We just returned from an epic trip to the Caribbean to learn the fine art of sailing! I have a personal dream of someday selling everything and spending several years of my life on a boat cruising the Caribbean and South Pacific. Unfortunately, there are many hurdles I will have to overcome for that dream to become a reality. One thing is certain, however. I must learn how to sail a boat. While I have gained alot of experience on boats over the years, especially with my 56 foot Hatteras, I can not take that behemoth into the ocean. First, my boat isn’t built for blue water travel. Second, it uses a ton of diesel at a high cost. And finally, it’s simply too big and complex to maintain. I am looking for simple, cheap, and seaworthy!
As such, I am currently listing my boat for sale and starting the process of learning a new skill. I’ve done a ton of research on how to achieve my desired result. After looking into the various certification schemes, I felt that the Royal Yachting Association, based out of South Hampton, United Kingdom, made the most sense for me. They offer a variety of certifications starting what they refer to as Competent Crew, Day Skipper, Coastal Skipper, and Yacht-Master. Since I only have limited sailing experience, I was able to use my hours on Lake Michigan to qualify for the Day Skipper Certificate. Natalie took the competent crew course, which was a breeze for her.
The course is comprised of two parts. The first is written theory and a written examination, and the second part is a practical examination on the water for a week practicing various maneuvers and scenarios with other people. Natalie tagged along and took her Competent Crew training. We found ourselves spending five days sleeping on a 35-foot sloop in various harbors on the southern and western coast of Antigua. Not a bad deal at all! While we met some challenges, primarily problems with the boat, we had a great time learning the art of sailing with our instructor and one other couple on board.
Despite missing our connecting flight in Atlanta and somehow pleasantly finding ourselves spending the night in San Juan, Puerto Rico, we had a fantastic time on this trip. And we passed! So now we can charter sailboats on vacation if we choose to. This experience has just fueled the fire for us to get our proverbial ducks in a row and start planning for future life on the water, able to experience our world in ways we never knew possible.

Somehow we ended up in Puerto Rico for an overnight which actually turned out to be a great time!

Dinner out in San Juan at Casita Miramar

Our bartender’s reaction when he learned we were going to try every signature drink on the menu! We almost made it!

Along the walk to Shirley’s Heights, Antigua for a kettle drum concert and barbecue

Rum Punch, Jerk Chicken and Steel Drums at Shirley’s Heights, Antigua

Overlooking English Harbor, Antigua.

Hanging out with new friends. Falmouth Harbor, Antigua.

Carib is the drink of choice with every meal.

Falmouth Harbor, Antigua

She should have done the Day Skipper certification. She did an excellent job.

Anchored out in Deep Bay on the northwest side of Antigua

Enjoying some sun. Deep Bay, Antigua

Our final night overlooking English Harbor.
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