12* Ways We Get Into Sailing Without Owning a Sailboat

If you’d have asked me 5 years ago if I’d ever thought about sailing, I would have guffawed – it’s not feasible, not practical, and frankly, not possible here in Iowa. (Isn’t Iowa a fly-over state?!) So when we tell people we’re learning to sail in Iowa, we sometimes get the side-eye.

I’m not saying it’s easy to learn how to sail in Iowa, but it has been easier than I would have imagined. Because we don’t own a sailboat, we have to find ways to keep our heads in the game. In order of hands-off to hands-on, here are ways that we try to keep thinking and learning about sailing.

1. Blog/Vlog About Sailing

Admittedly, this blog was conceived of as a way to keep our heads in the sailing game. While it is hands-off, it’s definitely intensive. In addition to the blog, I have a YouTube channel with videos of our sailing escapades! I invite you to take a look!

2. Videos

We started watching sailing videos on YouTube during the pandemic. At first it was sheer entertainment and escapism. However, we soon realized that our favorite YouTubers were just regular peeps so we thought, why not us? To this day, YouTube sailing channels are our primary entertainment!

Sailing videos are a great way to learn the basics, such as how to rig a boat, how to steer, how to tack and jibe, how to read the wind and the waves, and how to handle different situations on the water. It’s also great fun to watch experienced sailors who share their tips and tricks, stories, and adventures. 

I’ll share our fave channels in another blog post 🙂

3. Sailing Groups on Social Media

Most of the sailing groups I belong to on Facebook are about selling boats and catamarans. We’re not even close to buying a boat (and especially not a catamaran) but it’s fun to see what’s out there. 

One FB group is focused on sailing the Great Lakes and that has been very fun and helpful.

4. Books and magazines

• WoodenBoat Magazine
• Small Boats Monthly
• Cruising World Magazine
• How to Read Water by Tristan Gooley
• Go Sailing by Simon Jollands
• Sailing Alone Around the World by Joshua Slocum Audible 

5. Apps

ASA’s Sailing Challenge app on my phone is where I first started to really understand how sailing works. It’s not bad for learning the fundamentals of sailing, and it lets you practice sailing in a realistic (albeit tiny) and interactive environment, with different types of boats, weather conditions, and locations, etc. I’d really like to try Sailaway or eSail – virtual reality simulators! 

6. Courses

Early on we took a water safety courses, for which we are now certified. It seemed sensible since we have a small fishing boat with a motor, and love to do other fun stuff in the water, like stand-up paddleboarding.

7. Sailing Club

We learned to sail at the University of Iowa Sailing Club, a student rec club that is open to the public. At the club boathouse we have access to a diverse fleet of sailboats, lessons, clinics, and regattas. Experienced sailors are always there to share their knowledge and it has been invaluable to us. We’ve been members for 3 years and we’re starting to feel a little more confident in identifying ourselves as “sailors.”

8. Regattas

Regattas are organized sailing races (trust me, it’s nothing fancy). There’s nothing like racing to challenge yourself and improve your performance. I competed in a club regatta last year and won third place! (Full disclosure: The real 3^rd place winner didn’t make it to the awards ceremony….)

We also volunteer to help run club regattas. We have worked on the committee boat and driven the safety boat a few times, and it’s very fun to see the competition right on the water, in the thick of it.

At the professional level, this year we went to see the SailGP regatta in Chicago! From Navy Pier, we watched teams race on hydro-foiling catamarans. The races are short and intense, lasting about 15 minutes, and they are thrilling. The skill and teamwork of the sailors maneuvering their boats in the wind and water, and the beauty and speed of the boats as they glide across the water, well, it’s a sight to behold.

9. Sailing School

We attended Offshore Sailing School in St. Petersburg, FL in February 2023 and it was probably the most exciting week I’ve ever had. We spent 2 days day-sailing on a Colgate 26 with trainers and other students. Then we moved onto a 48 ft Jeanneau for 6 days with an instructor and 2 other mates. This immersive experience was life-changing. 

Because we don’t yet have a sailboat, one of our goals was to be able to charter a boat. It would allow us to go on sailing vacations before we retire, so that when the time comes, we will be prepared. The US Sailing Basic Keelboat, Basic Cruising and Bareboat Cruising certifications from Offshore Sailing School would allow us to do that.

I cannot say enough about this experience – another day’s blog post. 

10. Fractional Membership Boat Program

In the late summer, we bought into a fractional membership boat program in Chicago called SailTime. Through October, the end of the season, we have access to a 30 ft sailboat out of a marina on Lake Michigan. We’ve already sailed on Lake Michigan 4 times and let me tell ya, we’ve learned a lot….

We hope to do this again next sailing season.

11. Charter Boat

In July of this year, we chartered our first boat, which means we skippered. We were in charge. By ourselves. In Grand Traverse Bay, Michigan, we puttered around for four days and had the time of our lives. The weather was mild and the sea state was calm, it could not have been better.

To be able to charter a boat, you have to be able to prove that you are capable. We were happy to show Great Lakes Sailing Co. our certifications we’d earned at sailing school. 

12. Become Crew*

*This is something we’ve not done (yet). You can find opportunities to crew on platforms like Crewbay, Find a Crew, or Crewseekers where you can browse through different listings. The thing that appeals to me about this is that you get hands-on experience within the safety of an experienced crew. I don’t know if we’ll ever get the chance to do this but it’s definitely appealing.

Thanks for stickin’ with me here! I hope you found it interesting, if not helpful.

UPDATE: I did it! I got to crew on a boat delivery! You can read all about it here!