Truthfully, I wasn’t always confident that my full-time cruising dream would ever become a reality. I was petrified of failure but thirsted for a lifestyle I knew existed outside my orbit. Taken as a whole, the detailed legwork, crucial boating skills and financial commitment necessary for success seemed unsurmountable for a rookie sailor like myself.
Yet here I am meandering along a sensuous curve of sun-drenched sand. The warm surf rushing between my toes tickles like bubbling champagne. Lifting my face skyward to catch the celebratory rays, I reflect on how lucky I am to have landed in paradise and living my dream.
But maybe it was more than just luck. Like many of you, my husband and I fantasized about escaping the daily grind and sailing off into the sunset. I quickly learned that embarking on a major lifestyle change required steadfast devotion, determination and careful planning. Our efforts paid dividends, and before we knew it, we were casting off with our two daughters, ages five and seven.
Our minimalistic 33-foot sailboat Chewbacca carried us safely along the rugged shores of Mexico and Central America, through the historic Panama Canal and into the emerald waters of the Caribbean Sea. A decade of treasured adventures later, we sold our beloved catamaran and returned home to witness our teenagers come of age, complete high school and college, and launch lives of their own.
The nest was empty, and once again it was time to plan our next chapter — this time on our new-to-us 34-foot trawler. Believe it or not, sequestered at home during the pandemic proved advantageous as I had few distractions and plenty of time to prepare for our great escape.
Like planning our previous journey, we focused on five simple steps that have become a proven blueprint for taking our dream to reality:
Have a Realistic Goal
It’s OK to dream big, but make sure your dream is attainable. Any endeavor can feel like folly until organized into realistic bite-sized goals.
Prepare Yourself
Gain the knowledge and skill set you will need to be comfortable piloting your own vessel and feel at home in a new community. You can find many resources to obtain the necessary boating skills including U.S. Coast Guard Auxiliary Courses, one-on-one coaching, boat show seminars and online training.
I read books by experts, joined social media groups and perused forums that highlighted the cruising lifestyle gleaning practical information and advice. In addition, I inhaled information from guidebooks, marine magazines and browsed blogs specific to the cruising grounds we were planning to visit. Just as important, I made friends and contacts within the boating community who provided mentorship and inspiration that further fueled our resolve.
Purchase & Prepare your Boat
Buy the boat to best serve your cruising goals; whether frugal or flamboyant, your vessel must be safe, seaworthy and capable of exploring the areas that interest you. Realize that there is no perfect boat that fits every need. Every boat is a compromise. Your cruising grounds and comfort level may dictate the size and equipment needed on your boat. Don’t let the installation of “just one more piece” of gear derail your dream.
Create a Realistic Budget & Maintain Financial Affairs
Guessing what your new lifestyle might cost is just that, … a guess, but with a little research, you can make a pretty sound and educated approximation. Distinguishing needs from wants is a good foundation for building a realistic budget. In our case this time around, we own a more sophisticated boat, we are 20 years older and our cruising grounds are more expensive than the remote foreign destinations of the past. You’ll need to take all these different variables into consideration when constructing a financial plan.
A cruiser’s nomadic lifestyle can be challenging when it comes to maintaining ongoing financial commitments. Luckily, today’s technology is king. Keeping one’s affairs in order is just one or two keystrokes away. Internet access, paperless billing, online banking, mail forwarding and virtual mailboxes make it feasible to handle the personal and financial side of your wandering lifestyle.
And… GO FOR IT!
Remember that procrastination is the graveyard of dreams.
I hope you are inspired to turn your dream into reality and launch an adventure of your own, drifting off the beaten path, even for just a little while. Another love affair with the sea awaits us, and we look forward to calling ourselves cruisers once again, where last names and past occupations are irrelevant. It makes me smile knowing that soon we will be known simply as Bruce and April, this time hailing from the vessel, Rogue One. ml
Set Sail and Live Your Dreams (Seaworthy Publications, 2019) is the Winships’ book about their 10-year adventure cruising aboard their 33-foot catamaran Chewbacca. It is available in both paperback and e-book editions on Amazon.
