Our Back-of-the-Envelope Plan for Sailing Adventures

One of the first questions people ask us once they get over the shock of finding out we’re planning to live and travel on our sailboat for awhile is: “Where are you going to go?”. Because Megan and I have been talking about doing this for the better part of a decade, we’ve got a pretty good idea of world geography, major seasonal weather patterns, and generally where we can go and when; however, we’ve also said from the beginning that we weren’t going to have an end goal or specific destination for this adventure - we’d go where we felt good and for as long as it felt right.

So I wanted to share our current back-of-envelope plan for the next couple years, keeping in mind when I say “plan” I really mean a general sketch of where we’d like to be and when, subject to how we’re feeling, how much fun we’re having, how comfortable we are in our surroundings, and of course what the weather permits. So take everything that follows with several grains of salt, the further down the page the more salt you’ll need…

Leaving Milton

We felt that giving Liam, Aden, and Grace the chance to finish their school year was important. We wanted to give them some closure on this suburban chapter of their lives, so we’re holding off moving day until after their last day of school on June 28 plus a couple days for packing up last minute things and saying farewells. We also felt that before we leave Canada for awhile we’d celebrate one more Canada Day (July 1) on home turf. Our plan is to pack everything that’s coming aboard Matriarch into my father-in-law’s trailer and brother-in-law’s truck (thanks Mel & Kyle, don’t know how I lucked into such generous and helpful in-laws!), and hit the road on July 2nd.

Getting Comfortable in Chesapeake Bay

We’re planning to spend the summer of 2019 based at Herrington Harbour North which is about a 30 minute drive south of Annapolis, Maryland. Herrington Harbour is a great facility with a pool (key for the kids), contractors and maintenance facilities on site, nice showers, abundant wildlife, lots of other boaters, and in general a great jumping off point to explore the many, many, out of the way spots in the Chesapeake. We hope this will be a perfect spot for us to smoothly transition into boat life, learn all the in’s and out’s of managing Matriarch’s systems (heating, A/C, generator, navigation instruments, communications equipment etc.), refine our boat handling skills (we’ve only spent an hour actually sailing her as of yet), get comfortable anchoring a much larger and heavier boat, and generally getting used to living together in a very tiny floating house. Off the boat, we’ve got plans to visit Washington, DC and all its amazing museums and sights as part of the kids intro to homeschooling. We’ll also likely visit the Annapolis boat show the first weekend in October to pick up any last minute items we’ve realized we need before leaving the USA later in the month.

Heading South via Bermuda

When it comes to departing the USA and heading south to where winter is nothing but a headline we can read about on our Weather Network apps, hurricane season is the number one item dictating the timing and route. Hurricane season in the northern hemisphere runs June 1st through November 1st, with September typically being the most active month and big storms with geeky names impacting the North American coastline anywhere from the Gulf of Mexico to North Carolina (or even further north in a bad year). As a result, our boat insurance requires us to stay north of 30.5 degrees north latitude until after November 1st, just about the time to start worry about winter storms coming off the east coast of the US .

Given all this, a typical sailing route south is to leave the east coast of the USA sometime after November 1st (usually from a port in North Carolina where the continent pokes out to the east), then head east to cross the Gulf Stream (a major northerly running ocean current that can cause seriously bad sea conditions when it runs against a southerly wind), followed by turning south and heading for the BVI (in total about 1400nm or 10-12 days sailing). However, since this will be our first real offshore passage, we’re planning to make a stop in Bermuda to take a break and to see the island, followed by heading south to the Caribbean from there.

While this will lengthen the overall mileage a bit, it does allow us to break up the trek into two 5-7 day passages and hopefully gives us novices a bit more safety margin for selecting a good weather window. We’ll likely make landfall in the Caribbean at one of Tortola, Antigua, or St Maarten hopefully by the first week of December because Megan needs to catch a flight back home for Dec 13th to work (yuck!).

Rum and Sun in the Caribbean

Our plans for the Caribbean right now consist of not having any firm plans other than enjoying ourselves, keeping the kids on top of school, sharing the experience with some visiting family and friends, and not pushing too hard in an effort to see everything. We’ll see how far we get, but possibly as far south as Grenada if we skip some places in between.

And remember what I said about northern hemisphere hurricane season earlier? Well the middle part of the Caribbean island chain is not where we want to be any time between the middle of June and the following November. So when spring starts approaching we’ll have a big decision to make, either get far enough south or far enough north to avoid any reasonable chance of being in the path of a big storm. Right now we’re thinking north meaning we need to be back in the northern part of the island chain by beginning of May to prep for the next big passage.

Atlantic Ocean & Azores

Oh baby…as I sit here writing this and looking at the map it all seems very intimidating, so I’ll just do what I do best and compartmentalize until the time comes! Assuming we stick with the “plan” to leave north out of the Caribbean come late spring, our next stop will again be Bermuda; however, this time en route across the Atlantic to make landfall in the Azores which is a group of Portuguese islands a few hundred miles off the west coast of Portugal. From the Caribbean to Bermuda will be 6-7 days sailing (we’ll hopefully be comfortable with this by now), then after stopping to rest, provision, and get up our nerve, depart for 15-18 days sailing skirting the North Atlantic high to reach the Azores. If all goes well, this will be in the second half of June 2020, giving us plenty of time to explore the Azores and contemplate our next destination.

Portugal & Spain

Now firmly in the summer of 2020 our current thought it to make the jump from the Azores to Portugal and work our way down the Portuguese coast, through the straight of Gibraltar, and east along the Spanish coast. So far out, we really don’t have a clear idea yet of how much time this plan gives us in these areas, plus we’ve got EU travel visa details to work out. Any way you slice it, once we’ve reached this point it’s very likely we’ll end up continuing east through the fall and wintering the boat somewhere in Spain in preparation for the following spring when we can get an early start on the season and maybe get as far east as Greece before heading back west (now that’s really far away so don’t hold me to this…).

Christmas 2020 at Disney

Of all these wishy-washy plans, one sure-thing is that we will be flying home to celebrate Christmas 2020 with the Getty family at Disney World in Florida. After spending a little less than 2 years with the 5 of us crammed into a 49ft sailboat, I’m looking forward to seeing how big an average hotel room feels!

Then What?

The short answer to “then what?” is “who knows?”. Megan and I have decided we’re going to do our absolute best along the way to take things one day and one challenge at a time and not get locked into a definitive plan at any point unless we absolutely have to. What you’ve read is our current long term guess, with full realization that right now we’ll be completely happy enjoying a summer sailing around the Chesapeake then taking it from there. For now, we’d love to hear your thoughts, recommendations, and requests for time to come sail with us! Just remember, if you come to visit you have to pack light!