a conversation about the evolution of a sailor

An Honest Conversation About Buying Boats

Happy New Year friends!

Hopefully, this is the first of many in-depth conversations we’ll share in 2023.  And we’re starting off with our new friends Frank and Mary Grace aboard Ticket To Ride.  We spent a couple of weeks with them in the Tuamotus looking to gain some experience and insight regarding performance cruising.

They also started off in a great production catamaran and then moved on to a performance cat.   Spending time with them felt like a peek into what our own journey may be like.  And we wanted to know a lot more about that evolution.

Because there is no such thing as a perfect boat, but there are different boats for different types of sailors, for different types of cruising, and for different seasons of life.  As a sailor evolves, so does their boat.

So, grab a beverage and settle in for an insightful conversation about the evolution of these sailors.


If you enjoyed our conversation, these two keep a blog that is a lovely mix of personal musing and lessons learned.  Below are a few we recommend checking out.



Thank you for watching!  Ups, downs, and all around, we share it all. If you like what you see, there are lots of ways you can show your support.

Hello there! I honestly don’t know what to say, so I am going to tell you a bunch of random facts instead. I'm a fish eating vegetarian who hates spiders and loves snakes. I almost never took vacations growing up. I wanted to be Pippi Longstocking (still do). I misspell about every other word I write and still struggle with grammar. I love splurging on a good high tea (which is really hard to find these days). And whatever you do, don’t tell me I can’t do something, because then I'll HAVE to do it!

Comments (11)

  • Carol

    Sounds like someone is a Beatles fan! “Let It Be” and “Ticket To Ride.” 2 oldie Beatles songs.
    You guys already gave up everything you owned to take the first steps and buy Curiosity. Now that you’ve gotten your feet wet (so to speak) it’s time to move on. I feel like somehow you are being pressured into justifying your purchase of (Curiosity II-I hope). Maybe I’m wrong and I hope I am. But then too, if that’s the case, why are you? Is it really anyone’s business if you choose to purchase a different boat? I know you guys get donations from people and have taken a lot of criticism over it (another thing I don’t understand) but I have a feeling you aren’t monetized enough to use that money for the purpose of buying a new boat. I guess what I’m trying to say is I think people should mind their own business. You deliver what you say you will. Incredible travel videos of places I could never go to. It’s no different than if someone subscribed to say, Conde Nast Traveler. Except we’re getting it in real time…kind of. And if people want to go as far as joining your Patreon page, that isn’t anyone’s business either. I’m looking forward to seeing the new floating tiny house. BTW: I’m probably not getting the same ones you guys had but I ordered an electric bike and can’t wait to get it. Watching your videos is what got me interested in the first place so thanks much! God bless you both as you embark on this new phase of being “Curiouser and Curiouser.” Maybe that could be the name. Curiouser from Alice in Wonderland!

  • Paul Smyers

    Frank’s comment that “you can’t take it with you” is a lot to process for some people. But I’ve found it’s often the right mindset for seeking happiness. Spend the money, have fun, someday you won’t be able to anymore.

    That said – being boat poor is a real thing and often times people feel trapped in their fancy boat because they can’t afford to use it. Or fix it when it inevitably breaks.

    Everyone has to find the happy medium where they are in an amply comfortable boat and can still afford to operate and maintain it.

  • Alan Solomon

    Thank you so much for a great and informative video. Healthy, Happy, Safe and successful coming New Year to you both and frank and Mary Grace too.
    Frank and Mary Grace have a beautiful and remarkable fast, performance boat that is well-organized, with easy rigging, easy accessibility and is a fun, exciting, entertaining boat to enjoy. However, I like the space, roominess, convenient and luxury aspects in addition to the above.
    I loved that scene at 10:45 and 11:00 minutes of walking into the salon’ with the wood floor and the yellow highlights under the countertops and island. I would love to walk in to that every day and see that. I would have to pinch myself.
    Thanks, Wynns and Thanks Frank and Mary Grace.
    Happy and Joyous,

  • Michael Magill

    Good Morning, Thank you for a very informitive an iterestinmg chat you had. First of f let me send you all the best for 2023, and hope you both had a great festive time. Changing from one system of boating to another is difficult at the best of times. The owners of “TICKET TO RIDE” were the perfect couple to help you along with your new purchase. It will be different to be sure , but i feel Jason and you Nikki , will get to know the boat and will Master it very quickly. I also feel that if you have any issues that come up,you have boat ownrs that will stop and help you along the way. My best to you bith and thank you for letting me tag along with your new journey. Can wait for your next update.

  • Steve

    Jason, let me turn that back around on you. It takes a special knd of person to let all of US into that personal aspect of your lives. It’s not all gold amd glitter, but if it gets you out to shine that brass, you have found nirvanna

  • Steve Gibbons

    Happy New Year folks,
    Thats an excellent start to the new year. Some much detail that can be easily digested. So now I have to start thinking about what the right entry level boat for me is.
    Your miles ahead of my journey. But man, your all-great motivators. Thank you.

  • Bill Berry

    Not bad not bad at all. Very enjoyable conversation regarding what where why and becasue we wanted too.

  • aboyandhisdog

    Terrific conversation today! This morning NPR had a piece on how difficult it is to recycle fiberglass boats and that people don’t want to pay to properly dispose of them. They scuttle them in our coastal waterways where the fiberglass breaks down and gets into the water and food chain. So what happens to all of these boats when they reach the end of their useful lives? They are all pretty much fiberglass, carbon fiber, plastic, and other synthetics. In the “sailing world” is there a good way to dispose of these boats? This may be a topic you could address for us sometime. Thank you, -Tom

  • James Dillon

    Great information!! All the best to you guys in 2023!! Greetings from Canada !! I have enjoyed your journey these many, many years from the VW van and then the RV all over North America!! Congrats on your “BRAND” standing the test of time!! Truly amazing!! Giddyup!!

  • Mary Van

    Happy New Year! What an exciting year it is going to be for the Wynn’s!

    Ticket to Ride is a beautiful boat! It must have been great to experience it first hand! Hopefully it enabled you to make some of the boat decisions that you needed to nail!

    I plan to check out the Alaska adventure!

  • Jeff Forgey

    Wow ! What a Happy group of 4. You guys all are living the dream. Amazing how much knowledge you have about sailing. I am a pilot and it is the same in our industry. Many, many more years of happiness on the water for you all.


Post a Comment