March 6th to 18th, 2025: Sanibel Island to Stock Island

Wednesday the 6th was a busy, social day.  Early in the morning, I met our slip neighbour just as the harbourmaster delivered fresh, hot, blueberry muffins to our boat.  Our neighbour had just taken possession of a 15-year-old Back Cove, and was preparing to take it across Florida and then north to his home in Cape Cod, after some much needed work in a couple of boatyards along the way.  Dick took MOKE for a final run to stock up on heavy grocery items, while I worked on getting the next issue of the blog completed and published.

Local Harbor Hosts Mike and Deb came over from Fort Meyers and we had a pleasant lunch at the onsite restaurant.  Later in the afternoon, we enjoyed a great reunion with Jim and Marilyn, who we met in 2021 on Lake Michigan.  We all tucked into cheese and sausage and exchanged stories of our various boating experiences, as well as interesting international business travel stories.

Very high winds and waves were forecast for the next day, so we stayed put.  It was a good day for boat chores.  In the afternoon, we took a walk to have a look at the beach – we were very glad we weren’t out in that weather!

Our voyage to Naples was straightforward, with relatively smooth seas, although unfortunately in a direction that gave us a certain amount of corkscrew motion.  Not enough to require medication or wrist bands, but I certainly was not going down into the cabin in those conditions.

Naples is reached by turning into a very narrow and shallow channel with a lot of shoaling.  We could see breakers on one side of us, and an optimistic surfer waiting his chance.  I can’t imagine a more dangerous place to surf, one miscalculation could put you right into the path of an oncoming boat.  Once you are through the cut, the waterway opens up and winds north for several miles.  The shores are lined with beautiful homes.  Here again, the speed limit in the channel is 30mph, and outside is a no wake zone.  This is to protect the manatees, but it makes things difficult for slower boaters, as they are subject to wakes they can’t avoid or turn into.

On arrival at the city marina, we went straight to the fuel dock for a pump out.  Staff were efficient, answering the radio when we called, and helping to tie up.  I would not call them friendly, as some reviewers have experienced, and as often happens, the man who took the midships line refused to cleat it tight, making it difficult for Dick to bring the stern in. Our overnight dockage was just along the dock, but it required slotting between two large sportfish boats, so Dick had to go out, turn around, and then maneuver back in.  This time the dock hand was more understanding of how Nine Lives ties up, having seen what is needed.

Our spot on the outside dock meant some motion from passing boats, but it was worth it to be able to watch the traffic.  There is no security in the marina, and it seems to be a “thing” to walk around the docks and look at the boats.  One man was explaining, quite loudly, to his family that we obviously bring Nine Lives from Hilton Head and stay for the winter.  When he saw me looking, he asked how long it had taken us to get to Naples.  I was amused at the look on his face when I told him, 8 years!  Explanations were then offered, but it’s always fun to be able to correct mansplaining.  There must have been at least 50 people wandering around and commenting on the various craft.  I have never seen so many tourist boats, all doing a roaring trade.  There were lots of tiny floating tiki bars with just 4 or 5 people sitting on bar stools while the vessel puttered around the harbour.  There were the usual dolphin watch pontoon boats, also at least 2 very large sailing cats as well as monohull sailing boats heading out for cruises in the Gulf.  There were also the expected sport fishing boats, and a large dinner cruising yacht.

Dick took time to explore the town, finding a couple of very interesting shopping precincts that we would plan to return to later with a rental car.  In the evening, we walked to the nearby Bleu Provence, another outstanding French restaurant.  Service was excellent, and the food was delicious.  Once again, the noise was incredible, it seems to be the main downside of dining in Florida.  Dick commented that it has been our luck lately to be seated at a table next to one with a particularly loud man who holds forth at length on topics that are of zero interest to nearby diners.

We didn’t have far to go to Marco Island, so we left at 11am.  It should have been an enjoyable trip through the Naples channel, looking at all the beautiful houses.  Sadly, because of the 30mph speed limit and the huge number of Saturday boaters, it was just an unpleasant half hour of being thrown around by wakes.  Not the fault of the boaters, they are doing the speed limit that they are allowed, and looking forward to getting out onto the Gulf.  Once we got out there, it was unpleasant in a whole different way.  Long, rolling waves on the bow meant that wristbands were required, and I was very unhappy.  The official trip planner, when questioned, indicated that the sea state was not at all as predicted.  Fortunately, it wasn’t a long trip, and once we were into the channel for Marco Island everything calmed down.  All the waterways around the Island are strictly minimum wake or no wake, so travel is much more enjoyable.

We arrived at our marina, and our slip neighbour offered to catch our lines.  For a change, when asked to cleat the midship line tight, he did!  Docking was very quick and easy with such great help.  Dick checked in with the dockmaster, and then walked over to the other marina on the bay, hoping that one of the two would have had a cancellation and we would be able to avoid some or all of the expected nights at anchor.  No luck.

In the evening, we walked to a nearby steakhouse.  They have very good reviews, but sadly, our experience did not live up to expectations.  My steak was charred on the outside, and the asparagus was yellow and bitter, should never have left the kitchen.  The dessert we shared looked gorgeous, but it did not taste very good and neither of us wanted to finish it.  It was a very pricey meal for what it was.

Next morning, Dick checked again to see if we could remain in the marina.  He was offered an 18-foot-wide slip, and thought we might just squeeze into it (one thinks about a large lady and a corset). At the waterline, we are less than our 18’8” width at the widest point, our rub rail.  We untied and made the attempt, but sadly, we couldn’t fit as the dock was just that bit higher than we had hoped.  Instead, we anchored just outside the marina, between 2 sailboats as planned.  We spent an interesting afternoon watching boats to-ing and fro-ing.  There was a small cruise ship in port (100 passengers).  Some of the passengers were taken on a dolphin cruise, and their boat got into trouble and had to be rescued and towed back by Sea Tow.  An interesting experience for the passengers, if not quite what they were expecting.

After a quiet night, we re-recorded the podcast we had done earlier for AGLCA.  The topic is “Segment Looping”, that is, doing the great Loop in segments rather than all at once as is more usual.  We were asked about how we chose our boat, how we decided on the length of the segments, where we put the boat when we were not aboard, and of course, the advantages and disadvantages of segment looping. 

We dropped the dinghy, and Dick set off to collect the rental car he had arranged.  The weather in the afternoon went from interesting to exciting.  We started with heavy rain and some rumbling thunder.  After the rain stopped, the wind really came up and we began to swing from side to side.  There was a small craft warning for the entire west coast of Florida.  The wind howled, and we swung faster through 180 degrees.  Earlier, Dick had chatted with the couple on the sailboat anchored next to us.  They were having a bad week.  They had gone out in rough weather, and were lifted by a big wave and slammed down on something, debris, sand bar, possibly the broken marker off the Marco Island Channel?  The impact was enough to bend their floorboards, so they had concerns that there was serious damage to their hull.  A haul-out was scheduled for later in the week, and meanwhile, they were anchoring while they waited for their appointment.  Next piece of bad luck, their dinghy motor died.  Dick gave Bill his card, and offered a ride if needed to shore the next day, to save them having to row.

A couple of hours later, the phone rang, it was Bill to say that their dinghy had broken free and was floating away.  Fortunately, it was floating into one of the canals rather than out into the bay.  Dick quickly donned life vest and shoes, and headed out.  He managed to capture the runaway, not without some challenge, as it had slid under the only open dock on the canal.  He returned it to the sailboat, and in due course it was pulled up onto its davits, instead of just being tied.  Everyone then settled back to what they were doing, and listened to the wind howl.

The afternoon excitement was not over by any means.  I looked over at our sailboat friends, and realized they were dragging their anchor.  As I tried to work out the best way to get their attention, they noticed the situation, and started their engines.  They began the process of resetting their anchor.  Dick decided to check ours, and saw that one of the lines of the bridle had come off.  Life vest, headsets, start engines, and we began a little resetting of our own.  It didn’t take long, and once we were set again, we poured well-deserved adult beverages and sat watching.

A small trawler that had come into the bay, and anchored behind us, decided to relocate for the second time that day.  Meanwhile, our sailboat friends seemed to be set, and put on their snubber (this is a line that functions as our bridle does, taking the weight of the anchor chain off the anchor roller).  Within a few minutes they were in motion again, and trying to get the anchor to set.  We suspect a couple of issues.  The type of anchor they have does not appear to swivel like ours, so as the boat swings back and forth it is less likely to remain set.  We also suspect that they are backing down too hard and too soon, and then not putting out enough rode (that’s the chain, rope, or combination of the two that goes between the anchor and the boat).  Dick and I always put out at least 7:1, that is, 7 times the depth from the bridle attachment points.  We have seen advice for 5:1, or even 3:1, but 7:1 was what we were taught for an overnight stop.  Ultimately, they were unable to get their anchor to hold, but meanwhile, Dick left a message to tell them about the vacant slip we couldn’t fit into, or the alternative of tying up at the fuel dock, since it was now after hours.  They chose to head for the fuel dock.

Just to finish their rather sad story, Bill let us know later that after the haulout and inspection by the insurance adjuster, it is certain that their beautiful Oceanis 45 will be written off, as it cannot be repaired.  They are selling everything portable and fortunately had an “agreed value” insurance policy, so they will get back what they paid for the boat.  An object lesson, reminding all of us not to go out in conditions that are worse than we should be in.

Eventually, the chop subsided, but the wind was still high, so Dick had to cook the burgers on the frying pan in the galley.  The wind would have blown out the flame under the grill!  As it happens, the burgers were delicious, and perfectly cooked, and in my opinion, we should always do them in the frying pan in future.

Tuesday turned out to be a busy and interesting day.  After a leisurely start, we got into the dinghy and motored over to the fuel dock, which doubles as a dinghy dock.  There is a $10 plus tax charge, which is pretty unusual, although it does allow in/out privileges.  The biggest issue is that after 6pm, you are supposed to have left, because the dock is behind the security gates and they do not provide the code to dinghy owners.  Fortunately for our plans, we already knew the code, although we kept that quiet and told the cashier that we had friends in the marina who would let us in.

Our first stop was a high-end shopping center at another marina.  Dick’s sources for marina selection had suggested that it was not suitable for boats of our size, and that the access was too shallow, so he had not tried to get a reservation there.  Having seen 2 Looper boats in there this week, we could have fit.

The shops were disappointing, with the exception of a jewellery shop that offered unique pieces of shells and marine glass, set in silver.  We would have bought something there, but the saleslady was unable to help us while a couple dithered over their purchase.  After a very long wait, we gave up.

Next, we drove to the end of the island, marvelling at the sheer number of high-rise condo buildings.  Assuming that each unit has one vehicle, the traffic jams must be horrendous, and we now know why the restaurants at that end of the island are fully booked.

We parked in another shopping centre that happened to have a branch of my favourite ladies’ shop, as well as being the location of our (early) dinner reservation.  Having bought two nice things at Chico’s, I was delighted to discover that there were more shops with very unusual, and flattering, clothes that just had to be added to my wardrobe.  Dick can occasionally be a good shopping buddy, and this was one of those rare times.  He selected several garments that subsequently found their way into shopping bags.  Exhausted by our efforts, we fortified ourselves with ice cream before heading out for some grocery shopping.  It was late enough by the time we finished that we decided not to return to the boat, instead we went directly to the restaurant.

Da Vinci’s is a huge venue, that was completely filled by shortly after 5pm.  Many of the diners appeared to be family groups, grandma and grandpa, parents, and grandchildren on vacation.  Dinner was excellent, and service was also very good.  It just shows that having enough staff makes a big difference to success, especially in restaurants that cater to families and vacationers.

Returning to Nine Lives was accomplished without drama, and we had a very peaceful night.  We suspect the anchor had dragged a small amount with tide changes, but it always dug in again and we remained within the circle I set for the anchor alarms.

The next morning we were fascinated watching TowBoatUS retrieve the derelict sailboat that had been anchored beside us.  Derelict boats left at anchor are a huge problem in southern US, especially in Florida.  Wealthy homeowners don’t want to have to look at deteriorating vessels outside their expensive properties.  We find this completely understandable.  The problem comes when communities and counties try a shotgun approach and put forward legislative bills to forbid anchoring entirely.  There are already laws and procedures in place to deal with the situation, but instead of following them, a draconian approach is proposed again and again in the form of new and ever more restrictive laws.  Concerned boating organizations do their best to counter the proposals but are not always successful.  We were happy to see the derelict retrieval, as it shows that measures can be taken to handle the problem.  It took less than an hour from the time the towing company came out to dropping the derelict at the dock and heading out on another job.

We were able to get into our slip across the bay a little early.  The anchor took a while to come loose from the mud – three days of wind and fetch with almost continual swinging back and forth meant it was well dug in.

As soon as Dick had retrieved the rented vehicle, we set off for Naples.  Another successful shopping day!  I said to Dick, we have made up in just 2 days for 3 years of scarce shopping on the inland rivers.  This extravaganza was a little more even, 2 shirts for Dick, a necklace and an outfit for me, and a very nice silk flower arrangement for the condo.

Next stop was Bha! Bha!, a Persian restaurant.  The food was beautifully presented and absolutely delicious.  I started with gravlax, while Dick had lamb meatballs.  His main course was the Persian chef’s interpretation of paella, which he loved.  I had a wonderful dish of beef tenderloin pieces with tomatoes, eggplant, and red peppers in a spicy sauce.  The desserts were also beautifully presented, but sadly they were too sweet for our taste.

On our travels to and from Naples, there was a road sign warning about panthers crossing.  I would have loved to have seen a panther.  Instead, I saw two wild pigs foraging along the verges. I suppose they would make a good lunch for a panther…

The next day was another full day.  We returned to Naples, to the second upscale shopping precinct that Dick had scouted earlier in the week.  We found a couple of very interesting, eclectic boutiques with things for the home.  The clothing shops were less interesting, probably just as well!  Lunch was at Alberto’s, an Italian restaurant.  We chose the cauliflower soup to start, which was delicious.  We both ordered salads, Dick’s with mixed seafood, and mine with lobster and shrimp.  They were excellent.  Desserts were interesting.  Dick enjoyed a parfait made with limoncello, and I ordered Grand Marnier crème brulee.  It was a bit startling, as it arrived with 5” of flames creating the sugar crust.  I can’t remember a dish being delivered on fire before.

We returned to Marco Island, and after Dick returned the rental car, we spent a quiet evening.  We hoped to have an evening drink with our slip neighbours, fellow Loopers, but it didn’t work out, so we made plans to get together in Key West.

It was an early start for our second Gulf crossing.  This one would be daylight only, with plans to shorten the duration by running fast.  We ran the whole way at about 85% of WOT (wide open throttle, that is, the fastest the engines can go), giving us between 13 and 15 knots.  This was partly for comfort, but also to make sure that a prolonged journey at this speed was fine for the engines.  One unexpected challenge was the crab pots.  We did not expect them so far off shore and in water depths of 50 feet.  The pots are marked by floats, each about 6” to 8” in diameter.  Here they were mostly in groups of 3, but they were still very difficult to see.  They bob up and down in the waves, and between the sun glinting on the water and the small whitecaps, they were practically invisible.  Dick’s chair is further forward than mine, and of course he is taller, and with the bow slightly elevated at the speed we were travelling, I had no hope of seeing them except through the side window.  By then they are pretty close for Dick to find the next in the line and maneuver around it.  These crab pot floats are not something you want to just run over.  If you cut the line or damage the float, you are hurting the fisherman’s livelihood.  Also, you risk damage to your hull and running gear.  Get the line wrapped around the prop and you are instantly dead in the water.

We arrived at the marina in Key West by 3pm.  The basin is huge, but there are 4 separate marinas, and it is both crowded and higgledy piggledy.  Nine Lives was salt encrusted after her fast run, so Dick’s first order of business was a washdown of all the decks, railings, and windows.

In the evening, we joined fellow Loopers Beth and Calvin for dinner at a local steakhouse.  The food was very good, as was the service, and they were great company.  Their boat was behind us in Marco Island, and they made the same crossing a couple of hours after us.

We set out to explore Key West the next morning.  Dick booked 2 days for the hop-on-hop-off trolley tour, so we began by taking the full 90-minute round-trip tour of the island.

The Saturday before St Patrick’s Day is a big celebration in Key West, so students on spring break, cruise ship passengers, and hundreds of other tourists wandered the streets, in and out of the many bars, and generally enjoyed a raucous good time.  Crowds and drunks are never my thing, so I was reminded of being told by friends that you either love it or hate it when speaking of Key West.  I was well on the way to the latter until after dinner, as we walked back to the boat along quiet, leafy streets of gracious old houses with lovely tropical gardens. 

There were some interesting stories on the trolley tour.  One must always assume part fantasy, I have heard the most outrageous lies told by tour guides!

One story goes that in the mid 20th century, the island was populated by the navy and the shrimp fishermen.  These groups hated each other, but there was only one bar on the island at the time, so they found themselves drinking together after hard days at sea.  The bar, The Red Doors Saloon, was also known as “The Bucket of Blood”.  Fights broke out regularly, and brawling was a way of life.  Apparently, when you arrived at the bar, you were searched for weapons before being allowed to enter the premises.  If you didn’t have one, they gave you one – just to ensure that everyone had an equal chance. One can look up the true story.  Research shows that the building dates from 1868, and was at various times, a cigar factory, a ship’s chandlery, a grocery and hardware store, and a bar.  It was always a shrimper’s bar, and its reputation as a place of beatings, stabbings, assaults, and even quiet murders was well earned.  By 1972, the regulars had moved on and the bar was no longer viable and closed its doors.  Today it is an upscale lady’s boutique. There is another story about this building’s colourful history.  At one time, the upstairs was used as a bordello.  When the building was renovated, inside one of the upstairs walls were found a great many mens’ wallets.  Apparently, the ladies of the evening would rob their patrons and toss the empty wallets into a cavity in the wall.  The tour guide commented that given the clothing sold today in this shop, men are still leaving without the contents of their wallets.

In the 19th century, many Cubans came to the island to avoid troubles in their own country.  They brought with them their culture and cuisine, and also their chickens.  These ran loose, and inevitably multiplied.  Early in the morning, while I sat in the cockpit enjoying coffee, I could hear roosters crowing all over town.  I imagine that would not help much with the inevitable morning-after hangovers suffered by the St Patrick’s Day revelers. The chickens are feral, and are considered a nuisance by residents, but they are an important part of the island’s history and are now protected.

The southernmost part of USA is supposedly on the south side of the island.  There is a marker to designate the spot, and it is considered obligatory for visitors to have their picture taken in front of the large painted concrete buoy.  The queue was a block long.  We decided to pass on that particular experience.  In fact, the marker is not at the southernmost point of the US, it’s not even the southernmost point of Key West.  It is also not the remains of the Key West lighthouse that was wrecked in a hurricane.  It was set up as a tourist attraction in 1983 by the city.

When the navy first arrived, with the mission to clear out the pirates in the Caribbean, Key West was a one mile square island.  The navy needed more space, so they started dredging, using the coral they dug to fill in the wetlands and increase the size of the island.  By the time it had grown to 4 miles square, it became clear that they were dredging faster than the coral could renew, and doing irreparable damage to the only coral reef in United States waters.  The expansion stopped, and that end of the island is called “New Town”, as distinguished from “Old Town”, the site of the original settlement.

Sloppy Joe’s Bar officially opened in 1933, the day that Prohibition was repealed.  In fact, the island was full of speakeasies, the Island being a bastion of free-thinkers who considered that Prohibition was an amusing exercise dreamed up by the government.  It was Ernest Hemmingway’s favourite bar, and while it originally had several other names, Sloppy Joe’s was the one that stuck.

Dinner was at Café Marquesa, a beautiful, elegant restaurant that is part of a very upscale hotel, spread over several historic homes.  The owner (manager?) met every guest as they entered, and checked back with them during the meal to make sure everything was as expected.  The restaurant offers what is described as “gourmet coastal cuisine.”  The meal was excellent, starting with an interesting amuse bouche, a small beignet, filled with cotija cheese, resting on a lightly spicy chili sauce.  The courses and portions were designed to put together a 4-course meal, so Dick enjoyed what was very similar to a tasting menu.  I decided to try the salad to begin, and Dick had she crab soup.  After a small pasta dish with crawfish tails, Dick’s main course was duck breast, while I had filet mignon Oscar, topped with a small crab cake and served on a perfectly executed roesti potato cake.  We shared a dessert trio.

As we walked back along the beautiful streets of the residential part of the old town, we saw a hen shepherding her chicks across the road, watched by an interested golden retriever, fortunately well secured on his leash.

We sat in the cockpit and enjoyed a nightcap.  Clearly, the Key West spirit is contagious, because we decided a second glass was called for, and we stayed up long past Looper midnight!

We set off the next day to repeat the trolley tour – different guide, different stories, and sitting on the opposite side to get different pictures.

From my perspective, we probably couldn’t have chosen a worse week to be there.  It was hot – between temperatures over 80F and high humidity, it felt like 90F, and the sun beat down on the concrete sidewalks.  The St Patrick’s celebration and spring break combined to create my most disliked scenario, crowds and drunks.  The next week might have been a perfect time, cooler, quieter, but we are not there then.

The tour driver had a great sense of humour, but he was clearly hungover and did not have as many interesting stories as the previous day.  Afterwards, we did the Key West thing, and repaired to a bar for tropical beverages.

Our dinner plans were for a late meal at Hot Tin Roof, having reserved one of the coveted outside tables.  It was still hot and muggy, and on arrival we realized that the outside tables are on a balcony overlooking a popular bar with live music, all very loud!  We were able to get a table inside instead.  The meal started with delicious and unusual garlic toasts with Manchego butter.  Dick’s choices for the meal were good, but I found that my food was overwhelmed by the sauces.  The key lime pie for dessert made up for everything.  It was delicious and nothing like what we have had before.

We were not able to stay longer in the marina in Key West because they had a previous booking, and we don’t fit into the slips that were vacant.  Dick booked 3 nights at Perry Hotel Marina on Stock Island, which is across the bridge from Key West.  It would take just an hour, especially if we ran fast, to get there from Key West.  We knew that conditions would be bad.  The wind was howling.  Calvin helped us untie, if he hadn’t been there, we would have had trouble.  Dick had spoken with a couple of fishing boat captains, who confirmed his expectation that the worst would be just outside the harbour, with the wind coming from the north and the waves directly on the beam.  Once in the lee of Fleming Key, it would be better, and then as soon as we rounded the point and were on the south side of Key West we would have greater protection from the wind.

The “adventure” unfolded pretty much as predicted.  Dick was pleased with the way Nine Lives handled the conditions, although he commented that we have never had the waves splash the roof of the cockpit before.  Later, after we were safely tied up, the Coast Guard issued a small craft warning for the Florida Keys (by definition, Nine Lives is a small craft).  The winds were predicted to get worse through the day, hence our 8:30am departure in 25 knot winds.  On arrival, I felt that a large whiskey was required, but given that it was not even 10am, I settled for coffee.

We travelled through part of Hawk Channel, the passage that connects the Atlantic Ocean with the Gulf.  The Florida Reef Tract, the only living coral barrier reef in the continental USA, lies along the channel and helps to protect the Keys (and us) from heavy surf.  Pink shrimp are caught by shrimpers anchoring between the reef and the shore.  These shrimp are nocturnal, that is, they move around at night, and bury themselves in the sand and mud on the bottom during the day.  The story goes that they were discovered by accident, when a shrimp boat captain left his nets down in the water overnight, and when they were lifted in the morning, they were full of a new species of shrimp.  A nice story.  As we made our way along the south shore of Key West, we could see the fishing boats anchored, with their nets out but not down in the water.  One presumes that they had already lifted the nets and were processing the catch.

In the harbour we saw a saildrone, a very interesting unmanned vessel that Dick had read is being used by the Navy and by NOAA.  The Saildrone website is very interesting, these vessels can be used for infrastructure on oceans (think undersea cables), offshore energy surveys and development, ocean monitoring and climate science, and of course national security and defence.

We arrived at the Perry Hotel and Marina, quite relieved that we were there as planned and without extra drama.  It is a nice facility, with many features including swimming pool, fitness center, onsite restaurant and a bar with live music nightly, laundry, bath house, captains lounge, etc etc.  They even have an hourly shuttle to Key West Old Town, that runs until 10pm, so all of the restaurants of Key West are easily accessible.  We saw as we came in that there was an Endeavour Trawlercat Skylounge called Remember When.  The name was familiar, Dick thought we had met them on the Alligator River in North Carolina in 2017.  When we looked at our filed boat cards, there was their card, and Dick was quite right.  He chatted with them later, and they remembered us too.

We are planning a quiet few days here before leaving for Marathon.  A good time for laundry and boat chores, and a rest from the hustle and bustle of Key West.