Last month, I had the opportunity to spend a week with college friends on a catamaran in Puerto Rico. I had hesitated to write about the trip as it was a solo one with only half of the Traveling Ridleys team represented. However, based on the encouragement of my better half, here I am, sharing it with you.
First, I have to admit that this was a once-in-a-lifetime opportunity. Most people don’t get the chance to live on a sailboat for a week cruising around from archipelago port to harbor to bay to inlet for seven days. It just reinforced how fortunate I am to have a wife who would support such an activity and friends who impressed me daily with their sailing skills.






I flew into San Juan, arriving after midnight after winter storms across the central part of the USA diverted me to a new itinerary through Houston. Alas, my arrival and departure to meet amigos in port did not permit any time to explore Old San Juan or much of Puerto Rico proper aside from the views from the windows of my transport. After a quick stop at the grocery store and CVS to supplement supply procurement from the day before, I was delivered to port and craft.
We set sail (or I should say set motor) at around noon on a Saturday and headed north to swim and lounge before mooring off the shores of Cayo Icacos for the evening. This particular boat had four bedrooms (mostly bed) and four private toilets which made for some pretty luxe living onboard.


We spent the next four days on and around the island of Culebra. Poking into inlets for snorkeling, swimming or fishing. During the day, the bright blue skies reflected on the water below where various shades of blues, greens and aquas marked the depth of the seas and existence of coral beds like a colorful depth chart. There was little wind to speak of, so our movements were all motorized.








On board, life was at an easy-going pace, up early to watch the sunrise, up late playing cards, listening to music and downing tequila and beers (or, in my case, NA beers and Coke Zeros). Meals were grilled on the stern deck. We barely left the boat and then to swim, stand-up paddle or snorkel or for only brief beach strolls, hikes or supply runs to town. As such, I cannot really comment on Culebra itself, or any of the islands we visited for that matter.
Our captain had an Ahab-like obsession with landing a tarpin in one of our nighttime inlets and his zealous obsession was rewarded on our final night. They aren’t edible – too bony and man, do they stink – but his gamesmanship and persistence prevailed before we cut said fish loose and returned him to sea.




On our sixth day, we set sail (finally blessed with enough wind to do so) for Vieques. The western tip of the island is a former military installation with a bay used as target practice by the Navy before heading out to sea. Signs warn of danger and substantial fines for entering the bay, so we took heed and continued on to Playa de Chiva for the night. The beaches of Vieques are pristine, uncrowded (at least in early March) and provide ample opportunity for strolling, snorkeling or sunbathing. During our traverse, we hooked a wahoo and served up some of the freshest and most delicious fish tacos I’ve ever tasted for dinner.



Our final full day was our roughest and windiest of the week and we sailed west back towards Puerto Rico nearly the full length of Vieques with a goal to set anchor closer to our final port. The choppy seas and wind near the western end of the island did not make for a good anchor spot, so we returned east to Sun Bay for our final night on board, a pre-dawn rise and final motor back to Vajardo to return our trusty craft.





After a week on board, with very little boots (or flip flops, as the case may be) on terra firma, my head was still rocking with the waves for days. I carried home with me the souvenirs of memories of the easy life on board, with few interruptions from the outside world and normal life, plenty of stunning sunsets and moon and sun rises and the positive vibes of good decades-long friendships.
“Haul the sheet in as we ride on the wind
That our forefathers harnessed before us
Hear the bells ring as the tight rigging sings
It’s a son of a gun of a chorus.” – Jimmy Buffet





Hello David and Melissa,
I LOVED reading this recap of David’s sailing adventure. You two really inspire me. I am so very sorry and sad that I had to cancel next Friday’s dinner with you all. I needed to make sure I was there for my friend who’s son took his life earlier this week. It’s so sad and really makes you appreciate those you love. I hope you understand.
I know your leave for traveling again and I sure hope we can continue to stay in touch. I am forever grateful for your continued help with my career decision and so happy to watch you all continue on with this dream of yours. We may be coming to Portugal next year and I will definitely be in touch.
XO
Kelly
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