This Was A Bad Idea – Sailing With My Brother

Jason’s brother joins us aboard CURIOSITY in Tahiti for our last hurrah!  From swimming with sharks to hiking to the top of volcanoes, we made sure to give him the full Polynesian boat life experience. Complete, of course, with local concoctions and Tahitian fire-dancing.

At the end of his last night on board, we sit down for a conversation and he shares what he really thinks about our alternative lifestyle on the sea.  It’s a different perspective on our lives as sailors, creators and family.

We were sad to see Jacob go. 😢 Being away from family is hands down the hardest part of this unsedentary lifestyle.  We often find ourselves a little blue thinking about family and friends back home. The milestones and everyday moments we’re missing out on…the ones we’re having and wish we could share.  The late nights of playing games, laughing and razzing each other…we miss it all.

Endless horizons and swimming with all the baby whales in the world can’t replace the connections we have to our families.  So when someone takes the time (and long flights) to come and spend time with us, we try hard not to take a single second of it for granted.

jason and jacob aboard s/v curiosity in moorea french polynesia

jason and jacob swimming in Tahiti french polynesia

Boat life isn’t always easy but being able to share a slice of our life with family is priceless!

Jacob, thanks for the memories and the supplies delivered.  And don’t sweat it city boy, we’ll work on getting an Air Conditioner just for you. 🤣


More Family Sailing Adventures Here:


Brother On Board Timecode

Just in case you want to skip ahead or revisit any specific answers.

03:58 What do you find to be the biggest adjustment to Boat Life?
04:27 What fun behind the scenes things don’t we get to see on Gone With The Wynns?
05:50 Seeing how much fun your brother is having does it make you want to do similar things?
08:28 Do you watch all Gone With The Wynns videos?
09:13 Name one thing you’re envious Nikki and Jason get to do.
10:35 Do you feel stir crazy on the sailboat? Is there enough to keep you busy?
11:55 What was the biggest change going from land to sailboat that surprised you?
15:45 What have you noticed Nikki and Jason doing differently this trip vs. your first times on the catamaran?
17:22 Which cat likes you better?
18:19 When will we see full time family crew aboard s/y CURIOSITY?
19:24 If you could instantly relocate your sailboat anywhere in the world, where would it be?
20:16 How much filming goes into a Gone With The Wynns episode? Have you thought about a Bloopers episode? What is Nikki and Jason’s work to play ratio, and how much sleep do they get each day?
23:22 Get that fly! Singa goes a little crazy.
23:51 Now that you’re years into full time sailing can you see yourselves doing it for the rest of your lives, or will you come back to land and settle down in a few years?
25:02 Do Nikki and Jason’s adventures make you long for your own? Would you start with an RV or Boat Life?
25:51 If someone told you 15 years ago that Jason would become an explorer traveling the world, what would have been your response?
28:54 Would Jason be skinny or heavier without Nikki’s cooking?
29:38 Does the filming schedule get in the way of your vacation fun?
30:20 Oh man…bring on the tears!
32:58 Damn Cat!!!
34:41 I would like to see a video about the composting toilet on a sailboat. Jacob, what are your thoughts about peeing and pooping in the composting toilet?
37:16 Jacob, any thing you want to share about Jason and Nikki?



Ups, downs and all arounds, we share them all.  We’re able to do so because you beautiful people show up each week, read, watch, comment, share, shop our gear store and put tips in our production jar. If you like what you see, there are lots of FREE ways you can show your support.  Thank you for being a part of the journey!


🎶AWESOME tunes:

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 (36)

  • Al-Claudia

    Hi LOVE and miss my family too.

  • BrendaB Jones-Schneeberg

    Jason is 37!? Mind blown

  • John Lockhart

    It’s a week since I watched this, and realized I never stopped to comment. Your videos are always chock full of amazing sights, always shot and edited to high professional standards. This one was less amazing scenery, but the sit down with Jacob was an amazing look into your lives, what keeps you going and what you do through someone else’s eyes! Great job, and hopefully you can do a few more like this with your crew and other family members.

  • Steve Nicholls

    Such a cool vid! Loved it! Really. But the best parts were when Singa gate-crashed the view! He’s a gem!

  • Ron Stein

    Do you ever see yourselves cumming to Western Australia ( Perth )

  • cynthia williams

    So good to see the 3 of you share… I teared up when you did Jacob… so sweet!!! The time you spent together was so precious I’m sure!!! So glad you were able to make that investment of time.. Love all of you. I don’t have a Sunday Jason and Niki matinee, but I do tune in without always, and leave out much commenting, but I do enjoy chiming in when family members show up. Miss you all!!! We are all so spread out getting together from time to time is priceless!!!
    Jason was coming out to California on the plane traveling alone under age (couldn’t travel under 5 alone, maybe that has changed) but his mom lied about his age… shush!!! so I would say YES Jason had a travel bone at 5 because he did not miss a summer coming for a visit!!! Skipped 1 year, the following year brought Niki out. Love you guys!!! Enjoyed!!!
    Aunt Cindy

  • Alan Solomon

    Thanks for the video. ALL the videos are great. Thanks Nikki, Jason and Jacob and Singa was in there too.

    Jacob says that he works remotely. I was just wondering what does Jacob do?

  • Deborah Oliver

    I would LOVE to have your (Nikki’s) salad recipe(s)!!! Or any recipies for that matter. I try my hardest to eat ‘real food’ and on one episode I heard some of the ingredients you were putting together, and it sounded delicious!

  • Paul VanCompernolle

    I don’t post comments very often, not a big social media guy. I watched Jason and Jacob grow up and the bond they developed, with my daughter Lauren as well. We were always a close knit family and did so much together; from pool time and grilling out in the backyard, bike rides, sports (Lots of Sports), family tennis on Sundays, volleyball with friends and family at the frequent get-togethers at our house and wake boarding on our boat. Lots of snow skiing and snowboarding with all three kids learning to ski at three or four years of age. I remember Nikki’s first ski trip with the family, I’m pretty sure she had never skied before, but as you know by now that Nikki is not afraid to try anything, so by Day 2 she was skiing the blue slopes with us and taking on the blacks by the end of the week. We enjoyed camping trips throughout Colorado including hiking, white water rafting, climbing (and rolling / sliding down) the sand dunes at Great Sand Dunes National Park and Preserve. For a change of pace, laid back trips to the beach. Our immediate family always spent Christmas together even after Jason and Nikki started their RV adventure. I’m so proud of all of them for their special bond with each other, what they continue to accomplish and the wonderful persons they are.
    Love, Dad

  • Jana

    This was so cute. A few things:
    Brotherly love is awesome.
    Loved Jason’s little “I been drinking / sleepy time blinking”.
    Singa going for the fly was hilarious.
    Best quote ever: “If you know what you’re going to be doing in 20 years, there’s something wrong with you.” I’m going to steal that, Jacob.
    Nikki (adorable as always), please consider making an e-book we could buy/download with some of your mixology. I swear, girl, your drinks always look so damn good.
    And Jason, good job on just scooping the damn fly out. 🙂

  • Dinah Rogers

    HI Mary, I had that thought while watching Jacob and Jason interact and noticing their similar expressions and little likenesses. . . “I bet Mary is so happy to see the boys together.” I’m a mother of grown sons, so my reaction to things I see often reflects how their mother must feel. You’ve done a great job raising them, obviously, and it’s wonderful that your family remains close . . . and how blessed you all are to have Nikki as a part.

  • Jeanette Brennan

    Thanks for sharing this awesome video – you are all blessed to have each other. Really loved the Q&A. Sweet of Jake to share his experiences with us. Enjoy your family time and come back soon! Adventures await… 💓🙏⛵️🙏

  • Don Capellani

    Another blogger I follow ran in to you guys in Colorado recently how did that happen did you leave the boat somewhere and come back to the states for a while. Just asking

  • Tom Fitch

    Do either of you have issues with depression when people leave? I get pretty severe melancholy when friends visit and then leave.

  • Lisa Day

    Loved seeing Jake and hear his him answer the q&a. You are blessed!

  • Mary

    I loved the video. I just wish I could have been there too! It makes a mom happy when she has all her family together.

    • Dinah

      HI Mary, I had that thought while watching Jacob and Jason interact and noticing their similar expressions and little likenesses. . . “I bet Mary is so happy to see the boys together.” I’m a mother of grown sons, so my reaction to things I see often reflects how their mother must feel. You’ve done a great job raising them, obviously, and it’s wonderful that your family remains close . . . and how blessed you all are to have Nikki as a part.

  • Stoney A Shukat

    I too bought a Bounder. My wife said, “I’ll give it 2 maybe 3 weeks. “. That was 10 years and 82,500 miles ago. Since 1970 I’ve had a boat from 17ft to 45 ft.
    You and only you, will know when the time for change comes. Keep living your dream.

  • Jonni

    Jacob, could not be anything other than your brother, seriously.
    Lovely guy, heartfelt and as straightforward as you two.
    The trip back to the boat after the airport dropoff , without him, would have been a hard one.
    Till next time

  • Roy Hardcastle

    Jason Enjoyed your info with Jacob. It is heart warming to see you 2 so close. Mom did a good job. Look forward to see you and Nikki.

    Roy (grand paw)

    • Mary

      And all the stories grandpa could tell about Jason… 😊❤️

    • Mary

      And all the stories grandpa could tell about Jason… 😊❤️

  • Rob Dawkins

    Love your videos
    Time to watch is always peaceful
    Thank You

  • tom tordel jr

    “This Was A Bad Idea – Sailing With My Brother.. what? why? was great

    • Dinah Rogers

      Oh yeah, what was the “bad idea” part?

        • Steve

          No, no, no, it was a great idea. A lot of work for you, but a blessing forus.

  • Jo

    At the end of the day, experiences are great, memories are cherished but family is everything.

    Great video thanks Nikki, Jason and Jacob.

  • jim

    As always thank you for sharing your lives. Keep trucking with that JD hat. If you ever need some more JD paraphernalia let me know I am 10 minutes from the source. ( it is starting to look a bit worse for wear)


Post a Comment