learning to sail

Sailing Schooled Ep. 1 – Miami, The Crew & Scarface

Conventionally, the majority of people would learn how to sail and then eventually buy a sailboat.  But we’re not much on convention, despite our deceivingly conventional appearance.  It may sound crazy but why not put the cart before the horse?

wing on wing

Truthfully we don’t know a lot about sailing and we have little sailing experience.  So, when we put every penny plus a few borrowed ones into purchasing a sailboat and moved onto it without really knowing how to sail, we received a “boat-load” of mixed reactions.

A lot of people are terrified of the ocean. Some think if you didn’t grow up sailing or already have years of experience on the water, you can’t just decide to go buy a sailboat and go sailing.  Ah, but you can and we are doing it.

Much like riding a bike or driving a car, we’re not born knowing how to do it.  We hop up on that seat, or get behind the wheel, and learn by doing. In the beginning we’re not the best drivers, or maybe we need training wheels, but it’s the real-world experience that makes us more confident and pushes us to refine our skills.

Learning to sail and sailing across oceans isn’t an unachievable goal.  We want to explore the world and as much of our oceans as we possibly can.  We think the best way for us to accomplish this goal is by sailboat.  What better way to get started than to buy a boat, be 100% invested in learning how to use it?  Our passion for exploration is deep and when you’re passionate about a goal (or a dream), anything is possible.

Is it the easiest way to go about it?  Probably not.  But I can also think of easier ways to get to the top of a glacier than hiking up…but where’s the fun in that?  If we wanted easy, we would’ve never hit the road six years ago in the first place.  Our adventures have been life changing and sailing is simply the next iteration of our crazy way of life.

Now here we are, settled into our new home on water, fully invested and ready to learn how to move it about the globe!



Why Sailing School?

You don’t have to go to sailing school to learn how to sail.  We’ve talked with a lot of fellow sailing cruisers that taught themselves how to sail or learned from friends (lots of great sailing books and websites out there).  We could have easily gone this route (and we heavily considered it) but it would take a lot longer to grow our skills and confidence.  Not to mention, we really want that need to have an experienced sailor on-board limitation removed from our insurance, and our insurance broker said an ASA certification might do the trick.

When we announced we were sailboat shopping, there were a lot of you out there that recommended different sailing instructors and schools (thank you!).  One school that was recommended numerous times was Blue Water Sailing School.   After reading some reviews, chatting with those of you about your experiences and realizing we could knock out four ASA certifications in one week, on our own boat, we were sold on the idea!

learning to sail a catamaran


What We learned On Day One

This first day was all about getting in the grove, getting to know each other, the boat, the lingo and making the journey to our first anchorage.

We went over daily cruising checklists, weather logs, navigation log, used paper maps to plan our route, water depths and any possible obstructions along the way.  It was a nice introduction and not too intense on the information.  However, we know the next few days will be non-stop learning.

learning to sail

anchoring out key Biscayne

anchoring out key Biscayne


Captain Jennifer Wirth

I was sure with our luck we’d get stuck with some uptight, super strict instructor that was reminiscent of a military drill sergeant.  Luckily, that was just my nerves and imagination getting the best of me.  Captn’ Jen is great so far.  She’s a laid back sailor with heaps of great stories and experiences to share. She doesn’t get flustered and isn’t an old grumpy salt.  She knows her fish and can fillet up a mean mackerel.

 learning from captain jen


Our Camera Man

Terry works at Just Cats and we somehow convinced him to take off a week of work and come along with us for this sail.  We were concerned if we spent all our energy filming we might not be able to do much learning or vice versa.  As we mentioned in the video he’s spent a lot of time on cats in the past (his dad is currently sailing around the world) but he’s never filmed anything before.  We figured it’s better to have a boat smart person on board with no camera experience than a camera person with no sailing experience…although an impromptu camera-man overboard drill would have made for great footage.

luckily Terry was happy to be compensated in food, beer and quality conversation, for that we will be forever grateful to him.  I don’t think this is the last time we’ll see Terry…I mean we’ve already broke him in on being camera man so maybe we can convince him to come along to the Bahamas for our first crossing.

terry from catamaran impi


The Sailing Course and Certifications

We’re taking the A+ Cat Course: Bareboat Catamaran Skipper through Blue Water Sailing School.  (Side note, we just got an email from Bluewater Sailing School saying they would offer any of our readers a 10% discount!  Just use the code word Curiosity when booking to get the discount. I guess they liked our video!)

If we pass all the tests, at the end of the week we will be certified for bareboat chartering and big boat sailing. It’s a short, intensive, live-aboard cruising course that combines the Basic Sailing (ASA 101), Basic Coastal Cruising (ASA 103), Bareboat Chartering (ASA 104), and Cruising Catamaran (ASA 114) curriculum.

We picked up our books (4 total, one for each course) up a few weeks ago after signing up for the course and because we have very little experience (which is totally ok, you don’t have to have any experience to sign up) we’ve been warned to “study and prepare before the first day of class”.  I wish I could say we fully heeded that warning.  We’ve been so busy with moving in, outfitting and servicing the boat that we’ve only made it through the first 2.5 books.  Yikes!  We’re banking on a little down time to read (cram) each night.  It really does feel just like being in school again.

learning to sail


Equipment used to film this video:

See all of our camera/editing equipment and how we use it here:

Find all of our favorite gear and toys here: 

Also, if you want to begin the education you can find our sailing school books here:  and the flashcards we used to study here:

Sailing Report

Date – 6/19/2016
Weather – T-Storms in the PM
Wind – Northeast 10 knots
Seas –  2-3 feet
Route – Sailed from Harbor Towne Marina to Key Biscayne
Anchor Spot – Key Biscayne Bight (you can see the exact spot on our map). West side of Key Biscayne near the site of what used to be President Nixon’s Florida White House and the Scarface house (Al Pacino movie).

anchoring out key Biscayne

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 (53)

  • Tim

    Starting my Blue Water Sailing course (same as you guys) today! Thrilled to see our instructor is Jennifer! Feel like i know her from watching your videos! Nervous and excited all at the same time! Hope i studied up enough.

  • Anjeli Sonstegard

    Nice video! I just noticed you were docked right next to Tanda Malaika. Wonder what they are up to these days? Any plans to get back to the boat life?

  • Kevin and Audra

    Yay!!! So thankful I was sent a link to your blog/vlog/life story. My wife and I are in the research phase and are headed down this same path (well, maybe not buy the boat first). So, so crazy how stars, planets, and worlds can seem to align sometimes (we are from the North Texas area.) We’ve been looking at sailing schools and the week+ live-aboard courses for the last couple of months. Excited to see your journey and learn from your experiences.

  • Theresa

    I can’t find anything about how you decided a catamaran was the way to go, can you break down your reasoning on that?

  • Dave Bobo

    Hello Nikki – my wife & I just discovered your video series, and I have to say, you guys are da bomb!! (Don’t read that out loud in an airport!) We are in the education/planning stages of our lives right now – that being we are going to retire early (by American “standards”, that is), and buy a catamaran & make our own history on the great, big Blue. One question for you; after starting to watch your series on your sailing school, I was wondering – did you both take (pay for) the class for certification or did you just pay for 1 of you? I read in one of your earlier posts that due to the fact of getting the ‘need to have an experienced sailor on board’ statement removed from your insurance, if you felt you needed to fork out all the $$$$ for the both of you to get certified? I completely get & understand the need to gain knowledge & experience from the class, but didn’t know if there would be any kind of a requirement from your insurance company to have you both certified. We are looking to do the same (obtain our ASA 101, 103, 104, 114) within the next year or so, but didn’t want to spend more than what we needed to. Obviously, those courses aren’t cheap & every little bit of saving money helps!

    Thanks for sharing your awesome experiences, it helps more than you know! I certainly hope to cross wakes with you guys someday!

    Dave & Michelle Bobo
    Noblesville, IN

  • Paul

    Did you change your boat’s name from Curiousity to Reset? I heard you use Reset while you were doing a radio check. BTW, really enjoy your videos.

  • Rick & Brock the dog, WA

    Love your blog…I’ve been following you through your RVing and now the sailing. Very cool. My dad built a 27ft sailboat and always wanted to be a “cruising sailor”. When I graduated from highschool in 1978 my folks sold the house and with my middle brother and a buddy of his sailed the boat down the Mississippi to the Gulf and over to Dog Island off the coast of Florida. I joined them there and sailed with them for another year down the Gulf coast of Florida. Very cool trip. Mom and dad continued sailing until they reached the Keys. By then it had been almost five years so they headed back up the coast. They settled in DeFuniak Springs FL and dad set about building the house they lived in last 30 yrs. The boat got sold so it’s hopefully still out there somewhere. So I love watching you two learn to sail…it’s a great thing. Enjoy!!

    • Thanks for the kind words Rick! It’s amazing how long travel takes when you really slow down and enjoy it.

  • Brenda King

    Outstanding video…so much fun to be there with you two. We learned to sail in Marina de Rey ..boating has changed our life. You build such a great partnership with your mate, trusting in each other skills and relying on each other when the water gets tough. 12 years on the water with my Hubbie and we are so excited to retire this year, go PT on the boat and pt in the big ass RV. Life is good but so short…keep living your dreams!!

  • Nikki B.

    So happy for you guys.

  • illya

    Thanks for the video 🙂 What great guests to have, both seem like a lot of fun. For an on the cheap camera angle of Curiosity going by you could make a Styrofoam pad and put a camera on it for some drive by distant shots. you sold the flyer right if i’m remembering right, which i quite often don’t. You guys do the very best camera work around it seems. Of course for a more expensive option an RC boat with weed whacker engine would be much more fun. I used to have a few of them and they were a blast to run. I don’t feel you’re putting the cart before the horse, I feel you’re doing things your way and it may be different but that how new discoveries are made, That’s how new ideas are formed, following some by the book been there done that theme is not the way everything should be done. You guys are awesome in all the ways you do things, inspirational, don’t ever change because of the geniuses out there advising you or challenging your way of doing things. It’s your constitutional right to do things as you see fit. Keep up the great work, i found your site looking for solar advice, but what i found was a whole new attitude and breath of fresh air in this stuffy and confined world. We are born new daily just as the earth is with new land formed by lava, you remind us of this with your optimistic presence.

    Thanks, illya

  • Jannie

    Hi, i’ve stumbled on your site by chance, as it so happens i’ve been following the ‘tahina expedition’ that was a five year circumnavigation but finished now. So i’ll start follow you now. I want to use ‘vessel finder’ but needs your ais imo/mmsi nrs please. I am from South-Africa so English not first language so bear mistakes pls. Favourable wind and following seas.

  • Heedong Choi

    Jason and Nikki,

    Aloha! My wife and I are big fans. Was up in Seward, Alaska recently and ran into Jesse and Samantha Osborn who run Seven Seas Sailing Logistics LLC. They charter a sailboat “Extraordinary,” Jesse is a sailor and Samantha is a bush-pilot. Since your Alaska RV adventure was a big hit thought you might want to do an Alaskan Sail odyssey with Jesse and Samantha’s help. Please check them out and blog

  • Gina

    What about your fur kids?

    • Rick

      Agree, what did the cats do?

  • Christopher E

    You’re really hitting your stride! Great vid! Like the brief sailing report on your post. Keep those coming. And congrats on your first catch! Hope the kitties got a treat. Your product & people recommendations are really valuable.

    I know the chief at Biscayne NP. Best way to visit is by boat. Remember to share some national park adventures between your sailing lessons!

  • Leslie Sharpe

    I love following your adventures, whether on land or at sea. As someone who suffers from motion sickness, I’m glad that doesn’t appear to be a constant problem for Jason while at sea. Do you take anything for prevention?

  • Debi

    Thanks for taking the time to make these outstanding videos..and Jason, thanks so very much for doing the editing..your work is greatly appreciated. I can never watch only one time…I try to limit it to…nah..I watch over and over. The picture quality..color…composition…and subject are outstanding. You two set the standard for adventure really.
    I am so excited for you two..keeping including me and all of your followers…we love your sharing.

  • Jerry

    Another really great video!

  • Lucille Hjort

    I would think that to buy your sail boat first, is best. Cleaning it, loading it with your things and installing your add-ons all helped you to become familiar with your boat and to know it as one does when living in a new home an thereby making it your own. I also would think, just as you did, that to figure out which one to buy took a lot of research much the same as we do when we buy a new car and then we have to get to know that one, too, as different makes of cars have their operating controls in different places, etc. It makes sense to me to buy the boat first and then take sailing lessons as learning by doing is much better for me than trying to learn from pictures and imagining you are right there or with descriptions only. I agree with you. Just as in learning to drive a car, we learn by doing, that is how I would imagine it would be with a sail boat, too. Practice makes perfect and while reading and studying, you can go to the area and look at your boat and see your your own operational devices and get to know their names. I am proud of you. You are much braver than I am as I have an immense fear of water, and I do not swim, but I love it and respect it and love to ride on boats on it, with a life jacket on though on the open sea. You not only have to know how to operate your boat and those great big sails, but you have to be aware of the weather and as you say, obstructions under the water. Again, I am very proud of you. You are doing a fine and orderly job of learning to live on and to care for and to operate your dream boat. Wishing you a lot of fun along with the stresses and hard work of sailing on open water to destinations that you have never been to before. Good luck and have fun. You both look very physically fit, but a little on the too slim side I think for the hard work you may have on the open seas, but maybe if you are fortunate to plan ahead weather wise and make it to a safe harbor, your work will not be as difficult or stressful that it otherwise could be. Sending you my wishes for good luck and love to you and thanks for sharing you adventures with us.

    • It’s true, learning by doing is much simpler to take it all in and begin to understand. The caveat to that is if we would have done the classes first we could have likely saved on our insurance and not had the “captain on board” restriction.

  • cindy

    WOW!!! You guys look like naturals!!! Especially the beard Jason!!! The barnacle look-lol… Morro Bay Ca. clad…You are making this look much to easy watch out of you will fill the sea with newbies!!! Enjoy the journey.

    • Have fun in Morro Bay, we do hope to sail over there one of these days 🙂

  • -cb.

    looking forward to the person/critter overboard drills….very important skill for you to master!
    where are your pfd’s?

    • Yes, the MOB drill is quite the task…and we will need to practice a lot!

  • David Thatcher

    My wife Nancy and I just love to watch the Two of you with each of your adventures. Keep the vedios coming.

    • Thank you so much David, glad to have you guys on board with us.

  • Dave Tousseau

    Have always wanted to sail. Grew up in Southern CA and was always around the water. Went in the Navy after high school for 20 yrs and was around the water, now live in the Midwest, no ocean around here. Going fulltime in our motorhome in Jan so will be able to travel. Guess I can get my sailing fix through you guys, this video did put a smile on my face. Thanks for the videos.

    • Safe travels Dave, we wouldn’t change anything about our motorhome trips…what a life 🙂

  • Hi,

    Two quick questions. When you are on the hook or at dock does your boat have ac? Also you mentioned that your instructor cruised for 7 years in a 23ft boat. Do you know what kind of boat and does she have a blog or website? I guess that’s three questions! Really enjoying your blog. Good luck with the classes. I often wonder how I filled my time before I knew how to sail.

    • Dominic,
      Our instructor does not have a blog but she does have a website called BikiniSailing
      We do have A/C and we’re planning to run it off our lithium batteries and solar array, so stay tuned.

  • Nancy Fernandez

    Another great day on the boat. Love every video. Please use those gloves. See you next time 🙂

  • Leslie

    I’m really enjoying watching you guys. Thanks for including me in your journey. ?
    Looks like you’re doing an awesome job, and great teamwork!

    • Glad to have you on board Leslie and thanks for the thumbs up!

  • I’m not sure Biscayne Bay can be considered “wilderness,” but I do appreciate your enthusiasm.

    • HA! Although it was pretty dead during the week, I think we only saw a few boats the entire trip!

  • Jon

    If you don’t want to answer the question no worries, I looked at the blue water sailing school rates and saw they could be quite expensive. I take it a lot of that cost relates to they use their own boat. since you guys have a boat did that decrease to the total amount by a large percent I Hope It did ? I would video the courses just for your enjoyment as I would bet information overload occurs quickly !! And GIRL wear those Gloves !!!!!

    • John Anderson

      I did BWSS a number of years ago (like 10) and I do know they have a private lesson rate. If memory serves, the private lesson rate is actually a touch higher because while the regular rate includes the cost of the boat, it also assumes they’ll have 6 students sharing the cost of the boat and the captain.

      • The class was actually slightly less expensive than their standard…but not by much. I’ll try to find my receipt and get back with you.

  • Troy

    Aside from saving your skin, sailing gloves might also protect your finger joints from RSI, all that grabbing of lines, anchor chains, and levers takes a toll that results in arthritis eventually.

    I learned this the hard way when I was opening & closing a rental cargo truck’s roll-up door a lot — the sharp metal of the hand grip repeatedly “cut” into my finger joints, making them rather numb and stiff for a couple of years (they’re back to normal now).

    • Thanks Troy, we are trying to remember to wear them 🙂

  • William

    You two are very entertaining to watch! Please keep making great videos. Ignore the haters; I am a military pilot and saw the same attitude from old salty flight instructors who couldn’t (or wouldn’t) allow themselves to believe that women were tough enough to be fighter pilots. Well, the jokes on them, because as it turns out, in many cases, the women tended to be the best in the class! Why? it’s because the women listened to instructions and didn’t have anything to prove. You two are obviously very green (for now), but have the right attitudes and are not too prideful to accept instruction from the experts. Fair winds, and best of luck as you continue your adventures!
    (Also, I hope to see Nikki or Jason filleting the next catch)

    • Thanks for the words of encouragement William…and yes we’ll be filleting many times in the future, I hope 🙂

  • Love your videos! We’re FT RVers and will probably never get the chance to FT on the water, but we can live vicariously thru the two of you.
    Can’t wait for the next installment.

  • Capt Chef Mark

    Sorry to say but it’s not a map it’s a chart.

  • Scott

    Sorry to pick nits here, but the Scarface house is sort of on the other side of the country; in Santa Barbara.

    It’s not really important. Just thought you’d like to know.


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