Key West has a way of pulling you in, but how it greets you depends entirely on where you drop anchor.
In 2024, when we first arrived in Key West, we treated ourselves to a stay at The Perry Hotel and Marina. It was our holiday gift to ourselves, and it felt like one. The Perry is where “working waterfront” meets high-end hospitality. Even though we had just checked into the marina, we weren’t just guests; we were part of the family, even getting invited to the Christmas White Elephant gift exchange. If you’re looking for first-class service and a sense of belonging in a luxury setting, that’s the spot!
But 2025 called for a change of pace. We bypassed the docks and headed straight for the Garrison Bight Mooring Field.
At less than $450 a month (weekly pump out included!), it’s arguably the best deal in the Keys, but the value isn’t just in the price tag. It’s in the community. Out here, the rules of the land don’t apply. We learn the names of the dogs before we learn the names of the humans. It’s a place where we look out for each other…especially when the northern winds begin to blow. When the weather turns, the radio comes alive. Whether it’s a dinghy assist or just an extra eye on a wandering anchor, nobody hesitates to help. You have to stay sharp because abandoned boats are a reality out here, but that common challenge only knits the community tighter.
A City Built on Bones and Shipwrecks
Once you tie up to the dinghy dock and step onto the streets of “Cayo Hueso” (Bone Island), the history surrounds you. Long before it was a tourist mecca, Key West was the wealthiest city per capita, built on the wrecking industry which was the salvaging of cargo ships that met their end on the treacherous Florida Reef.
The island’s spirit of “making do” and “doing it your own way” still define the city today. It’s why Key West famously seceded from the Union in 1982 to become the Conch Republic, a tongue-in-cheek protest that turned into its permanent identity.
Shore Leave: The Tour Guide Itinerary: Bones, Bars, & Treasure
Every city we visit, I spend days researching the “why” behind the place. What makes the place exceptional, what is it famous for, and what ghostly paranormal shit can we find? Our friends have even started calling me “The Tour Guide” because I can’t help but plan one day of perfectly curated fun based on the deepest local lore. So, here is your “Tour Guide” day for Key West:
- The History of Wealth and Wrecks
Start at the Mel Fisher Maritime Museum. It isn’t just about gold; it’s about the staggering history of the 1622 Spanish plate fleet. To see the reality of the island’s past, move from the treasure to the City Cemetery. The epitaphs are legendary, as are the mausoleums themselves. Including the former burial site of Elena Hoyos, whose body was stolen by a local man who lived with her for over 7 years.
If you want a smaller, more intimate look at some of our history, stop behind St. Paul’s and look at their graveyard. Call out to John Fleming, one of the four founding fathers of Key West who is buried there, after his family donated the land to the archdiocese…
Finish your history walk by grabbing a drink at Captain Tony’s Saloon. It’s the original Sloppy Joe’s, but it holds a darker secret. Inside this small bar is Key West’s hanging tree. There are two headstones and a spirit that haunts the women’s restroom…but that’s not all. When they were renovating the pool room, they discovered that the building was built over a shallow burial ground. The removed 13 skeletons. 12 were interned at the city cemetery, but one remained. Stop by the bar and say hi to Fred–the skeleton behind the bar who still keeps watch over the patrons.
- The Local Table: Better than the “Famous” Spots
People will tell you to go to the places with the longest lines. Don’t. If you want the real Key West, follow the salty locals:
The Best Key Lime Pie: I don’t think I’ve ever seen a local I know enter Kermits. No, if you want the real deal, it’s a toss-up between Blue Heaven (for the atmosphere and the meringue) or Moondog Cafe.
The Cuban Secret: Most tourists flock to Cuban Queen for breakfast and coffee. If you want the best Cuban food on the island, go to Kim’s Kuban. It’s authentic, no-frills, and vastly superior.
The Sailor’s Happy Hour: For a perfect “dinghy-up” experience, head to Mac’s Place. It’s right outside the mooring field, under the bridge next to the dinghy docks. It’s the perfect spot to grab a drink and a bite while catching live music. Our other favorite place for happy hour is The Boathouse. Located just off the water, you can park your dinghy here for $15.
Key West isn’t just a destination; it’s a vibe. Whether we’re taking a cooking class at The Key West Cooking Show, or grabbing things for dinner from Fausto’s, this island has a way of making sure you never truly want to weigh anchor.