I‘ve been sailing for a number of years. And by sailing, I mean drinking on a boat that happens to have sails. My buddy Liam and I have that was passed down to us by our fathers (primarily because neither of them wanted it in their yard). While over the years we’ve gotten better, we were long overdue for some more official training, so we decided to take our first ASA certification. A bit of research uncovered that we could take our course in Puerto Rico, USA so we figured why not make an adventure out of it.

After a day or so to stock up on supplies (rum and ice) and relax, we met our captain Pedro in Farjado on the east coast of the Puerto Rican mainland at 7 a.m.. After a very quick ferry ride to his marina, we boarded our transportation/accommodation for the trip – Blue Runner, a 32 foot Beneteau.

Our destination for the day was Culebra, a small Island community situated between PR and the U.S. Virgin Islands.   A 6 or so hour sail was between us and our destination, so we had plenty of time to get comfortable with the open ocean, Blue Runner, and Pedro. Most boat captains have a reputation for being pretty hard-ass. Pedro is not one of those captains.  He was happy to have us do as much or as little as we cared to, and was good at giving some instruction and then backing off and letting us make our own mistakes.

After about 6 hours of sailing, we pulled close to Culebra and stopped for a bit on a deserted beach for some snorkeling and a couple beers before heading into our anchorage for the evening in the “main” port on the island.

The island of 2,000 is fairly quiet on a Sunday evening, with a mix of locals and salty gringos filling the streets and bars. After a few token rum drinks and a walking tour of the town, we headed back to the boat for cocktails and a steak dinner ala Pedro. Sleeping aboard offers a few options, Topside, V-Berth or Main Cabin. Our first night, Liam and Pedro took the topside and I snagged the v-berth. I believe I got the short end of the stick.

The following morning we went back ashore for a quick run. Which was made interesting with one pair of shoes between the two of us, which made for a relay style tour of the island. Nonetheless, occasionally you need to punish yourself for what you have or are about to do to your body with a 95 degree run.

Before departing to Vieques, we had our first knot lesson which proved to be the hardest aspect of the course. Vieques is a larger island 10 or so miles nautical miles south. The island is most well know as being the center of years of conflict and protest between the locals and the US Navy, who used the east end of the island for bombing and missile testing for years leading up to the disarmament of the island in 2003. Since then, there has been ongoing clean up of unexploded and defunct munitions which leave a good chunk of the island unaccessible. Cruising along the northern coast, no a person was to be found for miles and miles of uninhabited beaches.

Our trip took about another 6 hours which Pedro filled with man-overboard drills, more knots, and sailor terminology quizes (quick: where is the clew?). After a while at the helm you begin to get accustomed to the swells and become more comfortable trimming the sails.  With confidence building, we went in search of a mooring for the evening in a small ferry port on the north side of the island.

Once moored, we spent another hour or so practicing knots and sipping 7 ounce beers before heading ashore to explore the local watering holes. Vieques is known as being a bit more dangerous than Culebra, so Pedro opted to stay and guard the boat as dinghy theft is fairly common. Upon return to the Blue Runner, we were served another fantastic meal while relaxing over rum drinks.

After drying out from a quick downpour during the night, Pedro served us breakfast while we studied up on terminology and more knots (quick, what’s a beam reach?).  After clean up, we departed back towards the mainland by way of some barrier islands. After another 5 or so hours of sailing we made our lunch mooring & snorkeling spot at a reef five miles off the mainland.  After days of very limited contact with other boats, we were most surprised to pop up from our snorkeling to find ourselves surrounded by 5 catamarans and 200 pasty American tourists on a half day snorkeling trip – All of which made the impeding torrential downpour much, much more entertaining to watch.

After a break we navigated ourway between the massive catamarans back towards Fajardo. After docking for the final time, we settled in for our exam. Having not taking a test (or used a pencil) in a decade or so, the process was fairly nostalgia inducing. Liam and I bet dinner on our test scores. However with our final results coming in at – Neil 99/100, Liam 99/100 – neither of us had the real taste of true victory as we both missed the same question. (side note: 5 Horn blasts = Danger)

Nonetheless, we left the dock as ASA certified sailors – which really means we can now take the more advanced courses that will allow us to charter up to 45 foot boats. All in all the experience could not have been better. Three full days aboard is the perfect amount in my book. The price was right, the beer was cold, and Pedro didn’t jump overboard after 72 hours stuck aboard with us. We managed to learn a lot, but not so much to keep us from enjoying a healthy amount of cocktails and soaking in the Caribbean breeze.

A few highlight videos below. (excuse the wind noise)