• Gypsy Days Crew

Going From a 3-Year Plan to a 3-Month Plan


When we first bought Gypsy Days, we bought her as a learner boat, a liveaboard boat, a boat that we could make mistakes on but that would ferry us safely through the process of those mistakes. When we first bought Gypsy Days, we had plans to use and abuse her for three years while living aboard in Boston and saving up money for an epic cruise to faraway places. When we first bought Gypsy Days, we never would have imagined we would have three short months to prepare her for a trip south and into the unknown.


The marina crew breaking up the ice that formed in the marina

Throughout the endlessly long winter that we lived aboard at Constitution Marina, we did very few of the 'over the winter' projects that we had originally set for ourselves the previous summer. It was cold, it was dark by the time we got home from work, and we reasoned that we had plenty of time to get those things done. In early 2018, Aaron found out that he was going to be losing his job as of August 31st. His company worked within Wheelock College which announced they had been purchased by Boston University. Unfortunately, BU already had a program like the one Aaron worked with so they had no use for his company in the new restructuring. His company offered him a retention bonus to encourage him to stay to the bitter end, and would also provide him with a severance package. Faced with the daunting task of job applications (does anyone like applying for jobs?!) and with both of us feeling the two year itch of staying in one place too long, we had some serious discussions about our future.

We had been saving a chunk of money from each of our paychecks every week without fail since we moved aboard so we already had savings. When we looked at how much Aaron's retention bonus and severance package would add, we calculated we should have enough for a year of cruising. We had just returned from an amazing trip in Brazil in May and dearly missed the travelling lifestyle. With that realization, we decided to throw ourselves in to the wind and prepare to leave Boston at the end of the summer, bound for the Bahamas.


Some of the amazing water we saw while touring around Rio de Janeiro

All of a sudden, we had to really get serious about the projects on our boat, and about learning how to safely operate the boat. We had moved aboard in November and therefore hadn't yet taken her out at all, let alone all by ourselves! Thankfully, we had based ourselves at the largest liveaboard marina in New England with the most amazing people. Everyone took us under their wing offering advice, support, and gear. We spent the entire summer fixing things, adding things, and preparing ourselves for the voyage.


Our most difficult task by far was removing and installing a new steering pedestal.

You often hear of people who have a plan to do something that drags into years and maybe it never happens at all. We are so proud of ourselves for taking this daunting step and just doing it. We have learned so much is such a short time but we are incredibly motivated to make this journey and will do what we have to do make it happen, and make it happen safely.

If you are unsure about whether or not you can make something happen for yourself, consider us two crazy kids and what we were able to accomplish. We are not special, we are not rich, but we are willing to work hard, ask for help, and dig deep to make our dreams come true. Tomorrow is not guaranteed so don't wait for forever to follow your dreams.