OUR LATEST POSTS
San Carlos Institute in Key West: The Duval Street Landmark With a Big Cuban Story
Did you know one of the most important places in Cuba’s fight for independence is sitting right in the middle of Duval...
Best Things to do In Key West in September (2026)
Is September a Good Time to Visit Key West? You Bet It Is! https://youtu.be/7gUv-LciYn8 Welcome to the heart of...
Our Latest Key West Trip: New Favorites, Old Standbys and a Few Surprises
https://youtu.be/hVJ2HBoJPLw There are some trips to Key West where you arrive with a color-coded itinerary, dinner...
DIVE IN
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 Best Hotels and Resorts in Key West for families
Are you looking for the perfect place to stay in Key West with your family? Look no further! Let's explore some of the best hotels in ... read more

Key Largo vs. Key West: Which Destination Is Better?
Planning your next trip to the Florida Keys and stuck between Key Largo and Key West? Don’t worry—I’ve got the lowdown on both ... read more

Sawyer-Navarro House in Key West: The Historic Home That Was Moved Off Duval Street
Did you know there’s a house in Key West that used to sit on Duval Street... until they moved the entire house? Not the ... 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
Out A
Here Travel
The Keys
Travel Tips
& Insights
Advertise with Us
Podcast












