Cheeky Monkey is Seeking Adventurous Crew!

in Life at Sea / Sailing the World

Announcement: Cheeky Monkey is sailing across the Pacific Ocean!


We are looking for crew!

S/V Cheeky Monkey is about to embark on the ultimate sailing adventure from the Caribbean to Panama to the Galapagos to the South Pacific islands and we are seeking the right crew to join us on this adventure!

If you’re a Turf to Surf Newsletter subscriber, you may remember me recently writing that “I’d like to slow down in 2016 and look around more” – well, that outlook lasted a whole month before we decided we’d had enough pause and, instead of spending a year in the Caribbean on Cheeky Monkey, we’re heading towards the South Pacific instead! (By the way, if you haven’t yet subscribed to my monthly newsletter, you can do so here at Turf to Surf’s Subscription Page by entering your email address.)

If you’re interested in crewing for us and want to find out more about us (Tasha & Ryan), the crew we’ve had on board so far, and the kinds of adventures we’re out chasing, catch up on our story by watching our YouTube Channel, Chase the Story:


So, let’s get down to it — are you the next crew member we’re looking for to join the party on Cheeky Monkey?

Have a look at the list of qualities we’re looking for below, and let us know if you’re serious about joining us on this adventure!

Essential Qualities

  • Adventurous
  • Good sense of humor
  • Open-minded
  • Young at heart
  • Fun
  • Sporty
  • Friendly
  • Easy-going
  • Good personal hygiene
  • Not allergic to or afraid of cats

Extra Qualities

  • YouTube creator / Videography experience
  • Creative abilities
  • Social Media / PR expertise
  • Sailing experience
  • Good at fixing things
  • Good chef
  • Good at water sports (and are willing to teach us some things)

Application Requirements

  • Please submit the following 2 items by email: (1) Answer the question “Why do you want to be a part of this adventure?” in the form of either a 2-minute personal video (include link to video) or a 300-word personal written statement. And feel free to be creative with your answer and how you choose to answer it either in video or in words. (2) Resume / C.V. – we ask for this because we want to get an idea of your professional experience and/or adventuring experience.
  • Application Deadline: March 23rd, 2016
  • Email submissions to


  • How much will it cost? You only need to cover the cost of your flights and any personal necessities you care to purchase in ports. Board, food, booze and adventures covered by us.
  • How long will I be crewing for? No adventure of this magnitude can be achieved on a two-week vacation. We are looking for crew who can commit to a crossing or two.

Crew Expectations

  • All crew share equally in the duties on board Cheeky Monkey, including keeping watch, cleaning, cooking, maintaining the boat, repairs, provisioning runs and cocktail making.
  • We expect crew to contribute to the creative process on board, using whatever skills they have or are willing to learn – i.e. video-making, posting on social media, photography, website building, etc.
  • We expect crew to have fun and enjoy the adventure!

Note from Tasha & Ryan

We look forward to hearing from you and getting to know more of your story! We’ve had great experiences so far with crew on board who embody all the qualities we’ve listed above. So let us know if you’re the missing link in this next great adventure — we’d love to meet you! Or if you know someone who would love to sail with us on Cheeky Monkey, share this opportunity with them!


Tasha & Ryan

0 Comments... Be the first to comment
  • Jessica March 7, 2016, 9:44 am

    Wow, that is a HUGE change in plans! You know Matt and I would apply in a heart beat if we wren’t so determined to get the new boat in the water this summer/fall. Are you planning to make it all the way to NZ by the fall or will you leave it in the islands for hurricane season? Can’t wait to keep following along with your adventures. 🙂
    Jessica recently posted…One Step Forward, Two Steps BackMy Profile

    • Ellis April 24, 2016, 2:45 pm

      Sent you an email in case there was a change in plans, in which case I’ll app sine I came across the board and your post today. I’d also be interested if you know of any other vessels heading Caribbean to Pacific, my end destination goal is currently NZ by December 2017. I’m in Belize now, and unless I find a boat first, I may shift down to Rio Dulce in late May. Thanks!
      Ellis recently posted…Sell Art Online: More than 300 places to sellMy Profile

      • Tasha April 25, 2016, 1:28 am

        Hi Ellis,
        Thanks for your message — our crew spots are all full for this trip, but keep in touch as we’ll have more openings in the future 🙂

  • Michael Carter March 7, 2016, 12:52 pm

    I would love to go with you, but I am 73 and I don’t think you would want a old dude like me.

  • Ryan March 8, 2016, 4:49 pm

    I just stumbled across you blog and wow, what an amazing opportunity! As a sailor, traveler, adventurer, and aspiring photo/videographer I think I’d be a great fit to join the adventure! I’m very excited to put together my info for you to consider, keep an eye out for it!

    • Tasha March 9, 2016, 3:24 pm

      I look forward to getting your application!

      • Peter March 10, 2016, 9:10 am

        Expect one from me as well!

        • Tasha March 10, 2016, 2:00 pm

          I look forward to reading / watching it!

  • Mandy Rosello March 9, 2016, 7:23 pm

    We absolutely LOVE what you guys are doing! We’d love to apply but are working towards purchasing an Orana in September. Hope to meet up with you guys at sea in the next year or two! We’re bringing our furbaby on board too, so keep posting how the kitties are doing at sea!!

    • Tasha March 10, 2016, 1:58 pm

      Wow, how exciting! The Orana is a great boat – keep in touch and hopefully we’ll cross paths out there!

  • Robert Trautman March 10, 2016, 12:24 am

    Hi Guys,

    I’d love to join you on a adventure!!!
    Until recently I was the proud owner of a 38ft Pout Catamaran, which I sailed single handed around the South African coast. I work as a navigation officer on Gas Tankers. I love scuba diving (have qualifications), spear fishing and just overall being crazy…

    I’ve done basically the whole world on ships.

    Let me know.


    • Tasha March 10, 2016, 1:59 pm

      Hi Robert,
      I look forward to receiving your application. The deadline is March 23rd, so you’d better get cracking!

  • Lucinda March 10, 2016, 3:09 am

    Wow I’ve always been looking to travel abroad through au pairing but haven’t had a chance due to certain circumstances… think it’s time for my gap year 5 years later 😀

  • Kait March 10, 2016, 6:19 am

    This sounds amazing ! Where can I send my application too?

  • Tom March 10, 2016, 9:01 pm

    Hi, shame I’m set for this season or I’d have to apply! If you call in to Niue on your way through the South Pacific would be up for a beer and I can recommend some incredible places to visit on the island.

    • Tasha March 12, 2016, 9:53 am

      That would be amazing – I’ll keep it in mind!

  • Emmauel March 11, 2016, 4:50 am

    Hi iam interested in joining the crew

  • Raul Lucas March 11, 2016, 10:23 pm

    A opportunity of a lifetime.. I would love to be part of your crew, my wife and I are in the planning of buying a 40 Nautitech in the next 3 years.. We are in Fort Lauderdale FL and are dreaming of sailing the world and living aboard.. Was looking into sailing school for my Bday this summer but I’m a firm believer experience is the best teacher

    I would love for the opportunity make the Pacific crossing with the Cheeky Monkey crew.. Found your channel 2 weeks ago and binge watched all of your episodes.. Lol you guys are living our dreams 🙌🏾⛵️⚓️🏝

    I am a United States Marine vet.. I have crossed the Pacific Ocean from San Diego California to the Seychelles islands and the Middle East 3 times goin west.. and 3 times back east to come home to the west coast of California .. Marines motto is to Improvise Adapt and Overcome.. I believe I would be a great addition to you crew

    • Raul Lucas March 12, 2016, 12:58 am

      I am also a Golden Shellback ⚓️

    • Tasha March 12, 2016, 9:55 am

      Hey Raul, congratulations on working toward your dream and thanks for watching! We look forward to reviewing your application!

  • Jan Ferreira March 12, 2016, 10:13 am

    Wow wow wow! I’ve sold my house and quit my desk job to go on an open ended adventure exploring the world and today (on my 29th birthday) this cape town boytjie got sent your post by a friend. Best bday discovery ever! Expect my video soon soon! Peace. Jan

    • Tasha March 12, 2016, 12:46 pm

      Looking forward to watching it!

  • Michael March 12, 2016, 10:29 am

    Wow! this is such an amazing opportunity! I cannot wait to submit my application!

    • Tasha March 12, 2016, 12:46 pm

      I look forward to reviewing your application!

  • Douglas March 13, 2016, 9:22 am

    Just putting together my application! Look forward to your feedback, positive or otherwise!

    My application will be in your Inbox before the deadline!

    Fair Winds!

    • Tasha March 13, 2016, 11:51 am

      I look forward to reviewing it!

  • Catherine March 13, 2016, 10:48 am

    I miss living at sea, worked for Rccl would love to be back at sea, can’t imagine leaving my daughter behind unless you guys wouldn’t mind having a 3 year old on board.

  • Sam Satlker March 13, 2016, 3:15 pm

    This would be great!
    I dreamt of sailing the world last night.
    For the years this has been a big topic of interest to me.
    I have not done much sailing but feel a big draw towards that level of world exploration and study.

    I will work on the application immediately.
    Sam Stalker

  • Natassja March 14, 2016, 7:00 am

    This could NOT have come at a better time. I am so ready and will be submitting my credentials to you guys as soon as I get out the office !!! Can you tell how ready I am ??? #WatchThisSpace

  • Linda March 14, 2016, 7:16 pm

    Hi guys! You’re amazing! This is like… my dream! But still I didn’t get it: how long will the adventure last at least?

  • Stacey March 17, 2016, 5:31 pm

    Hi Tasha,

    When do you need your crew for?


    • Tasha March 20, 2016, 8:37 pm

      It depends where the crew decide to get on. We’re leaving St. Maarten at the end of this week (end of March). We’ll be in Colombia a week after that, then Panama ready to leave by second week of April. The trip from Panama to Galapagos to the South Pacific will take about 4-5 weeks.

  • Ric March 17, 2016, 8:19 pm

    Not a chance I could qualify, although it looks like a great opportunity. I’m sure you will find just the right person.
    I’m way too ugly to put on video, so that is out. I could help you with your writing though; Of course that’s just my opinion.
    You are doing a pretty damn fine job with all this without my help.
    You might forward some of those lady contestants for when I finally empty my nest and hit the waves myself! Just kidding, I’m planning on going it alone for reasons I can’t go into here. On the other hand, who knows what the future holds?

  • Ettie Hauptman March 19, 2016, 2:02 pm

    Hi Tasah,

    I will be more than happy to join you guys for this adventure. I just sent you the all the applications. Waiting to hear from you. Ettie

    • Tasha March 20, 2016, 8:38 pm

      Great! We’ll look forward to reviewing it!

  • Emily March 20, 2016, 12:25 pm

    This sounds absolutely incredible!!! i would love to do this and will definitely apply! Just 1 question, when are you guys thinking of heading?? Thanks!

    • Tasha March 20, 2016, 8:39 pm

      Leaving the Caribbean March 25th. Leaving Panama around second week of April.

  • Christina March 21, 2016, 8:23 pm

    Expect my application as well! 🙂

  • WIlliam Taudien March 24, 2016, 8:39 pm


    My name is William Taudien. I have a dream of sailing around the world, thought it would be great to go with you guys for a while 🙂

    See my personal video I put together!

    // William

  • Yachtside April 6, 2016, 6:04 pm

    Beautiful trip !

  • Joel April 10, 2016, 11:38 am

    What a great idea. Looking forward to seeing who you selected.
    My wife and I really really really enjoy your videos and now are reading your blog.

  • Jason April 11, 2016, 2:02 am

    The site states your boat is “Hide Away”. Is “Cheeky Monkey” someone else’s boat you’ll be sailing on?

    • Tasha April 22, 2016, 4:15 pm

      Cheeky Monkey is our new boat and Hideaway is our old boat, which we’ve just sold 🙂

  • Mycophile May 7, 2016, 3:48 pm

    Wish I could unplug and join you guys; but for now being inspired by you will have to do. Do let us know about your experience with FP, noticed you guys had some issues but don’t go into much detail.
    Clear sailing!

  • Daniel McGarrigle May 31, 2016, 6:04 pm

    My name is Danny. I live in New York City. I have been sailing for 8 years. I currently work in television production. I mainly do reality television and have filmed shows like “Party Down South” “Beachfront Bargain Hunt” and NBC’s “The Voice”. I would love to be considered for this position, if your former applicant doesn’t work out.

    • Tasha June 5, 2016, 2:16 pm

      Hi Daniel! Great to hear from you — we’ve got a full crew for the Pacific crossing but keep us in mind for future journeys! We’ll be recruiting again, I’m sure!


  • Ed June 15, 2016, 11:05 pm

    Hey guys,I just started watching your videos. Love what you guys are doing and hope to do it myself sometime. So cool! I wish I could have made the deadline to put in an application. Let me know next time you are looking for crew members and need a bartender!

    • Tasha June 18, 2016, 9:32 am

      Hey Ed,

      So glad you found us! Keep up with our social media and this blog for announcements of future crew opportunities!


  • Jim and Peggy Larson December 2, 2016, 12:29 pm

    We love watching your video on YouTube! Can’t wait for more!

    Be safe and have a great day!

    Jim and Peggy Larson
    Manitowoc, WIsconsin

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