There and Back Again, Key Largo, Islamorada
Posted: Sun Feb 15, 2026 7:21 pm
Departed Keylargo, bay side, not too early, with the idea to "both ways" the coming front. In the past, this stunt required a few days commitment at least. I was betting I could do it in two. Bailed out of Sunset Cove on Easterly 15 knot winds, main and brand new working jib which is still not cut correctly imho. My goal is to sail the boat as hard as possible given the conditions. Weekend warriors in powerboats make me feel like I'm Sailing on I-95 and no one slows down in narrow areas. Sailing seems to be becoming a novelty. It's quite possible my boat is the first actual sailboat some of these kids have seen. Making good way with winds on the quarter, exit Sunset Cove to the west and make a beeline to the small cut to shoreward of Pidgin Key. This saves a dogleg if following the ICW. Of course a dozen powerboats are converging and none slow down, and I'm not shy about taking up space. And the jet skies. I just do NOT see the appeal.
Oh hey, theres is the red marker I hit last year! Right off Tavernier creek. I'm doing 5 knots now, a collision with a marker at this speed would be an insurance claim, not merely a torn sail. Up until now I've had the board up, SOP for me now unless its really needed. The next short leg to the Toilet seat Pass entrance might need it, as its slightly to weather. While I am pondering this, it suddenly gets a lot more windy and the boat heels in a manner that my dogs both hate. I am obviously over canvassed on this point of sail but I just have to make the pass where I can bear off again. Looks like she'll do it without the board. There seems to be a large, abandoned motor yacht half blocking the pass but I can clear it. It's pretty nice looking boat to have red "Abandoned Vessel" sticker on it. Toilet seat pass is always a hoot, since there are new seats every time I traverse it. The west end of this pass seems shallower than the east, and I predictably drag the rudders over the same mud the powerboats are churning up. Im back off the wind again and once out of the shallows, boat speed picks up to five knots again. One of the reasons I like TS pass besides the visuals, is that I can usually sail it in the wind conditions I typically have when I make this trip. By comparison, I can NEVER sail Cowpens cut, no matter how favorable the winds outside the cut may be. Plus there are a lot of large powerboats that use Cowpens. In a few more miles, the entrance to Snake Creek is abeam. This is the only passage to the ocean side for sailboats or large boats, in a nearly 35 mile stretch, and its pretty busy, but thankfully I am not going in there. The bascule bridge only opens on the hour. I bet its a total cluster today, with everyone waiting around. There is one more shallow pass inside Cotton Key to negotiate before I arrive in the Lorelei/Worldwide Sportsman district. The outer anchrage is filled with the same mostly derelict boats, only a small number of the vessels present appear to be cruisers. Of note, one Very Ugly Catamaran, and a quite shipshape gaff rigged 22 foot sloop. I strike the jib, to make anchoring easier. I have a place I like, past most of the larger boats and closer to the little unnamed keys to the SW. I have to go behind VUC and the pretty sloop, and notice ANOTHER abandoned and sunken power yacht. Like wtf, its palatial. The paint is still shiny. What a waste. I wonder where I can get one. I drop the anchor in three ft of water, secure the boat, and take the dogs to the public access, which was rumored to be closed, but it appears they just replaced the barricade that was always there in some form. Its a dawn to dusk ramp with no trailer parking. But people in dinghies can still access it by walking around the gate. There is a huge pile of junk that looks like it was once a houseboat, nearby. One piece has a nice outboard bracket on it, but I have no need of it. Dinner back on the boat is some shrimp I netted several days ago.
The next morning is breezy. As expected, the wind had shifted more from the South, but was stronger than the forecast had mentioned. I contemplated staying a day, but I suspected that once the winds were out of the west, they would go to the NW and N, quickly. I wanted to be back in Key Largo by then. So, no lollygagging. I sure dont need a headsail today. Or maybe a double reefed main and a small jib. But I needed a full main to get the anchor up to get out of here, and reefing it and setting a jib once clear of the anchorage seemed like too much work. I never have a jib up while pulling the anchor. And the main does make the task easier. It's another lovely day for sailing and I'm the only one out here. Not as much powerboat traffic, as its choppier than yesterday. Except for at least 50 jetskies all in a line. The wind isn't quite as behind me as I thought it might be, and the broad reach with the full main up begins to feel like I'm needlessly lugging sail. In years past, the boat would just round up to let me know I was being lazy, but we fixed that nonsense. However, to be a bit more in control, as I tried to see if the abandoned boat that was partially obstructing Toiletseat Pass yesterday was now fulling obstructing it, I took the first reef. Then I jammed the boat into the wind and studied the situation with binoculars. I sure didn't want to get down there and have the pass blocked, under sail with 20 knots behind me. Was it clear? The boat HAD moved, now it looked like it was stuck on the other side of the pass. A few open fishermen roared past me. Well if they could make it, so could I. I followed them. I wondered if I could just claim that hulk for myself? Unlike the one down by the Lorelei, it was floating high and dry, and had expansive windows and a lot of stainless railing. Once back through the Pidgin key pass, I stuck very close to land, and admired the fancy houses and resorts that line the shore in this locale. Some had their very own tiny secluded beaches, and one place boasted a pristine, immaculate miniature catboat resting on a special boat lift. It looked as perfect as a ship in a bottle. The resorts had roped off beaches full of sunburned bathers and float loungers. This is one of my favorite passages, in the lee, just a stones throw away from some of the priciest real estate the Keys have to offer. There are also very many less powerboats, and the ones that are in this area are going slow, so close to swimming areas. There is nothing else of interest to the sailing cruiser here except for a kayak trail beach, accessible to non motorized craft. (Anchor and dinghy in) On anchoring in Tarpon Basin, I notice that VUC and pretty sloop are here also. They must have left the Lorelei/Worldwide Sportsman district earlier than I did, because they didn't pass me. The wind dropped off later and was now Westerly. Tomorrow I bet it will be from the North.
Oh hey, theres is the red marker I hit last year! Right off Tavernier creek. I'm doing 5 knots now, a collision with a marker at this speed would be an insurance claim, not merely a torn sail. Up until now I've had the board up, SOP for me now unless its really needed. The next short leg to the Toilet seat Pass entrance might need it, as its slightly to weather. While I am pondering this, it suddenly gets a lot more windy and the boat heels in a manner that my dogs both hate. I am obviously over canvassed on this point of sail but I just have to make the pass where I can bear off again. Looks like she'll do it without the board. There seems to be a large, abandoned motor yacht half blocking the pass but I can clear it. It's pretty nice looking boat to have red "Abandoned Vessel" sticker on it. Toilet seat pass is always a hoot, since there are new seats every time I traverse it. The west end of this pass seems shallower than the east, and I predictably drag the rudders over the same mud the powerboats are churning up. Im back off the wind again and once out of the shallows, boat speed picks up to five knots again. One of the reasons I like TS pass besides the visuals, is that I can usually sail it in the wind conditions I typically have when I make this trip. By comparison, I can NEVER sail Cowpens cut, no matter how favorable the winds outside the cut may be. Plus there are a lot of large powerboats that use Cowpens. In a few more miles, the entrance to Snake Creek is abeam. This is the only passage to the ocean side for sailboats or large boats, in a nearly 35 mile stretch, and its pretty busy, but thankfully I am not going in there. The bascule bridge only opens on the hour. I bet its a total cluster today, with everyone waiting around. There is one more shallow pass inside Cotton Key to negotiate before I arrive in the Lorelei/Worldwide Sportsman district. The outer anchrage is filled with the same mostly derelict boats, only a small number of the vessels present appear to be cruisers. Of note, one Very Ugly Catamaran, and a quite shipshape gaff rigged 22 foot sloop. I strike the jib, to make anchoring easier. I have a place I like, past most of the larger boats and closer to the little unnamed keys to the SW. I have to go behind VUC and the pretty sloop, and notice ANOTHER abandoned and sunken power yacht. Like wtf, its palatial. The paint is still shiny. What a waste. I wonder where I can get one. I drop the anchor in three ft of water, secure the boat, and take the dogs to the public access, which was rumored to be closed, but it appears they just replaced the barricade that was always there in some form. Its a dawn to dusk ramp with no trailer parking. But people in dinghies can still access it by walking around the gate. There is a huge pile of junk that looks like it was once a houseboat, nearby. One piece has a nice outboard bracket on it, but I have no need of it. Dinner back on the boat is some shrimp I netted several days ago.
The next morning is breezy. As expected, the wind had shifted more from the South, but was stronger than the forecast had mentioned. I contemplated staying a day, but I suspected that once the winds were out of the west, they would go to the NW and N, quickly. I wanted to be back in Key Largo by then. So, no lollygagging. I sure dont need a headsail today. Or maybe a double reefed main and a small jib. But I needed a full main to get the anchor up to get out of here, and reefing it and setting a jib once clear of the anchorage seemed like too much work. I never have a jib up while pulling the anchor. And the main does make the task easier. It's another lovely day for sailing and I'm the only one out here. Not as much powerboat traffic, as its choppier than yesterday. Except for at least 50 jetskies all in a line. The wind isn't quite as behind me as I thought it might be, and the broad reach with the full main up begins to feel like I'm needlessly lugging sail. In years past, the boat would just round up to let me know I was being lazy, but we fixed that nonsense. However, to be a bit more in control, as I tried to see if the abandoned boat that was partially obstructing Toiletseat Pass yesterday was now fulling obstructing it, I took the first reef. Then I jammed the boat into the wind and studied the situation with binoculars. I sure didn't want to get down there and have the pass blocked, under sail with 20 knots behind me. Was it clear? The boat HAD moved, now it looked like it was stuck on the other side of the pass. A few open fishermen roared past me. Well if they could make it, so could I. I followed them. I wondered if I could just claim that hulk for myself? Unlike the one down by the Lorelei, it was floating high and dry, and had expansive windows and a lot of stainless railing. Once back through the Pidgin key pass, I stuck very close to land, and admired the fancy houses and resorts that line the shore in this locale. Some had their very own tiny secluded beaches, and one place boasted a pristine, immaculate miniature catboat resting on a special boat lift. It looked as perfect as a ship in a bottle. The resorts had roped off beaches full of sunburned bathers and float loungers. This is one of my favorite passages, in the lee, just a stones throw away from some of the priciest real estate the Keys have to offer. There are also very many less powerboats, and the ones that are in this area are going slow, so close to swimming areas. There is nothing else of interest to the sailing cruiser here except for a kayak trail beach, accessible to non motorized craft. (Anchor and dinghy in) On anchoring in Tarpon Basin, I notice that VUC and pretty sloop are here also. They must have left the Lorelei/Worldwide Sportsman district earlier than I did, because they didn't pass me. The wind dropped off later and was now Westerly. Tomorrow I bet it will be from the North.
