The One With The Hardest Parts of Looping

“What are the hardest parts of Looping?” It’s a question we hear all the time.

If you ask me in person, 9 times out of 10 you’re going to get a smile. And I’ll tell you that nothing about the Loop is all that hard. I’m a positive person, in general. However, if you catch me after a harrowing docking experience, there’s no telling what I’ll say!

I’ve heard several wise people describe the Loop as being just challenging enough that you feel a huge sense of accomplishment upon completion. I couldn’t agree more. Some days are cake walks. And other days you’re up before sunrise staring at dense fog, wondering if you can make it to a lock on time and reminding yourself that this is supposed to be fun.

Let me say that again, it’s supposed to be fun.

To me, that is mindset that you have to maintain while Looping. If at any point we begin to stress, we realize it’s time to take a deep breath. We also give ourselves permission to laugh when we begin to take boating too seriously. Zooming out always puts life in perspective.

Are some days on the Loop long? Yes. Is it frustrating when it takes 3 tries to set our anchor? Of course. Have I ended a day with several new bruises from the physical effort it takes to untie lines or move fenders? More times than I care to admit.

But I still wouldn’t say the Loop itself is hard.

However, there are some things that are more challenging than others. As I’ve said before, not every moment includes sunsets and chardonnay.

Here are some of the things that I would classify as the hardest parts of the Loop:

Logistics: The Loop is circle around the Eastern half of the United States, most often traveled in a counterclockwise direction. Sounds simple enough, right? But then factor in the thousands of marinas, town walls, mooring fields and anchorages. Suddenly, there are some decisions to make.

Of course, you have to take into consideration available daylight, speed of travel, and the number of miles you want to cover. Oh, and don’t forget that some locks and bridges have specific operating hours.

Every day presents possibility: new water to navigate and new places to explore. I’ve yet to meet any Looper that’s gone everywhere. Even those with the most unlimited time and resources are forced to make decisions regarding their logistics.

And I haven’t even mentioned side trips!

To put it bluntly, if the logistics of looping isn’t at least a little bit difficult, you may not be doing it right!

Maintenance: If I’ve ever looked you in the eye and told you the Loop was easy, I take that back now that I’m thinking about it. Boat maintenance is hard. Especially when you’re Looping!

For starters, boat issues rarely happen at convenient times. Inevitably you’re dealing with maintenance in the most difficult place. Lining up someone to do work and finding the correct parts can be really challenging. (See above, logistics!)

Most Loopers want work done right away. Fortunately, the community is so amazing and somehow we almost always pull it off. Between using resources of harbour hosts, marinas and other boaters- we’ve never had a major problem with maintenance.

I think it’s safe to say, boat maintenance is my least favorite part of Looping!

Laundry: Once upon a time, I had a huge laundry room that belonged to me. I had cute baskets for sorting, nice cabinets to store supplies in, and even a sink for whatever you’re supposed to do with a laundry room sink. All of this was just steps from my bedroom.

And I used to think laundry was hard.

So in all fairness, maybe it’s me. But boatlife laundry will always be my “walked to school in the snow, uphill both ways” story. We don’t have a washing machine or dryer on our boat, so I use the marina facilities. Not all marina laundry rooms are created equal. Some are fancy, but most are not. One was so bad, I marched my dirty laundry back to the boat and decided it didn’t really need to be done.

The hardest part of laundry is the timing. In my cushy home laundry room, I was known to leave things in the dryer for a few days. But they frown on that in marinas.

Let’s be honest though, life looks pretty good if I’m considering laundry one of the hardest parts of Looping.

Weather: When people picture boating, I know it’s 75 and sunny in their mind. Unfortunately, not all days are picture perfect.

Ideally, you stay in relatively warm weather while Looping if you follow a traditional travel route/time. That being said, we’ve seen snow on our boat. It was in October in Chicago. We’ve had our water line freeze. That was in December in Florida. Cold weather happens. You deal with it.

But the weather that I’m referring to is the stuff that impacts boating. Like fog. Or wind. And even, sometimes, rain. There’s not many things more miserable than docking or locking in a torrential downpour. We’ve done both. And not on purpose.

I’d be remiss if I didn’t mention hurricanes and tropical storms. Those happen occasionally too. You make the best decision you can for your boat and your crew, and there isn’t much more you can do.

Fortunately, weather is also one of the best parts about looping!

Goodbyes: I saved the worst part of Looping for last.

Boats move. Which means it’s inevitable that Loopers spend a lot of time saying goodbye to friends. There’s really no way to describe the bond that forms in this community. After spending days/weeks/months together, going separate ways is so difficult.

Loopers spend so much time together, that it’s almost like you have to re-learn how to exist without each other every time you part. Fortunately, the friendships we’ve made over the last few years are ones that we will have forever.

Of course, I have to end this post with some good news: For every hard or negative thing about the Loop, there are at least 10 positive things.

As always, thanks for keeping up with our adventures. You may also enjoy reading:
The One About Boatlife Logistics

Hotel 101: Selecting The Best Place To Stay

Booking Airline Tickets: Don’t Overpay

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  1. David on March 18, 2023 at 3:32 pm

    A down side that some, certainly not all, loopers will have is finding crew.
    The Admirable, died Dec31 ’22. We were pretty much just starting our looping experience. We had a great boat. We’d gone from the Ches Bay to Fl. and back, we were ready to head north the next season. I was not to be. So the Captain lost his crew in addition to his lifetime best friend.
    That’s all sad, to be sure. Now the captain wants to continue the Loop. Trying to find crew who actually CAN join the boat even for a week seems to be a significant challenge. Most folks have the Wxxk thing going on. Or there are health issues, or ??? Sometimes it’s fear of the unknown, or the different. Whether that’s boating itself, or visiting new places, it still results in not being available to crew. Finally and very important there’s the need to find crew that you can live in close quarters with for days, weeks, months at a time.
    So for me, for now, one of the downsides of the Loop is finding crew.

    • momwithamap on March 18, 2023 at 10:05 pm

      Aww, big hugs. This is, for sure, a huge challenge. I’m so sorry you two were not able to complete the Loop together. We actually just had a boat come through our marina that was in a similar situation. His wife encouraged him to finish the Loop and he is currently traveling portions with friends or family members. It’s definitely not what he set out to do, but he’s honoring his wife’s wishes by making the most of it. My heart goes out to anyone facing challenges like this one! We will pray we get to meet you out on the water one of these days- keep us posted!

  2. chrisensing52 on March 18, 2023 at 9:16 pm


    • momwithamap on March 18, 2023 at 10:01 pm

      Thanks! Hopefully this came across as more of an inspiration than a warning! Ha!

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