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Sailing in Seattle seemed like the perfect activity to experience what those in Seattle call a right of passage to being a true Seattleite.

Note: This post is NOT, I repeat…NOT sponsored — I am simply sharing my love for Sailing after my first experience with the best Captain & Sail boat on the planet.

Booking a Sailing in Seattle Trip:

Sailing in Seattle

When you decide to book your sailing, I would highly recommend the captain and SY Cynthia R Boat (unless you have a group of more than 6 people). I found the captain through the Airbnb experience page, but he also has a website Emerald City Sailing you can book your unique adventure through. If you do have more than six people just let Michael know and he can make arrangements for parties of 12, 18 and 24 on other ships that have that capacity.

Traveler Tip: Never tried Airbnb Experience? Get $40 off your first stay by signing up with this Airbnb link.

Getting to SY Cynthia R Boat:

Sailing in Seattle

The Pier that the boat departs from is north of Seattle, about a 25-minute ride from Pike’s Place Market. I took an Uber Shared ride and it cost me about $14, but I would allow for extra time. Once you get to the Pier, there are private docks that you have to have a card to get into; so be sure to get Captain Michael’s number. It is a short walk to the boat itself, and then you have to board the boat via a small plastic step stool with 2 steps. Your captain can help ensure you get on safely. We had one passenger who recently had a pelvic fracture was on crutches and still was able to safely get on the boat. Once on the boat, you want to make sure you have your footing, so hang onto something as you make your way around the boat.

Meeting the Captain

Sailing in Seattle

Captain Michael Schaible was born in Seattle Washington. He is a certified PADI Master Diver, licensed boat captain and was part of the US Coast Guard in 2014. He is certified with the American Sailing Association levels 101, 103, 104 barebones charters and 105 coastal navigation, Instructor level 201-204. So needless to say he has quite the resume and knows what he is doing. The thing I found fascinating about the Captain was that he can read the wind based on the texture of the water.

Sounds like a false claim doesn’t it? Nope, I was able to identify what he was talking about based on the water texture, but my goodness, to have the razor sharp eyesight to see that far ahead of the boat (I’m talking several miles) without binoculars was quite impressive. He is a second generation vendor at the world famous Pike Place Market. His family runs a textile business that his father established in 1973, El Gringo Imports. He is very excited about this textile business, and even has some amazing sweaters to keep you warm while on the boat — which are also available for purchase, should you so desire. For those traveling from abroad, he also speaks Spanish fluently, so can accommodate International passengers as well.

The History of the Boat

Sailing in Seattle

Cynthia R is a historic and classic modern sailing yacht measuring 44.4 feet long. Designed by John Alden Company as a ketch rigged Pearson custom center cockpit sailboat. She was first launched in Thomaston Main by the Morse boat building company in 1967! You wouldn’t think she is this old when looking at her, but age is just a number, she is beautiful just the way she is 😉 If you go below deck, ask Michael for the history of the boat book collection he always has stored on board. Here reflections of the original owner’s voyages across the Atlantic four times, the sailing path of his trip with his wife through the Mediterranean and across the world are laid out in a storybook-like way to keep you enthralled for hours.

These voyages are also chronicled in Robert Carter’s book: Sail Far Away, Reflections of Life Afloat. This non-fiction book is an account of the 10 years in Europe Robert spent with his wife, sailing Parts of the Boat It is important to know what the parts of the boat are, especially when sailing in such frigid waters in Seattle. I personally didn’t realize that if someone falls into the water here (even if it is in summer) without a wetsuit that they can go into hypothermia very quickly. So in order to not get knocked into the water here are some main points.

Rule One: Stay in the boat

Rule two: Stay behind the Mast when the wind is blowing

Rule three: Don’t get on the boat if you have problems with dizziness or can’t keep your balance on solid ground.

Rule Four: Stay in the boat (there are loads of jellyfish right off the coast of Seattle)

Other than that, its all a matter of getting to know the boat. Michael is actually a sailing teacher and is really patient and open-minded about those who want to learn. He even let me cinch down the jib halyard and jib sheet (aka the ropes that tighten down the sails and control them). Here is what I personally learned on my first sailing trip about the boat and all its parts:

  • Mainsail: Catches the wind
  • Jib: Helps with turning the boat and also catches some wind
  • Mast: Holds up the sail
  • Boom: keeps mainsail stationary and helps to keep constant sail trim
    • This is what will hit you push you right off the boat should the boat need to turn quickly to not run into a sandbar or rocks. So as I pointed out before, stay behind the mast & the anchor point of the boom if the sails are out.
  • Keel: Stabilizes boat and also uses water pressure to propel the boat forward.
  • Tacking: turning the boat through the wind (but requires a lot of velocity to do this)
  • Jibing: turning the boat through downwind point of sail, requires a lot of weight management and distribution.
    • So ladies, don’t be offended if he asks you to step into a certain spot to help maintain the boat direction. It is for your safety and has nothing to do with you being fat or the anchor of the boat — it could be he is trying to even out the heavy stove downstairs.
  • Trim: A way of sailing the boat so as to create less resistance and faster sailing time like they do in racing.
Sailing in Seattle

If the sails are too tight the wind will bounce off of them like bouncing off a brick wall. If the sails are too loose they will ‘luff’ is the technical word, but I prefer ‘laugh’ at you by flapping in the wind. When they flap I feel like they are saying, ‘HA! You think you’re going anywhere? THINK AGAIN!’. Lastly, make sure you bring a snack, something warm to wear (that is wind resistant), and be sure whatever you bring (including cameras/hats/shoes etc…) are secure and won’t roll off the boat when you start sailing. The flat floor of the boat when sailing goes to about a 50-degree angle at times to help with speed and trim.

Passengers on the Boat

In total there were 6 passengers on the sailboat, and it was just the right amount for everyone to have a place to sit. One thing I would mention, don’t expect a cushioned seat of gold with servants to place grapes in your mouth gingerly. This is a boat, with a place up front for about 5 people to sit/lay (Michael does provide cushions, but no gold or servants). There is a place for 3 people to sit behind the wheel, although you will have to move quite a bit for Michael to be able to actually sail the boat.

Sailing in Seattle

The other 5 passengers were all from the Greater Seattle area. There were two other couples and then 2 single women. I became friends with one of them, Berkley, she had this bubbly personality that was so infectious. I personally get nervous in groups of people more than three, so it was nice to have someone to connect to. Berkley was so interested in my website and instantly wanted my Instagram handle. She didn’t care to talk much about herself, just wanted to know everything about me. She helped me take photos, asked about trips I was going on – and each time I tried to ask a question about her…..she played it off as if she wasn’t that important.
So Berkley, on this public platform, I want to thank you for being so kind and making me feel included and comfortable with your group. I think you have are a beautiful human being inside and out & hope we can have another grand adventure in the future.
You see, my Culture Trekking friends, it doesn’t matter if you travel solo or in a group — there will always be a kindred spirit whom you can connect with. They will teach you how to be a better friend, and maybe even become a lifelong friend. So please do not be afraid to travel alone — or start a conversation with a local. In doing so, it enriches your soul and provides a memory that will be forever burned in your mind.

Helping Sail the Boat

Sailing in Seattle

Not only was Berkley kind and inclusive, but Michael was a fascinating individual as well. If you put a California Surfer Yogi Master onto a sailboat…..Micheal would be the definition of that image you just conjured up.


He had a Jewish Star with each of the Chakra stones in it on a leather cord, a hat to control the long slightly curly sun-bleached hair, sunglasses and a smile that took up his whole face. Although there was a certain amount of shyness that was hard to pinpoint. So I decided to try and make everyone feel more comfortable by doing something a little silly, try to help out on the boat.

Michael let me cinch down several lines, and the rest of the group watched as I put my back into it. If you try and do this, just know your triceps are going to be in outright protest when you do. Luckily I had Berkley and the rest of the group as my cheerleaders, which ended up putting a huge smile on my face. I even got to sit behind the wheel!!!!! I steered us out to the Puget Sound while Michael got our sails ready to go, and then BOOM! Sails were out, lines were tight, and I WAS SAILING A BOAT!!!! GAHHHH!!!
I became so comfortable about an hour into it, I just felt like jumping into the water (fully clothed mind you). We were relaxing in front of the gorgeous view of the Seattle skyline and I just wanted to jump in. Luckily, Michael told me, ‘uuuuhhhh, that wouldn’t be a good idea, but I mean if you really want to I guess we could make it work.

The problem is, the water is cold enough that you could only be in there for about two minutes before I would have to pull you out because you could easily get hypothermia’.
So professional of him to say not say what he likely should have said ‘that’s a stupid and dangerous idea’ in such a nice way. Thus the Rule ONE from above, stay in the boat with your seatbelt fastened and arms and legs inside the ride at all times (unless your in warmer waters that is).

Embracing Freedom and Feeling

Sailing in Seattle

When you get me on any kind of boat, I feel like I am home. When we were kids my parents had a boat, most of our summers we were out on the water trying out the latest water toys. I remember the air chair, the chariot, the doughnut tube roller coaster thing that would spin you over the wake & roll you over and over until you finally just drop out the back of it because you get so dizzy.

So as soon as I stepped on Michaels boat, I felt at home, I felt peaceful and immediately took my shoes off and walked every inch of the boat. (I’m a little nosy and slightly impaired when it comes to being appropriate in social situations). Luckily Michael was laid back and let me snoop around his boat home.

Once we got out to the water, surrounded by the serene beauty of the Puget Sound and the Seattle Skyline — I couldn’t help the feeling of freedom. There was an inherent sense of feeling free — like I was away from the crowds, the cruise ships, the taxi’s the muggy heat of the city. I had the wind blowing in my hair, a fabulous group of passengers around me, a Captain who regaled us with stories of the boat crossing the Atlantic four times….I felt at peace there. I could have stayed out on the ocean for hours on end. At one point I even thought, ‘I need to get my own sailboat so I can live in it like Michael’.
Once the wind hits those sails, and you feel the boat tilt, the water lapping at the sides of the boat, the sun glistens on the water, and the only sound you hear is the wind whistling in your ears telling tales of adventure……nothing can beat this feeling.

It was the perfect timing for me to experience sailing. My Mom had just discovered after 35 years of marriage that my Dad had been living a double life. They were in the process of getting divorced and all the drama that comes with that. No matter how old you get, finding out your Dad was not who you thought he was, is always hard, and I was going through a significant mourning period.

So being able to be on this boat, imagining disappearing into the great blue beyond was just what my soul needed. I can’t tell you how grateful I was for this experience, for the freedom I felt and it truly helped peace return to my soul. One of Michael’s goals for his passengers is to have this type of spiritual experience. To have a sense of calm in a world that never has enough time for the quiet moments of life that are so precious and rare.

In Summary

Sailing in Seattle

If you are going to Seattle, and have a chance to hang with Michael on his boat…..do it…..no matter what the cost is. I promise you won’t regret sailing in Seattle with him. It isn’t like the commercialized sailings that are right off the main pier, this experience is unique because he and his boat are unique.

Michael has been sailing for so long, through so many countries, has so many adventures to tell — there was not one minute I felt bored. You will get to help sail the boat, feel peaceful away from the rat race of life, and see the Seattle Skyline without having to fight others for the perfect picture. You will capture moments that more commercialized boats don’t allow the time or space for. Most importantly, it gives you the perfect setting to connect with people in a way that will make your trip to Seattle even more memorable.

This was NOT a sponsored post, everything in this post I shared with you was to help you see how doing the unique things…..even if they are a little more expensive, can have the greatest return in meaningful memories that will fill your soul. Personally, I cannot wait to book an overnight (or maybe a few nights) sailing trip up through Canada and through the plethora of islands that surround Seattle.

As Always Happy Travels, Happy Tales, and See You on the Flip Side. 


Where to Stay in Seattle

Booking.com

To book a Sailing in Seattle Tour with Michael visit Emerald City Sailing Website.


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