If you’re planning to do the Great Loop, you’re probably excited — and maybe a little overwhelmed. Between choosing a boat, budgeting time and money, and figuring out where to start, it’s easy to feel like you need everything perfect before you ever leave the dock.
I’ve been there.
I started the Great Loop in 2021, logged over 2,000 miles, completed the Florida Mini Loop, and learned many lessons the hard way. This article isn’t based on internet research or theory — it’s based on real experience on the water.
Here are the five biggest mistakes new Loopers make, and what you should do instead.
Mistake #5: Buying Too Much Boat
Many new Loopers think they need a big boat to be safe or comfortable. In reality, bigger boats often create more stress.
Larger boats mean:
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More systems to maintain
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Higher fuel costs
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More difficulty docking in wind
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More things that can fail
The Great Loop rewards simplicity and confidence, not size. The best boat is one you know well, can afford to maintain, and feel comfortable handling in tight spaces.
Mistake #4: Underestimating Time and Budget
Almost everything on the Loop takes longer and costs more than expected.
Weather delays, maintenance issues, and unexpected repairs are part of the journey. When people try to stick to rigid schedules or unrealistic budgets, they start making dangerous decisions — pushing through bad weather or ignoring warning signs.
You need time margin and financial margin. Those two things reduce stress and keep you safe.
Mistake #3: Waiting Too Long to Start
I hear this all the time:
“Someday I’m going to do the Great Loop.”
Someday isn’t a plan.
Overplanning and waiting for everything to be perfect prevents many people from ever starting. The truth is, you’ll learn more in your first 100 miles than you will in years of preparation.
Your health, energy, and circumstances can change quickly. If the Loop is something you want to do, set a real start date and begin working toward it.
Mistake #2: Not Learning Your Boat Before You Go
If you don’t know your boat, you’re setting yourself up for stress.
You need time on your boat — not just surveys and low engine hours. Knowing how your boat sounds, runs, and behaves builds confidence. It helps you stay calm when something goes wrong, and it helps you recognize small problems before they become expensive ones.
At a minimum, you should spend months — not weeks — running your boat locally before attempting the Loop.
Mistake #1: Starting the Loop on Someone Else’s Engine
This is the biggest mistake I see.
Low engine hours and surveys do not replace real experience. Starting the Great Loop on an engine you haven’t personally run and trusted is a recipe for breakdowns, delays, and stress.
Put real hours on your engines. Learn their sounds, temperatures, and quirks. Confidence comes from familiarity, not paperwork.
What to Do Instead
Before committing to the full Loop:
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Run your boat locally
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Do mini-loops like the Florida Mini Loop
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Take multi-week trips
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Learn how your boat behaves in different conditions
Problems almost always start small. When something doesn’t sound right, investigate early.
Final Thoughts
This advice isn’t meant to discourage you. The Great Loop is one of the most rewarding adventures you can experience. The stories, friendships, and memories last a lifetime.
Preparation builds confidence. Time on the water builds calm. And confidence makes you a better captain.
If you’d like to hear these lessons explained in more detail, along with real stories from my own journey, you can watch the full video here:
👉 The 5 Biggest Mistakes New Loopers Make (Learn Before You Start)
I document real-world boating decisions and lessons learned throughout my Great Loop journey. Check back often or subscribe on YouTube to follow along.
