If there’s one thing I’ve learned over the years, it’s this: curiosity is a slippery slope.

You start by wondering what’s down a side road. Next thing you know, you’ve got 42 browser tabs open, a half-finished coffee, and you’re building websites at midnight because “this idea won’t leave me alone.”

So yes. That happened again and yet again.

Today I’m officially announcing two new digital projects I’ve been quietly working on. They live at the intersection of travel, curiosity, and my background in information technology. Which is a long way of saying: this is very on-brand for me,  Curious Craig.

These projects join postcardstoryco.com, which came from a simple idea. Places tell stories, and sometimes a small moment or image captures a place better than a long explanation ever could.

As it turns out, that idea didn’t stop there. It just kept wandering. Occasionally toward food. Occasionally toward great new business idea . Or just wanting to ‘play” with the latest techie stuff.  Most often C:  All of the above.

A Little Backstory (Because Of Course There Is)

I’ve always loved travel, but not just the checklist version.

I’m not chasing passport stamps for bragging rights. I’m chasing moments. The quiet coffee shop you didn’t plan on. The coastal town that smells like salt, sunscreen and fried seafood. The realization that the best part of a trip often isn’t the destination, but the little discoveries along the way.

At the same time, I come from an IT background. I like systems. I like structure. I like solving messy problems with clean solutions.

Travel, if we’re being honest, is messy.

So naturally, my brain decided this was a problem worth poking at.

Project One: Weekend Getaway Planner

Let’s start with the project born from mild frustration and one too many Google searches and doom scrolls.

WeekendGetawayPlanner.com exists for one simple reason:
planning short trips shouldn’t feel like unpaid consulting work.

You know how it goes:

• “What should we do?”

• “I don’t know, what do you want to do?”

• “Did anyone book anything?”

• “Wait, the museum is closed on Mondays?”

Weekend Getaway Planner helps take the guesswork out of short trips by curating itineraries that actually make sense. Not the “wake up at 5 a.m. and sprint between attractions” kind, but realistic, human itineraries.

The kind where:

• things are close together

• downtime is intentional

• and no one ends the weekend more tired than when they started

This is where my IT brain kicks in. Flow. Structure. Patterns. What works well on Day One versus Day Two. When to plan and when to leave space for wandering.

It’s part travel guide, part decision-fatigue reducer.

And honestly, it’s built for people like me. Curious, eager to explore, but not interested in spending three nights researching blogs written in 2011.

If that sounds familiar, you’ll probably enjoy poking around here:
👉 https://weekendgetawayplanner.com

Project Two: The Lobster Trail (With a Twist)

Now let’s talk about Maine. And food. Specifically, coastal food.

Some projects start with a detailed business plan.
This one started with a question:

“Why is it so hard to find consistently great places to eat along the coast?”

That question became TheLobsterTrail.com.

At its core, The Lobster Trail helps people discover great eateries along the coast of Maine. Not just the famous spots, but the places that feel right. The kind locals mention casually. The places where the menu is short, the butter is real, and no one is trying too hard.

But here’s where it gets interesting.

Not everyone explores the same way.

Some people like wandering. Others like goals. Some folks secretly love checking boxes, earning badges, and saying things like, “Okay, but how many have you done?”

So I leaned into that.

The Lobster Trail isn’t just a list. It’s a trail you can follow.

There’s a light gaming layer built in for those who enjoy the chase. Visit places. Track progress. Unlock badges. Collect bragging rights. It’s optional, tongue-in-cheek, and designed to add fun, not pressure.

Think of it like this:

• If you want to casually explore and eat great food, you can.

• If you want to turn it into a coastal scavenger hunt with seafood rewards, you can also do that.

No leaderboards yelling at you. No nonsense. Just a gentle nudge for people who enjoy a little structure with their spontaneity.

This is where my IT side really shows up. Systems, tracking, progression, all layered quietly beneath something that still feels human and playful.

Yes, lobster plays a starring role. But the real point is the experience around it. The drive. The view. The conversation at the table. The “we should come back here” feeling.

You can start exploring the trail here:
👉 https://thelobstertrail.com

Why These Projects Belong Here

Curious Craig has always been about ideas, exploration, and asking “what if?”

These projects aren’t random side hustles. They’re experiments. They’re what happens when curiosity meets structure and decides to build something useful instead of just thinking about it.

They all share the same DNA:

• a love for travel

• a fascination with place

• a desire to make exploration easier and more enjoyable

• and an IT background that likes turning ideas into systems that actually work

They’re tools, yes. But they’re also invitations. To explore differently. To slow down. To follow curiosity instead of an algorithm.

What’s Next?

Honestly? I don’t know. And I’m okay with that.

There will be more writing here. More ideas. More late-night “this might be something” moments. Probably more experiments. Some will stick. Some won’t. That’s part of the fun.

For now, I’m excited to finally share these projects and let them grow out in the world.

If they help you plan a trip, discover a new place, or turn a meal into a small adventure, that’s a win.

And if nothing else, maybe they’ll save you from one more group text that starts with, “So… where should we go this weekend for a good lobster roll.?”

Stay curious.