Go Sea the World

Begin, Begin: How We Started Sailing (and Why Discomfort Changes Everything)

In this episode of Go Sea the World, Aubrey O’Hare and Jordan share how they got started living an unconventional life at sea—and why taking the first step matters more than having a perfect plan.

Recording from a 51-foot sailboat in Mexico, they talk about choosing freedom over comfort, overcoming fear, and how discomfort often leads to growth and inspiration. From sailing for the first time to swimming with dolphins, navigating fear, and preparing for a passage toward Panama, this episode explores what it really takes to build a life outside the traditional path.

Topics include sailing around the world, personal growth, adventure travel, living aboard a sailboat, women in sailing, leadership, fear, and staying inspired while choosing an unconventional life.

Behind the Collab: Sailing Doodles, Dating Myths & YouTube Reality

In this episode of Go Sea the World, Aubrey O’Hare and Jordan share what it was really like sailing in Greece with Sailing Doodles—from collaborating as creators to navigating chemistry, expectations, and the reality of life on YouTube.

We talk candidly about creator burnout, work ethic, thumbnails and algorithms, and what happens when an online connection meets real life. From age gaps and dating myths to sailing YouTube growth and collaboration dynamics, this is an honest, behind-the-scenes conversation about building a life—and a career—at sea.

Filmed during our time sailing the Greek islands, this episode pulls back the curtain on what it’s actually like to collaborate with another major sailing channel while staying true to yourself and your story.

Topics covered:

• Sailing Doodles collaboration in Greece

• Life as a sailing YouTube creator

• Chemistry vs commonality in relationships

• Online dating vs real-world connection

• YouTube thumbnails, algorithms & burnout

• Sailing, travel, and life at sea

Subscribe to Go Sea the World for honest conversations about sailing, travel, relationships, motherhood, and choosing an unconventional life on your own terms.

Dating on the Move: Love, Co-Parenting & Life Afloat in Mexico

We’re recording from a 51’ Formosa in Mexico with a squealing baby in the tub and a whole lot happening in a tiny space. In this episode, Aubrey and Jordan talk about what dating looks like when you live on the move—how relationships become pressure cookers at sea, why “normal” timelines don’t exist for travelers, and what it means to protect your peace while still wanting love.

Then the universe drops a full telenovela plotline in our laps: Aubrey accidentally meets Violet’s paternal grandfather in the street… which turns into a sudden, emotional introduction to Violet’s extended Mexican family—tears, laughter, healing, and a whole new perspective.

And just when we think the day couldn’t get wilder? A 3AM “surprise” arrival at the boat sparks a hard boundary conversation, a co-parenting reset, and a surprising moment of hope for what a healthier future could look like—maybe even tandem-sailing around the world.

In this episode:

• Dating abroad vs dating on the move (and why it gets intense fast)

• Protecting your peace without closing your heart

• Meeting family you’ve never met—by total accident

• Co-parenting while traveling

• The dream of “together, but with separate boats/houses”

If you’ve ever loved unconventionally, lived nomadically, or tried to co-parent while building an extraordinary life—this one’s for you.

We Didn’t Plan This: Motherhood, Risk, and Choosing the Wrong Way

We didn’t set out to do this.

What started as a quiet morning at anchor in Zihuatanejo, Mexico turns into a reflection on how quickly life can change—and what happens when you say yes anyway. In this episode, Aubrey and Jordan sit down over coffee aboard a classic pirate ship to talk about the unexpected chain of events that led to three women and a baby preparing to sail the wrong way around the world.

There’s no master plan here. No polished answers. Just honest conversation about motherhood, risk, trust, and the strange clarity that comes when familiar paths fall away. From failed plans and near-misses at sea to the quiet confidence of choosing a different kind of crew, this episode sets the tone for a journey shaped more by instinct than expectation.

Along the way, Aubrey opens up about leadership, fear, and the weight of making decisions that affect everyone on board—while learning that there may not be a “right way” to do something as wild as circumnavigating the globe.

This isn’t a how-to.
It’s a beginning.

And the story is just getting started.

How can YOU complete a SUCCESSFUL boat Flip

Fan Mail! Jake reach out by email and asked us a few really great questions about purchasing a boat for the first time or trying ones hand at buying a boat and selling it for a profit, or what we have been calling a "boat flip". 

Hi, love following your YouTube channel. Your pretty much living the life I want.  My plan is in about 3 years to sell my business and live aboard a sailboat at least half the year. 

My question is how do you find the boats that you flip?  I’ve been casually looking for a boat for several years and I rarely come across a good deal.  Is it mostly knowing people and right place right time or are there websites that I don’t know about! 

I look at boat trader, eBay, Craigslist and even Facebook market place with very little success. 

My other question is how do you manage having multiple boats? 

My concern with buying something now (assuming I could find something) is I live in Montana and can’t be there to take care of most of the time.  Do you have any suggestions or recommendations for me?

A BIG thank you to Jake for his email! 

Questions Answered Part One

Hello, and welcome! This Podcast is geared towards some of my most frequently asked questions by those of you watching Sailing Miss Lone Star on Youtube! If you have any topics or discussions you would like to hear about, send me an email at misslonestaradventure@gmail.com

• “Tell me more about your background” – perhaps when did you start sailing/how did you start sailing/what did you do before you started sailing.
• What is your favourite destination that you’ve travelled to so far?
• What destination is at the top of your bucket list?
• What was your first crossing? / Longest crossing? How did it go?
• How do you prepare for long crossings?
• What are some of your go-to meals for long crossings? Ie. how do you manage meals with limited space & for long time periods offshore?
• What is the biggest lesson you have learned while sailing?
• What is your number 1 tip for new sailors?
• What is the most unexpectedly difficult thing about a sailing lifestyle?
• Where did you get the inspiration to start learning to sail?
• What is your biggest intimidation/fear of the lifestyle you live?
• How long does it usually take you to do a boat flip?
• When you flip a boat, how do you choose where to start?
• What was your goal/ambition when you started out with the sailing lifestyle/your channel?
• How do you decide where to draw the line between what you share on social media and what you keep private? 

How much does FREE actually cost? Buying a boat for a dollar.

In this podcast you will find out where to find your own dollar boat and NOT make the same mistakes that I did. I bought a boat for a buck and refit it myself. Find out what I wish I would have known back then. 

What sailing has taught me about fear

How I became a sailor

Welcome! This is my very first podcast. My name is Aubrey, and I am Youtube personality, single mom, sailor, captain, photographer and former Playboy Playmate. 

Today I give you a little background on how a girl like me found herself on a 29 foot sailboat living on the ocean. In the episodes to come I will give you some insight on what it is like living this lifestyle and how I navigate the hard stuff.

You can find the video version of this Podcast on Vimeo On Demand 

https://vimeo.com/sailingmisslonestar/vod_pages