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A Timbers Ohana Sailing Adventure

Updated: Mar 30, 2022

Right now it’s a dark, starry night and we are bobbing gently off the coast of St. John. Everyone has gone to sleep and it’s time to wind down after a fantastic first day of sailing. Sitting up here on the top deck of our beautiful 51 catamaran I can’t help but think about how damn lucky I am.


The magic hour on St. John

The friends we have on board this week – Art, Victoria, Mike, Traci, Dan, & Kathy have never been on a trip like this before. To say that they were anxious sailors is a deep dive into the world of understatement. For months we’ve had video calls focused on what to pack, what to wear, how many types of sea sickness medicine to take, what the alternatives are to sailing, is the boat big enough, EXACTLY how much sailing do we absolutely NEED to do? You get the idea. They were nervous.


However… they were committed. Each one of them fought through their fear and apprehension and climbed on board. You could almost feel the tension in the air as the crew walked down the dock looking like a tropical alternative interpretation of the Reservoir Dogs. Each time we passed another massive mega-yacht Victoria would half-jokingly ask if we “could just take that one instead”. As we rounded the last corner of the pier, our home for the week was tied up at the end looking relatively small next to the 260’ monsters around us. But she was still a beauty. Custom designed for the Moorings charter company, this model of catamaran is set up for fun and comfort. Upon boarding “Annilola” the first order of business was to get a rum drink in everyone’s hand and introduce them to the boat.


Our first toast on board Annilola

Working with me this week are my dear friend Mia, and Darby – the wonderful eldest daughter of another great friend from Virginia. Mia and I have done this before and know that we make a great team. Darby was with us for the last couple of days in St. Thomas and has already proven to be an invaluable addition. We are stoked a ready for a great time and a lot of hard work in the week ahead.


Between the 3 of us, we get everyone’s luggage stored, cabins prepared, and most importantly nerves calmed (thank you Capt. Morgan for the assist). After everyone knows where the lifejackets, life raft, safety lines, radio, and bar are, it’s time to explore the boat. With a large dining table and seating area on the stern, another large lounge on the stern rooftop deck, a small chill-out spot between the main salon and the trampoline, there is room for everyone to get comfortable, find some privacy, and relax. The cabins each have private full bathrooms, and the main salon / galley area has more than enough room for us to cook, tend bar, and keep a little reading nook available.


As we cast off our lines and head out into the Caribbean, everyone seems to be getting comfortable, relaxing, and settling in for a nice day of sailing over to St. John. Aware that today will set the tone for the whole week, I’m careful to keep the boat moving slowly, avoid chop and ferry wakes wherever possible, and let everyone get their sea legs under them as easily as possible. It’s a short shot over to St. John, but it still took us over three and a half hours.



Darby workin' the lines


Art was a great student at the helm & an awesome co-captain to chat away the hours with.

Art and Victoria are all smiles as we wrap a day on the water

As we pulled up to the mooring buoy in Caneel Bay, Victoria walked over to the base of the cockpit and asked the best question I could have possibly hoped for: “Do we have to stop sailing already?” My wonderful crew of nervous first-time sailors was happy, excited, and ready for more! I promised a full day of sailing tomorrow, started making a round of sundowners, and encouraged everyone to go for a swim.


After a fun filled dinner, a couple bottles of wine, some impromptu floating karaoke, and a beautiful moonrise, everyone is tucked in down below and I have the top deck to myself. And I’m still thinking about how damn lucky I am.




It's a bird! It's a plane! It's SuperDan!

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