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15. Cabbage Key, Florida

Dates: March 14-17, 2022


This is one of my most unique solo-stops so far: Cabbage Key Island.


I booked this place last fall before I decided to sell everything when this was just going to be a 6 months excursion. I wanted to stay on a real island. One you couldn’t drive to. I had to get a boat taxi to get there! I wasn’t sure if this would be like a resort in Mexico or Jamaica. Or something else.


It was something else.


The boat taxi has a route to 3-4 islands. I was the only one getting off at Cabbage Key. We pull up and it’s a bumpin’ place! There are boats lined up in the marina and people everywhere on the island’s hillside with loud music coming from the restaurant up the hill.


Captain Ted grabbed my bag and said to check-in at the gift shop on the dock. The lady only asked for my name and said my room was ready and Capt. Ted would take me up there. We walk up the hill then through a back door he says is someone else’s room who hasn’t checked in yet so don't enter in this way again. We round a corner and enter my suite. It’s all wood floors with a fireplace that doesn’t work.


Capt. Ted: Here’s your room.

Me: Thanks! Where’s the key.

Capt. Ted: We don’t have keys.

Me: Uhhhh what about my stuff?

Capt. Ted: We’ve never really had a problem.

Me: I have 2 laptops on me.

Capt. Ted: We’ve never really had a problem. Just don’t leave stuff out. Someone may peek their head in so just hide it in a closet. And at night, you can lock yourself in with this latch.


I’ve been in bathroom stalls that were more secure than this door!


Island life takes on an entirely different meaning at this point.


Time to work

I get hooked up to Wi-Fi in time for a Zoom meeting with a client. The internet is unstable.


Oh s*(%#)8.


Turns out a storm the day before knocked out technology and Wi-Fi is down. No one can do anything. We're on an island. The connection is enough to send email but that's about it.


I cancel all my meetings for the week and resort to email communication only. It works. Mostly. Thankfully my clients are super understanding and very supportive of my new lifestyle! Lookin’ at you Drew Bird. he was the first meeting I had to cancel. He’s in the leadership development biz. I don’t know when I’ll meet him IRL (in real life) so will do a shoutout now. You can read about his work at eqdevgroup.com.


Back to Cabbage Key…

The staff are all friendly and get to know the guests staying on the island. I hear there are maybe 50 guests staying and my room is 10 steps from the restaurant and bar. Staff can see my door so I feel safe. It’s a whole other world for sure! The staff of about 30 live on the island full time. Some commute in for the day via boat.


The main house is a restaurant and bar with a couple rooms for let on either end of the building. Six cottages are scattered along the shore line. Supposedly this is where Jimmy Buffet wrote Cheeseburger in Paradise. The burgers here are ok. I’m pretty biased when it comes to beef though so it’s not fair for me to judge.


The first sunset was beautiful. I watched from the dock.


My first full day there I woke up at sunrise and ran the entire island. It was less than a mile. (haha) I didn’t trip over anything though so I call it a win.



Since I was meeting-free, and semi unconnected, I was able to focus on a big project all day. I worked from a corner of the bar. By now I’m friends with the bartenders. I told them I can’t have anyfun until I get my task list done. It was a successful day and by evening the head bartender Andrew sent me to borrow his kayak and checkout a neighboring island.


Me: Do I need a lifejacket?

Andrew: If you fall out, just stand up.

Me: Ha. Got it.



I’m still in awe of the vegetation around the islands. This pic captures it perfectly.



I kayak around a nearby smaller island and resist the temptation to call someone. Anyone. To share this moment with. It’s peaceful. I’m guessing God is trying to tell me something? Slow down. Be still.


Ok. Ok. Fine.


And so I float in the water.


I get back to land in time for sunset from the water tower. Here I'm pointing to where I just was on the kayak. Exciting stuff, huh.


Then I head back to the main house for dinner where I made some new friends: Mark, Parke, Kevin, Chris & Leon. One of them just bought a boat in the Keys and they’re all driving it up to the Florida Panhandle. I had so much fun hanging out with these guys! Music, dancing, watching a thunderstorm roll in… by far the most fun night I’ve had so far.


They only stopped for a night, but left me with an armful of water. The tap water here tastes absolutely awful and bottled water costs almost as much as a beer!


Lots of animals call this place home.




The downside are the bugs who also inhabit this island. And it turns out they really love me. I was eaten alive. They even got my scalp! I’m assuming it was no-see-ums. These bugs are horrific creatures. I survived to tell the tale thankfully.


Would I visit again?

Only if I got a cabin. The restaurant menu is limited. It would’ve been nice to boat in with groceries.


Would I live here?

I think I’d get island fever after a week. Or less.


Enthusiasm level: 8 then down to a 6. My skin is on fire from all these dang bugs. It was a unique stop though!


Here’s to screened in porches,

Megan “Not Into Bugs” Giles


Placeholder for a fun shirt design.


Unedited by another. Typos are on the house.

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