Flip-Flops, Fun Boxes & a New Year in the Keys 🎉


Hey Reader,

We rang in 2026 with sunshine, live music, and… one very oversized red flip-flop. Kevin and I spent New Year’s Eve wandering around Margaritaville in Orlando — not quite Key West, but hey, it was warmish, and there were zero snowflakes in sight. That’s a win. 🙌

✨ We snapped a photo in front of the giant flip-flop (because of course we did) — you’ll see that we started the year with smiles and maybe a margarita or two.


🎉 And the Winner Is…

Our December Fun Box winner is… Sandy G!
I’ll be packing up a box of island-inspired goodies and shipping it her way.

Now it’s a brand new month and a brand new chance to win — and we’re kicking off the January trivia with a little island history:

💭 Who purchased the island of Key West in January 1822?

(Hint: He had big dreams and divided the island into four pieces… the names live on as some of Key West’s streets.)

Hit reply with your best guess — and yep, correct answers get entered into the January Fun Box drawing!


📚 Book Club Corner

Did you know we also run a fun Key West-themed book club?

Here’s what’s new for 2026:

  • ✅ Fresh calendar of monthly reads
  • 💌 Free access to our digital magazines with cocktail recipes, playlists, and fun extras
  • 💬 A new Skool community — where we chat about books, food, travel tips, cocktails, and everything island life

🎤 This month I’ll be doing a live interview with Chris Harvey, author of Son of a Son of a Pirate, our January read. If you love Key West (and maybe a little mischief), you’ll want to tune in! (Click here for the YouTube link)


👉 Check out the Book Club »


Thanks for being here and for letting me bring a little bit of sunshine and rooster energy into your inbox each week. I’ve got some new videos and blog posts coming soon, so stay tuned.

Cheers to 2026 — may it be filled with laughter, palm trees, and your favorite frozen drinks.

💛
Michele
Your Flip-Flop-Wearin’, Rooster-Lovin’, Fun-Filled Tour Guide to All Things Key West
(Still dreaming of palm trees over snowflakes)

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.