Cruising the Great Loop is an adventure many boaters spend their lives dreaming about. Most of them realize they have countless things to learn before casting off on an adventure of this scale. Ask 10 loopers about the lessons learned on the Great Loop, and you’ll likely get 10 different answers. Yet, certain themes tend to surface repeatedly.
The best way to embark on any new challenge is to learn from others’ mistakes and narrow your own margin for error in the process. Here are some lessons boaters have learned during their time on the more than 6,000 miles of the Great Loop.
Of all the lessons Great Loopers carry home from their journey, this one seems to come up most often. Slow down. Do not be tempted to make this journey a race to the finish line. This is especially true if you’re still operating on land time. Schedules, deadlines, and productivity expectations keep us moving at an unsustainable pace. Life on the water, however, flows at a much slower pace.
I could spend years exploring the Intracoastal Waterway. I find that little else can beat the experience of waking up on the water while the fog slowly reveals the calm and quiet surroundings. The air feels rich as the landscape comes to life with the sun. The ecosystems are unique. The scenery beckons for you to stop and take it all in. Time has a way of pausing in perfect interludes of quiet and subtle perfection.
It’s not like this in the Caribbean, on the ocean, or anywhere else I have spent time on the water. It’s a singular experience, and I treasure every moment I have spent exploring it.
Time is everything on the water. While you may be tempted to rush the experience, stop, slow down, and resist the urge. Like so many loopers, I rushed my time on the ICW. Looking back, I should have embraced the journey and all the little moments that were lost to the hustle and hurry.
My advice: Enjoy yourself. Make friends, eat local food, and get to know the communities you travel in. For most boaters, this is a once-in-a-lifetime experience. Don’t rush it!
Believe me, by the end of your trip, you will be docking like a pro. But give yourself some grace in the beginning. The learning curve is steep. In the early days, you will almost certainly make a few embarrassing mistakes. Don’t be discouraged. You will get better. And then you will get really good. Remember that as you watch a line of people file up at the dock to watch your docking skills in action. You have nothing to prove here. Slow is smooth and smooth is fast.
There is only one speed you should be docking your boat: the speed of the dock. When my husband and I first embarked on the Great Loop, we headed south from Washington, D.C. He made me dock the boat for the first two weeks of our trip. I was so nervous about it, but after a few days, the anxiety burned away and my confidence grew with experience.

I learned to turn around if it didn’t feel right, to go even slower, and to use the forces under the boat to my advantage. If conditions are adverse—25-knot winds poised to slam you into a megayacht, for example—sometimes the smartest move is to abort altogether. More than once we dropped anchor and hauled our diesel aboard in jerry cans. It was exhausting and time-consuming but a better alternative than an insurance claim.
This is one of the lessons learned on the Great Loop that we learned more than once. Many parts of the Intracoastal Waterway on the Great Loop intersect with busy inlets. Shipping vessels, barges, and commercial traffic frequent these waters. If you can avoid these areas as darkness arrives, do so. Monoliths of the sea tend to embark at dusk, often passing each other in impossibly narrow channels.
I remember a tugboat hailing us in the dark, asking us to stay out of the channel altogether. That’s a big ask for a sailboat that must watch out for shoals outside the channel to avoid running aground. The point is, little moments like these are best navigated during the daylight hours.
The Great Loop is sheltered from the dangers of the open ocean, but don’t let that fact lower your guard. Many other bodies of water can be perilous. The ocean is monstrous and deep. Bays and sounds are small and shallow, with plenty of obstructions. These large bodies of water carry echoes of the forces traveling in from the ocean, but with less depth and fetch to dissipate the energy. This leaves short chops and steep waves in many of the sounds and bays on the ICW. If you lose control, you will have to avoid shoals, shorelines, fishing contraptions, and other obstructions.
I remember being in a marina north of the Albemarle Sound on the ICW. A trawler pulled into the slip next to us. The couple looked like they were on the verge of tears. Their faces were white and their hands were shaking. As they stepped onto the dock, I intercepted them under the guise of casual conversation. The woman aboard quickly described their white-knuckled crossing of the Albemarle Sound. The winds were building all day. They underestimated their arrival time to the sound and crossed later than intended. By the time they were in the middle of it, the chop was severe enough it almost capsized their boat.
The next day, my husband and I left in the predawn to cross the Albemarle Sound. We were so nervous we even tied lifelines and tethered ourselves in. But the winds were light that early in the morning, and there wasn’t a ripple on the water. We felt, and looked, utterly ridiculous. But you are better served by overestimating these large bodies of water than underestimating them. Let that be one of the lessons learned on the Great Loop by others that can benefit you.
It’s easy to overlook the forces working under your boat. But the tides and currents will factor into your schedule more than you expect. Bridge openings alone can wreck your schedule. I can’t tell you how many times we raced toward a bridge, begging the tender to wait for us.
“Just hang on three more minutes! We can see the bridge!”
If we missed that opening, we were going to miss the next one, too. If you are waiting a long time for a bridge to open, you will be contending with a variety of forces. With boats waiting in a line behind you in a narrow channel, you’ll need to work with the wind, current, and tide to stay put.
To choose a marina or a suitable anchorage, you have to time your arrival. My salon table was always full of open books, charts, and digital devices. To make these calculations with accuracy, I used a variety of tools:
Tip: It won’t take you long to learn this, but with all the forces working on your boat, it’s a good idea to have a backup anchorage or marina in mind. I like to have one ahead of our intended arrival point and one after it.
If you feel like making strict plans to meet anyone on a particular date, maybe reconsider. I can’t tell you how much stress these ‘meetups’ added to our trip on the Great Loop. This is especially true when flights are involved. A friend of ours bought tickets to join us on part of the Florida section of our route. The minute she sent me her itinerary, the pressure was on.
But what about that northerly blowing in on Thursday?
What if we have to stop and wait for engine repairs?
What if the flight is delayed?
Once you have to adhere to a strict schedule, the pressure builds. Do yourself a favor and be upfront with friends and family about your schedule: It could change. Keep it loose and spontaneous.
You are trading the rigidity and pressure of sedentary life for the fluidity and freedom of life on the water. That’s one of the lessons learned on the Great Loop. Here’s another: Don’t forget to allow yourself the time and independence to enjoy it.