From sunset sails to spooky October fun — catch up here! 🌅🎃


Hey Reader, 🌞

Guess what? I’m back on the road again — yep, road tripping my way through Florida and spending a little time in Orlando for another conference.
(Yes, another one... what can I say? I like to learn things and then tell you all about them 😉)

You might see a few updates pop up in our Facebook Stories this week — a little behind-the-scenes from the road, maybe a margarita or two 🍹

But in the meantime, here’s what went down last week in our little slice of paradise:


🏛️ Historic Marker Monday: The Old Custom House

This week we visited the stunning and history-packed Old Custom House — right near Mallory Square.

Have you stayed here?
Grabbed a drink at the Smallest Bar in Key West just next door? 🍻

There’s more history packed into this one block than you’d expect, and we dove right in.

🎥 Watch the video on YouTube


🌅 Sunset Cruises: So Many Choices, So Little Time

On Tuesday we talked all about sunset cruises — and believe me, there are so many options.

From wine-tasting sails to party catamarans to romantic schooners... there's something for everyone. I even shared how you can book your own right from the blog!

🎥 Watch the Sunset Sail video
📝 Read the full guide + book online here

What’s your favorite sunset cruise in Key West? Hit reply — I’d love to know!


🎃 October Happenings in Key West

We wrapped up the week with a full rundown of what’s going on in October across the island.

From Fantasy Fest to zombie bike rides to low-key spooky fun — this month is stacked with events. 🎭🧟‍♂️

🎥 Watch the video roundup
📅 Check out the full calendar of events here


🧠 Trivia Time!

Last week’s question:

The Conch Republic was created in what year?
✔️ Answer: 1982 — following a very Key West-style “succession” in protest of a U.S. Border Patrol checkpoint. Only in the Keys, right?

Now, ready for this week’s trivia?

How many Civil War forts are in Key West?

Got a guess? Just hit reply and tell me — correct answers get entered to win this month’s Key West Surprise Box 🎁
(Spoiler: it’s full of tropical fun you didn’t know you needed in your life.)

🕛 Deadline to answer: October 31 at midnight EST
🎉 Winner will be picked on November 1st!


Alright, that’s it for this week!
Thanks for sticking with me — whether you’re here for the history, the happenings, the happy hours, or just dreaming of that next escape to paradise... I’m so glad you’re part of this crew. 💙

Until next time,
🌞 Michele
Fun in Key West

P.S. Don’t forget to check out this week’s videos, hit me with your trivia answer, and keep an eye on our Stories for some road trip chaos 😉

Check out the Fun in Key West Book Club - Every month we read a book with a Key West connection... learn more and sign up (it's free) here!


Ready to plan your escape? Or next adventure? Check us out at...

Out A Here Travel.