The Florida Keys are America’s tropical island paradise. Islands that promise island life that you can drive to, without ever setting foot on a boat.
Of course, boaters like to boat there, too. Home to the continental US’s only living coral reef, the Keys have clear water, great diving, world-class fishing, and some of the country’s most interesting boating.
But boating and sailing in the Keys isn’t for the faint of heart. The water is shallow, the area can be open and rough, and safe, protected anchorages are few and far between. Here’s a look at boating in the Keys for the first-timer.
Florida Keys Boating Overview
The Florida Keys is a chain of islands that starts around Miami (Key Biscayne) runs southwest, 70 miles past Key West to the Dry Tortugas. Key West is one of Florida’s oldest port cities, and Henry Flagler dreamed of connecting the town to his railroad network in the early 1900s. The Overseas Railroad was an engineering marvel of its time, but it was destroyed by hurricanes after only a decade or so of service. Eventually, a highway replaced the railroad, traveling south from Florida City on the mainland and crossing 47 bridges on its way, island by island, down to Key West.
By land, everything in the Keys is navigable by “mile marker” since there is only one road. MM 0 is in Old Town Key West, MM 50 is about Maraton, and MM 100 is in Key Largo. The system stops at MM 127, where US 1 joins with the Florida Turnpike in Florida City.
The road might connect the islands for motorists, but it separates them for the boater — at least boaters with masts. There are only a few points where you can pass between the oceanside and the bayside, which means you have to plan how you want to cruise the islands. Cuts with no bridge or high-rise bridges include (listed from south to north):
- Biscayane Channel, Biscayane Bay
- Angelfish Creek, Key Largo
- Snake Creek drawbridge, Islamorada
- Channel 5 Bridge, Long Key (fixed, 65-foot clearance)
- Moser Channel on Seven Mile Bridge, Marathon (fixed, 65-foot clearance)
- After that, you’re stuck until you pass the west side of Key West
If it’s not obvious, the oceanside is the south and east side of the islands facing the Atlantic, and the bayside is the north and west side facing either Florida Bay or the Gulf of Mexico. In the Upper Keys, the bayside is formed by a series of sounds and bights that are part of Everglades National Park. As you travel south, the sounds open up into the wider expanses of Florida Bay. By the time you are past Marathon, the Keys are wider with more land area, and the bayside is the open waters of the Gulf of Mexico.
Florida Keys Cruising Conditions
The environment is king in the Florida Keys. The entire region is under the protection of one government entity or another, and there are special rules and regulations you should know. Patrol and enforcement of marine laws are heavy in the Keys.
The islands are part of the Florida Keys National Marine Sanctuary (FKNMS), which covers everything out to 200 fathoms. There are also Biscayne, Everglades, and Dry Tortugas National Parks, John Pennekamp Coral Reef and Bahia Honda State Parks, and dozens of other smaller wildlife refuges and protected zones. Each office has its own law enforcement branch, in addition to the Monroe County sheriff and USCG patrols.
The FKNMS was created to protect the delicate reefs and seagrass beds of the Keys after years of poor water quality and lack of management caused their decline. It’s a job they take very seriously, and as boaters, we are the ones they worry most about. Of the various high crimes and misdemeanors unsuspecting boaters may commit, the worst include discharging blackwater (sewage) anywhere in the sanctuary (which goes much farther out than 3 miles…it goes out to 200 fathoms/1,200 feet, which is more like 12–15 miles offshore) and anchoring on coral rock or seagrass. Running aground is also frowned upon, and fines may be levied for each square meter of damaged coral or seagrass bed.
In all seriousness, though, ensure your boat meets or exceeds the legal requirements before venturing south into the Keys. This includes putting some sort of lock (which can be visually inspected, if need be) on your overboard discharge through hulls and Y-valves. Also, keep a record of your pump-outs to prove that you have had one recently. You can be fined if you cannot prove that you’ve had a pump-out within at least the last 30 days. See Monroe County’s website for more details on the rules about pump-outs and record-keeping.
If you need a pump-out while in the Keys, you can arrange one through On the Hook Marine. They have a weekly schedule and can set up a recurring or one-time visit for most areas in the Keys. If you get recurring service, you’ll get a sticker that meets the record-keeping requirements.
To get you up to speed on the regulations in the Keys, an online course was created to familiarize boaters with the rules. You can access it on the sanctuary website.
Similarly, there’s a MANDATORY course for navigating within the waters of Everglades National Park. If you look at the park boundaries, it’s quite close to Key Largo. In the Upper Keys, everything north of the ICW is inside Everglades National Park. There’s a park ranger station in Key Largo at MM 98.7.
From north to south, here are the various zones or regions you’ll navigate on a cruise down the Keys.
- Biscayne Bay National Park
- Everglades National Park
- Upper Keys
- Middle Keys
- Lower Keys
- Key West
- Marquesas
- Dry Tortugas National Park
Keys Marinas and Anchorages
The Keys have many marinas, but most are small-boat facilities that can’t accommodate cruising boats due to draft or size issues. When you really start digging and looking for a catamaran, 40-foot monohull sailboat, or 50-foot trawler slip, you’ll find only a handful of options, all of which are very pricey. The going rate for a monthly slip in the Key West area is well past $2,000 a month.
Anchoring in the Keys is difficult for several reasons. Firstly, it’s nearly impossible to find all-around protection anywhere in the islands. Second, the bottom is often scoured rock with shallow sand or thick seagrass and weeds that can quickly foul even the best anchors.
Your anchorage choices are less limited if you have a shallow draft that allows more gunk-holing. Less is better — if you had a two-foot draft, you could find places to go no matter where you were—a typical sailboat with five or six feet of keel limits you to mostly exposed locations.
If you find a good spot, or the weather is good enough to anchor without too much worry, your next challenge is finding a place to land the dinghy. If you’re hanging out at a bar or eating at a dock-and-dine, it’s easier. If you want to tie the dinghy off and walk to the store, your choices are limited.
There are spots where you’ll find groups of liveaboard boaters on anchor or homemade moorings. When you see these boats, it may be wise to anchor your fine cruising vessel elsewhere. The Keys have a well-established community of folks who use their boats as affordable housing options. Their seaworthiness and the trustworthiness of their ground tackle are questionable. I also wouldn’t leave grabbable things like outboard motors or portable generators on deck, but that’s just me.
All of these factors, and a community-wide unfriendliness to anchored vessels in general, have led to the formation of two major mooring fields for boaters: One in Boot Key Harbor, Marathon, and one in Garrison Bight, Key West.
Boot Key Harbors is one of the most popular Keys bases for local liveaboards and cruising boaters alike. It’s a huge facility with excellent access to town and good protection from all directions. Make your reservations early because getting a ball during the winter season is nearly impossible.
Garrison Bight is easy to get in, but it’s got some big drawbacks. It’s very exposed from the north, so every cold front brings a big, uncomfortable chop through the mooring field. It’s also a long dinghy ride from the dock — well over a mile in exposed conditions. A mile doesn’t sound like much until you’re pounding into a three-foot chop in gusty, cold, northerly winds. It’s usually fine, but those few days for every ten days in the winter, after each cold front passage, are absolutely brutal.
Florida Keys Navigation Notes
There are two primary routes south through the Keys to Key West: On the bayside, you can take the ICW, and on the oceanside, you can take Hawk Channel.
The ICW route through the Keys is one of the most problematic sections on the East Coast. Commercial vessels do not use the route, so it is rarely surveyed and never dredged. In the open expanses of Florida Bay, markers are far apart, and it’s easy to be set one way or another out of the channel by crosswinds. Even in the channel, depths can be as little as 5 feet MLW in spots. Outside the channel, most birds can stand up and only get their feet wet.
The ICW route only follows Florida Bay until Marathon. At that point, it goes under the Moser Channel Bridge and joins Hawk Channel on the outside.
The number one boater complaint about the bayside isn’t the shallow water, though; it’s the lobster pots. Be sure to study up on your fishing gear, as you’re sure to share the water with tons of pots and stakes.
Generally, the route along the bayside has facilities only for smaller boats.
Hawk Channel runs along the oceanside of the Keys from Elliot Key (just off South Miami) all the way to Key West. Although it’s open ocean, the reef line farther offshore slightly protects it. While the reef won’t stop strong winds and chop, it does prevent big swells from working their way in.
Hawk Channel is the choice for most bigger vessels heading to Key West. There are a few stops along the way that allow for deep draft and larger cruising boats, including:
- Largo Canal with Key Largo Harbor and Marina Del Mar
- Three Waters (Postcard Inn), Islamorada
- Hawk Cay Resort
- Marathon area marinas and moorings
- Stock Island and Key West marinas
Running offshore of the reef line will put you in the Gulf Stream. If heading north or east to The Bahamas, this is a welcome help. But if you’re going south, it’s a no-go for slow-moving boats. Currents near the reef are usually around a knot and up to three knots farther offshore. It’s also worth noting that the Gulf Stream passage is an open water, bluewater affair, with big swell and big waves possible. Any amount of wind that opposes the current will stir up a nasty, square wave that no boater wants to deal with.
Keys Tides and Currents
Tides in the Keys are moderate, averaging only a foot or two and up to 3 feet at their max.
Generally, currents are also negligible. The exception is tidal currents between islands, which can sometimes run up to a knot. The outer reefs offshore are subject to the Gulf Stream, which sometimes dips close and can bring a knot or more of northeast-setting current to the reefs. Swimmers and divers must use caution and plan for the current.
Under the right circumstances, wind-driven tides can dramatically lower water levels in Florida Bay. Keep this in mind if you’re navigating the skinny waters along the ICW in the Upper Keys.
Boating Weather in the Florida Keys
When it comes to weather, boating in the Keys is much like boating in The Bahamas. There are two seasons: winter/dry season, and summer/wet season.
Winter, Boating in Dry Season
The dry season is denoted by low humidity and very little rain. It does rain occasionally, but it comes from passing squalls riding on cold fronts and is over quickly. It usually starts in October and goes through early May.
The weather follows a predictable cycle during this time of year. There is generally a moderate east-to-southeast wind. As a cold front approaches, winds calm while clocking to the south and southwest. The front usually brings a line of thunderstorms, including a sudden shift bringing the winds from the northwest. Gusts can be strong and sudden with the storms, testing the best anchor sets.
The storms pass as quickly as they came, and a cold wind blows out of the north for a few days. Then, the pattern settles back to the prevailing easterlies until the next front approaches.
The need to find shelter from clocking winds makes anchoring in the Keys during frontal passage tricky.
Summer Boating During the Wet Season
The wet season officially starts when humidity and temperatures rise, and it becomes hot and muggy. During this period, airmass thunderstorms build over larger landmasses, especially mainland Florida. The Keys are rarely affected by these storms, which push south and east every afternoon, but the backcountry of Florida Bay often gets walloped.
During the wet season, the weather in the Keys becomes nearly idyllic. Despite the name, it doesn’t actually rain very much. Winds are light, and the ocean is warm and calm, perfect for kayaking, swimming, diving, and snorkeling. It can be hot, but being near the water keeps temperatures much more manageable than on the mainland.
Of course, nothing is ever perfect. The Keys are smack-dab in the hurricane zone, and with storms taking aim from both the Western Caribbean and distant Atlantic, every system must be monitored closely. With only one highway out, officials issue non-resident evacuations early to prevent gridlock.
For boaters, options are very limited in the Keys during hurricane season. A few boatyards could potentially haul you out, but the highest elevation in all of the Keys is 13 feet, not enough to protect boats during a storm. The best option is to get out, but most storms will tend to veer north, making planning an escape difficult. Locals talk of finding hurricane holes deep in the mangrove creeks, but this isn’t a viable plan unless you’ve been there long enough to scope spots out and get there early enough to ensure you have space. It’s far from a foolproof or safe tactic, and you certainly wouldn’t want to ride out a storm out here.
Boating with Pets in the Keys
Overall, the Keys are a pet-friendly destination. As is the case in all of Florida, they are generally not allowed on sandy beaches — particularly when in a state park. The lack of places to land a dinghy means cruising with a pet on board is challenging when you’re between marina stops. Remember that landing on mangrove islands or small patches of sand might put Fluffy at a crocodile’s doorstep.
Landside, pets are usually good to go in outdoor restaurants, marinas, and parks.
Special Notes About Boating in the Keys
The FKNMS includes numerous no-take zones, including “Special Protection Areas” along the biggest reefs. These areas are marked with large yellow buoys. Taking anything from these areas, including fish, lobsters, or rocks, is prohibited.
Anchoring is frowned upon at the reefs because your hook or chain could damage coral, even if you are careful to anchor in the sand. The Sanctuary provides mooring balls for day use. There are hundreds of them installed all over the Keys, mostly at the reefs. All of these moorings are first-come/first-serve and free to use. The Sanctuary regularly maintains them, so they are usually some of the best around.
Be sure to review how to tie to a mooring properly; we often see boaters using these balls incorrectly and unsafely.
As you might imagine, fishing is regulated in all of the Keys. Be sure to have a current Florida saltwater fishing license on board if you’re doing any fishing. Double-check the FWC and any specific Monroe County rules, including bag limits and size minimums.
Like many areas in the region, the Keys are waging a war against invasive and hungry lionfish. These crazy-looking alien fish eat up everything on the reef and have no natural predators, so it’s up to us to kill as many as we can while we’re out there. Thankfully, plenty of tasty lionfish recipes have been concocted. Be sure to avoid those poisonous spines, though.
Keys Lingo — Talk Like a Conch
- Key — A small island, from the original native term “cayo.”
- Key lime — Tiny limes that are more yellow than green and more bitter than others. It’s the same as a Mexican lime.
- Key deer — A tiny species of white-tail deer that lives only in the Lower Keys and spends its time leaping in front of cars and eating expensive landscaping.
- Conch — A native-born person from the Keys. Also, a huge sea snail.
- Freshwater conch — An honorary conch from the mainland who has lived on island for seven years or more.
- Conch Republic — For an hour back in the 1980s, the mayor of Key West succeeded from the US and formed an independent nation. It was a publicity stunt, of course, and he immediately demanded foreign aid and then surrendered. But the spirit is alive, and you’ll see the national flag everywhere in the Keys.
- Florida Keys — Not Key West. The Keys are a group of smaller islands northeast of Key West, and the small towns on them are more conservative, with more of the feel of sleepy fishing villages that have a problem with second-home owners and wanna-be weekend pirates.
- Key West — Not all of the Florida Keys, but a small part of them.
- Oceanside — Anything south of US 1 (on the left as you drive toward Key West).
- Bayside — Anything north of US 1 (on the right as you drive toward Key West).
- Mangroves — Crazy-looking trees that grow on prop roots in salt water. The Keys are made from them, and they protect the islands from storms.
- Backcountry — The numerous shoals, sandbars, mangrove islands, and twisting channels on the bayside of the islands.
- Crocodiles—The Keys and Everglades are home to North America’s only saltwater crocodiles. They have a refuge in northern Key Largo but can be found anywhere in the backcountry or along the Keys. They’re generally shy but like to snack on small pets occasionally.
- Mile marker (MM) — Numerical markers denote your location on the Overseas Highway. MM 127 is in Florida City on the mainland, and MM 0 is in Old Town Key West.
- Square Grouper — An abandoned bail of week, coke, or drug money found floating or washed up on shore.
- Bugs — Lobster. Caribbean spiny lobster that is.
- Tickle stick — A plastic stick used to tickle lobsters. Stop laughing; that’s what you do.
- Mini season — Two horrible days in July when zillions of people descend on the Keys, clogging up the roads and boat ramps with nonsense and bad boating just to catch some bugs. It’s a good time to not be in the Keys. Many get hurt, and some die. The people, not the lobsters. Most of these people couldn’t catch a lobster if it walked into their net!
- Chickee — Local native style of a tiki hut with palm-frond roofs
- Too cold — For the locals, that’s water below 80 degrees or air below 70 degrees.
- Dolphin — Local name for mahi-mahi, a pelagic fish that tastes great in tacos. So, when you see it on the menu, it’s not Flipper.
- Green Flash — An elusive atmospheric phenomenon that occurs the moment after sunset when viewed over the water.
- The 18-Mile Stretch — The long stretch of road across the Everglades marshes between Florida City and Key Largo.
Florida Keys Boating Places of Interest
Here’s a list of places people love to hang out, plus some spots you should visit.
Major Ports and Florida Keys Cruiser Hangouts
- Key Largo marinas
- Boot Key Harbor, Marathon + marinas
- Key West and Stock Island marinas
Cute Places You Ought to Visit in the Florida Keys
- Pennekamp State Park (docks, moorings, mangrove kayak trails, reef tours)
- Coral reefs for diving and snorkeling
- Sandbars for parties
- Mangrove creeks for kayaking/paddleboarding
- Backcountry of Lower Keys (good gunk-holing possibilities)
- Bahia Honda State Park (descent anchorage for big boats between bridges, small-boat marina, beautiful beaches)
- Dry Tortugas National Park (idyllic and stunning, but its remote location requires good weather and passage planning)
Florida Keys Special Events for Boaters
Here are a few events of interest to boaters.
Lobster Season
Florida lobster season runs from early August through the end of March. Monroe County has special lobster regulations, so look up the state requirements from FWC and have the lobster stamp on your saltwater fishing license.
Lobster carapaces must be more than 3 inches. Make sure to have a gauge with you and check your catch, releasing the small ones. You don’t want to get caught with undersized bugs on your boat.
Mini Season
Mini season is the local name for spiny lobster sport season, two days of madness that occur every year during the last consecutive Wednesday-Thursday in July. For those two days, lobster is legal to take by recreational lobster hunters even though regular season hasn’t opened yet. For some reason, this is a big deal in the Keys, and people come from all around (although it’s a thing in all of Florida).
Fantasy Fest
Key West has festivals throughout the year, but the biggest is Fantasy Fest, which occurs at the end of October. It includes all sorts of debauchery and naughtiness, plus a few family-friendly events sprinkled around the island, like the Bahamas Village Goombay Fest, which kicks the event off.
Other famous Key West festivals include Pride Week and the Hemingway Days with its lookalike contest. There’s also the Conch Republic Independence Day and countless seafood, film, and art fests.
Places to Get Boat Work Done
The Keys are mostly a vacation spot, but plenty of people live there full-time and work on their boats there. There are boatyards in Key Largo, Marathon, and Key West. Key Largo has a boatyard that can haul catamarans, but you should carefully check their reviews and references before using them.
Resources, Guides, and More Information
Many people feel that cruising the Keys is similar to The Bahamas, but in our experience they are very, very different. Read our Boater’s Guide to The Bahamas for a look at what to expect on the other side of the Stream.
🛒 Buy from Amazon — Waterway Guide Florida Keys Edition
Boater Education Courses: Florida Keys and Everglades National Park
Knowledge Base Articles:
How To Properly Tie to a Mooring Ball
Boaters, Don’t Run A-foul of Fishing Gear
Boater’s Guide to The Bahamas
Leave a Reply