We’re Not Locals. That’s the Whole Point.
We are Michele and Kevin O’Connor, and we have been exploring Key West and the Florida Keys since 2014 — not as residents, but as repeat visitors who keep coming back because we genuinely can’t stay away.
That distinction matters more than you might think.
Locals are busy. They’re running businesses, raising families, navigating daily life. They’re not taking the trolley tour, staying at the new inn on Duval, or trying every restaurant on your shortlist. We are. Every trip, we explore the way our audience would — if they had the time, the obsession, and the excuse to keep going back.
Over the past decade, we’ve stayed at dozens of inns and hotels across the Keys, researched more than 120 historic markers, eaten our way through hundreds of restaurants, and taken nearly every tour worth taking from Key Largo to Mile Marker 0. Kevin photographs everything (beautifully — that’s his department). Michele writes, researches, hosts the podcast, and runs the book club. Together, we cover Key West and the Florida Keys the way our audience actually experiences it: as visitors who love this place deeply and want to help others love it too.
Come for the Tips. Stay for the Community.
That’s really the whole site in one line. You’ll find real, tested recommendations here — where to eat, where to stay, what to do, and the history behind all of it. But the tips are just the front door. The community is what people actually stay for.
120,000+ people follow us across Facebook and Instagram, where our content gets 3+ million views a month. Add in 19,000+ more visits to the site itself, plus an email community of 7,000+ subscribers opening our newsletter at a 50%+ rate — well above the industry average. And inside our private Facebook group — yes, it’s called Book Club, but it’s really our whole Key West community — we trade stories, plan trips together, and once a month dig into a book (with a real shelf at Key West Island Bookstore for anyone who wants to go deeper).
If the tips are what bring you here, the group is where you’ll actually feel like part of something — a place to hear from us between trips, not just during them.
Join the Fun in Key West Book Club group
Real Visits, Real Opinions
Every piece of content on this site reflects real visits and real opinions. We write about what we’ve done, where we’ve stayed, what we’ve eaten, and what we’d do differently. You get our honest take — always.
A toast to all of you…
You’ll also find island-inspired recipes here — because the best way to stay connected to Key West between visits is to bring the flavors home.
Our own Tiki Bar… or what we call the O’Connor Bar
For Brands & Destinations
We partner with brands, destinations, and tourism organizations who want to reach an audience of passionate Key West fans — past visitors, repeat visitors, and devoted fans of the Florida Keys lifestyle. This isn’t a side note: it’s the same trust and repeat attention described above, and it’s exactly what makes a partnership with us different from a one-off ad placement.
If that’s you, visit our Advertise With Us page for reach, audience data, and how a partnership works — or just reach out directly.
The Bottom Line
I think we can all agree that Key West is paradise and one of our favorite spots. If you have not been yet, well sit back and read about how much this place has to offer, and like I tell everyone, you will very quickly plan your return trip!
Cheers,
Michele