Fort Myers to Key West by Boat
Last Updated on September 26, 2024 by Boatsetter Team
If you’re planning a passage between Fort Myers and Key West, you’re in luck, it’s a great stretch of water to explore with a few fun stops to drop anchor or tie up in a slip and enjoy the scenery. Much of your experience will be dictated by the type of boat and the weather but other than the hurricane season of summer, you should be able to enjoy a great boating adventure.
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Distance, direction, and time
The total distance is about 140 miles which a fast powerboat going 30 knots can cover in five hours, non-stop. However, keeping that kind of consistent speed may be fatiguing so plan on a more conservative 20 knots which would take 7 hours. That said, unless you’re truly in a hurry or are on a sailboat that can conservatively move at 5 knots, you’ll want to plan 2-4 stops along the way so plan a few days or a long weekend.
Whatever vessel you choose, it should be offshore capable for coastal or near-coastal work. At the most remote point on a relatively direct route, you’ll be roughly 30 nautical miles west of Everglades National Park so be prepared to be out of the sight of land.
Planning
Key West is nearly due south from Fort Myers which means 180 degrees on your compass if you go direct. If you follow the west coast of Florida, you’ll eventually head more southeast. The trade winds generally blow from the east with some variation from northeast to southeast. This mean you should experience a beam reach when the wind will be coming over your port side as you head south. For sailboats, this can be a perfect reach. If the wind shifts to the south, you may get an uncomfortable bash and will need to slow down. Check the weather frequently along the way and don’t consider this trip July – October which is the height of hurricane season.
From one of the many marinas in Fort Myers you’ll head southwest along the Caloosahatchee River, to the southern end of Pine Island Sound and out into the Gulf of Mexico. You’ll have the Ten Thousand Islands off on the left. Once you reach Florida Bay north of the Florida Keys, follow marked channels to Key West, the southernmost point in the continental United States. Follow more markers to enter the harbor and its many marinas.
Bring drinking water, food, sunscreen and layered clothing because you can’t guarantee to be at a dock in a marina every evening, especially if there is an emergency or a change of plan. For at least part of the trip, you’ll be out of cell phone range so make sure there’s a VHF radio aboard.
Routing and stops
Depart Fort Myers and follow markers toward Sanibel and Captiva, two barrier islands that are worth a visit. From here, you can either follow a marked channel under the Sanibel Causeway, or spend a day anchored in the Sound and then exit via Boca Grande Pass, a deepwater channel that leads into the Gulf of Mexico. You’ll cover 20-30 miles that day depending on your routing and may end up anchoring near the barrier islands.
From Sanibel to Naples, you’ll be covering about 18 miles on this stretch. Naples is a lovely area to spend the night at anchor. You can enter via Gordon’s Pass or tuck up near Keewaydin Island Beach for some fishing (with a license) or a shelling along the beach.
Next, make it a leisurely day from Naples to Marco Island that covers only about 20 nautical miles. Call ahead for transient dockage in one of the many marinas and enjoy the waterfront restaurants including Snook Inn, Capri Fish House and the Dolphin Tiki Bar. Take in a round of golf at nearby Hideaway Beach Park or go paddleboarding at Tigertail Beach Park.
The next day will be your longest as you leave the shallows of Ten Thousand Islands and Everglades City to port and head south 80 miles. Following channel markers in Florida Bay and on to Key West will be slow going so plan ahead and get an early start.
The bulk of this passage will be in open water so know what the weather is doing and bring seasickness medicine if needed.
Exploring Key West
Guest dockage is available with prior arrangement in one of many Key West marinas like Key West Bight Marina. Once tied up, head out to Duval Street for nightlife, Mallory Square for its sunset celebration, and the Ernest Hemingway Home and Museum. Of course, you’ll need to take a selfie at the Southernmost Point concrete buoy along with the rest of the tourists.
You don’t need to add all the stops outlined above but you’ll be boating through some phenomenal places so why not slow down and enjoy your time on your own boat or one rented from a peer-to-peer sharing service like Boatsetter?
Learn more about Key West
Key West Water Activities You Must Experience
Private Boats from Miami to Key West
Zuzana Prochazka is an award-winning freelance journalist and photographer with regular contributions to more than a dozen sailing and powerboating magazines and online publications including Southern Boating, SEA, Latitudes & Attitudes and SAIL. She is SAIL magazines Charter Editor and the Executive Director of Boating Writers International. Zuzana serves as judge for SAIL’s Best Boats awards and for Europe’s Best of Boats in Berlin.
A USCG 100 Ton Master, Zuzana founded and manages a flotilla charter organization called Zescapes that takes guests adventure sailing at destinations worldwide.
Zuzana has lived in Europe, Africa and the United States and has traveled extensively in South America, the islands of the South Pacific and Mexico.
