What Are the Best Hotels in the Florida Keys for Fishing?
BY AMY BURDICK AND RYAN GOLOVERSIC, WITH MATT SEXTON, OWNER OF GRASSY FLATS RESORT AND BEACH CLUB
Matt owns one of the hotels on this list, so take that for what it's worth. He'll say so upfront, and he won't pretend the other places here are bad, because they're not. Book Hawks Cay or Faro Blanco instead and he'd tell you to go get after it, those are real fishing hotels with real marinas. But he's fished this whole chain for years, he knows what these places actually offer versus what their website says, and he'd rather just say it straight than pretend he doesn't have a stake in the answer. Ask him which hotel is actually best for a fishing trip and his answer isn't just "the one with a dock," it's the one that gets you on the right boat with the right captain, and puts your catch on a plate that same night.
Does Grassy Flats have its own marina or fishing dock?
Sort of, and Matt won't dress that up. What's on property right now is a dock, not a finished marina. Pilings are going in, boat storage is planned to go with it, and there's more construction coming over the next couple of weeks. In the meantime, guests can already tie up and launch from it. It's just not the full-service setup a name like "marina" implies yet.
What's less obvious, and probably more useful, is that Grassy Flats also runs a private fish camp a couple miles off property. It's not on the hotel grounds, but it's exclusive to guests, with a place to tie up a boat, a fish cleaning station, and deep water access that puts you right out into the better fishing water in the Middle Keys. Guests can dock their own boat there too, at a rate that varies with the length of the stay.
So the honest version is this. The on-site dock isn't a finished marina yet, and Grassy Flats isn't going to claim it is. What it does have is real deep water access, just a short drive away instead of a walk out the back door.
What's the difference between booking a fishing charter through a hotel and booking one independently?
At most hotels, not much. The front desk hands you a brochure or a partner's phone number, and that's the extent of it. At Grassy Flats, when a guest books through Rhum Line Charters, they're booking through Matt directly, and he either puts them with one of his in-house captains or works his way through a network of guides he's vetted personally over years of actually fishing with them.
He'll tell you plainly why that matters. The worst thing a hotel could do, in his words, is put guests on something like a booking platform for guide services, the fishing equivalent of an Airbnb, where the captain who shows up first is just the one who paid the most to be in front of your face. That's not how he does it. No commission changes hands on any of it, so the captain he connects a guest with is based on who's actually right for the trip, not who's paying for the placement.
It also means the matching happens based on a real conversation, not a form. Depending on what a guest wants to catch, what kind of day they're after, and what price point makes sense, Matt goes through what he calls his rolodex and connects them with the right guide. Some of that happens with guests already staying on property. Plenty of it happens the same way it always has in the Keys, a conversation at the market while someone's waiting on a coffee, someone mentions they want to get out fishing, and a couple of phone calls later they're set up with a guide who's already been vetted.
Which Florida Keys hotel is best for offshore fishing versus flats and backcountry fishing?
It depends less on which hotel and more on what the day actually calls for, and Matt builds the trip around that instead of locking a guest into one category before they've even landed.
A half day trip is four hours and stays close, working the reef and the mangroves for snapper, yellowtail, mackerel, whatever's biting that morning. A three-quarter day runs six hours, and a full day is eight, running twenty to fifty miles out for mahi, tuna, sailfish in the winter and spring, wahoo year round. The choice isn't really about which hotel to book, it's about how far out someone wants to go and how long they want to be on the boat, and that gets figured out the day of based on conditions and what the guest actually wants, not a package picked off a menu months in advance.
For hotels built around one type of fishing specifically, there are real options elsewhere in the Keys. Hawks Cay leans hardest into offshore infrastructure, with a marina built for it. Cheeca Lodge carries the Islamorada sportfishing pedigree, tournament history included. Faro Blanco sits closer to the bay side, better suited to backcountry and flats trips. Grassy Flats isn't trying to be the one-note version of any of those. It's built for a guest who might want reef fishing on Tuesday and an offshore run on Thursday, and wants the trip shaped around the actual day rather than booked into a fixed category.
Can you eat what you catch at a Florida Keys fishing resort?
At Grassy Flats, yes, and it happens the same day. A half day trip out chasing reef fish or a full day running offshore for mahi and tuna both end the same way, boat comes in, the catch gets cleaned and filleted, and it goes straight to the Rhum House kitchen.
Matt describes one trip where the boat brought back five or six tuna and a couple mahi. The guests didn't want to spend the rest of the day cooking or cleaning anything themselves, they wanted the pool and a cocktail, so the kitchen took it from there. That night they came up to the Rhum House and had their catch three different ways, blackfin tuna sashimi, a tuna tartare, and mahi prepared three separate ways, an actual feast built entirely out of the same fish they'd been reeling in that morning. They still had enough left over to vacuum seal and take home the next day.
A full day trip runs longer, out from seven to three, and guests usually come back tired enough to want a shower and a painkiller by the pool before anything else. Same result by dinner, though. The fish gets prepared the way none of them could manage on their own, and the day that started on a boat forty miles offshore ends at a table.
How much does a private fishing charter cost in the Florida Keys?
It swings hard depending on the boat and how far out you're going. At the low end, a small boat and a half day trip runs around $650. A full day now can top $2,000, mostly driven by fuel, and that's before anything gets added for how the catch is packed up afterward.
Matt won't pretend chartering is cheap, either. He's had guests bring a cooler up to their room, grab some rods, and post up at Tom's Harbor Bridge with frozen shrimp instead, and walk away with close to the same amount of fish as someone who just spent $1,200 to fish the reef with a guide. Both are real ways to fish the Keys.
What the guide buys is what the bridge can't reach. A captain who knows grouper isn't biting today but yellowtail are thick at the 74 line, right now, not from a week-old report. A boat that can actually get out to where the mahi and tuna are running. And someone setting real expectations before you leave the dock instead of finding out three hours in. The bridge is a fine afternoon. The charter is how you go after the fish you actually came for.
Do you need your own boat to fish in the Florida Keys, or can the hotel set it up?
No boat required. Book a charter through Grassy Flats and the boat, the captain, and the gear are all covered, a guest just shows up and fishes.
For anyone who does have their own boat, the option's there too. Guests can tie up at the on-site dock or Grassy Flats' private fish camp a couple miles away, at a rate that depends on the length of the stay. Matt docks his own boats there, so it's a real option, not just something offered on paper.
The Grassy Flats fish camp in particular is built for exactly this kind of guest, the one who'd rather run their own day than book a charter around someone else's schedule. It's got a cleaning station and deep water access straight into the better fishing grounds in the Middle Keys, so a self-sufficient angler isn't giving anything up by skipping the guided trip. It's a different kind of trip than a charter, not a smaller one, just for someone who already knows exactly where they want to go.
So, which Florida Keys hotel is actually best for a fishing trip?
Most of the answers to this question stop at whether the hotel has a dock. That matters, but it's not the part that actually decides whether the trip is any good. What decides that is whether you end up on the right boat with the right captain for what you're actually trying to catch, and whether anyone does anything with the fish once you're back on land. That's the part Grassy Flats has actually built out, dock construction and all.
Matt's said from the start that he's got a stake in this answer, and that's still true here at the end of it. But the comparison holds up on its own. A dock that's honest about still being under construction. A private fish camp already running for anyone who wants deep water access without waiting on that construction to finish. A network of captains booked with no commission, matched to the day's conditions instead of a fixed package. And a kitchen that turns whatever comes off the boat into dinner the same night
Book a private fishing charter through Grassy Flats, and let Matt's network match the boat to the day instead of guessing.
Want the captain-level detail, who's who and what they specialize in? The full captains guide has all nine, named, with real specifics on each.
