WON Landing Page March 2022

Retro WON: In Windsurfing, There is No Such Thing as a ‘Beginner’s Guide’

Sometimes as an outdoor enthusiast, I get a little overly excited to talk about my adventures. I list off activities like as though they’re accomplishments on a resume … Ever since I was about 16-years old, I have proudly listed “windsurfing” as one of the outdoor activities I enjoy. I haven’t embellished so much as to call myself a “windsurfer” or even say that I was successful in my windsurfing attempt, but I usually leave out the gory details of that 1 grand windsurfing trip, and just smile and nod and say, “It was really exciting,” when anyone asks how I liked it. But, in the interest of giving you all the backstory to my most recent windsurfing adventure, I’ll share the reality of my first “windsurfing” trip.

As I mentioned, I was only 16, and summer break was in full swing. One day, I had planned to meet up with some of my friends in the extremely rural farming town of Gaston (population around 650). Hanging out usually involved driving around, listening to tunes, going on a hike, 4-wheeling on the dusty gravel back-roads, or going over to Hagg Lake.  Those days – all golden and shimmery, warm and carefree – they created some of the best memories I have, stored like little snapshots in the photo album of my brain.


Ah, to be 16 and on summer break again! Here I am with my dear friend Betsy Hartner on one of our adventures – the same dear friend who came along to help photo document my windsurfing attempt.


On this particular day, my friend thought it would be fun to take his parents’ super old fiberglass windsurfing board out to the lake. We pulled it out of a pile of dusty toys in their storage shed; he cleaned out an old bee’s nest and globs of mud and mildew, scrubbed off the sail, threw it into his truck, and headed to the lake.  It was a beautiful day at the lake. The sun beat down overhead. The stagnant heat formed little beads of sweat that dripped down my forehead and back as we unpacked and hauled the heavy 1980’s-style board from the parking lot down to the shore. The glittery cool blue lake beckoned us as we attached the gigantic heavy sail to the huge boat-like board.


Here I am around 16 years old trying different “boarding” sports. Body boarding, in my opinion, was much easier than windsurfing…

My friend had been windsurfing a few times before, but I knew that although he knew a ton about different outdoor adventures, he was not the best teacher. This was the same friend who had promised to teach me to snowboard, took me to the top of the mountain, pointed me at a double black-diamond run, said “I’ll see you at the bottom!” and took off – leaving me there to figure it out. He had the same type of approach to teaching me how to windsurf. He told me that all I had to do was balance on the board, pull the rope attached to the sail and hang on. So, that’s exactly what I did. I stood up on shaking legs, trying desperately to balance while hoisting up the sail, I grabbed onto the mast, and I held on.  I moved the sail back and forth a few times, trying to find and catch the wind. As I shifted the sail around and balanced gingerly on the board with my knees flexed and center of gravity low, I found a few little gusts and I giggled and clung to the mast each time I felt myself propel in any direction. I felt like I was in love with this amazing sport.

Then the wind stopped.  

The sail deflated, I wobbled as I tried to maintain my balance, and finally dropped the sail and fell into the water. I turned back to see how far I had gone, and was shocked to find that I was smack-dab in the middle of the lake. I swam around and tipped the nose of the board toward the shore, thinking I would just catch a few more gusts and get straight back to shore. I hopped back up, hoisted up the sail, balanced, and waited … no wind.  After a few minutes, I wobbled and fell back in.  I tried again, frantically hoping for just one teeny gust – anything to help me to move – but nothing.

I wasn’t prepared to handle this. All I knew was that I was too far away from shore, and the only way I would move would be by swimming. I grabbed the rope attached to the front end of the board, and I started swimming. The sail dropped completely under water, serving as a kind of parachute, drastically impairing my attempts to move forward. I tugged and fought and battled with the board, and felt like I was making only inches of progress. I kept my eyes on the shore, which didn’t appear to be getting any closer. I made progress slowly, but my muscles were beginning to shake, ache and burn. When I was about 50 yards away from the shore, I took a break and pulled my limp body up onto the board and laid down my head and just tried to catch my breath. I heard a boat nearby, and looked up to see an older man and woman, both looking at me, headed in my direction. They threw me a rope, told me to hold on tight and they gently pulled me to shore. It may sound dramatic, but at that moment, I felt like they saved my life.

So, yes – I have been windsurfing before.  But, the honest answer to the question I usually get regarding how I liked it would actually be more along these lines: “It was absolutely horrible and exhausting, and I felt like I was about to die by the end of the day, and I hated it.”

That type of answer didn’t really feel like it aligned with my enthusiasm for all other outdoor activities, so I have always been a bit elusive with my smiley vague answers to questions about the experience. But ever since that failed (and exhausting) attempt, I’ve always felt like it was a sport that I genuinely wanted to learn, and I genuinely wanted to love! So, when coming up with ideas about topics to write about, I was so excited to give windsurfing another try.  I wanted to write an article about how awesome this sport is, how other interested beginners can get started, and how much I genuinely (honestly) love this activity. Sadly, I couldn’t do it.

If you are an avid windsurfer or a considering getting into windsurfing, please don’t misunderstand or feel disheartened. I can honestly say that windsurfing is totally amazing, but, it requires far more skill and talent and athleticism than any bystander could possibly imagine.  It is truly a very cool sport and I admire and respect those who participate in it. I cannot personally claim to genuinely love windsurfing – at least not yet.

Windsurfing is really, really hard and physically demanding, and it’s important to understand this concept before your first experience. It is not like paddle boarding, kayaking, or snorkeling – all activities that are demanding and awesome, but that you can really scale to the level of adventure that you’re looking to have.  You can learn the basics about any of these, then go out on your own, feel confident, and have a lot of fun on your first day. That was not the case with my most recent windsurfing experience.

Back on board

I signed up for a 2-hour lesson in Hood River, followed by 1 hour of additional equipment rental for extra practice. I asked my friend to come with me to take photos and help me to document the experience. I asked if she wanted to take the class with me, and she said, “Absolutely not – I’ve tried it before, and it is way too hard and tiring.” The tone in her voice was alarmingly serious, in contrast to her usually bubbly and optimistic demeanor. I giggled and said “Oh, it couldn’t be that hard!”

Oh, how foolish I was!


This is right around the point where the instructor asked if we had any questions… If you can’t tell by the look on my face, I am extremely nervous but also really anxious and excited to get into the water. The lessons were fantastic, and were even more helpful once we were in the water and had the instructor right there to answer any questions, and provide reassurance when you just wanted to know whether or not you were doing things right. (Betsy Hartner photo)

The class started on windsurfing boards balanced on top of rotating blocks on shore. We spent about half an hour practicing getting onto the board, hoisting up the sail, holding the mast, controlling the sail, moving the board in different directions, finding the cross-wind, tail to sail to adjust direction and speed, balance, center of gravity, etc. The instructor was great, but the concepts are extremely difficult to explain and understand. At the end of the 30 minutes, he looked at us all and said, “if you’re confused, don’t be afraid to speak up.”

I said, “I’m confused.”

He grinned and chuckled; I didn’t. I still didn’t have any sense of what the correct position would feel like, and when it had been my turn to practice directional maneuvers on the blocks, the board just spun in all directions.


Here I am really trying to learn all of the ins and outs of windsurfing, but it’s really hard to completely grasp the concepts being taught until you’re in the water and able to feel what they’re talking about. The lessons were great, though, and I would absolutely recommend at least 1 lesson to learn and practice the basics. (Betsy Hartner photo)

We headed down to the water, and we each received a board and sail.  We learned about the correct way to paddle the board with the sail secured on top of the board and out of the water, held between the feet.  We stayed within a shallow swimming area that was roped off. One at a time, we each got onto the board, pulled up the mast, and practiced different sail and body positions as the instructor called them out.  “Tail to Sail!” “Swing your mast!” “Tuck your hips!” I nervously shuffled my shaky feet around on the board, moved my body slowly, and moved the sail side to side, trying to keep up with the instructor. Every now and then, I sheepishly glanced up to make sure my friend was capturing my hilariously awkward positions on camera and I saw her laughing and waving, amused by my lack of success.

Windsurfing_So_Tired-wind surfing

Ok, seriously… If you haven’t already picked up on it by now, you should know that windsurfing is REALLY tiring! It’s important to give yourself a break when you need one. Safety first! I think I did this probably 20 times during the 2.5 hours we spent in the water. Plus, taking a break allows time to enjoy the gorgeous scenery. (Betsy Hartner photo)

I was able to catch the wind a few times, and I did get a sense of what balance felt like, and how to use the crosswind to control the direction and speed.  I was able to get from the starting point down to the end of the swimming hole, then secure the paddle and swim back to start.  I successfully sailed from one end to the other end of the practice area several times. I did not, however, feel in control or truly balanced or confident at any time during my lesson or practice.

At time, glimmers of enthusiasm appeared, but for a majority of the experience, I felt uncertain and uncomfortable.  I don’t want to come across as a pessimist, because I truly did want to fall in love with this sport, and maybe after a few more lessons, I will.  At the end of the day, however, I was exhausted, shaky, frozen to the bone, and so indescribably frustrated. Above all else, I walked away with such a great respect for those who actively practice and participate in windsurfing.


Ok, so I saw this picture and I thought I looked pretty cool here – like I’m totally cruising… But the truth here is that I’m barely moving at all, and wobbling around so much that it was hard to balance on the board. Nevertheless, I stood up! And I stayed up until I got to the other end of the teeny roped off shallow area…like 20 minutes later….. (Betsy Hartner photo)

After the lesson, my friend and I went to the portion of Hood River that sits on the Columbia River Gorge shoreline, had some amazing pizza, and watched the scores of windsurfers and parasailers playing in the water. I watched the windsurfers yanking the mast with all of their bodyweight, leaning against it so hard that they were almost sitting on top of the water, catching the crosswind and using it to lift them into the air as they cut into the waves ripping across the gorge, and I was absolutely in awe. To all you windsurfers out there: I want you to know that I think you are so totally awesome.


After an exhausting morning of windsurfing lessons followed by individual practice, Betsy and I headed out to the beach for some lunch, rest, and sun, and I sat on the shore in absolute awe of the talented windsurfers cutting across the waves, flying into the air, speeding along the top of the river like water skippers, and practicing special trick moves. It was inspirational and amazing to see what skilled windsurfers are capable of.

For any enthusiast thinking about giving windsurfing a try, I made a few notes that I hope you find helpful, outlining few things I wish I had known prior to my experiences:

1.A lesson is ALWAYS a good investment.

Not only will you learn the basics about safety, movement, and body / sail positions, but you can also try out the sport before investing in your own equipment. Most places that offer lessons also can provide all other equipment like wet-suits and water-socks, and a safe place to practice with certified instructors.

2. Be prepared for an extremely physically demanding activity.

Eat a great breakfast packed with protein, and pack snacks. Drink a bunch of extra water leading up to the day of your activity, and be sure to pack a water bottle and stay hydrated throughout the day. To be extra prepared, ramp up the exercise as far in advance as possible to make sure your muscles are prepared for an extremely demanding day. Also, be sure to stretch before and after your adventure. I failed to do this entirely, and ended the day with stiff muscles and a super sore back that hung around for a couple days after my lesson.

3. Know your limits:

If you need a break, feel too shaky, dizzy, cold, or exhausted, don’t be afraid to take a rest. This sport is extremely demanding, and your instructor and classmates will certainly understand and respect you for respecting your body’s needs. If you have any special medical concerns, please talk to your doctor before engaging in this activity – I cannot stress enough how physically demanding it is.

I am very proud to say that I have been windsurfing twice.  I still cannot claim to be a “windsurfer,” but maybe someday (after LOTS of lessons and practice) I will get there. I adore the idea of harnessing the natural power of wind, and learning how to work with it to create movement. I watch intermediate and experienced windsurfers with complete respect and appreciation, and I admire the commitment and dedication that I know it took to perfect their skills. I see other beginners and feel a sense of camaraderie and empathy for the journey they are attempting to embark on.  Windsurfing is a magical and amazing sport, and I still dream of one day calling myself a windsurfer.  Until then, I am a girl who has experienced two “really exciting” windsurfing trips, who has a deep respect for this difficult sport.

This Retro WON first appeared about windsurfing first appeared August 24, 2016.

  • About Casey Monteleone

    Casey Monteleone is excited to be a guest outdoor columnist at The WON. She is proud to work at Columbia Sportswear Company, where their motto is “We Connect Active People With Their Passions.” Seeking to live out this motto, she hopes to inspire others through her writing to get outdoors, get active and live life to the fullest. Born and raised in Oregon, Casey spent the summers hiking, camping and fishing in the majestic mountains of rural Eastern Oregon. Her parents taught her from a young age how to survive in the wilderness with bare essentials, and how to truly appreciate the beauty and tranquility of the great outdoors. As she grew up, Casey continued to pursue various outdoor activities … From exciting adventures like kayaking, canoeing, hunting, and skiing ... to relaxing outings where she plays on the beach with her family ... to taking her yellow lab to the Columbia River Gorge for a swim. Casey went on to earn her degree in Mass Communications with an emphasis on Environmental Studies from Linfield College, and happily resides near Portland with her 2 amazing girls, loving fiancé, and sweet dog. Casey is passionate about sharing her love of the great outdoors, and is so happy to have the opportunity to contribute to The WON, and work with such an amazing team of inspirational women.