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Learning To Sail
20 Oct

Learn To Sail in a Weekend and Discover a World of New Horizons

Discover Your Inner Swabby by Learning to Sail in a Weekend

How can two land-locked adventure seekers with the dream to sail around the world learn to sail? By taking lessons, of course.  The dream of sailing around the world in our first few years of retirement has been ours since we first met. But life is short and we figured we’d better not wait until then to begin the adventure.

We were in love with the idea of sailing, but we really didn’t know if we would like sailing. Good news– It’s even more fun than it looks. It’s hard to describe the inner calm that develops while quietly gliding through the water powered only by wind – it’s truly addicting.

Learning To Sail

How do beginners learn to sail? Usually by attending classes along the coast. In our case living along the Ohio River we had to choose between going north to the coasts of the Great Lakes (Erie, Huron, etc) or to the Atlantic Coast. Of course there are sailing schools along every coast. Here are some tips to get you started in sailing school:

Pick Your Sailing School with the Destination in Mind.

There are many types of sailing schools taught by sailing enthusiasts. To pick the school best for you, figure out what you eventually want to do after you learn to sail. Do you want to buy or rent a boat? Will you be sailing in local lakes? Renting boats in other countries? How big of a boat do you want to sail? Figuring out your goal will help you sort through all the different learn-to-sail options.

If you want to rent or buy a boat to use on your local lake or shoreline you can simply attend your local learn-to-sail school. The course certificates they offer don’t ‘transfer’ but it doesn’t matter since you will be sailing from your home port. You will have learned how to sail the type of boat available near your home.  We wanted to learn to sail 40 ft cruising boats so that we could travel around the world visiting places. These are large boats, it’s important to be sure you are competent before sailing off in one of these beauties. With this in mind we embarked on a learn-to-sail adventure that will be spread over a few years.

Sailboat on the bay

We had fallen in love with the idea of sailing in Croatia after seeing the wonderful photos and constant over-the-top recommendations of fellow travelers. Due to regulations it became apparent that we would need special certificates from the American Sailing Association (ASA) to vouch for our proficiency before being able to rent boats in Croatia. That requirement helped us narrow our search to ASA accredited sailing schools. We chose to learn to sail in Annapolis because it was close by and has a great nautical reputation.

Choose Your Class to Match Your Schedule

A deep dive on the internet turned up learn-to-sail courses in a week, in a half week and in a weekend. We were a little short on vacation time this particular year so we chose the accelerated weekend option.

There is a lot of prep work if you choose the accelerated schedule…but it’s worth it. Plan to spend 10+ hours reading the sailing course book, taking on-line practice tests, and learning the knots ahead of time. The compressed weekend schedule means you need to complete the classroom work independently and be ready to go out on the water when you arrive. Your instructor will spend a few hours in the classroom reviewing the material but most of the time is spent on the water. Yipee!

Classes are Practical Hands-On Workshops

You cannot learn by watching. The instructors know this, so they pair up 4 people and one instructor in a boat for the weekend. Our boat mates were another couple learning to sail in preparation for joining a flotilla in the Greek islands next spring.

Our instructor patiently showed us how to trim sails, how to turn the boat, how to stay out of the way of others, and even how to do doughnuts in the water! Each of us was allowed ample time to learn each task, and as is often the case, we learned from each other as well as the instructor. We were delighted to find that sailing is more fun than we had imagined.  Keelhauling buoys was by far my favorite activity. I don’t know what it says about me…but it’s really fun to run over a nautical speed limit sign (buoy) as part of the man-overboard drill. By the end of the weekend each of the four of us had to demonstrate we could easily knock over the buoy, turn the boat around and stop the boat right next to it without using a motor. We were using the buoy as our pretend man overboard since it stayed still in the water.

Sailing Lessons

How to Dress for Sailing

Sailing classes are only cancelled in the event of lighting — that leaves a lot of weather possibilities. In just 48 hours on the Chesapeake we experienced scorching sun, light breezes, pelting rain and squalls. We had a blast trimming and changing sails to match the weather. Good thing we brought clothing to match too.

Lightweight quick-dry clothing is essential, including quick-dry undies; sitting on a wet seat all day is very uncomfortable. Your gym clothes are perfect for the first layer; avoid cotton clothing it just soaks up the water and makes you miserable the rest of the day. Add to your bag a lightweight shirt, fleece jacket, rain jacket, sunglasses, brimmed hat with chinstrap, water bottle, sun block and you are good to go.

Pass sailing exam

Learning to Sail is Just The Beginning

Just like you don’t learn to play tennis in one lesson, you can’t learn everything about sailing in one weekend. The learn-to-sail courses are designed to teach you the fundamentals of sailing a keelboat and becoming proficient enough to rent a small (20 ft) boat to practice. To achieve our dreams we plan to practice our skills on the weekends and take more classes. As a bonus, you can take the next level courses while vacationing on a live-aboard boat in coastal waters close to home, along the coasts of Florida and even in the British Virgin Islads. What fun– a vacation coupled with a path towards our retirement goals. Count me in!

Do you have a lifelong dream or goal? What is your plan to get there? Share your dreams in the comments below:

About The Author:   Sarah Kohl was practically born with a suitcase in her hand. She is a doctor trained in travel medicine and loves to share tips about how to make your next trip happy and healthy.  Does packing for a trip stress you out? Learn 10 tips to making packing easy:  Get in touch with her or
Photo Source:  Sarah Kohl