December 24, 2022
What a long, strange trip it’s been! We have just spent 65 days traveling 1720 nautical miles through 13 states from South Portland, Maine to Miami, Florida, not including the six weeks we spend in Rhode Island working on the boat in preparation for the trip. In all honesty, nothing could have prepared us for this trip. Which is not to say we were unprepared; we had the requisite guide books, navigation equipment, boat gear, and very importantly, food larder. We understood that there would be passages off the coast and inland on the Intracoastal Waterway (ICW). While I’ve traveled extensively on the West Coast, Europe, the Adriatic, and the Caribbean, much of it on a sailboat, I’ve spent almost no time of substance south of New England on the East Coast. And I’ve never sailed coastwise outside of Maine, nor spent any time making tracks in a boat on one of the largest connected bodies of water in the world, the ICW; neither has Will.
It’s been eye-opening, fascinating, amazing, challenging, disheartening, scary, and yes, fun too, although fun has not been the operative word in my experience. “Has it been fun for you?” I asked Will. “Yes, I’ve enjoyed most of it, with the exception of all the motoring we’ve done on the ICW.” Tallying it up, we’ve spent 23 days motoring on the ICW, 21 days sailing on the outside, and 21 days mostly at anchor, with a handful of days at mostly free docks or at a marina. That’s a pretty healthy balance, although we’ve spent many more days motoring that we’d hoped and, in retrospect, we now agree we should have spent more days at anchor, relaxing.
Now that we’ve “arrived” at the end of this major leg before we “jump across” to the Bahamas, it feels incredibly satisfying that we’ve made it this far. At the same time, we’re taking some much-needed time for rest and relaxation, as well as some deep reflection—about our country, our boat, our journey, and each other.
Miami
Our Country
America was built on the backs of slaves. As one immediate example, we traveled on canals that were hand dug by slaves. Having grown up in New England, I’ve had very little exposure to the South and the history of our country. After the slaughter of the Native Americans when the Europeans first arrived, the worst scar on our country is surely slavery and its ongoing repercussions. We have been reading Heather Cox Richardson, a political blogger pop-star of the liberal persuasion, who happens to live in Round Pond, Maine where I used to keep my boat. It’s where we get our news—as much as we can tolerate. She is a genius about reflecting on our political, economic, and social state of affairs with an historical lens, particularly as it relates to the Civil War. (You can sign up for her daily “Letter from an American” here.) While the Civil War was “won” by the North, the endemic injustice that’s baked into our institutions—and now even into our laws—prevails, and we’re still fighting over what was never fully resolved by that very uncivil war.
This trip took us to Elizabeth City, Belhaven, and Oriental, NC on the ICW; Charleston, NC, where the Civil War started; Savannah, GA, which was spared when captured by the Union army, leaving the beautiful architecture and landscape in tact; Fenwick Island, SC, where freed slaves created a thriving community post-Civil War; Beaufort, SC, which we learned was a model for Reconstruction after the war; St Augustine, FL where we met up with Will’s 96-year-old mother; New Smyrna where we met up with a friend and saw a rocket launch from Cape Canaveral; and West Palm Beach, FL where we stayed a few nights at Will’s brother’s poolside cabana and king-sized bed, a most welcome break from boat life.
Elizabeth City, Belhaven, and Oriental, NC
Charleston, NC
Savannah, GA
Fenwick Island, SC
Beaufort, SC
St. Augustine, New Smyrna, and West Palm Beach, FL
While the South is seemingly integrated now, we all know that our country is still racially charged and divided along so many different lines. Having grown up in the South, Will observes that while it might have more overt racism, many blacks and whites at least know the others’ families, whereas in the North, very little exchange seems to occur. As for our experience, some of the friendliest people we’ve met on this trip are casual encounters with people of color, whether at the grocery store, post office, or fishing pier.
And speaking of eye-opening, the over-the-top presence of the military as we’ve moved south has been beyond astonishing. In Norfolk, VA, we passed the largest Naval base in the world; in Sunny Point, NC, we passed the largest ocean terminal for military munitions in the country; and just before Cumberland Island, GA, we passed the Kings Bay Naval Submarine Base, the largest nuclear submarine base in the world. And that says nothing of the military-industrial complex that lurks at every port and is hidden behind Restricted Zones on the chart. I found it excruciatingly difficult to observe, but it is our reality.

We’ve also seen some of the most overt displays of wealth ever as we passed house after house along the ICW, with lifts to hold motor boats out of the water so as not to get them dirty. The further south we traveled, the larger the houses and yachts have become to the point of being mind-numbing. When personal wealth is the yardstick upon which so much of this country is based, it means “development” rules the day, leaving nature to the tree-huggers who have to fight battles with the behemoths to preserve what’s left.
One such fighter is our friend Sidney VanZant who fifty years ago founded the Groton Open Space Association in Connecticut, which has preserved hundreds of acres of land, the first of which we had the good fortune to visit at the very beginning of our trip south. Another is Carol Ruckdeschel, a self-taught biologist/activist now in her 80s, who has almost single-handedly been responsible for preserving much of Cumberland Island, GA, where she lives off the land and wild horses roam freely amidst the ruins of mansions built by the wealthy in the mid-1800s. We’ve been reading her fascinating story Untamed: The Wildest Woman in America and The Fight for Cumberland Island. And right next door on Jekyll Island is an almost Disneyland display of wealthy Americana that we found hard to take.
Cumberland Island and Jekyll Island, GA
On the positive side, we’ve observed some magnificent wildlife both “inside” on the ICW and “outside” off the coast, including a whale, porpoise, dolphin, manatees, armadillos, pelicans, ibis, and many other species of birds. While most of the waterfront is residential, there have been stretches that are beautifully pristine, in particular the marshlands of South Carolina and Georgia, no doubt because this land cannot be developed. And as we’ve traveled south, the temperature has warmed while the breezes over the water keep it from getting too hot, so we’re enjoying much more time in the cockpit, with few insects to send us inside at night.
So after this very looonnnggg leg of our journey, we are somewhat disheartened by the onslaught of humanity and are longing for nature.
Here are some of Will’s photographic impressions from this leg of the trip.
Our Boat
Our Freedom 36 is incredibly well built and is listed as one of the top 100 best production sailboats for its overall construction. This is good. Despite having upgraded much of the equipment on the boat, under the careful guidance of a world-class Freedom expert, you can’t upgrade everything, and so things break, and they did, starting on our first day out of Rhode Island. And they continued to break on our way down the coast to Norfolk, and beyond.
Some of it was old equipment: we chose not to upgrade our 34-year-old forestay, for example, and so it nearly broke the first day out on rough seas. Some of it was a big surprise: our older chart plotter that worked fine in Maine ran out of charts once we hit Long Island Sound. Some of it was bad luck: we pushed our sailmaker to deliver our sails while I was in Portland in October, resulting in less-than-robust batten receptacles and reinforcements. Some of it turned out to be our lack of understanding: we broke our boom vang not once but twice because we were pulling it too tight when it’s really just there to hold up the boom (who knew?). And on and on and on…
I say, “Damn it, why are so many things breaking? It’s all too daunting!”
Will says, “A boat is a mechanical object. Things break. We can fix them.”
And so we fix things, little by little, accumulating replacement parts in our ever-growing “project box,” which sits in the aft cabin, aka “garage,” waiting for time and motivation to install them. Meanwhile, our older autopilot has served us well enough while motoring on the ICW until we upgrade to the newer model and synch it up with our chart plotter. Our refurbished water maker is back from the manufacturer and ready to install. We’ve installed a “soft vang” while our new boom vang collar is being manufactured and shipped to us in Miami. And I have a glass of wine to calm my nerves while Will drills holes in the deck to install a pad eye so our jack lines don’t chafe.
My growth edge is coming to accept that “fixing stuff” goes along with the watery territory when you live on a boat and, more importantly, none of it is a catastrophe. Will’s growth edge is coming to accept a side of me that he hasn’t seen much before this trip and not fear that I’m going to flee the boat as a result. It’s a work in progress…
Our Journey
There are a number of ways to get from New England to the Bahamas on a sailboat. Starting in Norfolk, you can motor on the ICW all the way down to Florida. You can sail within a few miles of shore, passing in and out of inlets each day to avoid sailing at night. You can do 1 – 3 day hops offshore between major inlets to put in some serious miles and avoid motoring inside. Or you can sail offshore all the way, stopping in Bermuda on the way.
While each have their advantages, they each also have their challenges. Going outside means you get to sail, but it also means you typically have more wind and rougher seas and you have to go in and out of inlets, which can be hairy. Motoring on the ICW is the safest and most direct way to travel, but a) you’re not sailing, b) it can get pretty boring, and c) especially in Florida, there are a lot of opening bridges you have to contend with.
As this is our first time, we’ve been learning what works for us. We’ve done a combination of day hopping off the coast when the conditions have been favorable and motoring the ICW when they have not. We did most of our sailing outside in the first half of the trip and most of our motoring on the ICW in the second half due to extreme waves caused by a huge system in the mid-Atlantic.
Sailing at night or offshore is not something we’ve done yet and involves a whole other level of preparation and psyching up for. After our experience coming down, I imagine we’ll do longer hops offshore when the conditions allow for it, which will likely require bringing on another crew member. (Let us know if you’re interested in the position!)
Also, as we got a late start from New England, we were pushing much of the way down the coast from Rhode Island in order to stay ahead of the cold, with many 50-60 mile days. It turns out it was reasonably warm, the wind was largely favorable from behind, and we seemed to be up to the challenge. Somewhere around North Carolina, however, the pushing caught up with us and we realized we needed to slow our pace. There were more 20- and 30-mile days where we slept in and had time after we arrived to relax or go ashore. We spent time in some of the more interesting cities like Charleston and Savannah. There were some breaks where we visited with Will’s mom in St. Augustine, his brother in West Palm Beach, and a friend in New Smyrna. Mostly we anchored, but we have stopped at the occasional marina, which is always a treat for a real shower and laundry. And much to a sailor’s delight, we’ve stayed at a number of free docks in North Carolina and West Palm Beach.
One thing we’ve come to recognize is the importance of going ashore and doing something completely un-boat-related to change things up. These have been some of the most interesting and fun days of the trip.
Each Other
Will and I make a good team. I like to be creative in my cooking, and Will is an enthusiastic recipient and is happy to clean up after meals. We take turns making breakfast and our daily salad for lunch. I have a head for technology so have taken on most of our electronic route planning. Will can take on mechanical things without feeling daunted so has gotten his hands dirty more times than I can count. As a former technical writer, I like to document things so am the keeper of the logbook and blog. Will enthusiastically spots dolphins, birds, and other wildlife with the eye of a child. I usually steer us in and out of inlets, on and off of anchors, and onto and off of docks. Will takes the helm when my arms and nervous system can’t take the wild seas, raises and drops the sails, drops and hauls the anchor, and hops on and off the boat with dock lines. And we each take our turn at manipulating the autopilot on the long legs of the ICW while the drone of the engine largely prevents conversation.
I like to organize things so have created most of our storage systems aboard our tiny craft and help Will find things when he can’t. Will appreciates my organizational talents and is learning the benefits of keeping a tidy ship. I am an emotional barometer for much of our experience. Will appreciates that “shit happens” and usually finds a silver lining in what initially looks like a dark cloud. Given our different approaches to living aboard and having this kind of adventure together, we both allow each other to be ourselves and influence each other in subtle ways, which is as it should be in any good relationship.
And so, the end is now once again the beginning as we prepare for and anticipate what our cruising friends have called “the pot of gold at the end of the rainbow”: The Bahamas!
Congratulations! Miami is a big milestone. 1700 miles under the keel that you won’t soon forget. Looking forward to seeing you on the other side.
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Yes, congratulations to both of you for making it all the way to Miami. I’m so excited for you and very interested in reading about your journey. A friend and I are planning to sail to the Bahamas next November and will probably sail down to Norfolk or Morehead City and sail from there to the Bahamas, pending weather conditions of course. Can’t wait to hear about the next leg of your trip. Duane
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Good to hear about your trip south. It’s a long way and agree offshore is probably a better way to go if you’re up for it!
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