Sailing Vagabonds: A Life of Travel, Incrementally Achieved

555886_472392866142920_324682394_nMy friend Anne is on a boat, and has been for the last year. She and her partner Colin—and their dog, Maye—left the comforts of living on land for a life on the sea, going where the wind takes them (mainly, south) and enjoying time on the water while still working real, full-time jobs. I asked Anne how she decided to make the jump to a full-time vagabond, and what she, Colin, and Maye do to keep themselves happy in their lifestyle.

I just celebrated St Patrick’s day in Savannah, GA. I live on a 32′ wooden sailboat and it took three full days of sailing to get here in time for it. When I was on the street, waiting for the 4 hour parade to start in the warm Georgian sun, I met kindred from, of all places, my home state of New Hampshire.

As it happens normally, my lifestyle comes up in conversation. It’s my work that allows me to live this way, and people are always surprised when I’m not a trust fund kid or something. Nope, I work for this.

“I wish I could live like that,” they say. Do you? Do you really? Well boy howdy, you can be free, free, free. A little bit of escape velocity, and you’re on your way.

How I Went Virtual

I lost my job in fall of 2009. I had already been looking for jobs and was unhappy there, and was toying with the idea of being a professional organizer. You know, work for good money and thankful clients spiffing up their offices and basements. I still looked for a traditional job at first, because I did want to do copywriting and there were a few jobs available. I was also applying for unemployment and had to keep up the look that I was really interested in getting a new job.

Then the floor fell out. Because of something my previous employer said on the phone with the Bureau of Labor, I was denied my claim. Rather than keep on fighting that, I had rent to pay, so I ran with it. I took the one client I had, saw that she wanted me for my admin skills foremost and figured that’s what the world wanted me to do. I never imagined that it could be all virtual, and I hadn’t really even heard of virtual admins before.

However, there was news everywhere that businesses were growing but couldn’t hire people full time. Surely I could find these people and pick up 10 hours here, 5 hours there, and so on.

I didn’t get more clients right away, but at least what I had almost paid my rent.

549205_485361414846065_1227865476_nHow I Grew

My next clients came from my job at Bard Coffee, a local shop known for its smarty pants baristas and alternative brew methods. By being in a public place that has savvy customers and seeing so many different faces everyday, the right people heard eventually that I did admin work. BAM. I started working for Donald Verger the photographer and Chris Brogan, a prolific writer and speaker.

And it’s gone on from there. I’m the go-to gal at an online triathlete community for administrative help, I do some press releases and strategizing for an OSHA trainer in New Hampshire, I write web copy for a branding firm in North Carolina, I plan to freelance write for a couple of magazines who have asked me to tell my sailing stories, and I look forward to a day when it all lines up and the travel IS the job.

How I Came to Travel

Toe dipping. I always tell people self employment is like this: Day 1 through day, oh I don’t know, 60- you get up everyday and can’t believe that you’re allowed to work in your pajamas. So you do, and it’s fun and comfortable and you eat a lot of grilled cheese.

Then you start going out to cafes and wearing pants more often, because you crave contact (and possibly, faster internet). Then it radiates out—the possibilities become endless. You take a train trip to NYC to see friends and work the whole time, you go to Seattle to feel spring time in March and bring your computer along, keeping people happy and having good coffee the whole while. Then, if you’re really nutty like me, you live aboard a boat and make travel your life.

425615_445915955457278_1557238145_nBut It’s Not All About the Job

The biggest mistake people make is assuming they need to make more money or that they’ll make more money tomorrow or the next day. The only thing you can really control is your expenses.

Live simply. Save money. Barter. That’s REALLY how I’m doing all of this. I’ve cut so many of my expenses that I don’t need to work as much. Eliminate your debt, only own a car if you really truly need one, and take a good hard look at your “goin’ out” money. If you find that you’d rather, truly in your heart, stop working for the weekend and start taking workweek time and turning into adventure time, it’s the limitation of your expenses that will set you free.

Anne and Colin are loving the simple life they lead, and you can keep up with their adventures by reading their blog From Pine To Palm, liking the Mimi Rose on Facebook, or following Anne on Twitter @FromPineToPalm.

Anne is also for hire as a Virtual Assistant! Check out her credentials at

*All Photos courtesy Anne Bryant/SV Mimi Rose

Chris Cavallari

About Chris Cavallari

Chris is a longtime digital content producer based in Maine. Since 1999, he has been an early adopter and active participant in blogging, podcasting, and social media, and has been guiding small and mid-sized businesses in leveraging video, social media, and digital publishing to the fullest. With an avid love of travel and the outdoors, Chris started in 2009 to give him a platform to showcase his outdoors and travel adventures, and to help educate others in doing the same.