Other, Personal

Sailing Trip – American Sailing Academy

I have been enamored by sailing ever since I saw the first Pirates of the Caribbean movie. Its been a life long dream of mine to sail the seas. So when a couple of my friends decided to organize a sailing trip in Florida and invited me along, I was exceptionally excited. The six of us booked a stay with the American Sailing Academy in Key West to get our ASA sailing certifications.

ASA Sailing Certification

As far as I know, if you want to sail you are in no way required to have any sort of certification. The benefit of these classes is purely for show, to put on your ‘sailing resume’. So in the future, when you want to rent or charter a boat, or be part of a crew, you have something to prove that you have at least some idea of what you are doing. If you don’t have any experience or connections to sailing, certifications like ASA are a really helpful gateway to get into the scene. ASA is by no means the only organization that offers classes like these, but it is one of the most prolific and reputable.

We decided to get our sailing certifications with ASA. In one week we would get certified for 3 courses, 101 Basic Keelboat Sailing, 103 Basic Coastal Cruising, and 104 Bareboat Cruising. A month or so before the trip, we got our coursebooks. The academy recommended that we read the books beforehand but told us that it was not required. I read the first book before going, but didn’t manage to make it through the other two. I still managed to pass all the courses with flying colors, but had to read and study pretty much every evening of the trip. If you are planning on taking similar trip, I do highly recommend reading all of the course materials beforehand if you want to have any time to do anything other than study during your stay.

Day 0 – Arrival

We flew into the Miami airport in the evening and Lyfted down to Key West to the American Sailing Academy. When we got there, we were greeted by Captain G, who showed us to our room, and introduced Captain Laurel and Captain Bernard who would be our instructors. We chose our bunks, and then went out to dinner at an awesome place down the street called Mrs. Mac’s Kitchen. The food was phenomenal. And they had a really fantastic Key Lime Pie.

My little cubby in our lodgings.

Day 1 – First Day of Class

I love getting to vacation lodgings at night. Because it is a wonderful treat on the first real day of vacation to wake up let vacation literally dawn on you. I woke up early and walked down to the dock, and got to see all the boats floating in the crystal clear water for the first time. I knew that in a couple hours I would be sailing one.

First day crystal clear waters.
Our Classroom.

We started our first day of class brushing up on our sailing terminology in the classroom. After lunch we got to sail for the first time. We split into two teams of three. I went with Captain Laurel on the Blue Dragon. We learned the basics of how to manage the sails, about tacking, and the various points of sail. We also started our MOB, (man over board) training. We named one of the life jackets Oscar and would throw him overboard, then tack around to go and pick him up. After rescuing a couple Oscars, we went back to shore. We watched the sunset on the dock, and drank some rum.

Sunset on the dock with my buds.

The captains very generously invited us to partake in an absolutely fantastic BBQ with them. We studied our books, and went to bed.

Day 2 – More 101 Training

Foggy morning.

Woke up the second day to see some beautiful fog over the waters. We had class in the morning, and by lunch it had cleared up. We switched up our crews and prepared to set sail. Before we could, we saw a manatee swim under the dock. This was my first ever manatee sighting. Captain Laurel told us that manatees were actually quite common in the area.

My first manatee sighting!

Eventually we confirmed the manatee had vacated the area, and we set sail. By now, we were tacking and sailing pros. We came back to shore and one of our member made us fried fish for dinner! We studied up because the next day was our 101 test.

Day 3 – The 101 Test

Windy weather for our first tes.

The morning of our 101 test I went to shore and looked at the waters. It was the windiest that it had been since we had been there. Luckily, our instructors were very accomodating, and decided to let us to our practicals at a later time that day.

I sailed with Bernard on the Aleena for the first time. She was much more finicky (IMO) than the Blue Dragon. I was quite nervous doing my practical on a different boat, but Bernard was understanding and I passed.

I’m sailing awaaaaay!

After sailing, we went to lunch at a delicious sushi restaurant down the street. Then we had our written test, and we all passed with flying colors! After our practicals, we got to celebrate by sailing the boats by ourselves for the first time. My friend and I sailed the Aleena by ourselves, and as we were heading out our motor died. Needless to say I was quite stressed. Luckily my friend was very calming. We got the motor working, tacked a few times, going slowly and taking our time while our friends on the other boat sailed circles around us. I was quite glad to take the boat back in.

We said good bye to the Aleena, because the next day we would start our 103 training on the catamaran.

The sweet Aleena.

Day 4 – 103 Training

On our fourth day we started our catamaran training aboard the Endless Summer. I found the catamaran to be a lot more fun than the smaller boats. It handled much more smoothly and predictably. My favorite part was that I got to be the ‘running fender’. I ran up and down the side of the ship as we were docking to make sure that the boat didn’t get damaged running into the dock.

That night we did a lot of cramming because the next day was our 103 test.

Hauling up the mainsail on the Endless Summer.

Day 5 – 103 Test

With only a couple days of training on the catamaran, we took our 103 test. Needless to say, we all passed. After a great day of sailing, we went on a mega shopping run to stock the catamaran, because the remainder of our days would be spent sleeping on the catamaran.

The Endless Summer.
An epic day of sailing.

Day 6 – The Proposal

I did not sleep well our first night on the catamaran. I went out on the boat early in the morning when it was still dark. It was wonderfully peaceful.

Night aboard the catamaran.

That day for class we learned about charts and plotting courses. We plotted a course to a destination not to far away through a channel.

Our chart table.

At lunch we anchored the catamaran and went swimming! We all jumped off the bow of the catamaran, and swam through the middle.

That evening, as we sailed in at sunset, my best friend got proposed to by her long term boyfriend. It was a beautiful moment. The captains were wonderfully obliging, keeping us out on the water for sunset so we could have the best possible lighting. We celebrated with lots of drinks and card games. And of course, a cheezy love song playlist playing through the catamaran speakers (Starting with Can you Feel the Love Tonight).

The proposal.

Day 7 – Last Day Out

The next morning was a beautiful day for our last day out on the water. We all passed our 104 practical exam.

The majestic captain Kersti steers the Endless Summer.

After our day out sailing, we said goodbye to captain Bernard. That night we moored the boat off the dock.

Our sailing team! Thank you so much Captain Bernard and Captain Laurel. They made our stay so fantastic! Could not have asked for anyone better.

Day 8 – Stormy Weather

That morning, we were supposed to take the dingy to the dock to take our last 104 exam. However, there was a bit of a storm that morning, and the waters proved far too turbulent for our limited experience. So captain Laurel came to us on the catamaran. We all passed our 104 exam, and we said goodbye to captain Laurel.

The storm aproacheth!

After passing our 104 test, we mostly slept the rest of the day. In the evening, a few of us decided to try and get some dinner on shore. However the waves were still quite large. Regardless, the brave and stalwart among us decided to try their luck. We lowered the dingy, and one of the brave adventurers got in. After bobbing about on the massive waves for a bit, he decided it was probably a bad idea. So he got back on the catamaran and we hauled the dingy back up. While doing so, we were able to use one of the knots we learned during class in a practical real life situation. We are fab students.

We got a nasty override in our winch as we were hauling the dingy back up. This gave us a perfect real life practical use for the Trucker’s Hitch.

Day 9 – Last Day

We said goodbye to the Endless Summer the next day. We took the dingy back and forth to unload all our stuff off of the catamaran. It took several trips but we were efficient. We went to Snooks for lunch, quite delicious. We drove down to Miami Beach and walked around for a bit. After some people watching we went to the airport, and went back home to Colorado.

The return was a shock to the system. From warm sunny beaches, t-shirt and short weather, to winter storms, snow, and freezing temperatures. Regardless, we were happy to be home.


Money to cover this trip was one of the few things I asked for for Christmas. I am eternally grateful to the people who helped me pay for the trip, because I had a phenomenal time. I accomplished a life long goal, and now have a good-for-life certification that I can use to charter my own boats and go on my own sailing adventures. Not to mention, I did it with several of my best friends.

I will never forget this trip. And if you are thinking of doing something similar, I highly recommend the American Sailing Academy. Everyone I met there was super nice and fun. We all had a great time, and I would do it again in a heartbeat.

1 thought on “Sailing Trip – American Sailing Academy”

  1. Wow, that voyage looks like so much fun! I’ve never gone sailing, but I’ve always wanted to. But to get certification is so amazing, even if you don’t really need it to sail.


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