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Frequently Asked Questions

Curious minds welcome. Nervous beginners encouraged. Sea monsters optional.​

Sailing can feel like a mystery at first. What do you wear. Do boats really tip over. Are pirates still a thing. This page has answers to the questions most new sailors ask, and some they are too afraid to ask out loud. If you still have questions after reading this, just reach out. We love questions almost as much as we love snacks onboard. Almost.

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What is SkyWind Sailing?

 

We are a friendly, down to earth sailing school on the Columbia River that teaches real hands on sailing skills without the fluff. Our classes are practical, engaging, and fun. No yacht club snobbery allowed.

 

Do I need any experience to take a class?

 

Nope. Zero. None. If you can smile and step onto a boat, you are qualified to begin.

 

Will I actually learn to sail or just sit there while someone else does it?

 

You will sail. No ride alongs in disguise. You will take the helm, trim the sails, and learn by doing.

 

Where do your lessons take place?

 

Lessons depart from Hayden Island, in Portland, Oregon on the beautiful Columbia River.

Exact dock locations are provided when you book.

 

Are the courses ASA certified?

 

We are not currently part of the ASA certification system. Our classes are fast, practical, and designed to give you real skills without the time or cost of long certification tracks. If you want ASA later, you will already have a strong foundation! We can also provide recommendation to local ASA-affiliated schools if needed. 

 

Safety and Comfort

 

Is sailing safe?

 

Yes. Safety is our number one priority and we take it seriously. We follow Coast Guard safety requirements, carry proper equipment, and teach with intention.

 

What if I am nervous about heeling?

 

Heeling is the lean of a sailboat. It can feel wild at first, but you get used to it quickly. We start gentle and keep things comfortable. Sailboats are designed to heel! 

 

What should I wear?

 

Layers are your best friend. Bring a windbreaker, non cotton layers, and shoes with good grip. Bonus points if you wear something with pockets.

 

Do you cancel for bad weather?

 

Rain does not stop us. Really high winds and lightning do. Safety comes first, and we will reschedule if the weather is not safe. Part of good seamanship is knowing when to stay in the harbor. It's always better to be at home wishing you were out sailing, than out in a storm wishing you were home!

 

Can I get seasick?

 

On the river it is rare, but it can happen. The river is calm compared to open ocean, so most people are fine. If you are worried, take motion sickness medicine before you arrive. We recommend an over-the-counter medicine called Bonine (meclizine) - it is easily found in most local stores and pharmacies, and it is non-drowsy. 

 

 

Booking and Rates

 

How do I book a class?

 

Super easy. Click here and choose from our available options, and checkout online! 

 

What is your cancellation policy?

 

Life happens. Cancellations made more than 48 hours in advance receive full credit toward a future class. Less than 48 hours means we have already prepared the boat, but we will be happy to reschedule with a 30% booking fee. 

 

Are private lessons available?

 

Yes. Private lessons are perfect for individuals, couples, or small groups who want custom pacing.

 

Do you offer gift certificates?

 

Yes. Sailing is the greatest gift other than a puppy or a pizza.

Is there a minimum age requirement? 

Participants ages 13 and up are welcome. At this time we do not offer youth sailing for younger children, but we recommend checking out Willamette Sailing!

On The Water

What if there is no wind?

 

Calm days are still valuable training days. However, if there isn't enough wind to make the boat move during class, we have a sign-up sheet for students who want to come back for the afternoon portion of class another day (at no charge). We want students to really experience the wind!

 

Can I bring food or drinks?

 

Yes. Snacks are encouraged. Hydration is important. Alcohol is allowed after lessons, not during training.

 

Do lessons still run in winter?

 

Yes. Sailing is a year round sport here. We just add more layers and maybe a thermos of cocoa.

 

Will I get wet?

 

A little breezy mist or splash sometimes, but we are not trying to swim. That is a different class.

 

Gear and Boats

 

Do I need to bring any gear?

 

We provide life jackets and all boat equipment. You bring clothes, water, and adventure energy. Some students may wish to purchase sailing gloves before class. These help prevent rope burn! Sailing gloves can be found at Sexton's Chandlery and/or West Marine on Hayden Island. 

 

What kind of boats do you use?

 

We teach aboard comfortable cruising sailboats designed for learning, not racing you into terror. Stable, safe, and fun! Click here to read more about our boats!

 

Can I bring my own life jacket?

 

Yes, as long as it is Coast Guard approved.

 

Random but Real Questions

 

Do I need to know knots?

 

Not yet. We will teach you a few useful ones and make sure you can do them without googling.

 

Are pirates real?

 

Only the friendly Portland kind.

 

Can I fall off the boat?

Please do not. We show you how to move safely so everyone stays onboard.

 

Will I look cool?

 

Absolutely. Nothing says cool like taking the helm under sail with the wind in your hair.

 

If we missed something, send us your question. Odds are someone else has asked it too but in a weirder way. We are happy to help.

Send us a message!

How did you hear about us?
What are you interested in?

© 2025 SkyWind Sailing, LLC

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