5 Simple Prompts to Help You Remember Your Great Loop Journey (Even if You’re Not a Journaler!)

Let’s be honest: documenting your Great Loop journey sounds lovely in theory… but in the chaos of lines, locks, weather apps, and provisioning runs, journaling often falls to the bottom of the to-do list.

But here’s the thing: you don’t need to write a novel. A few simple prompts can help you capture memories you’ll actually want to revisit later—whether you’re using a fancy leather-bound notebook, a note-taking app, or one of the Loop journals we created.

Whether you’re already cruising or still dreaming, here are five easy prompts you can reuse every day to reflect, record, and remember the journey.

1️⃣ Where did we go today?

This one sounds obvious, but jotting down the name of the marina, anchorage, or waterway you were on helps you track your route and sparks memories later. Bonus points if you note the weather, tide, or how the travel felt—was it glassy calm or an “I-need-a-nap” kind of day?

2️⃣ What surprised me today?

The best parts of the Loop often come from the unexpected: dolphins playing in your wake, a friendly dockmate sharing fresh muffins, or stumbling into a parade you didn’t know was happening. Capturing those little surprises adds personality to your story—and reminds you how magical this trip can be.

3️⃣ What did we learn?

Every day on the Loop is a chance to learn something—whether it’s a new knot, a historic tidbit from a museum, or how not to enter a current sideways (oops). Kids especially love this one, and it makes a great prompt for homeschool logs or roadschool journals too.

4️⃣ What made us laugh?

From boat bloopers to family inside jokes, these are the moments you’ll want to remember. (Like the time your kid named every spider aboard. Or when the autopilot tried to steer you into the marina bar.) Keep it light, silly, and honest.

5️⃣ What do I want to remember about today?

This prompt is wide open. Maybe it’s the sunset, a delicious sandwich, or the feeling of finally nailing that tight docking maneuver. This question invites you to pause and be present—even if it’s just for 30 seconds.

Want more guided journaling ideas?

We created a set of Great Loop journals for kids, and teens, and grown-ups to make documenting this journey easy and fun. They include ready-to-go prompts just like these, so no one has to start from a blank page.

Check them out:

Whether you’re anchoring off a quiet cove or rafting up with new friends, take two minutes at the end of each day to jot something down. Trust me—future you will be so glad you did.


We’d Love to Hear From You!

How do you like to remember your travels?

Are you more of a writer, a photo-taker, or a storyteller around the dock?

Have you tried journaling on your Great Loop journey—or would you consider giving it a shot?

What’s one moment from your trip you never want to forget?

 

Want more of what you see here?

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Alison Major

Alison Major is an author, experienced sailor, and the founder of Loop Life Academy, dedicated to helping families navigate the adventures of America’s Great Loop. With over a decade of remote work experience leading international technology and software engineering teams, she brings her expertise to the nautical world.

Alison lives full-time aboard a 2005 Beneteau 423, SV Fika, with her husband, Chris, and their two children. She has sailed over 7,000 nautical miles. She writes about remote work, cruising, and family life aboard, sharing practical insights for those embracing a nomadic lifestyle. Her most recent book is Remote Work Afloat. An educator and lifelong learner, she teaches Software Architecture to graduate students and mentors cruisers, providing guidance on life's technical and logistical aspects on the water.

https://looplifeacademy.com
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Why We Had the Kids Journal on the Great Loop (and What I’d Do Differently)

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