LAHOWIND » Just you, me, + the dog.

We quit our jobs to sail the caribbean! And so the adventure begins…

We are letting our dreams set sail.  Both literally and figuratively.

We’re planning to cruise south to the Bahamas + Caribbean, island hopping along the way for the next year (or so).  Don’t worry, Oliver is coming too!

Jereme and I officially put in our notice at work earlier this week.  I suppose this whole thing is legit now.  😉

Let me just tell ya, it feels pretty.freaking.amazing.  We’ve decided to wake up and live.  While we’re young.

Awhile back, a spark ignited for us.  We decided to give up staring at computer screens for 9 hours a day, 5 days a week at our corporate jobs, and instead experience a little more while we can.  Why wait until we’re retired to live it up?

Basically, we’re simplifying. We’re moving onto our 37ft. sailboat with way less “stuff” than we’re accustomed to.  And traveling by boat from island to island in the (eastern) Caribbean — think St. Lucia, Anguilla, USVI’s, Martinique, etc. etc.  And there is not a morsel of my being that suspects we will ever regret this decision.

Live, love, travel, and don’t be sorry, right?  We are enjoying life NOW, since as they say, “this is not a rehearsal.”

^^totally overusing this photo (hello! blog banner, christmas card, etc.) but I don’t care — I LOVE it!^^

In the past month or two, we’ve pretty much sold off nearly all of our worldy posessions. We’ve literally whittled down an entire 3-bedroom, 2-bath home into one small walk-in closet.  Don’t even ask me how that was possible, but we did it.  We’ve also rented out our house and have been living three blocks over at Jereme’s parents’ second home since November (give us a shout if you need our new addy).  And we’ve been working our little butts off to save as much $ as we can.

And for those of you who may think we’ve lost our minds (and you certainly could be right), this isn’t something we decided on a whim.  This dream is three-plus years in the making.

We’ve been researching, planning, saving, working, and doing everything in our being to make this a reality.  We weren’t ever sure our dream would come true, so we’ve stayed pretty tight-lipped about it until now. More than anything, we didn’t want our friends and family to worry or doubt us while we figured it all out.  And now that we’ve offiically let the cat out of the bag (where did that saying come from btw?), everyone has been amazingly supportive.

But believe me, there is a TON that has gone into making this a reality. And it’s certainly not as easy as just buying a boat and throwing up the sails. If it were, we would have set sail years ago. You wouldn’t even believe everything that has gone into making this dream come true…

  • First we had to learn to sail. Jereme took the ASA courses, and I’m constantly learning from him. And then there’s anchoring and docking, and lots of other fun stuff. The basics really.  And sailing is the easy part of this whole adventure.
  • Then we had to buy a boat. That only took two years of searching, learning the market, talking about buying a boat, calculating what it would cost, searching a ton more, talking about it lots more, and then we finally bit the bullet. Back in March, we found our perfect boat.
  • Over the past year, Jereme has pretty much become a certified boat mechanic and electrician.  For you non-sailors, you can’t even begin to imagine the intricate systems he’s had to learn and maintain.
  • He’s also a bonafide handyman. But we already knew that. Installing things like our custom water tank, replumbing the head from top to bottom, (soon to be) installing solar panels, and successfully completing an exhausting list of boat projects to get the boat in ship shape for our big “cruise.”
  • Know anything about reading nautical charts?  Neither did we!  But we’re learning. Slowly.
  • How about all the different islands/countries in the bahamas, caribbean, and south america (and beyond) and each of their rules and regulations on importing (i.e. traveling with) a pet. I’ve spent countless hours making sure we have our i’s dotted and t’s crossed when it comes to traveling with Oliver. There is no way in hell I will let anything happen to him in one of these places or have him quarantined (which is why we will be selectively skipping certain countries because they require pet quarantines of anywhere from 2 weeks to 6 months – not happening).
  • How about finances? How the heck can we just quit our jobs and sail off into the sunset without a steady paycheck coming in the door. Well, we’ve been working on that part too for awhile now. Luckily, we’re DINKS (dual income, no kids — thanks Aubri for the acronym). We have ZERO debt (other than the mortgage – and we’ve got that covered with renters) and have saved our little butts off so that we can comfortably cruise for at least a year, but hopefully longer.

And that’s just scratching the surface!

We know that we still have a ton to learn and figure out along the way. There is no finite plan carved in stone. But that’s the beauty of it.

We have no agenda, no schedule, no rules.  We’re ready to see new places, meet new faces, and learn a ton along the way, while soaking up every single second of our little adventure.

And we’d love for anyone to join us along the way. Wanna hop a flight to some exotic island in the Caribbean for a week or two?  Visitors are always welcome aboard s/v LAHO. Give us a shout anytime!

>>Thanks for visiting LAHOWIND sailing blog! We’d love for you to get to know us and follow our story as we attempt to navigate a whole new world of sailing.

Michelle SauerDecember 6, 2013 - 12:31 am

How incredible Kim! I can’t wait to live vicariously through you! It will be awesome to follow your journey!

Melissa R.December 6, 2013 - 1:43 am

I don’t know you, but found your blog through your sister’s blog. Just wanted to say I think what you are doing is INCREDIBLE and I wish you safe travels and happy adventures!

Anthony M.December 6, 2013 - 4:13 am

Congrats! Don’t know you, but your story sounds amazing and inspiring to us all.. We wish you all safe travels and loads of fun.. Love it up DINKS! I’m jealous. 😉

JackieDecember 6, 2013 - 2:09 pm

Words cannot express how much I LOVE LOVE LOVE this post!! I could have written this post myself…years of planning…renting the house…cruising with a dog…learning along the way…wow! Can’t wait to hear about it all! Although I’m hoping you can eek out more than a year of cruising so we can meet up somewhere in the Carib! Can’t wait to read about your adventure!! Cheers to you guys! (wow, that’s a lot of !’s…sorry, I’m just SO excited for you ;))

Mark and Cindy - s/v Cream PuffDecember 6, 2013 - 8:55 pm

This is such a cool post!

CONGRATULATIONS on being unemployed!!!!!

We wish you nothing but fun in the sun, fair winds and calm seas.

See you “out there” sometime soon.

Mark and Cindy
s/v Cream Puff

Kevin (SailFarLiveFree)December 9, 2013 - 4:12 pm

I know you know this already, but the “we quit our jobs” post is a total game changer. It’s all real now and you’re doing it the right way. Can’t wait to follow along on the adventure! Hopefully you’re also planning to document the experience through your Instagram account too.

LahoWindDecember 9, 2013 - 11:47 pm

Thanks SO much everyone!!! We are VERY excited to begin this new chapter now that we’ve made it “official” so to speak. We hope you all will follow our journey. :) -Kim

[…] awesome love and support we received from this announcement about our cruising plans knocked my socks off.  Ya’ll are amazing! Thank you thank you thank […]

Taryn Heaps YanceyDecember 11, 2013 - 2:21 am

Wow! This is Awesome! Good luck, stay safe & enjoy the beautiful journey your about to embark on! :-)

Marcus NethertonDecember 11, 2013 - 5:53 am

Congratulations YOU TWO!!! That’s the way to do it, take the leap to full time cruising. We have been on our E37 for two years preparing our boat, our finances and ourselves for our own departure. I can say living on a boat and rebuilding it at the same time is like remodeling the same room your living on. I wish you all the best of times and luck on your adventures.

LahoWindDecember 11, 2013 - 1:16 pm

Thanks Marcus!! :) We are very excited! Let us know when you start cruising. And btw, I cannot even imagine what living on our boat would have felt like when we were replumbing the head. I’m not sure I would’ve survived. lol. -Kim

[…] this time in our lives while we have the ability and means to do so.  And now that we have “officially” confirmed our plans to set sail in 2014, we can chat a little more about what all we’ve been up to over the past few months to make […]

MarlenaJanuary 28, 2014 - 1:55 pm

I am so thrilled for your adventure and cannot wait to follow along electronically. I’ve got a few food/bar/beach recs for St. Lucia, Anguilla, Turks + Caicos, and St. Barths so let me know when you are ready to set sail! Bon Voyage!

LAHOWINDJanuary 28, 2014 - 2:44 pm

Thanks so much Marlena!!! :) I definitely will take you up on those recs! Any good tips you can send our way, would be super appreciated. xo -Kim

[…] knows what’s up! This is what our little adventure is all about..taking the time now, while we can, to enjoy […]

Jerry cAugust 18, 2014 - 11:28 pm

Ok now that it’s been awhile maybe ya could help us all with a guide or shortcut to do the same thing. Pretty much for me it’s how to navigate the sailboat in open water, what routes and dates to follow and where to start. I know you birth went through this and just wanted to ask ya “where to start?” My main concern is safe travels and heading in the right direction on correct headings.

God bless

[…] been such a good little traveler, soaking up lots of new experiences and loving every minute of this little adventure with […]

Kerri GardnerOctober 1, 2014 - 4:41 pm

wow, you are exactly what we need to read. Our dream is to quite suburban life with kids (3) ages by then 17,15,and 12 and hit the RV road with a new truck to boot. We have already planned our adventurous itinerary courteous of my awesome hubby. We plan on a years adventures travels and vloging as well. I will learn quite a bit from you both. I encourage you to never go back to corporate and to have kids if you wish and raise them on the boat or where ever. Have a different life than in the typical box. Great job and so happy for you!!! I look forward to reading more :)

Jason McMillanOctober 1, 2014 - 10:56 pm

Congrats on your journey. My wife and I have been planning doing the same thing. We are still hunting and researching boats but haven’t found right one yet. We plan to leave September 2016 heading out through Chicago. We hope to see you in passing and share some stories

[…] December, I wrote about our big plans to “let our dreams set sail.” This was way back when we were still working, planning, but all along dead set on making our dream […]

federico LandaNovember 26, 2014 - 6:48 pm


Just looking to do the same one day… At least I started with the boat. I already have a Beneteu Oceanis 40. My idea is to spend one year in the Caribbean.

Do you have any guide that you suggest to me?
Average how much money I will need to do the caribean ??

I am working in Aruba Island and living onboard in order to obtain experience as a sailor and as a handyman in order to do my own maintenance and reparation on board.

If you pass by for Aruba my phone +297 5936342

Thank you in advance



RockDecember 30, 2014 - 3:07 am

I came across your blog 12.29.14…very interested in following and learning from your experiences…I have one friend taking sailing lessons in Charleston, SC and another living on a 40.6 Atlantic Power Cruiser in North Myrtle Beach, SC. Safe Sailing!

Jeff ClementsJanuary 13, 2015 - 2:58 am

Hi I just came across your blog. I am in route from California to Florida where I will purchase a sailboat and join you in the Caribbean. I will save your site and see how y’all are doing. Smooth sailing.

Laurie McCauleyApril 21, 2015 - 9:50 pm

I just started reading your blog and we are in the planning stage of our adventure. Can’t wait to read about your travels.

Juan Carlos GomezJuly 7, 2015 - 7:31 pm

My family and I are also planning such adventure, My wife is very scare. I am also have been learning the skills of a sailor.
Hopefully, my wife can trust me .

LouiseOctober 5, 2015 - 6:01 am

How inspiring ! My husband and I just returned from a three week sailing trip in Greece and considering a lifestyle of sailing for three months and wondering how to work at oh s the logistics of keeping our business running while we travel .
How gas tour trip being going? Are you still at sea? Would live to hear more
Any regrets ?

wayne junikerOctober 11, 2015 - 4:22 pm

Tks im leaving out this January to start my adventure. Happy sailing and share the love.

QueenAugust 26, 2016 - 4:15 am

I Have Leaving soon sailing To The Bahamas. I Think You All Are Courageous. Enjoy Yourselves
Wishing You All Safe Travels.