Key West, FL to Hobe Sound, FL

Upon reaching the Keys, we found ourselves tied up again for stays longer than we’d planned.  In Key West we divided our time between 2 marinas, one within walking distance of Duval Street and the other on Stock Island which is a few miles out of town and has a slightly more refined reputation than our “downtown” stop.  We spent a total of 4 nights in 2 Key West marinas and were ready to move on.

In case you get lost in KW …

In case you get lost in KW …

For us the Key West part of the trip was more about taking our loop all the way around the southern tip of Florida than visiting Key West itself. Though I did want to spend some time exploring the Keys by water since I don’t expect we’ll cruise this way again.  The first marina was congested, a little gritty (at least we thought so) and very, very expensive.  Good news, though; the washers and dryers were free(!), and they were excellent machines in a wonderfully air conditioned room.  So after all the time spent in coin laundromats on this trip, we took advantage of good and blessedly chilly facilities and washed everything we could get our hands on.

Despite the laundry surprise, we felt like the pricing of everything greatly exceeded its value … and our budget.  But ya know, it’s Key West; what did we expect?  We did like being docked alongside the Harborwalk with its abundance of restaurants and watering holes, not to mention the people-watching opportunities.  It really does take ALL kinds.  We sampled a beer flight and hand-made pretzels at The Waterfront Brewery YUM!, enjoyed a cocktail and a sunset at Sunset Pier and spent one night bar-hopping because, ya know, it’s Key West. And although fun, enough was enough.  It was time to move on and give our wallets and our livers time to recover.

These pretzels are delivered warm. Can’t you just smell them?

These pretzels are delivered warm. Can’t you just smell them?

Sunset Pier

Sunset Pier

Bar hopping (the middle-aged version anyway)

Bar hopping (the middle-aged version anyway)

The next day, February 26, we reached the southernmost point on our journey, another trip milestone, and rounded the tip of Key West from west to east. From there we would be moving north for the remainder of our journey. The cruise from downtown Key West to Stock Island Marina was a short one. This particular marina is very popular among loopers because it offers a quieter, more resort-type experience than its downtown counterparts.  We were eager to leave downtown so we didn’t pay too much attention to the weather even though we knew the winds were blowing pretty seriously from the south.  It was a short but very bumpy ride.

Southernmost point of our Great Loop!

Southernmost point of our Great Loop!

Stock Island was a nice marina but still too expensive for us to fully enjoy it.  The pool was a nice touch, though, and offered relief from the tropical temperatures. What made it really worth the stop was the chance to see a former neighbor and friend who moved to Key West 14 years ago.  He operates a successful charter fishing business and took us to his favorite local hangout for dinner.  We still haven’t had any success fishing, so he was kind enough to let us ask him stupid questions, such as “How do you kill a fish with kindness?” or “Actually, how do you even catch a fish?” We had a great night and enjoyed catching up, though we were sorry to have missed his wife who was visiting family in the chilly northeast.

Our plan upon leaving Key West was to make our way through the middle and upper Keys pretty quickly.  However, once again we had a couple of important decisions to make that would impact our course and travel schedule - and I use the term “schedule” very loosely.  The first decision had been the subject of much indecision for a couple of months.  The Captain wanted to earn his open water SCUBA certification while in tropical waters but couldn’t decide whether to spend the money or not.  This wasn’t only a bucket-list item (and on that score alone I encouraged him to go for it).  Having the knowledge and proper equipment would better position him to deal with issues that could arise below the boat, such as clearing a fouled propeller should we run over one of the many crabpots we’ve worked so hard to avoid.  Because our boat is single-screw (only one engine), losing the ability to maneuver due to a fouled propeller could pose a significant safety risk.  And we’d probably have to hire a diver at high cost. There are other reasons to hire a diver as well, or even have the boat hauled, like cleaning organic material off the bottom or changing the anodes (I’ll spare you that explanation, but it’s important).  And none of those other options are cheap. So, the Captain found a good diving school in Marathon, and there we stayed for a week.

Seven-Mile Bridge (between Key West and Marathon)

Seven-Mile Bridge (between Key West and Marathon)

Well, Marathon isn’t cheap either, but interestingly enough one of the nicest marinas in the area was among the cheapest.  That’s because the property was initially developed in 2008, right when the economy started to go downhill. Development was halted until very recently, and the property is now undergoing major renovation. I expect prices to rise dramatically when the project is complete, but in the meantime, we and a handful of other loopers had the resort, with it’s gorgeous harbor and pool, almost to ourselves. The location also offered a front-row seat to wildlife and, of course, more sunset viewing.

Oh yes, and this happened too, but only for a moment …

Oh yes, and this happened too, but only for a moment …

This was a great place for me to hang out while the Captain did his online coursework followed by 2 days of diving.  Needless to say, he passed with flying colors and is now certified. And he’s been outfitted with exactly what he needs should he have to do some underwater troubleshooting.  Congratulations, Captain!

Now with our wallets really hurting … we had another decision to make.  To cruise from the lower Keys to the upper Keys, you can go the inside route through Florida Bay (on the Gulf side of Florida) or the outside route via the Hawk Channel (in the Atlantic).  The Florida Bay route is the most protected with lots of anchoring opportunities. That would really help with wallet recovery.  But the waters in Florida Bay are very, very shallow. Stout draws about 5’ and most loopers and looping “experts” agree that boats drawing more than 4.5’ are well advised to go the Hawk Channel route.  That was our original plan, but as we looked for places to anchor, the few options we found were too exposed for our liking.  So we did a little more research and decided we could cruise in Florida Bay, albeit very carefully.  And that’s what we did.  We monitored our tide charts and used a rising tide to get through the sections with “skinny water.” 

The Florida Bay route allowed us to spend 3 nights at anchor—in Tarpon Basin near Key Largo the first night, off Sands Key apx. 10 miles south of Miami the second night (a favorite) and in busy Lake Sylvia in Fort Lauderdale the third. All worked well and were cheap.

Miami skyline moving north from Sands Key anchorage

Miami skyline moving north from Sands Key anchorage

In transit from the second to the third anchorage, we experienced another cool little coincidence.  On March 11, 2019 we passed through Port Everglades and went right by the Yacht Express yacht freighter getting ready to unload the following morning.  Three years ago, almost to the day — March 12, 2016 – the Captain, his cousin and I boarded Stout to take possession of her for the first time on the East Coast after she had arrived in Port Everglades from Mexico via Yacht Express.  Yacht Express was the freighter that moved her from the West Coast to the East Coast through the Panama Canal shortly after we bought her on the West Coast.  And we cruised past the same freighter in the same place on the same date 3 years later.  We did not plan it that way.  Dozens of decisions we’ve made could have placed us anyplace else on this particular date.  But instead of questioning these little coincidences, we spent some time reminiscing.

And here’s the original footage …


We entered the Atlantic Intracoastal Waterway (“ICW”) in Miami earlier this week and immediately went from leisurely cruising on open water and around barrier islands to a much busier experience.  

Our Fort Lauderdale anchorage was much more urban and congested than our previous anchorages

Our Fort Lauderdale anchorage was much more urban and congested than our previous anchorages



Some call the section of the ICW between Miami and West Palm the concrete canyon or concrete jungle.  There are lots of bridges to plan around, huge yachts in the waterway and docked alongside it as well as crazy boat traffic that has no problem passing within a few feet at high speed and throwing a serious wake in your direction. This section also reflects an enormous amount of wealth.

We took 2 cruising days to go from Miami to North Palm Beach.  During that time we went under 37 bridges, 27 of which were drawbridges that either open on a predetermined schedule or on signal.  We did 20 of those on the second day with a strong north wind blowing directly on our bow for over 50 miles.  We were pooped, and it wasn’t even the weekend (we’d been warned to avoid the concrete canyon on the weekend at all costs).  So we tucked into another marina in North Palm Beach for a couple of nights.  We rested a bit, filled our water tanks, pumped out our holding tank and otherwise prepared ourselves for a few more cherished nights at anchor.

One bridge at a time …

One bridge at a time …

And that’s where we are now.  We’ve decided to slow down a little and enjoy a few shorter cruising days which means longer evenings at anchor.  Yesterday we cruised a mere 14 miles and are anchored in a lovely little cove in Hobe Sound, a bit south of Stuart, FL.  Cooler temperatures and breezes have arrived.

We’ll hoist the anchor shortly and continue our slow push north.

Only in Key West can you wake to the sound of feral roosters crowing and the Star Spangled Banner being broadcast in the streets

Only in Key West can you wake to the sound of feral roosters crowing and the Star Spangled Banner being broadcast in the streets