Not Just A Dream – Reflecting on Our First Year As Sailors
It’s been one year since we signed on the dotted line, hit the transfer funds button and purchased our first sailboat that we didn’t know how to sail. That last part, the part about not knowing how to sail is my favorite. Because it’s absurd.
Calculated absurdity could be used to describe most of the significant decisions we’ve made in our life.
Our first time ever on a sailboat was in January 2013 but the dream had been swirling around in our heads long before that. So, the idea to go sailing about the world wasn’t a dream born from experience but rather from a romantic curiosity for the adventure it could be.
We figured whatever we lacked in experience could be made up with enthusiasm and determination.
Once we started sharing our salty dreams, plenty of people wanted to influence our expectations along the way. We’ve heard everything from “you are going to do great, you’ll love it” to “you are going to get yourselves killed” and possibly my favorite “you don’t just go buy a sailboat and go sailing”.
Between myself and Jason I don’t know which of us is more stubborn. We’re not easily deterred once we’re on a mission, especially when that mission is following a dream. If you’ve been along for our journey, then I’m sure you’ve already figured that much out.
We took in the encouragement and words of caution in equal parts. But at the end of the day, we know our limits and what we’re capable of. For us, there were never any doubts, we knew we would push ourselves to learn and it was as simple as that. Well, almost.
In case you are wondering, I really do dream I can fly and it’s wonderfully magical. I went hang gliding once, which is as close to flying as I can get (minus a squirrel suit, which I’ll happily try given the opportunity). So, I’ll stick by my “if you can dream it, you can probably do it” statement.
One thing we forgot to mention in the video: We always had a contingency plan! If we disliked sailing for some crazy reason we could always tie up at a marina and have ocean front property for a while. We figured a sailboat is still less expensive than most coastal real estate! Thankfully the past year has convinced us to push ourselves even further for year two. South Pacific, here we come!
Reflecting on the peaks and valleys of the past year reminded us of how much we’ve experienced, learned and how much is still to come. It always seems the bigger the dream, the harder we have to work to make it a reality and the more we savor the achievement.
If you want to travel back in time to hear some of our calculated absurd ideas on what we thought sailing life would be like…and our present day responses, click over to this post: Full Time Sailing – Thoughts, Expectations & Uncertainties
Thanks for being a part of the journey and sharing in our calculated absurdities. It wouldn’t be as fun without you! And a big virtual bear hug to all of our Patreons who keep us focused on sharing the adventures instead of peddling wares at the docks. We couldn’t have shared this new leg of the journey without you.
Are you dreaming of sailing?
If you missed our sailing school episodes or want to watch us squirm as we tackle mods & maintenance, head over to the sailing page. You can use the category tabs at the top to filter down to the posts you’re looking for: gonewiththewynns.com/sailing
Looking for some of the nitty-gritty details? Check these out:
gilbert williams
congrats!!!!ben following you for a long time along with eric, nomadic fanadic ,chris &chere tecnomadia and a bounch of others i’m all alone and started boondocking 1 yr. ago. just like you I learn asi go .I used to live in maine now I travel to fla. this year possibly Arizona. bounce around and stay out their on the rd the. best of good times, hopefully safe!!!! god-bless ,happy sailing…….
Tom Klein
So Jason adjusts his hair and Nikki does a second later. I notice this and then I hear Jason saying “When I do this, you can’t do it too.” LOL
You two should feel so proud of yourselves. Learning all of this and putting it to practice and literally putting your life into your hands. I think this sort of edge in your life makes you experience it so much better. And then where you are experiencing life just amps the whole thing up even more.
Teresa
Love your blog! I’ve been dreaming of living in an RV or a b oat and trying to decide between the two. I may follow in your footsteps and do the RV first, then the sailboat. Time will tell. Thank you for the inspiration!
Michael
We’re all glad you made the leap and just did it. What a wonderful encouragement to so many people around the globe.
Thank you.
Bob Goforth
Ever since I learned how to sail back the 70s, I have dreamt of living on a sailboat but “life” (i.e. fear, lack of funds, cancer, etc) have always gotten in the way. Found your videos about a year ago while researching cruising catamarans and have loved watching them ever since. Hopefully, one day soon my wife and I will move on board but until then, your videos keep my dream alive. Thanks for the inspiration.
Phil & Rita
Brilliant stuff. Many congrats. Can’t wait to see the French Polynesia vids in the not too distant future! Have fun and keep living that dream guys.
al ciauri
I have been following you guys for years and you just inspirer so many of us to take a chance at life . I wish I was a lot younger than 70 and had you back when . You have made me laugh and made me cry over your adventures and loved every minute of it . Keep it up and keep reaching for the stars . Al from Mckinney
Jennifer Thomas
So proud of you guys!! Such an inspiration to watch your videos each week!!! 🙂
Chris
Congrats on 1 year! Like most people, I first found your site by doing some research on RV’s, but LOVE your videos from your sailing adventures!
Jim Tatum
Love the videos. My wife and are are getting ready to take delivery of our Leopard 40 at the end of May…..
Question: Which do you find more useful. Cell signal booster of Wifi booster? Seems like Wifi booster would be great except most signals are password protected making them useless….Your thoughts?
Jim
Curious Minion
As you pointed out, WiFi networks are often password protected and their range is generally not far at all. So unless you’re planning to stay very close to land-based businesses that offer free WiFi it’s not going to help you much. A cell signal booster can turn a weak signal into a very usable one and will extend your cruising range.
Nikki Wynn
We do find our cell booster to be used more often. That said, the few times in the last 6 months that our WiFi booster worked at an anchorage was a dream! We weren’t using our expensive data to update our computers, download new music, videos and get a lot of work done. If you can swing it, we thing both are very worthy of having and come in useful. You can see more details on our boosters (we do think they are the best out of all the options) in our gear store here under the wifi & cellular tab: https://www.gonewiththewynns.com/store
Brenda Savage
Congratulations on Year One! I am so inspired by you both! I’ve learned through the years to listen to the cautionary tales and try to take the precautions necessary, but also to not allow the ‘dream crushers’ to crush my dreams. And, I’ve taught my son that as well, and he makes me proud as he follows his own dreams. Your videos make me happy, they calm me (I love being near or on the water)… and again, they inspire. Thanks for sharing! Safe travels!
Lisa
Does the South Pacific include a trip to New Zealand?
You would be very welcome!!
Johanna
Congratulations Nikki and Jason on reaching 3000 nautical miles!
Yvan Dion
Inspiring ! Thank you for sharing !!!
Luc L.
Congrats for the first year and the many more to come. You inspired us so much back in your RV years that we finally decided to buy one for ourselves. Bought it in December and went on our first trip this winter. Lots of fun. Even though we had watched all of your videos, we have to admit that we were still beginners… But we laughed a lot.
Just a few questions. Do you know any people you have inspired to follow your sailing route (e.g. buy a sail boat, maybe with the help of Just Catamaran, etc.)? Is it harder to meet people sailing than RVing? If so, do you miss that?
Steve Edison
Enjoy you guys alot. My wife and I are starting out on the RV route (which is how I found you)…It is really an adventure vehicle (Sportsmobile) and we’re headed to Alaska next May. We’ll do that a few years, and then may follow in your footsteps. True motivation. Thanks!!!
Michael Beal
Great job you two. Thank you for sharing.
Donna fennell
Love you and your spirit!
Had our maiden voyage in our rv. Can’t wait to head to Alaska! Sail on!?
Hugh R-J
Aww,…..we knew back in 2014 you guys would do great as sailors….Congrats on getting this far!
Fair Winds and Smooth Sailing!
H
Pam McClure
A year! ??. I so enjoy watching what you do and love your positive selves. Here’s to another year of growth and knowledge and adventure! Glad I can help just a little.
Pamela A. Mederos-Streetz
WOW!!!!! I can’t believe it’s been a year!
Your videos have helped make a tough year bearable. More than that, watching your videos has been inspirational. Although I would consider Victoria and me “late bloomers” we are both now retired and are making some MAJOR changes in our lives the first of which will be moving out of the “snow belt”. If things go as planned we’ll split our time between the home we just inherited in the SF Bay Area and a place in the Florida Keys.
About six months ago I began what I call “fantasy” shopping for an RV. After watching your RV videos we were able to indentify exactly what we want, what we can afford and how to get it. Without watching your videos the task would have been soooooo much more difficult. I went to my first RV show last month!
Nikki Wynn
Awe you guys…know I am giving you a virtual hug and high five right now. It is music to my soul to hear you are going for it! Split time between the Keys and SF Bay Area, that’s the best of both worlds! The road trip between the two each year will be half the fun. So many different routes to take and so much to see and do between those two points. Super exciting!
Laura
OMG one year already… we just got our RV on Friday 4/28 and are selling our house. We follow in your footsteps.
You guys are amazing, and you can do this. Go for it.
Nikki Wynn
Whoo hoo, congrats on the RV!
TOM
We hope that in all the times, when you kids get in the water, that you never encounter any of those “Man Eating” sharks. So be careful. We really enjoy your programs and especially your videos!
Nikki Wynn
I think the same thing every time I get in the water. 😉 Luckily, man eating sharks are super rare.
Cathy Stanley
Ahoy Mates: Congratulations on you amazing year. I just can’t wait to listen to your podcasts when they pop up. You are an inspiration to many of us. Keep on enjoying each other and the many adventures ahead.
Deborah Kerr
There was no doubt in my mind you could do this!! I can’t wait for the South Pacific – that’s 1 place I know that i personally will never get to visit, so thank you so much for sharing your adventures!! I just noticed, Jason always looks like he knows a good joke 🙂 You 2 are so cute!!
Lori
Wow, it’s been a year already? Congrats. Seems like yesterday you left your RV. I do miss your RV travels, but I am enjoying your cruising videos. So glad you are able to follow your dreams. Here’s to another great year!
cindy
seems like you announced this yesterday!!! I can’t believe it’s been a year. I see you mom, sis, and brother this coming Wednesday. Miss you both. Be safe! love you
Ellen Matthewson
You guys just rock! I was just looking back over some of your motor home videos, and I have to say that sailing looks very good on you. Both of you are totally buff with all that physical work of sailing, and you looked good before!
My husband and I just bought a 5th wheel, then a truck, then the hitch! This our first and it is something we talked about for YEARS! I have had a dream since childhood of being out in nature and NOT sleeping on the ground. We both want to visit our national parks all over the country. He has to work a few more years, but out first adventure is just around the corner. We live in the great northwest so there are so many parks on the ocean, in the mountains and even in the sagebrush just a few hours from us. We are young at heart, in our mid 60s.
Thanks for your inspiration!
Ellen
Sue Goetzinger
Congratulations! You are an inspiration to all of us to pursue dreams! We can’t wait to keep following you on the next big adventure leg.
Gerri Lilly
Best of luck to you. Love the videos. Guess I am living vicariously through your experiences. We have a motorhome and explore areas in our comfort range. Go for it!
Mike
Congratulations you two. It’s hard to believe it’s been a year already. Im glad to see that most things are working out the way you planned. And I’m also glad to see that you’re planning to improve your skills on MOB training and a few others. As a career firefighter we trained constantly for things that hopefully would never happen, but if they did we would be ready. It’s nice to see you’re taking the same approach.
Sail on and stay safe.
Roger B
Totally inspirational. It definitely requires a can do attitude to realize your dreams. By the way, Going RV just aired
S1, E2 again last week in your search for your RV.
Lisa Bee
Wonderful for you guys! So awesome! Who will your crew be in Florida?
Jason Wynn
We still have to choose! Lots of videos to watch 🙂
Angelack
Thumbs up all the way!
Kimberly
Is the timeline correct? The years seems wrong. Sorry… I was just trying to figure it kjt
Jason Wynn
Good Catch! You’re right, the hurricane was 2016…but all else is correct. Updating now 🙂
Nancy Fernandez
Congratulations on your first year! It’s been a pleasure and will continue to be following you two. Your smiles are contagious. Love every video! Safe and happy sailing and to another year. 🙂
Candace
Happy Sailiversary. I’ve followed you for years and the thing I admire the most is that you’re always growing, always have more you want to do and accomplish, not just reaching that peak and feeling satisfied. I mean, your life is great and I know you’re satisfied but you’re just not content to ride that familiar current. Onward and upward. It’s very commendable.
Jason Wynn
That’s it exactly! We get there, then we say how can we go further 🙂
Brette DeVore
Nikki and Jason – Thank you for sharing the adventure with us! I absolutely love the real life humble and honest videos like this latest one. So good!
As my husband and I have been saving up for the dream ourselves (currently 35), I’ve been curious about a couple of things :
– My husband has been a vegetarian for the past 15 years, should he consider introducing fish in to his diet so that we can rely on catching fresh seafood while living aboard? Or would you say it’s not necessarily essential to the lifestyle?
– My biggest fear is mechanical and electrical maintenance skills despite taking ASA 101/103/104 at Bluewater ourselves. Loved your section on learning from the repairs in FL, but wondering how much knowledge you all have found necessary to feel confident out on the water. Does engine or electrical failure keep you up at night and what all do you do to keep learning that side of living aboard?
Thanks again and huge congratulations on the first year!
– Brette and Dave
Jason Wynn
Being a Vegetarian can work but you may be stuck with a lot of beans and rice. Fish and eggs are such a wonderful source of protein that can be found just about anywhere. Fresh veggies or fruit are difficult to find and EXPENSIVE on the small, remote islands.
As for mechanical, there are classes you can take that give the general maintenance and repair of sailboats, engines, etc. Like we mentioned in the vid, when you’re surrounded by it (and all in) you quickly become in-tune with your inner mechanic. Remember, you have sails if your engines fail and you have multiple sails on board if you lose one of those somehow.
John Schretlen
It’s amazing how fast that first year went by. When you announced your sailing plans I was on the “GREAT IDEA!” side of the fence because you had the right enthusiasm and attitude about learning.
There was one concern that I kept to myself and one that I posted about.
The concern I kept to myself was about maintenance and mechanical issues. The memory you planted in my mind in the ‘Crossing the Alaska Border and Getting Screwed’ video about Jason being like Time the Tool Man Taylor – and then Jason proving it by running the ViAir with the filter plug in – was still very much in my mind. But when I saw how you were able to watch & learn from the Just Catamaran guys I was confident that you’d make do. Education is never free and sometime the school of hard knocks is the best place to learn. Remember that when you are knocking about in heavy rollers below decks.
The concern I did post about was about being aware of safety. Sure, everyone knows about life vests and other PFD’s, sure you were taught MOB drills, sure you are becoming super-aware of weather and tides and currents. But sometime new boaters do not realize that they are doing something unsafe, or in an unsafe manner.
As others have also suggested I hope you make some very never-break safety rules for yourselves. (Please) One idea: NEVER go out of the cockpit at night without being attached to your jack line and having somebody on watch.
I’m excited for you and hope for all the best in year two.
Jason Wynn
You’ll be happy to know off-shore safety gear and practice is a top priority for our return to FL.
michael robinson
you are both my sailing heros for your determinations to know and to do and to learn what is needed to succeed and do…some day when my aspiration turns to being a sailor i will remember nikki and jason did it with fortitude in the doing…blessings as you journey..m
George
I’m happy I found you two (back in the RV era) and thrilled to watch the progress, and the planning.
So much to say but I’m lost in the words.
Have fun
Stay in love
Onward!
Karin@yumandmore
That was so great to watch and listen to!!! Hoot hoot! Happy sailaversary wow have you come a long way since Jasper and I stayed with you in June. The vessel looks gorgeous and you two look happy and excited. So pleased for you. Good luck gor the next steps and we/I hope to see you again somewhere in the ocean. Huge hugs Karin and Jasper xox
Jason Wynn
We look forward to breaking bread with you again…and actually going for a sail this time 🙂
Jay & Leslie
Congrats!!! WOW, so proud of you & super jelly! We discovered your RV blogs & videos several years ago, as we full-timed across the states. They were a breath of fresh air, just like your current videos…ya’ll are the cutest couple!! We are looking forward to new adventures…the waves are calling to us!!! We hope to join ya’ll on part of your journey…how exciting!!
Mike DiMaria
Have you taken any precautions in case of piracy
Connie
Congratulations you 2 and the kids!!! It has been a wild ride for sure, watching you get this far and doing what you dreamed about……Wow! So proud of you!! I knew you could and would do it!! I’m so excited to see what’s next! Cheers and Big Love??Always!!!
Jason Wynn
Thanks Connie, it’s people like you that keep us pushing the limits 🙂
Dinah Rogers
Congrats, Nikki and Jason! One question: Have you experienced sailing in a storm? You can only prepare so much through role play. I wondered how you’d handle that inevitable.
Nikki Wynn
We’ve had up to about 35-38 knots of wind and storms. The smaller squalls help get us in the groove and practice for the bigger ones. For now, we watch the weather close enough to avoid sailing in anything to crazy. But I am sure it will happen one day.
Peter DeMichiel
Congratulations Nikki and Jason. Always enjoy hearing that you are challenging yourselves as you journey through life.
Sharing your life in love makes anything possible.
Steve LaChance
“If you wait for the boat to be perfect, you will never leave the dock”. Sounds like a perfect metaphor for life!
Congratulations on your milestone. Best of luck in the future. I am sure many like me will be waiting to live vicariously through you two!
Doug Carlson
Congratulations on completing Year 1! We love watching your channel and hopefully one day our paths with cross out on the blue!
Charles Babb
After your repairs in Florida and picking up the new crew, look into sailing down to Bonaire and enjoy over sixty diving reefs. Bonaire is below the hurricane belt.
Cherie @Technomadia
Big super congrats to you guys on completing your first year of the new dream! You’ve been a huge inspiration & encourager for us as we’ve geared up for pursuing our next adventure too.
I so fondly remember those nights spent years ago of us all sharing our eventual goals of exploring life on water. And here we all are.. doing it!
Dinah Rogers
Living vicariously through the four of you (and soaking up the intel–thank you!) inspires and encourages my husband Terry and me, not quite through our first year of FT RV life. Keep on with the love and fun. Safe travels.
Nikki Wynn
Thanks Cherie! It does seem like yesterday we were all sitting around dreaming and scheming together and now here we are. I wonder what we will all be dreaming about the next time we’re all sitting around pondering the future.