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

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 Best Dinner in Key West: Where Paradise Meets Your Plate
Let's be honest—planning dinner in Key West is like trying to pick your favorite Jimmy Buffett song. There are just too many good ... read more

Our Quick Key West Getaway: Where to Eat, Stay, and Play
https://youtu.be/ILTWpyW9Eaw Let’s be honest, any excuse to hop on a plane to the Florida Keys is a good one. Kevin ... read more
Out A
Here Travel
The Keys
Travel Tips
& Insights
Advertise with Us
Podcast













