The Crossing

  • Apalachicola to Clearwater Beach, Florida

A portion of the Great Loop route requires crossing the Gulf of Mexico. Individual loopers decide whether they want to cross during the day or do a crossing that includes overnight. A fast boat can complete the crossing in a day by leaving Carrabelle at first light and taking a direct shot toward Tarpon Springs. Most loopers, certainly those with full displacement trawlers, choose to make a night time crossing for several reasons but the most prominent consideration is the ability to complete the trip given short November or December days. Although our boat is fast enough to make the crossing during the day we opted to go slow and enjoy the night crossing.

Monday / Tuesday good weather window 1 source out of several we monitor

Weather is a major factor when making the crossing. Perhaps for someone in a sport fisherman style boat designed for rough water they don’t need to be quite as concerned but for the typical looper who has all of their possessions necessary for daily living aboard a boat that is designed for comfort it is a major concern. Think 4-wheel drive truck versus family sedan, one is great for bouncing through muddy fields but do you really want to drive it for a long trip? 

Typically there are only a few days/nights that a crossing can be comfortably made each month. While we were sitting at the The Wharf in Orange Beach, Alabama, we learned of a possible crossing date where the weather was going to cooperate the following week. If we didn’t arrive in time we would need to wait for the next crossing which was projected 10 days later. While in Pensacola the weather window continued to be favorable. We decided to make a run for it and set a fairly aggressive timeline to bring us to Carrabelle Florida which is the typical port of departure for a crossing.

We were limited by several factors and in this case it was daylight to complete the panhandle portion of the journey as well as our specific need to end up in a marina every night. Pressing to make the crossing during the good weather window, Now or Never decided to bypass motoring to Carabelle and get set from Apalachicola.

Carrabelle’s Police Station!

We would however, miss the world’s smallest police station on this trip by bypassing Carrabelle. We had the pleasure of visiting the station several years ago.

The last few days as we were moving through the panhandle, we had been communicating with our good friend Doug, who has wanted to make the overnight crossing voyage since he first heard of our adventure. It looked like the stars were aligning with his schedule and he had about a five day window to travel and join us within the weather window. But, what to do with his truck since he would end up close to 200 miles by sea or over 300 miles by car at the end of the voyage? Since we had not done our due diligence in preparing Remy for this trip and pottying aboard, and frustrations for all on the river, Tasha volunteered to take Remy and drive the route while David and Doug handled the crossing. Doug’s boating experience and resourcefulness would certainly be a welcome addition to this voyage and the captain. In addition, Remy was about to have a much smoother trip.

After driving all day from Louisville, Kentucky, Doug joined the crew late the night before the crossing. Tasha and Remy loaded up and pulled out of town the next morning for their 5+ hour drive to Clearwater. With a large group making the crossing (12+ boats), Tarpon Springs and Dunedin had no room in their marinas. Those are typical landing spots for boats making the crossing. We found dockage at Clearwater Beach Mariana where several other loopers had already set up camp from their crossing the week prior.

The day began in Apalachicola and the crew would add the 24 mile journey to Carrabelle onto the crossing. After fueling, Now or Never made the casual trip to Carrabelle for a 3PM departure. Timing the arrival on the West coast of Florida is imperative so one isn’t staring into the rising sun preventing the from seeing the crab pots from the morning glare. Crab pots are like boater land mines as they are randomly scattered throughout the Gulf and they are easily sucked into your propellers which will certainly disable your engine should you run over them. If that happens your only option is to jump overboard with a sharp knife and start cutting the lodged line from your running gear underneath the boat. While David dreams of being like one of our nation’s special forces boldly jumping into the water with a knife in his teeth and fighting off sharks while he frees our vessel from the treacherous forces which restrain it, reality sets in and he knows he wouldn’t want want to do that. (Have you ever seen Jaw’s?)  

Now or Never leaving Dog Island to head southeast

Making the way to Carrabelle a little before 2 pm, the crew dropped anchor to take a relaxing break and eat lunch before starting the next leg. At 3:15 pm, the engines were fired up and Now or Never pulled into the Gulf of Mexico.

As promised by our weather expert Eddie, the seas looked calm as Now or Never entered the waters and the winds were 4 mph from the east. Perfect! As the crew motored into the Gulf with a handful of other boats the realization that the dream was morphing into reality began to take hold. As Now or Never continued on, the coast was beginning to disappear. Although with extensive planning and prepping for this journey, one begins to question . . . is all optimal with the running gear, and was the research sufficient as to what we are going to experience?


The captain’s anxiety continued to increase as the sun was setting and land was no longer in sight. Two boats were off to port but were headed in another direction (towards Tarpon Springs). From radioing them, it was learned that their plan was to go straight toward the west coast and then turn south once nearing shore. The course David planned was different in that it set a straight SouthEastSouth course that was shorter but would take the vessel much further offshore. The crew was learning that they were going to be all alone if they didn’t change course. Nervously, David asked Doug (since it was his safety as well) if the course should be changed to be part of the group? Doug questioned if the other boaters had ever made the crossing. As David did not know that answer, Doug indicated that he felt they should hold the course that was plotted. David appreciated Doug’s belief in his abilities and hoped he was correct!

An eerie fog was surrounding the boat as the sun continued to set. The conversation turned to movies like The Final Countdown and The Fog. It reminded David of being a child and watching scary movies on a black and white television in the dark. It was time to change the topic. As they watched the sun drop over the horizon the feeling of being alone in a tiny boat in a great sea was obvious. At midnight, while plotting out the position of Now or Never, the chart plotter indicated the boat was now in 84′ of water and the nearest land was over 70 miles away in any direction. The boats that were seen earlier were no longer in sight but were still on radar and slowly continued their different course. At one point Doug saw a flashing red light in the darkness ahead. Turns out it was a 120 foot tower out in the middle of the Gulf. Who would do that? It was discovered to be a military tower. It was steered around, as if there were a choice. Nonetheless it inspired the crew to keep a better lookout for the rest of the trip.

David’s vision of this trip had always been crossing in calm water, warm temperatures, and a sky full of stars. Against all odds it was just that. The seas were flat, the temperature was comfortable, and the stars were abundant. At one point the International Space Station was seen flying overhead and Venus looked like a spotlight.

About 3:00 am the winds picked up to about 12 miles per hour. Not bad, but they created following waves that make steering a straight course difficult. The autopilot got quite a workout as you can see in the video. The bar above the word Menu shows the rudder position and you can see the rudder being shifted back and forth to maintain the course. This was a great time to have autopilot and not have to steer the course by hand.

The autopilot bouncing through the gulf!

It was at this time, the crew noticed that the other boats that were making the crossing had sailed out of radar sight and the solace previously given by their presence was gone. Phones no longer worked nor did internet connections. It wasn’t long and the bright moon set. It was officially dark! A couple of shooting stars flew through the sky. Can you guess what the captain was wishing about right then?

Moon rises and sets

With the sun & the moon both gone and with no city light pollution it gets really dark out there! Here’s a shot from the helm and as you can see there isn’t much to see. (Again, a reminder that it was 70 miles to the closest land and no communications were working on board).

Nothing to see but navigational aids

It was just a matter of holding on and watching the clock tick away while awaiting first light. The steady drone of those wonderful hometown Cummins engines gave a secure feeling as the crew continued to motor further into the darkness. The course was altered a couple of times over the evening so that it would make the eastern turn at least 10 miles off shore to avoid those crab pots. The crew joked and hoped that when the sun came up, land would be seen and they were not headed to Cuba.

Now or Never’s course across the gulf

The sun did come up as planned, and yes the crab pots where there. The crew, a bit punchy from being up way too long, stared anxiously into the water to avoid them as they are not easy to see especially if you arrive too early and have to deal with the sun on the horizon. Can you see this one? Now or Never dodged them all the way.

Now or Never and crew arrived safe and sound a little over 24 hours after departing and were only 15 minutes off the projected time planned. Blessed with good weather, good electronics, and of course a bit of good luck. The training received over the years from the American Great Looper’s Association (AGLCA) made this trip very doable and enjoyable.

Now or Never arriving at Clearwater Beach- looking good with palm trees!
Remy back on board in Clearwater with the crossing crew
Celebratory crossing evening

We “did it my/our way” as Frank would say by adding the extra miles both before and after the typical looper crossing. Memories to last for many years. Now it’s time to enjoy the beach.

Cheers! D, T & R

6 thoughts on “The Crossing”

  1. Very familiar with the Clearwater Beach marina. Dick, Alvia , Fred and Jay vacationed on the island evey summer from 1954 to 1960. It seems like every afternoon we would walk over to the marina to see the catches of the charter fishing boats.

    Once again thank you Tasha for including us on your adventure. We hope you celebrated your birthday and received our birthday wish.

    Cousin Fred & Marguerite

    1. What grand memories! The charter boats still coming in the marina each night and we have viewed their catches too! Thank you fof the birthday wishes – we were just getting settled in to Clearwater and celebrated with our first west coast Florida sunset!

  2. Douglas D. Ford

    Wouldn’t have missed it! Great job with the pictures, video and documentary!

    1. Thank you!! – So glad you were able to experience it with David – and Remy enjoyed the truck ride!

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