Punta Gorda, FL to Key West, FL

When I began writing this post, we were in the most remote and, for us, the most special place in all the miles we’ve traveled since starting our loop. And that’s saying something, because we’ve now traveled almost 4,500 miles and made many special stops along the way.

That place was an anchorage off Cape Sable Beach on the southwest corner of the Florida Peninsula. From there south, there’s nothing but the Keys. We cruised to Cape Sable from a river anchorage farther north in the Everglades and dropped the hook on the east side of the beach to make sure we were in the lee of the prevailing winds. We stayed 2 glorious nights waiting for the winds to subside so we could then make our long open-water reach to Key West.

A perfect little escape,  courtesy of Google Maps

A perfect little escape, courtesy of Google Maps

Other than a sailboat and sprinkling of fishermen, there was no one there.  And there was no sound other than the gusty winds, the surf hitting the beach around the point, some shore birds and raptors, dolphins occasionally surfacing and very large jumping fish we couldn’t identify. And we had zero cell coverage there, so none of the usual distractions. 

When we first got there, we settled the boat at anchor and then literally did nothing other than watch the blue-sky afternoon transition to a deep star-filled night.  We turned our chairs west at sunset and enjoyed a cocktail as the burning sun melted into the purple horizon.  And because there was no ambient light, we found ourselves under a blanket of stars.  That’s when we moved to the foredeck and laid on our backs to stargaze until it was time to sleep.  Fully in the moment, a very long uninterrupted moment.

After our second night at Cape Sable, which went very much like the first, diminishing winds were still predicted so off we went across 60-plus miles of open water to Key West. We bounced around for a good portion of the trip but Stout was happy and we were prepared. It was 89 degrees off shore with steady southeasterly winds. And it was another amazing open-water cruise. We started before the sun was fully up and tied up in Key West, hot and tired, 9 hours later.

Nothing but gorgeous blue-green water all around all day. Oh yeah, except for the crab pot obstacle courses that kept the Captain busy.

Nothing but gorgeous blue-green water all around all day. Oh yeah, except for the crab pot obstacle courses that kept the Captain busy.

Backing up a bit, I haven’t yet talked about the trip from Punta Gorda to the Everglades. So, I’ll do that now. From Punta Gorda we continued south toward Fort Myers, spending one more night on the hook before tying up again for a month.  Our original plan was to spend that night in Pelican Bay, an absolutely beautiful anchorage bordered on the west by Cayo Costa State Park and on the east by Punta Blanca Island.  Both are undeveloped, virtually in their natural state, and serve as bird sanctuaries.  A little like heaven to me.

The cruise to Pelican Bay was short, so we anchored with plenty of time to spare before dark.  We dropped the dinghy and had a great time exploring the shallow waters, including a trip through the so-called “Tunnel of Love.”  It’s a gap in the mangroves just wide enough and (barely) deep enough for our 9-foot dinghy.  The Captain carefully maneuvered us through, even paddling at times, while I was on high alert for ‘gators and snakes.  Fortunately, we didn’t come across any… But we did emerge from the tunnel into a small, mangrove-lined cove right on the back side of an utterly deserted Gulf beach.  Truly lovely and peaceful.  We spent some time walking the beach looking for shells and basically enjoying the peace and quiet before returning to the dinghy and retracing our steps to Stout.  That was definitely among my Top 10 ways to spend an afternoon.  Little did I know we’d encounter my No. 2 at Cape Sable (No. 1 will always be reserved for family).

Once we were back aboard Stout, the Captain became increasingly concerned that where we’d chosen to anchor was too shallow, and the tide was going out.  We’d had time to explore and still had a few daylight hours left, so we weighed anchor and moved a little farther south.  We ended up on the hook off Cabbage Key, the site of the inspiration for Jimmy Buffet’s Cheeseburger in Paradise.  We chose to forgo the cheeseburger and instead ate sandwiches as the sun went down.

In the morning we cruised past Pine Island, Captiva Island (a personal favorite) and up the Caloosahatchee River to Fort Myers.  In our loop planning we knew we’d need to find a winter “home,” a warm place to hold over until it made seasonal sense to think about starting the trip north.  On the recommendation of a fellow Vermont looper, we were fortunate to find a slip at the Edison Ford marina in Fort Myers.  We tied up there for a month.

View of the marina from Pinchers restaurant. You can see Stout on the left, the boat that’s bow in with a black bicycle cover on the upper deck

View of the marina from Pinchers restaurant. You can see Stout on the left, the boat that’s bow in with a black bicycle cover on the upper deck

The marina is right next door to the historic and lovely winter estates of Thomas Edison and Henry Ford. https://www.edisonfordwinterestates.org

It’s a small and extremely well run marina and within walking distance of the downtown River District of Fort Myers.  The small size and tendency of transient boaters like ourselves to stay there for extended periods creates the atmosphere of a little neighborhood.  Among our neighbors were two other Vermont boats, believe it or not, as well as boats we’d encountered along the inland rivers. 

While there we hunkered down inside the cabin and watched movies during a late January cold spell, toured some of the surrounding areas by rented car, spent some time downtown, completed small maintenance projects, enjoyed a few dinners out and docktails with our fellow travelers and did lots of reading. The highlight, though, was a visit from our daughter and her boyfriend in early February.  They managed to get a few days off from work and flew in from Vermont to escape the cold, snowy north.  We took them on a cruise to Tween Waters Island Resort on Captiva Island and spent a couple of nights there with access to a pool, private beach and other resort amenities. Our daughter was sort of obsessed with fishing while aboard.  That is, until she caught one.  This poor little catfish, whom she’d caught and released once, swallowed the hook so release wasn’t possible a second time.  Her boyfriend, who just happens to be a sous chef, came to the rescue.  He not only filleted it (with my knives that were in desperate need of sharpening which he very politely yet firmly pointed out), but served us all an amazing catfish lunch on the cruise back to Fort Myers the following day.  We are definitely getting spoiled on this journey.


By the end of the month, we’d grown fond of Fort Myers but were antsy and ready to get going again.  Barring unforeseen events, that will be our last extended stay of our trip.

For many loopers, Fort Myers is a turning point.  They continue up the Caloosahatchee River and cut across to Florida’s east coast via Lake Okeechobee and turn north from there.  We considered that … but not for long.  The Everglades were in reach, and we knew this might be our only opportunity to see them from the water.   And how cool will it be to cruise around Key West before turning north for the first time since Georgian Bay?! 

The forecast at the time of our departure from Fort Myers included strong winds every day for a week. So we took our time getting to Cape Sable which, as I’ve already mentioned, was the launching off point for our open water cruise to Key West. We cruised first to Marco Island and hung out there for 4 nights - 2 at anchor and 2 in a marina - and then anchored for a night in the Ten Thousand Islands (Russell Pass anchorage) before making the run to Cape Sable.  Marco Island is nice but a little too high-brow for me.

While both Russell Pass and Cape Sable offer unique and lovely Everglades experiences, they were quite different.  In Russell Pass we were surrounded by mangroves and by wildlife we knew was there but didn’t see, except for the no-see-ums!  They were everywhere, particularly toward sunset, and if you weren’t behind a screen, you were going to get eaten!  Tiny bug, big biter.  At Cape Sable the wide open spaces and strong breezes kept the air moving and the bugs away.

There’s more I’d like to say about the Everglades, but it’s time to explore Key West.  Let’s see what kind of wildlife we find here …