My Favorite Vacation Memories Usually Start With “Why Not?”

One of my favorite things to do with my Grandpa was troll fishing on Moyie Lake. Looking back, I don’t think I loved fishing nearly as much as I loved being out there with him.

I have a lot of memories from that time, but some of the strongest are tied to being out on the water with him. Fishing was never really about the fish. It was about the time together, the lake, the waiting, the talking, and probably a fair amount of just sitting there hoping something would bite.

Years later, when I was visiting Hannah and we found a Groupon for a chartered fishing trip on the Chesapeake Bay, I did not exactly stop and think, “Ah yes, this is a meaningful continuation of my childhood fishing memories.”

It was more like:

“This looks fun.”

“Should we do it?”

“Why not?”

So we booked it.

That random decision ended up becoming one of my favorite memories from the trip.

I think there is something to that.

Some of my favorite experiences haven’t come from checking off the biggest tourist attraction or following a perfectly planned itinerary. They’ve come from finding something a little unexpected, saying yes, and seeing what happens.

The Random Chesapeake Bay Fishing Charter

We booked our trip with Chesapeake Bay Sport Fishing, which operates out of Stevensville, Maryland, on Kent Island near Annapolis.

We knew very little about charter fishing going into it. That turned out not to matter much.

Today, Chesapeake Bay Sport Fishing still offers private and mixed-group charters, and rods, reels, bait, tackle and Maryland fishing licenses are included. In other words, it is very much the kind of experience where you can show up without owning an entire garage full of fishing equipment. Chesapeake Bay Sport Fishing

Once we were out on the water, the whole thing just became fun.

There was fishing, obviously. There was beautiful scenery. There was the general excitement of somebody actually catching something.

And then there was our captain.

Our Captain Was Half the Entertainment

Our captain was a hoot.

There really isn’t a more sophisticated way to describe him.

He had personality to spare, and that ended up being part of what made the day so memorable.

That is one of the things I love about experiences like this. You aren’t just seeing a place. You are meeting the people who actually live and work there.

You could spend an afternoon walking through the attractions everybody tells you that you have to see.

Or you could somehow end up on a boat with a hilarious Chesapeake Bay fishing captain.

I vote for doing a little of both.

You Don’t Have to Be a “Fishing Person”

This is probably the part I would have wanted to know before we booked.

You do not have to already be deeply invested in fishing to enjoy a fishing charter.

You don’t have to know which rod to buy, which bait to use or what half the fishing terminology means. A guided charter is actually a pretty easy way to try something completely outside your normal wheelhouse because someone else knows what they are doing.

You get to be the beginner.

That can be surprisingly fun.

And no, my takeaway from this trip is not that everybody reading Redcypress Designs now needs to become an angler.

My takeaway is that sometimes you should book the random thing.

“Outside Your Comfort Zone” Does Not Have to Mean Terrifying

Whenever somebody talks about getting outside your comfort zone, it tends to get very dramatic.

Jump out of an airplane!

Climb a mountain!

Go bungee jumping!

No thank you. 😂

Getting outside your comfort zone can be much smaller than that.

It can simply mean doing something you normally wouldn’t think to do.

Book a fishing charter.

Take a pottery class.

Go kayaking.

Try a cooking workshop.

Walk around an art market.

Take the ridiculous-looking local tour.

Visit the tiny museum you’ve driven past 47 times.

Go to a cultural festival where you haven’t tried half the food.

The goal isn’t to scare yourself.

It is to occasionally interrupt your normal routine.

I’ve Started Looking for the Things That Aren’t So Obvious

This is something I’ve noticed even at home.

When I started looking for more interesting things to do around Baton Rouge, I realized how much is happening beyond the standard dinner-and-a-movie routine.

There are markets, workshops, cultural events, exhibits and festivals that are easy to miss if you aren’t actively looking for them.

For example, Baton Rouge’s Night Market BTR is an Asian-influenced street festival built around food, art, music and cultural performances. Visit Baton Rouge

The Baton Rouge Arts Market happens alongside the farmers market and features local artists working in everything from pottery and glass to jewelry, photography and woodwork. Visit Baton Rouge

Events like Hot Art Cool Nights take over part of Mid City with local art, music, food and businesses staying open late. [225]

None of those require a major vacation.

Sometimes an adventure is literally twenty minutes from your house.

The hard part is remembering to look for it.

How I Find the Random Stuff

The Chesapeake Bay fishing trip came from Groupon, and I still think sites like that are worth checking when you’re traveling.

But now I look in several places.

I check local tourism websites and community event calendars. I look at Eventbrite and Facebook Events. I check museum calendars, markets, libraries and local businesses. Sometimes I simply search for things like “unusual things to do in ___” instead of “top attractions in ___.”

That tiny change in the search can turn up completely different ideas.

Atlas Obscura is another fun place to look when you specifically want the strange stuff. Even its Baton Rouge guide includes lesser-known attractions mixed in with familiar local landmarks. (Atlas Obscura)

When I’m traveling, I now think it is worth checking what locals are actually doing that weekend.

A farmers market, festival, neighborhood art event or workshop may tell you more about a city than another afternoon spent standing in line at the attraction on every travel website.

Try One “Why Not?” Thing

Sometimes, though, the “why not?” thing can be incredibly simple.

Maybe you notice the sky starting to change and decide to drive downtown just to watch the sunset.

No reservation. No tickets. No carefully researched list of things to do.

You just go.

That is what I mean when I talk about doing something a little outside your normal routine.

It does not always have to be a fishing charter, a kayaking trip, or some big once-in-a-lifetime experience. Sometimes it is choosing to leave the house when you normally would have stayed home. Sometimes it is driving somewhere just because the light looks pretty. Sometimes it is giving yourself permission to do something simply because it sounds nice.

You might discover a new favorite view.

You might find a place you want to come back to.

Or you might just spend an hour watching the sun go down and think, “I’m really glad I came.”

That counts too.

Sometimes “why not?” is an adventure.

Sometimes it is just a sunset.

Your “Why Not?” Activity Might Be Close to Home

You don’t necessarily have to be on vacation to do something outside your normal routine.

Here in Louisiana, that might mean renting a kayak and paddling through a swamp or bayou. I’ve done that too, and it is one of those activities that makes you see a place you already know from a completely different perspective.

Would I describe quietly paddling through a Louisiana swamp as my typical Saturday afternoon? No. 😂

Was it worth doing? Absolutely.

Canoe & Trail Adventures is one example of a local company that offers kayak and canoe rentals, so this is exactly the sort of thing I mean when I say to look beyond the obvious attractions.

A Few “Why Not?” Activities to Look For

If you want to add one unexpected thing to your next trip — or even your next weekend at home — search for:

• local fishing or boating charters
• beginner art, pottery or cooking workshops
• food tours or neighborhood tours
• farmers and art markets
• kayaking or paddle tours
• small museums and historic homes
• cultural festivals and night markets
• seasonal pop-up events
• unusual local tours
• classes taught by local makers

You aren’t looking for the activity everybody says you have to do.

You’re looking for the one that makes you say, “Huh. That could be fun.”

I think that’s really the point of all of this. You don’t need to become an adventurous person overnight or fill every weekend with plans. Just every once in a while, when something makes you think, “Huh, that could be fun,” maybe don’t talk yourself out of it. See what happens.

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