a massive steel-hulled, fully rigged tall ship that measures 442 feet in length. The ship can accommodate 227 passengers and a crew of 106. What a sight to see!

Next, we made a brief stop at the Island of Bequia just for the evening. We enjoyed a walk through town and a departure meal, complete with some metal drum island music. Just before midnight, we left the anchorage toward St. Lucia to check off my second request — a night crossing. The night crossing was an amazing experience. Watching the moon dance on the water, listening to the sound of the ocean in the dark, and taking in the breathtaking view of billions of stars under a clear sky truly gives you time and space to think. On the crossing, Captain Casey took cat naps in the cockpit while Steve, Erin, and I stood two-hour watches.

This is when I learned our second lesson — before heading out to sea or leaving the boat, always make sure your hatches are locked shut and not just on the vent setting. During the night, we had some rough seas and I happened to be sleeping in the forward berth. I was unpleasantly awakened by a gush of water coming in the hatch, soaking the bed and me. Casey and Steve laughed as I came up drenched in seawater. Apparently, it wasn’t the first time this had happened on their boat. Let’s hope it is the last for me!

The third and final lesson of the trip that we learned was to watch out for crab and lobster pots. This is especially true if you are sailing near land at night. On the way to drop us off in St. Lucia, we wrapped a line around one of the props. Casey jumped in to cut the line away, but with the swells, the task was too difficult. Fortunately, we were able to continue the journey into the anchorage on one engine until the line could be safely removed. These are the types of valuable lessons that you learn out on the water.

We arrived in St. Lucia the following morning with enough time to catch a taxi to the airport. We were reluctant to say goodbye. During the trip, we had really bonded with the kids and thoroughly enjoyed our time. We learned a lot from Casey who calmly assessed each anchorage for the perfect place to anchor — I liked his style. He and Erin worked well together using their “marriage saver” walkie-talkie headsets as they prepared to let down the hook. Erin was organized on board with her galley, gear, toys, and educational tools for the kids all in order. They were both so helpful in making suggestions for us to consider in our own cruising plans.

Overall, we felt like it was a very valuable trip, not just for the learning opportunities, but for our long-term friendship. It was a good experience to learn how to make our own guests feel comfortable and safe when we host them on our boat.

You can follow Casey and Erin’s story on IG and Facebook @endlessplaytime and @endlessboatwork.


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