jason wynn sailing

Bahamas Bound! Sailing Across The Gulf Stream

It’s 2:30am.  The power cord is being pulled, the fenders are being stowed away and the sails are going up. We shove away from the familiar shores of Florida, cross the notorious gulf stream and enter the clear blue Bahamian waters.

Bahamas baby!  It feels oh soooo good to finally be on our way again.  This time last year we had just exited Alaska which was our most epic stretch of road travels.   We were driving along the west coast of the US dreaming of sailing about the world. Now, that dream is our reality.  Watching those city lights slowly disappear into the night’s black horizon was a miraculous sight.

sailing to bahamas

We had oodles of meaningful little moments that seem as though they will be seared into our memories forever.  It was one of those big days filled with firsts and we tried to savor them all, but at the same time not get overly excited.  Our journey is only in its infancy and we haven’t seen or done anything yet!

sailing to bahamas

Spotting a cargo ship out at sea after hours of nothingness. When I was editing the images I noticed it’s carrying giant wind turbine blades!

sailing the gulf stream

Our little friend who stopped by to say hello and rest his feathers for a while during the storms (and was almost eaten by Singa).

Taking my first shift sleeping in the cockpit.

Taking sleeping shifts in the cockpit.

nikki wynn sailing

Tightening up the halyard on the new Genoa.

The dolphin escort

The dolphin escort…welcoming us after our first crossing.

nikki wynn sailing

Watching the water turn from deep blue to shallow turquoise.

anchored at mangrove cay

Dropping anchor at sunset after a long day.

I realize that we haven’t done anything all that remarkable and we’re still newbies at best.  But we have done something that many people tried to tell us was impossible, irresponsible, dangerous and blah blah blah.

The ocean is terrifying to a lot of people (fair enough, it should be feared and admired).  Then there is the crowd that thinks if you don’t have a ton of experience, you can’t take off sailing oceans much less the world.

We came at this new adventure with positive attitudes, an open mind and almost no real sailing experience.  We started looking for a sailboat in February, purchased our catamaran at the end of April and moved into the boat in May.  We took a fast-paced one week sailing course in June, worked on our boat a lot and practiced our sailing skills through October and now…we sailed across the gulf stream in November!  Sure, it took focus, work (ya know: blood, sweat and tears) and intense dedication but it’s all very, very doable.

You can do anything you put your mind to.  Seriously.  Don’t let the doubts and fears of others or yourself talk you out of your dreams.  There is a great saying, “dreams only work if you do”.  I believe in that 100%.

Everyone’s dream, ability, age, budget and so on may be different but I firmly believe we all have the choice to live life on our own terms.

We’ve met so many amazing people out in the world living and experiencing their dream.  From traveling families to single or widowed. Hitchhikers and backpackers and expats and work campers.  We draw motivation and inspiration from those that came before us and those out there making it happen right now.

sailing bahamas

This is only the first chapter of our aquatic adventures but our quest will remain the same.  We will let our curiosity choose the course and our heart determine the duration. There is no schedule or destination, there is only the journey.

Thanks for being a part of it all and I hope you are in for the long haul…because we are!

Sailing Report

sailing across the gulf stream

Weather: Low 70’s, Rain storms over open ocean, sunshine and high 70’s in Bahamas
Anchorage: Mangrove Cay
Nautical Miles Sailed: 100
Date: November 4, 2016

Crossing The Gulf Stream

For well over two weeks now we have had north and northeast winds at 20, 25 & even 30 knots.  The winds finally shifted from North to East/Northeast late Wednesday and Predict Wind was forecasting 10-15 knot wind speed for Friday. We waited over 24hrs for the seas to calm before sailing off early Friday morning. The worst seas we experienced were over within a couple hours of leaving Florida, about 15 nautical miles off shore. We’ll go into more detail on crossing the stream in the near future.  For now, know we were going by what other experienced sailors suggested.  Don’t cross with any winds over 15 knots, especially any northerly’s.

Gear You May Have Noticed

Cameras Used to Capture This Adventure:

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 (59)

  • Kerry Koontz

    I always wanted this live style for myself. One day it will happen. I love watching your adventures and seeing your excitement of your new encounters. Y’all are so funny and goofy its great. Believe in your dreams and fight with your hearts. Life’s all about learning. The knowledge we learn over life is the only thing we’ll take with us when were gone. Sense you started island hopping whats the good and bad you’ve encountered with port authorities, coast guard, check in processes and all that…

  • cindy

    Good job guys. You made it!!! Look forward to seeing you

  • Wow! Soooo beautiful with the dolphins! And, yes, so much work to keep the boat up, but it’s that way with anything, a house, a car, a boat, an RV, a marriage, your lives… maintenance! (And sometimes way more than you wish to deal with). Well done, I am so excited for you! Also, I love the excellent advice about safety, and look forward to your videos about that. Kind of cool that people care so much about you! Me too, and I think the cats are fine.

  • Joe

    Please include your cats when you purchase pfd’s. Flotation and tracking devices for the cats will spare you from experiencing some guilt and grief .

  • Shawna

    Love your videos and would like to see how you stow things. In particular vegetables/food. I notice you eat a lot of veg and have a good variety/selection so would like to see how you keep things fresh/stowed. Unfortunately, when cruising in some Caribbean ports I couldn’t find a lot of vegetable selection so would love to see your videos show shopping excursions! Keep up the great videos.

  • Robert Gould

    You two spent so much time making sure your boat was fixed up and in great shape before taking it out into the open ocean yet you seem to be totally unaware of any of the personal safety procedures you should have. Do you two drive around in the car without seat-belts? You really really really need to address safety. Try this experiment. Next time you are cruising along in rough water toss a soccer ball overboard, wait one minute (without looking for the ball) and then try and find it with only one person looking for it (because the 2nd person is in the water). Please put the same effort into life jackets and other safety devices that you put into camera choices.

  • karen lueck

    I’m so glad you finally got to get out of Florida. We crossed the gulf stream quite a few times and always seemed to have a tired bird hitch a ride. I sure hope the little guy was able to get to safety. Darn cat. Mine would have been all over that bird and probably gone overboard in the process.
    I have to agree with the others as far as PFD’s. We did some liveaboard dive trips in the Bahamas (and never wore PFD’s either. I’ve personally seen a scuba diver get away from the boat (me and hubby included) The boat looks huge to the diver in the water, but if you’re on the boat, the diver is almost impossible to see, even with a speargun waving in the air. We were on motorboats which are easier to turn. I also am extremely worried about the cats. I know cats and they get the crazies sometimes and a boat is not a good place for them at that time. Please be careful.

  • Rod

    You were lucky
    If one of you goes overboard at night, YOU WILL N-O-T BE ABLE TO LOCATE A HEAD STICKING OUT OF THE WATER.

    You have practiced with an orange floating vest in calm seas.
    Try that again with a brown jacket covering that float at NIGHT, with rough seas.

    You will not find it, I guarentee you will fail to find it in the dark with waves.

    Never think you won’t go overboard. IT HAPPENS all the time

    One thing that pilots say, applies to you guys too.
    “There are OLD pilots,
    and there are BOLD pilots,
    But, there are NO, OLD, BOLD pilots.

    A dangerous habit will eventually catch up with you.

    Sooo, listen to all those people talking about safety devices.
    All it takes is ONE wave to knock you overboard.
    Then you watch your shiny boat disappear in the distance.

    You got lucky
    Don’t do it again

  • robert tubear

    i admire you guys for following youre dream . it is said you have to follow youre dreams in order to acomplish what you enjoy….nikki you look so natural when you are at the helm . and youre guy looks like he makes it easier and gives you asurrance…..

  • al ciauri

    All I know is I love watching you . So many adventures and living the life most people would love . I’ll be back on the road soon with my livin lite 16 ft travel trailer . Just lost my 46 yr old son and I just need to get away for a while and decompress and gather my thoughts and heal . I wish you many happy years on the water and life . Blessing be with you both . Al from McKinney .

  • Frans

    The counsel of many is wise endeavor. You have many well wishers! FEEL BLESSED, sage advise. Love your vlog, blog whatever its called…
    Happy you shared the wonderment and newness of your adventure crossing Gulf Stream, etc. which brings joy Iam sure to your soul and online family!
    You only live once, so explore and thrive Wynns!

  • Pamela Mederos-Streetz

    Almost forgot …….. along with those PFD’s you should each have a Nautilus LifeLine Marine Rescue GPS ( ), AND a 10′ Surface Marker Buoy ( ). Currently the best price for the Nautilus LifeLine can be found on their website and the 10′ surface marker Buoy can be found at Amazon.

  • Pamela Mederos-Streetz

    Happy Post Thanksgiving to you two!!!!!!

    I know that space is at a premium but I think you should check out this scooter I found on called the Eon Scooter. It’s affordable, small, powerful and lightweight. Everything I had been looking at prior to finding this started at $700 and went up from there. This starts at $400 and fully kitted out is $547. HUGE price difference from other scooters. Maybe you could convince them to do a special deal with you.

  • Barbara Dobree

    Wear your PFD’s, always. And attached yourselves to the boat, always. Habits that can save your life when you least expect it.

  • mike scans

    You just upgraded one of the beds and I came across a product used to prevent condensation and dampness under the mattress . I thought of you when I saw it.

    enjoy your trip, I am with you in spirit.

  • Denise Fonseca

    Wow…adventures ho! Loved the wind and the little yellow visitor. I liked that the clouds finally parted and you could see blue skies for a good portion of the trip. Did you finally meet up with your friends? Do you have to file travel plans and get permission to come into waterways or bays? I will heed of the warning from Hap Camp if I ever go sailing…I like to err on the side of safety! Also, does Singa have a floatation device?

  • Over the last 2 years we sailed our catamaran from Florida to Thailand, 50K sailing miles. You guys are doing great, and filming along the way exposes so much – good and risky. You are doing fine and obviously enjoying the experience. I agree with others about life jackets and jack lines – we made rules on our boat – you should just make yours and then always stick to it. Ours; at night, outside the saloon, must wear a pfd ( we chose mustang off shore with ais units attached), forward of the cockpit, must clip in to the jack line, no bathroom breaks over the stern, wake the other person for major sail changes,etc. Especially with one person asleep, dark, autopilot on, in the gulf stream, sqalls ( winds can and do jump to 50 knots inside a squall) you really should have a lightweight pfd on. There are even some models that go around your waist ( I am not recommending them, but if the comfort factor is an over riding concern) . May be you can do a comparison video on off shore life jackets?
    Otherwise great sail and looks like you had the plan and wind forecasts. you guys are doing great. We will be over there in January and would look forward to hosting you guys for a sundowner.

  • Jeff

    Loved your video as I always do! So happy you had a great first experience. I follow a few others on the internet but no one knows how to do videos like you two! Best wishes.

  • Jayne

    Great adventure! Appreciate your sharing it.

    Not to also be a downer, but I agree about the tethers while on autopilot. I’ve heard stories…

    Otherwise, good luck, fair winds and smooth sailing to you both.

  • mary

    Following your dreams. We should all be so brave.
    I feel like I’m a part of your journeys. Thank you for sharing!

  • Congratulations! That must have been such an exciting moment to know you were really doing the thing you’ve dreamed of. I love reading (and watching) your adventures!

  • Nancy Fernandez

    That was awesome guys. I was so exciting watching this video. To see you finally make it across the Gulf Stream with no real problems is just awesome. The birdie was so cute, sure glad it made it before Singa had lunch. Seeing the dolphins was amazing. Jason did you ever get some sleep? Enjoy the bahamas, see you guys next time.

  • Hap Camp

    Please, please heed the good advice others have mentioned re safety when sailing offshore and especially at night. You were reckless and lucky, especially with all the dancing around when you were both forward on deck under autopilot with no one at the helm to implement man overboard procedures. Install jack lines both port and starboard, and always, always, always tether/clip in when on deck either to a fixed point or to a jack line. When on deck, always wear an inflatable pfd which doubles as a safety harness, with strobe light and preferably EPIRB. If one of you falls overboard, especially at night, it is a terrifying fact that it is nearly impossible to locate the overboard person. Same for daylight in rough seas when your boat is moving away at 5-7 knots. Think this is overly cautious advice? Then the next time you are out under sail at night, or in moderate to rough seas during the day, each of you – alone without help because one of you would be in the water – do a surprise man overboard drill attempting to recover a floating object without a strobe light on it. When you both fail you will have learned an important and life-saving lesson. Tethering is normal and basic offshore sailing practice based on centuries of experience, and is mandated by most offshore racing associations. And ignore any other comments you get that my comment is too “negative”, and instead ask the commenter if they will volunteer to join you under sail and jump overboard at night or in rough seas, without a pfd or strobe, while only one of you then tries to execute a man overboard drill and tries to locate and save them before they drown. I understand that you are beginners at this but your training on this critical safety issue appears to have been woefully deficient if not non-existent. Please understand that this is meant to be positive and helpful advice and I hope to continue to enjoy your posts in the future. You have made a lot of progress going from RVs to new sailors but are still low on the learning curve when it comes to offshore sailing safety practices. But the good news is that it’s an easy fix, just a matter of developing good safety habits and then following them religiously.

    • Roger

      Good recommendations….even if these options were part of their sailing process, it should have been shown in the video as a safety need to ensure we continue to see the Wynn’s blogs for many years to come.

  • Scott Cissel

    Great to see you making tremendous progress on your sailing journey. Have a great time in the Bahamas and congrats on your crossing and for such a good video.

    Scott & Tammy Cissel

  • Deborah Kerr

    Dolphins, cute little bird, healthy yummy-looking lunch, blue skies, wind & rain, an anchor that’s working, beautiful sunset!! Wow, just wow!! There are no words!! Thank you for sharing your journey! You made it across that Gulf Stream 🙂 Awesome…..

  • Go Wynns go! I so agree and if your dreams don’t scare you they aren’t big enough!

    If you’re not careful, you can find yourself stuck in life without even realizing it due to imaginary, self-imposed boundaries. The older we get, the easier it is to get set in our ways and subtly convince ourselves that we “can’t” do it. Life can become more scary as we age and hesitate to take on new challenges due to the perceived risks involved.

    Never say never… happy sailing!

  • So much fun to follow your first crossing. Well done!


  • Suzy

    I am learning geography. . Keep going.

  • You guys rock ‘n roll! So impressed with y’all! Wishing you smooth seas! Congratulations on this major milestone!

  • Alvin

    Great seeing and reading about your sailing adventure going so well for you both. I started following you a few years ago during the RV adventures.

  • Oh man, this video is awesome! So exciting!

  • Irv

    Why did you leave at night?

    • So they could arrive during daylight. Much safer to leave a place you know in the dark than arrive in an unknown place in the dark.

    • Curious Minion

      + wayne thomas has it: so they would arrive during daylight to anchor. It’s such shallow water sailing that it’s not advised to sail at night in the Bahamas.

  • Roeh

    Looks like so much fun!

  • I enjoyed this video the best! And I shared your excitement of finally going off, on a long trip, by yourselves!

  • Kathy

    I was so excited (and a bit scared) and I wasn’t on board! Thanks for sharing!

  • Ditto pfds.

    Get the inflatable type. Maybe two sets near shore and off shore. They are very comfortable. Ware them for a week and you will feel like something is missing when you are on deck without them. If you just cannot handle the vest style at least get a fanny pack with a light.

    Do youhave personal EPIRBs? Good to have as well.

    Do you guys know about the publication “Practical Sailor”. Get a subscription they have reviews of PDF and all sorts of gear.

    Seriously consider getting your boat fitted out with two bow anchors. I would hate to weather out a blow on a lee shore on one hook. I would put this in front of that radar for sure.

  • Mike macalpine

    You guys are an inspiration regarding challenging life, and you are able to portray that in an entertaining manner. Congratulations on that. I noticed you don’t wear any footwear, we had a rule on our boat that you had to have shoes on because a broken toe can so easily happen and can incapacitate you, something to think about. Cheers.

  • So cool to watch your new adventure! Good sailing!

  • John Schretlen

    Great addition to the sailing video collection. Love the colour of the water, and the escort provided to you by the local marine life.

    Not to be a downer, but I have one concern: has any of your family, friends or sailing buddies told you to always use a safety harness whenever you are outside sailing at night, especially if the wind is up? Perhaps you already know how fast one can fall over when a wave hits but you have no idea how hard it is to see a MOB in the dark. Believe the people who have tried – it is almost impossible.

  • Richard Cornelius

    Great job on your first crossing. Fair winds! We intend to follow in 2 years.

  • Norman Frenk

    Boy you guys have come a LONG WAY! (I still remember the fix-a-flat RV tire video). You guys ROCK leaving in the middle of the night in a storm on your first ocean solo! Great job, guys and let’s see more!

  • Congratulations! You two are amazing. Beautiful video and pictures! Well done. Looks like you two are on your way!

  • Mark

    Proud of you guys! You are an inspiration to those of us who are following your journey. Safe and adventurous travels.

  • Pam

    Thank you. That was fun. Very exciting.

  • David

    Loved it in your video when the bird came into the Living room and Singa’s attitude was “Out of my way Jason, never let a human do a cat’s job!”.
    Have you thought about naming your tender? I know that it’s not a good idea to write a name onto the tender itself, because it makes it easier for criminals to associate the tender with your boat, but I’m thinking just so that you can refer to it in your articles and videos. The Delos crew name their tender ‘Maggie’, the Sailing La Vagabonde crew name their tender ‘Cunningham’ and the crew of Ran have in their latest video named their tender ‘Quickie’. I was thinking that maybe you could call your tender Pippi after Pippi Longstocking…
    Do you follow flag etiquette and fly a Stars and Stripes from your starboard transom? I haven’t noticed one in any of your videos, I might not have been observant enough. I get the impression that in the USA, flag etiquette is largely ignored, but in other parts of the world is taken more seriously, so it might be a good idea now that you have left the USA to consider whether or not you wish to follow the traditions of flag etiquette. (It is worth noting that is some parts of the world, some parts of flag etiquette are law as well as tradition, so not following flag etiquette at all is both potentially offensive and illegal (possible fines)). Do you have a halyard suitable for courtesy flags on your starboard spreader?

  • Cam

    Congrats you guys! Ignore the haters. They’re just jealous that guys can afford to spend $$$$’s on the boating lifestyle without working full time jobs, and can stay in such amazing shape without appearing to have any excercise equipment or routine. Wait a second, I’m jealous too! 🙂

  • George Sears

    If you never mentioned the naysayers again, it would be OK with me. I’ve been out in the 18 foot travel trailer for 2 weeks, now. Travel is still just a filter, for me. It’s still your life, and it’s still a complicated world full of bad things. I don’t think you run off and just find perfection. Nature is too mucked up for that.

    I am fascinated by the idea of space, limited space, and making it work so well you don’ t think about it. Tiny details seem to make a huge difference. I’m annoyed that I haven’t found a way to carry the electric bike where it is more accessible, so I can just grab it and go somewhere. But it is heavy to get me up most terrain.

    Looking forward to how all this affects your view of the world. So much of what RV bloggers publish is sort of like Nature Porn. Yeah, it’s pretty, but is that really our relationship to nature or whatever? We are basically consumers of nature. I don’t know where that ends up. That’s a question to ask. I think a lot of people know the world is a very nasty and out of control place, and they wonder what you are doing. Just trying to do what you are doing is kind of profound.

  • Tim klenk

    Thanks guys for the video!

  • I loved the new video. SO awesome to see dolphins. The closest I have been is boogie boarding in Malibu, and they swim along the shore before sunset. Never gets old watching them.

    I am excited to see more videos.

  • Wolf

    Congratulations! But what about PFD’s when you are on deck? And jacklines when you are sailing at night?

  • Jane

    What brand of shoes do you have on Nikki? Cute!

  • Connie

    The Journey! May it never end!

  • David Simon

    Wonderful video, as they always are! Congratulations on your first sail across the Gulf Stream.


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