OUR LATEST POSTS
Stay Finder
Six quick questions, about a minute. We'll match you with Key West hotels, inns and guesthouses that fit your group,...
Best Things to Do in Key West in October (2026)
https://youtu.be/9ua4NQJwcZ8 The first time we visited Key West in October, we were excited to celebrate Halloween. We...
Runaway to the Keys: Finding Your Own Path with Author Miki Bennett
https://youtu.be/cXxNV3Kbqoo There is something about the Florida Keys that makes you want to change your plans. Maybe...
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Let Kevin help you book the perfect Keys Trip
HELLO THERE!
We are Michele and Kevin O’Connor and we love, love Key West. From our first visit, we have been smitten with this tiny Island. Probably a lot like you…. which is why you are checking out our website.
POPULAR POSTS

The Perfect 4 Day Key West Itinerary
We spent an amazing 4 days in Key West. Well, any time in Key West is amazing, right? The Kimpton Key West hosted us for a fun ... read more

When is Lobster Season in Key West? The Ultimate Guide
Have you been dreaming of warm waters, crystal-clear views, and tracking down Florida’s favorite crustacean? Then it’s time to talk ... read more

The Key West square you’ve walked past a million times
https://youtu.be/-KwSVddFQTQ You know that spot in front of the Custom House? The one you probably breeze past while ... read more

Ridley House Key West: The Turtle, the Fire, and the Story Behind This Historic Home
Did you know one of the rarest sea turtles in the world is named after a Key West furniture dealer... and you can actually stay in his ... read more
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