The One With Our Gulf Crossing and 20/20 Hindsight

Without a doubt, one of the most anticipated (and nerve-wracking) parts of the Great Loop is the Gulf Crossing.

150+ miles of open water. No land in sight for hours. Possible weather issues. Out of cell range.

This is the stretch of the Great Loop that puts your boating skills to the test. Along with your mental toughness!

Preparing for the Gulf crossing is half the battle. And, if done properly it will ensure a great experience. Quite honestly, we did a lot of things right. But we also did several things wrong.

Here’s the full scoop on our experience…

First, we had to get there! In my last post I detailed our trip down the inland rivers to the Gulf (check it out HERE if you missed it.) Once we made it to salt water, we still had some tricky areas to traverse before being ready to cross.

Unfortunately it was a tough year for the Panhandle. 2 different hurricanes hit the area- one causing more wind damage, and the other causing more water damage. The combination left many marinas unable to accommodate boats.

We spent 1 night in Mobile Bay before moving across to Fairhope for a week.

From there we went to a marina in Gulf Shores, then an anchorage behind Destin, before finally making our way to Carrabelle.

Carrabelle is one of two prefered places to cross- the other spot being Apalachicola.

One of the first questions I asked when we began talking about The Great Loop is “Why do we have to do a Gulf crossing? Why can’t we just hug the coast of Florida?”

In short, the water depth in that area is very unreliable and shallow. Can it be done? Yes. But it can be very tricky and stressful. Additionally, there are not many amenities for bigger boats (no marinas, fuel, etc.)

Unfortunately for those of us who prefer to see land, crossing is the best option.

For us, being in Carrabelle was both relaxing and anxiety inducing. With over 4,000 miles under our belt we felt ready for the crossing. However, we wanted to do our do diligence preparing for our furthest journey on open water.

Not only did we need to get a little work done before leaving. We also had to wait for an ideal weather-window.

In boating you can make plans, but they need to be flexible.

We initially planned to cross on a Saturday. For the week leading up to that day, it looked like the best weather. However, on Wednesday the forecast changed. Saturday looked okay, and Friday looked perfect.

With something as big as the crossing, you want perfect.

Another quirk to know about the Gulf crossing is that many boaters (specifically Loopers) go overnight. The thought process behind this has more to do with the arrival than the departure.

Some boats have a top speed between 8-10 mph. Even if boats can go faster, many choose to stay in that range for fuel efficiency. Doing the math, at that speed it takes about 15-20 hours to make it across.

Leaving Carrabelle mid-afternoon and traveling through the night allows boaters to arrive in daylight.

We debated this option. However, we chose the less popular crossing method I like to call “get it over with quickly.”

With our buddy boat we devised a plan to leave Carrabelle around 5:30AM, run at a high speed until lunchtime, and then slow down to arrive in Clearwater ahead of sunset.

In theory, our plan worked well.

The day before our crossing we did all the things we deemed important. We filed a float plan (more on that in a minute) with a detailed description of our itinerary. We did engine checks. And re-checked the weather a million times.

Several other boats in the marina departed for an overnight crossing. We enjoyed one final beautiful Carrabelle sunset and went out to dinner.

At some point I turned the corner from being overconfident and ready to go, to completely overcome with anxiety.

Adding to the stress, the weather alerts went off on our phones at about 10PM notifying us of a dense fog warning in our area. At that point we made the (bad) decision to push our departure time back to 7 to avoid the fog. Hindsight is always 20/20!

We prayed a lot that night for our crossing. And didn’t get much sleep.

Since I was wide awake I decided to check out the fog situation around 5AM, when we should have been starting our engines. It was crystal clear. Brent and I debated calling our buddy boat, but decided to let them sleep.

Little did we know, they were all awake (they were on the other side of the marina so we had no way of knowing.) They’d had a scare overnight and evacuated their boat due to a gas smell.

When we finally touched base with them, they were not sure we were going to be able to depart. They spent some time troubleshooting the issue and finally gave the green light.

We pulled out of Carrabelle just as the sun began to peak over the horizon.

The first hour was everything we dreamed it would be. A gorgeous sunrise, dolphins jumping in our wake, and very calm water.

But then it wasn’t.

The waves kicked up, big time. It wasn’t that they were that big (maybe 3-4 feet with an occasional 5.) We just weren’t prepared.

The forecast said 1 foot waves. Every boater in the area supported Friday being an ideal day to cross. And, unfortunately, we made the mistake of preparing our boat (and ourselves) based on the forecast.

Needless to say, we were scrambling while underway to secure everything on our boat.

The bigger waves also threw off our speed. We’d planned to run about 22 mph for the first 5 hours to get a huge bulk of the milage behind us before lunch. Unfortunately, in those conditions we could only do about 10mph.

At that speed, we were going to arrive at 2AM. Not good!

For about an hour we tried to increase our speed until we ultimately clogged the port fuel filter. Really not good!

Around noon we were chatting on the radio with our buddy boat. A series of things had gone wrong that day- starting with our decision to delay because of the fog forecast. We started making a list of things we’ll do differently next time.

Our biggest Gulf crossing takeaway: Prepare for the worst. Expect the worst. Be pleasantly surprised if it turns out better.

Thankfully shortly after lunch the wind and waves calmed down significantly. We were able to run enough fuel through the port engine to miraculously unclog it. And at that point we ran full throttle (literally) to Clearwater.

At some point we regained our cell signal and reached out to our emergency contacts letting them know we were arriving later than planned. However, we were safe and land was in sight.

We docked right as the sun set.

Crossing 153 miles from Carrabelle to Clearwater was a huge accomplishment under our belt!

One of my biggest regrets of the whole day was not having champagne in the fridge so we could toast the milestone. (Don’t worry, we improvised!)

The funny thing was after arriving there were so many mixed feelings. Our buddy boat (Full Count) couldn’t wait to get off their boat. They opted for dinner out and spent as many hours off the boat as they could that night.

On the other hand, I wanted to go straight to bed. It had been a mentally exhausting day. But I knew we needed food. The crock pot meal I’d planned to throw together while underway obviously hadn’t happened. We walked to a pizza place and brought it back to the boat.

We checked in with several of the boats that left Carrabelle the afternoon before us. They also faced conditions a bit worse than expected, but everyone arrived safely.

That night a big group of Loopers (at least 8 of us crossed in that 24 hour period) went to bed grateful to have the gulf crossing behind us!

And now, for all the things we know in hindsight of Gulf crossing that we’ll consider next time:


This might go without saying, but it’s not a good idea to set out if the forecast isn’t ideal. We like the app Windy to give us hour by hour reports on the wave height and spacing, as well as the wind strength and direction.


We made this mistake! Our fuel filters were not due a change and visually they looked fine. In hindsight, we really regretted not treating our fuel tanks and changing the filters. It wouldn’t have been a huge deal, but it would have saved some stress on the crossing.


When we received a report of fog, we completely altered our plans. Even before the weather actually changed! In hindsight, we should have left our alarms set and made any changes after doing a visual check that morning.

Loosing 2 hours that morning to non-existent fog almost cost us the ability to dock in daylight.


I can not tell you how comforting it was to have another boat in sight when we couldn’t see land. I knew that if the worst happened on our boat, we had a buddy looking out for us (and vice versa!) We were also able to help each other avoid crab pots and make wise decisions as to our speed.


A float plan is a document that you fill out with specific information about your boat and passengers. You also include a detailed itinerary including your departure and arrival ports, as well as the speed you anticipate traveling.

All of this information would help the Coast Guard locate you easier in an emergency.

We sent our float plan to two very experienced boating friends and told them to call the Coast Guard if they hadn’t heard from us by 6PM.

Knowing people were expecting us and know where to find us gave me great peace of mind during our Gulf crossing.


We had a solid plan. But in order for it to work, it needed to be executed perfectly. Mid-crossing we began to consider alternative routes that would have gotten us to land, or at least cell range before dark.


Our buddy boat learned this the hard way. They filled their fuel the night before the crossing and ended up having an issue.

Similarly, it’s wise to do all oil changes, and boat maintenance with a few days to spare just in case it doesn’t go as planned.


This was probably our biggest mistake of the whole crossing. We planned for a perfect day. I barely prepped the cabin. I didn’t pre-make any lunch (which we typically do when we anticipate a rougher day on the water.) And we had no sea-sick remedies on hand.

I’m not saying things will always be worse than you expect. However, if you plan for the worst you’ll have a much more enjoyable day either way!

As you can probably tell, there’s a lot we would do differently on our next gulf crossing.

One of the best parts about boating is that you can learn from your mistakes and make adjustments on future trips. We’ve already put several of these into practice.

Thanks for following along on our crazy adventures. This crossing was one of the craziest and most adventurous! You may also enjoy reading:

Montana Misadventure: Mistakes We Won’t Make Again

The One Where We Decided To Live On A Boat

The One With All Things Remote: Living, Working and Learning

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  1. Mendy on January 6, 2021 at 4:05 pm

    We are preparing for this exact crossing now. Great article! Thank you for sharing

    • momwithamap on January 9, 2021 at 7:29 pm

      Thank you! Hope this helps you out. Enjoy every second of it- it’s a gorgeous ride!

  2. onFIREfamily on January 6, 2021 at 5:23 pm

    WOW! Thank you for sharing the story of your crossing experience and especially all of your lessons learned! The more real accounts we read, the more we feel we’ll be as prepared as possible when we get there. Thanks for sharing!

    • momwithamap on January 12, 2021 at 1:39 pm

      Absolutely! I hope these lessons help others. As I mentioned, a few times, we should have done a better job preparing. After crossing Lake Michigan in rough conditions, I relied way too much on the “perfect” weather report and we were caught off guard. It would have been a lot more fun if we’d done a few things to prepare! When do you guys expect to cross?

      • onFIREfamily on January 14, 2021 at 5:08 pm

        We don’t start looping until 2022 so we’re just researching and preparing now. Your posts have been a valuable resource so far! Thanks for all the work you put into this effort!

  3. Megan Weaver on January 12, 2021 at 2:15 am

    This is all so fascinating-I remember talking to you right after y’all did this, but I had no idea just what an accomplishment it was. Champagne for sure next time ??

    • momwithamap on January 12, 2021 at 1:36 pm

      Aww yeah! I don’t even think I made a big enough deal of this before hand (obviously- I really should have prepared!)…definitely champagne next time!

  4. […] The One With Our Gulf Crossing and 20/20 Hindsight […]

  5. Jean Coleman on January 17, 2021 at 9:06 pm

    Great description and useful advice! We learned in Canada to batten everything down any time we were going to be in open water. It takes prep some time but, reduces stress when weather conditions take an unexpected turn. We’ve crossed the Gulf a number of times now, mostly in the slower 10 kt speed boats. Our BEST and most memorable crossing happened when we left Carabelle at midnight and had an amazing night – crystal clear and you couldn’t tell where the starry sky ended and the water began…it was that smooth! That timing took us close to crap pot territory as the sun was rising and we came into Tarpon Springs with good light and sunny weather. The other crossings have not been as nice…one time we crossed with zero visibility due to fog (Not a lot different than driving at night) which only became super stressful when we neared Tarpon and could only see the crab pots sliding by close to the hull! I agree, wait for a good forecast but be prepared for it to change!

    • momwithamap on January 20, 2021 at 3:39 pm

      Yes- prepping is so worth it! From now on we will always do it, regardless of the forecast! I can’t imagine crossing the Gulf in fog. We drove from Atlantic City to NYC in zero visibility fog (we had to get out of the anchorage at high tide and we assumed it would burn off quickly.) It was very stressful- not because of crab pots but because there were lots of smaller fishing boats heading out to sea that crossed our path with very little warning. In two cases we just saw their wake in our path, but never even picked up the boats on radar. Crazy! But making memories is what it’s all about!

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