We can help with that!
- Looking for some of the best Happy Hours in Key West? Get our Happy Hour Guide
- Need information about Key West? We have lots of ideas on Where to Eat, Where to Drink and What to Do
- Want to escape to the Island State of Mind? Check out our Fun in Key West Store
OUR LATEST POSTS
Best Things to Do in Key West in October (2025)
The first time we visited Key West in October, we were excited to celebrate Halloween. Little did we know, Halloween...
Chapters & Cocktails VIP Club
Your VIP Escape Awaits — Books, Cocktails & a Touch of Paradise What if your next getaway didn’t require a plane...
Best Sports Bars in Key West: Where to Catch the Big Game
Picture this: you're sipping a tropical cocktail under swaying palm trees, the ocean breeze is doing its thing, and...
DIVE IN
- First Timer
- Families
- Groups
- Couples
- Weddings

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

Best Restaurants on Duval – Key West’s Culinary Heart
Duval Street is the beating heart of Key West, where life is vibrant, the drinks are flowing, and the food? Oh, the food is legendary. ... read more

Is There Uber in Key West? (And Other Transportation Tips)
Planning a trip to Key West but wondering, “Is there Uber in Key West?” The short answer is yes—there is! But that’s just one of the ... read more

Hemingway’s Favorite Drinks and Where to Sip Them in Key West
Are you ready to sip like one of America’s greatest writers? Ernest Hemingway wasn’t just known for his adventurous prose and rugged ... read more

The Ultimate Key West Bar Crawl Guide: 6 Unique Stops to Savor Your Night
Planning a trip to Key West? Sure, you know about the sunsets, the palm trees, and maybe even the famous Key Lime pie—but did you know ... read more
Flip Flop
Gypsy
The Keys
Travel Tips
& Insights
Videos
Podcast