How to Learn to Cruise/Sail

Do you have a dream to go cruising someday, but don’t even know how to sail yet?   I was there.

People ask us all the time … how did you learn to go cruising – especially when I was living in landlocked Indianapolis Indiana!?

First I needed to learn to sail, since I’d never been sailing; and then to go cruising.  First a bit of background – my cruising dreams started when I was a single mom, no significant other, just two almost teenaged kids – I had no idea how to sail, but figured it would be cheaper than putting a swimming pool in the backyard so that the kids & I could enjoy something together.

I could have opted for the “cruising courses” offered by many reputable schools — Offshore Sailing is a very good one — but my budget didn’t allow for such extravagance.  As it turned out, learning to sail in small boats, in my opinion, is a better way to learn to sail than learning on a big boat. In a small boat, I could feel immediately the result of my actions — sometimes ending me upside down, so I learned that too!

I also found I could learn chart reading and navigation skills in a classroom locally rather than dribbling away my modest “cruising boat fund” and future “cruising kitty” spending money to go on vacation to learn the same skills.

If you too have a dream to go cruising, but like me, don’t even know how to SAIL, much less anything else about a complicated passion … here’s how I started….

1.  Took basic dinghy sailing classes from the Indianapolis Sailing Club at Geist Reservoir.  I didn’t have to be a member to learn to sail in this series of Adult Training Saturday classes offered in a variety of small boats – Lasers, Flying Juniors (primarily) as well as Y Flyers, Lightnings, Highlanders and Interlakes.

2.  One of the BIG bonuses of taking the sailing classes was that there were a large number of skippers looking for crew to race the next day – Sunday.   I was offered a variety of crew jobs on a variety of different types of boats.  The skippers didn’t mind I was a newbie, as long as I was excited and wanted to learn.   So I learned, and I sailed as often as I had the chance — keep in mind, at the time I was a single mom with two almost teenaged kids — both the kids tagged along and on many Sundays were asked to crew as well, or just hung out with the junior clan at the club while the adults raced.  Everyone enjoyed it.

3.  Then my entire family got involved with Y Flyer one design racing – traveling to regattas from Boston and Atlanta in the east to Little Rock and Kansas City in the west.  We raced all enjoyed racing Y Flyers – my daughter was a Junior National Champion Crew, my son was the runner up in the Junior National Championships and David & I raced and loved the cameraderie with all our friends from all over the country.  Before sailing – I had never imagined having friends from all over the country, but it was a precursor of things to come while cruising.

4.  By this time, I met a special friend – it was a long distance relationship but we met at a Y Flyer regatta.  To learn more about cruising rather than just sailing, I was hoping (plotting?) that my partner, best friend and future husband would teach me. After all, David had been a US Coast Guard Quartermaster 1st Class in a prior life — that means he was responsible for navigation on US Coast Guard Search & Rescue as well as other CG ships.  That’s all well & good, but we quickly discovered I was not a quick enough student for his rather heavy handed teaching style!  🙂  Oops.

5.  OK, so I needed another way to learn about cruising.  I found out about the US Power Squadron, yes, there were classes close to my home in Indianapolis Indiana, go figure!  Click the link and the drop down boxes to see the variety of courses and which courses are offered near you.  And if they don’t offer a class near you, I understand that now you can take the courses “online” or “remote” – I’m not familiar with that so you’d need to contact them.  If possible, I’d recommend a class setting because you’re working with other students and learning together which is fun and educational.

I took Basic Boating, followed by Seamanship, then Piloting, Advanced Piloting and Navigation.  I don’t remember how much it cost, but it was negligible, even for me!   At the time they didn’t offer the variety of courses they have now such as Weather, Diesel Engines, etc, but if they had been available, I’d have taken those too.   Small classes, experienced instructors and hands on figuring out how to read a chart, how to use dead reckoning, lots of great information that I would have never learned otherwise….  and I find it all a great backup and basis for using today’s more advanced electronics, GPS, AIS and such.  Kind of like old math — learning to add and subtract BEFORE they let you use a calculator?   🙂

The US Coast Guard Auxiliary also offers similar courses – if the USPS isn’t available in your area, check out the CG Auxiliary.

Now when David told me to plot our course every hour on the paper chart as well as include it in the log, I could do it confidently without his heavy handed help!   🙂

6.  From there, we wrangled as many invitations to friends big boats as possible – luckily Lake Michigan and Kentucky Lake were within easy driving distance.

7.  After that, we chartered a few times, some with friends, some just with the two of us to decide if we liked cruising and if we could stand each other on the boat long enough to actually get to that idyllic anchorage of my dreams.

We found cruising (albeit commuter cruising because David still wants to return in the summers to race Y Flyers … plus I love slalom skiing (on water, not that white COLD stuff) was fun for us.  We bought a sailboat and vowed to continue commuter cruising for as long as it’s fun.

So far, although we’re aren’t currently as far afield as we’ve been in the past, and as we may be in the future, we’re still having FUN.  And that’s what the lifestyle is all about.

So there you have it, the basics of how we learned to do what we do.  There are many other routes to achieve the same results – but if you’re landlocked with a dream, this one worked for us!    🙂   How did you learn … or are you learning to go cruising?  Leave comments and share with others!  CHEERS!  Jan



  1. Liz Burkle says:

    I’d like to communicate via email. I’m a single mom & dream to be on a boat. Maybe even call the boat home.
    I like your post a lot but wondered if you had an updates of where to take lessons? Still Indianapolis sailing club?
    I’m also limited on my funds.

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