Dinner Key to Key West, FL

This will be a rather lengthy post as we’ve been covering a lot of miles in a short amount of time, and I haven’t had access to internet to post.  Thanks for bearing with me!

On March 8, we left the Dinner Key mooring field for a short hop across Biscayne Bay to an anchorage off Key Biscayne.  We had a long day the next day, and any forward progress would make it that much easier.

The anchorage is relatively close to the Key Biscayne Yacht Club and is normally packed with boats on the weekends, but fortunately for us it was midweek.  When we arrived there were a couple of large motor yachts anchored for the day, and as the day wore on, many more motorboats of various sizes arrived.  The anchorage is known as a party spot due to its proximity to Miami and a walkable sandbar that appears at low tide.  You have to take the loud music and jet skis in stride during the day, but everyone was having such a great time that we couldn’t help but smile.  We did make one sociological determination:  at least on “party megayachts,” the ratio of men to women is approximately 1:10.

This day was 1 hour for 4.1 nm.

On March 9, we had a great day of motorsailing with the main and genoa from our anchorage at Key Biscayne to an anchorage at Rodriguez Key.  When we left Key Biscayne, we went through the Stiltville Channel.  This is the site of a clutch of get-away/party homes built on pilings in the water in what is now Biscayne National Park.  The buildings started appearing in the 1930’s, and at Stiltville’s height, there were 27 houses.  Time and weather destroyed many, and the seven remaining houses are managed by the Stiltsville Trust.




We took Hawk Channel along the ocean side of the keys.  No more ICW! It’s all offshore from here.  As the day progressed, we went from close haul to close reach to beam reach to broad reach.  We didn’t see much boat traffic.  We saw some more of the little sailing jellyfish, and the Captain saw a sea turtle (not sure what kind).

We anchored on the southeast side of Rodriguez Key to take advantage of the island’s protection from some northerly winds.  By nightfall, there were seven boats in addition to ours.  It was a quiet and peaceful anchorage.

This day was 9 ½ hours for 49.0 nm.

On March 10, we motorsailed from Rodriguez Key to Marathon.  We had the main and staysail out all day, although the winds were light.  The water got progressively clearer and more turquoise as we moved south.


Marathon has a personal significance for us even though we had never been there.  Years ago when saving money for a boat and planning our future, we would watch the Boot Key webcams that cover the mooring field (www.ci.marathon.fl.us/government/departments/marina-and-ports/marina-webcam/).  It became a little joke for us to guess whether a group was doing yoga in the Tiki Hut, whether the poop boats were out servicing the field, and what was happening in general.  To see the marina in person had turned into a challenge that we were eager to cross off our list.

Marathon is popularly known as a cruiser’s haven.  The city has a large mooring field for which it charges a ridiculously low monthly rate (in the $300 range).  Marathon itself has all of the restaurants and stores that anyone could want.  Many cruisers come here for the winter season, and the mooring field is also a popular choice for locals who would like to live more cheaply than on land.  For that reason it’s quite difficult to get a mooring ball much past December.  The city does have a waiting list, but you must come into the office in person to get put on it.  We had been calling ahead for a couple of weeks to check on the status of the mooring ball waiting list; it had gone from 40 a couple of weeks ago to 15 as we were nearing Marathon.

There are two main anchorages in Marathon; one is on the outer edge of the island on the west side, and one is inside the key itself through a channel.  This is where the city mooring field is located.  When we arrived in Marathon we went to the inside anchorage and immediately rejected it.  It is too tightly packed with boats for our liking.  We chose the outside anchorage and were very happy with our choice.  We had a great view of Seven Mile Bridge and the mangroves covering Boot Key.

This day was 9 hours for 48.3 nm.

The next day we went ashore, got fuel and water in our jerry jugs at Burdine’s Waterfront.


Burdine’s, home of fuel, water, ice, souvenirs, and an awesome upstairs restaurant called Chiki Tiki.

We also got on the city mooring field list, and checked out the facilities.  They are utilitarian but cover all of the bases:  large public space with free wifi, a couple of small lounges with TVs, book exchange, bicycles, laundry, showers, project rooms, and plenty of trash and recycling containers.


We got a kick out of the repurposed theater chairs in the TV “lounges.”

“Town” is essentially strung along both sides of Overseas Highway, so we walked a couple of miles up the road to assess what was there.  We had a great lunch at El Molcajete (the chilaquiles and chicken fajitas were fantastic) and a cortadito pick-me-up at a small Cuban food stand.


Being of the female persuasion, I didn’t feel I was allowed in this store.  But I’m sure it was awesome.

We wanted to keep going to Key West, and some heavy winds were predicted to begin moving in for a few days.  After analyzing the anchorages in Key West and comparing them to where we were in Marathon, we decided they were equal in terms of protection.  That being said, we decided to push on to Key West.

On March 12, we motorsailed to Key West with the main and staysail.  The winds were very light and fickle, but the trip was gorgeous.  It was sunny and hot and quintessentially “Keys.”  It was an uneventful day of sailing that culminated in an unexpected drama.

Not surprisingly, Key West is quite a popular place for boaters (this is an understatement).  It is also very expensive at marinas, and the one city mooring field has been full for ages.  The geography of the area leaves only two viable areas for anchoring:  off of Wisteria Island, which is very shallow, and off of Fleming Key.  We were hoping to anchor on the northern end of Fleming Key in order to stay away from the ripping current in Fleming Key Cut and avoid some of the boat traffic nearer to Key West Bight.  Our research into the anchoring options kept turning up complaints about the anchorages—the number of derelict boats, the homemade moorings, bad holding, constant traffic, etc.  We discounted the complaints somewhat as people tend to complain more than they compliment.

They were right.  The anchorage off of Fleming Key was crammed with boats, many of them clearly abandoned.  Boats on homemade moorings littered the north end of the field, making it off limits to us as the boats would not swing as we would swing (and heaven only knows the condition of the anchor and line they were using).  The anchorage itself was quite deep, up to 30 feet in places, which meant that we couldn’t put out the scope that we needed without potentially running into other boats.  We tried four or five spots and then found a spot about midway up the field that we thought might work.  We dropped the anchor and started putting out the 7:1 scope we’d need for windy conditions.  At a fraction of that, it was clear that we were going to run into the boat behind us if we kept going.  We raised anchor, moved up, and dropped the anchor again.  We got a scope of 5:1, and that was all it was going to support.  We gritted our teeth and accepted that, and then as we were backing down hard on the anchor to set it, it became clear that we were dragging.  This was the first time that our Rocna had dragged, and we took that as a sign.

We left the Fleming Key anchorage, went across the channel to Wisteria Island, and found a spot in Man of War Harbor that was 9.6 feet deep.  We dropped the anchor with the proper scope, held our breath as we backed down on it, and practically collapsed in relief when it held.  It took us an hour and a half to do what normally takes us 20 minutes, and we were beat.  We were still near some dodgy-looking boats and also close to some very shoal water, but at this point, beggars couldn’t be choosers.


This day was 8 ½ hours for 46 nm.

The next day, the coming high wind forecast had changed to the direction that offered the most exposure.  Since we were less than thrilled with our potential exposure, the number of derelict boats around us, and the constant wakes from high speed passers-by, we decided to cut our Key West trip short and just spend the day, returning to Marathon (and better protection if the forecast held up) on March 14.

We dinghied over to Key West Bight and got fuel at Conch Harbor.  It’s always funny getting our 5 or 10 gallons of diesel at a place that’s servicing sport fishers; the two boats that were there got $1200 and $1600 in fuel compared to our $15.  We then left the dinghy at the Key West municipal marina ($6.50 for a day pass) and went to Pepe’s Restaurant for an anniversary of sorts.  We went to Pepe’s for breakfast on our honeymoon almost 13 years ago, and we were hoping it was still as good.  It was, and it appeared that nothing at all had changed about it or the good food that we remembered.


We did the tourist thing, walking along Duval Street, Mallory Square, and associated areas.  We saw the chickens everywhere, the constant flocks of motorscooters, and the endless bars.


Who doesn’t take their parrot to the hardware store in a backpack?

What struck us most is how Key West has changed to cater to the cruise ship vacationers.  It was disappointing to see what had been the sort of grimy, free-spirited independence of the place spiffed up, mainstreamed, and marketed for popular consumption.  Even the weirdos were self-consciously, look-at-me weird as opposed to just authentically FU weird.  One day was all we needed, and we were ready to head on out.

Next stop:  back to Marathon.