The Plan

Our cruising plans were officially hatched on a hot summer day last August, although I'd been researching and thinking over the possibilities for much longer than that. Dawn and I had just returned from a weeklong low-season charter in the BVI with six of our friends on a 50' Beneteau, which was Dawn's 2nd time to the BVI and my 4th. Before the charter, I'd been thinking about the fact that with no kids and my flexible job with multiple bases available (most less senior than MSP), there was really nothing keeping us in Minnesota other than Dawn's middle-school teaching job - and she'd been increasingly talking about either taking a break or outright quitting. I'd had it with Minnesota winters and was ready to get out; the only question was where to move instead. The idea of moving onto a sailboat and going cruising had certainly crossed my mind, but I doubted whether Dawn would go for it. It would be an enormous, daunting, life-altering change, and Dawn has a fairly practical, conservative mindset compared to my own. That said, she also has a sneaky adventurous streak that appears when you least expect it, and over nearly 13 years of marriage I've learned to never count her out.

That August afternoon we were cooling off with old-fashioned malts at Tommy's Malt Shop in nearby Chaska when the topic of potential relocation again came up. I brought up my germ of an idea almost offhandedly: "You know, we could always become snowbirds... cruise the Caribbean from November through June, and come back up north during the summers." To my surprise, Dawn loved the idea. I guess we both had sailing on the brain, having just returned from the charter; none of our friends had sailed before, and so Dawn pitched in a lot on boat-handling duties until I got everyone up to speed, which I think increased her confidence level considerably. Now, instead of dismissing my idea as impractical dreaming, she seized on it and we immediately began scheming and honing the plan. Over the next three days we came up with a preliminary cruising route, a budget, a timeline, and a checklist of all the many things that would need to happen before we got on the boat. We hadn't decided to actually do it yet, this was supposed to be a theoretical exercise to flesh out our options, but we both got increasingly excited as we worked through the possibilities. At the end of the third day we sat down and went over the plan, and decided to sleep on it before making a decision. In the morning the answer was still yes, and that was it: time to get to work. I felt a bit like the dog who unexpectedly caught the car.

Here's the semi-refined plan as it existed by mid-fall of last year:

• Sell everything (Washington rental townhome, our Minnesota home, our cars, and our plane) by spring of 2017.
• Purchase an older refitted 40-45' cruising sailboat in fall 2016, do any additional retrofits and maintenance over the winter and spring,  and move aboard in June of 2017 to begin shakedown cruises. 
• Budget for the boat: $100-150k, plus $15-40k for retrofits depending on boat price.
• Cruise the Bahamas and the Caribbean for 3 seasons (Nov-Jun) starting fall of 2017. 
• First Season (2017-18): Bahamas, Turks & Caicos, Dominican Republic. Store boat on land in Puerto Rico for first hurricane season.  
• Second Season (18-19): PR, USVI, BVI, Lesser Antilles to Grenada. Store boat in Grenada or Trinidad for second hurricane season.
• Third Season (19-20): ABC Islands, Colombia, San Blas Islands, NW Caribbean, Jamaica, Cuba. Return to Florida to sell boat. 
• Spend the first summer in Minnesota/South Dakota with family; spend second summer living in the Northeast.
• Dawn quits teaching or takes a leave of absence starting June 2017.
• She will renew her 5-year MN license in spring 2016, so coming back to teaching after the cruise if desired will be easier.
• She's planning to tutor and volunteer for charities while cruising.
• Sam transfers to a more convenient/more junior base, works overtime during the summer and drops his schedule to a minimum during the cruising season.
• My airline & current fleet has large seasonal fluctuations in flying that make this possible.
• I also have enough scheduling flexibility to bunch the winter flying into several clusters of a couple weeks each, during which time Dawn, the boat and piperdog will stay at a secure marina in a major boating center with a major airport nearby (Nassau, Georgetown, Providenciales, Fajardo, Simpson Lagoon, Rodney Bay, etc).
• Writing will provide additional year-round income.
• A major part of our plan is inviting friends and family down south to sail with us for a week or two at a time. Will start with experienced sailors first season, then others as we gain experience.
• The boat will be ideally set up for 4 people, with two staterooms fore and aft, with additional room for a couple of kids to sleep in the salon for shorter stays.
•  Our budget is based on $70k/year income and provides for $10k/yr boat maintenance, 80% boat financing, insurance, provisioning, outside dining, marina fees while Sam works and 5-6 days/mo while cruising, and saving for contingencies or life after cruising. 

 The one major change to the plan already is that we decided to sell our Minnesota house a year early (ie now) due to extremely favorable market conditions and uncertainty surrounding the market (ie interest rates) after the election. Concurrently, Dawn has decided she doesn't want to teach another year and will quit or take a leave of absence in June 2016. So, we're now planning to buy the boat in spring/summer of this year, move aboard in the fall, and potentially begin cruising as early as January of 2017. We haven't decided yet whether to move the rest of the plan up by a year (i.e. cruise for 2.5 seasons) or simply treat the early start as a bonus shakedown/learning season. It'll probably depend on how smoothly things go from here on in. We've made a bunch of progress in our plan already but a ton of work remains, and the less familiar stuff that will involve a steep learning curve starts now as we get more serious about our boat search. If there's one thing I've gathered from reading cruising books and blogs over the years, it's that schedules and boats virtually never go together, and almost everything you do will take twice as long (and cost twice as much!) as you planned.

The other thing we haven't decided yet is what we'll do once we get off the boat in 2019 or 2020. We're purposely leaving that discussion for while we're on the boat; there will be plenty of time to talk about life after cruising. We did agree that we need to have an end date in mind and plan around that; of course the plan can (and probably will) change. Heck, we honestly don't even know if we'll like cruising and want to go all three years...not everyone does, and I don't think chartering necessarily gives you an accurate taste of what full-time cruising life is like. We've committed to go at least one full year while we build cruising skills; most cruisers agree that the first year is the hardest. Beyond that, this adventure is largely about experiencing a unique lifestyle and deciding if it suits us. If so, it's likely we'll end up building our long-term life goals around it; and if it doesn't, or if we've simply had our fill after three years, it'll be an interesting experience with lots of great memories while we move on to other land-based adventures. I'm a bit daunted and even a little scared when I look at the many challenges inherent to our ambitious plans, but I'm looking forward to taking them on with the love of my life at my side.