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Office of Greenways and Trails

Florida Circumnavigational Saltwater Paddling Trail

Segment 15

Florida Keys Overseas Paddling Trail

 Kayakers in open water in the Florida Keys
Kayakers on Open Water in the Keys

 Segment 15

Florida Keys Overseas Paddling Trail


Emergency contact information:


Monroe County Sheriff's Office: 305-289-2430

Florida Fish and Wildlife Conservation Commission 24-hour wildlife emergency/boating under the influence hotline: 1-888-404-3922


Begin: John Pennekamp State Park, Key Largo

End: Fort Zachary Taylor Historic State Park, Key West

Estimated Distance: 111 miles

Duration: 9-10 days


Special Considerations: The Keys are unlike any other segment in that you can paddle up and back and choose paddling on the Florida Bay/Gulf of Mexico side or along the Atlantic Ocean. Distance and duration will be determined by which side is chosen. The Bay side is longer as the shoreline is more sinuous and there are numerous opportunities to explore a multitude of islands, especially in the Lower Keys. You can also weave in and out between the bay and ocean through several creeks and channels, taking advantage of prevailing winds and weather conditions. Many of the same campsites can be utilized since they often border channels between the main islands. All mileage estimates in this guide are for the Atlantic side of the keys; they are measured in statute miles, not nautical miles. A global positioning system (GPS) unit is highly recommended to find campsites and points of interest.

For long-distance circumnavigation paddlers arriving from Everglades National Park and Florida Bay, the current point of connection to this trail is to come in from a primitive campsite at Rabbit Keys to the Indian Key Channel between Upper and Lower Matecumbe Keys. Efforts are being made to establish a primitive campsite to the south in Everglades National Park so long-distance paddlers have the option of beginning this segment in Key Largo.




 Paddling in the Keys is a great way to experience both tropical splendor and unique culture. The Overseas Highway is busy, powerboats abound on weekends and holidays, and some of the island towns can become congested during the peak winter tourist season, but by paddling just a short distance to lush, uninhabited islands or down winding tunnels through mangrove forests, it is easy to taste wildness and to experience solitude. Paddlers can enjoy viewing a rich diversity of marine life, ranging from manatees and sea turtles to lobsters, fish and stingrays. An array of bird life can also be spotted, from migrating hawks to magnificent frigate birds to brightly-colored warblers. Conversely, civilization in the form of great restaurants, lodging, and evening entertainment is often within easy reach of the water. Thus, the best of both worlds can be experienced!


History, too, is a strong part of the keys experience. Visual reminders of Henry Flagler’s overseas railroad of the early 1900s can be seen in the arching concrete columns of several old bridges, including the original Seven Mile Bridge between Knight’s Key and Ohio Key. Remnant railroad depots still exist, and the Flagler Station Over-Sea Railway Historeum can be visited at the Key West Seaport. The Labor Day Hurricane of 1935 destroyed much of the railroad.


Historic sites such as Indian Key Historic State Park and Fort Zachary Taylor Historic State Park can be visited from the water. Shipwrecks can sometimes be spotted in the gin-clear waters, testament as to how treacherous the Keys’ waters were for navigation. Salvaging shipwrecks, known as wrecking, was once the main industry in the Keys.


Because the Keys are a popular winter destination for tourists and snowbirds, advanced reservations for desired motels and public or private campsites are highly recommended. For reserving state park campsites as outlined in this guide, call toll free 1-800-326-3521 or 1-866-I CAMP FL, or go online to www.ReserveAmerica.com. There are some primitive campsites specifically for paddlers being developed at several state parks that do not require reservations at this time. Please keep these sites clean and follow all regulations in order for them to remain open for paddlers. Most of these sites are “pack-it-in, pack-it-out” only, with campers following Leave No Trace principles: http://www.lnt.org/.


Lodging is available in all of the Keys’ towns, and there are numerous private campgrounds. Log onto www.SEE-FloridaKeys.com, www.fla-keys.com or http://bestonkeywest.com/ , or call the Monroe County Tourist Development Council at 1-800-FLA-KEYS to ask for a free planning guide. Several outfitters in the Keys can also assist you in renting or selling equipment or in guiding trips. A Web search is the best way to locate them, or view the outfitters link on this Website.


Many important land areas and water bodies in the Keys are in the public domain, to be carefully managed for ecological, historical or recreational purposes. Visit the popular Florida State Parks  in the Keys. There are two Aquatic Preserves, Lignumvitae Key and Coupon Bight. The Florida Fish and Wildlife Conservation Commission manages the Florida Keys Wildlife & Environmental Area. Federal land and waters include Everglades National Park , National Key Deer Refuge, Great White Heron National Wildlife Refuge,  Crocodile Lake National Wildlife Refuge,Key West National Wildlife Refuge , and the Key Largo, Looe Key and Florida Keys National Marine Sanctuaries. The Florida Keys Marine Sanctuary covers most waters in the keys, encompassing 2900 square miles, and kayakers should be aware of regulations if planning to fish or snorkel.


A large number of shorter paddling adventures are available in the Keys other than the sections outlined here. To learn more, check out The Florida Keys Paddling Atlas by Bill and Mary Burnham (Falcon Press), The Florida Keys Paddling Guide by Bill Keogh (Backcountry Press) and Kayaking the Keys by Kathleen Patton (University Press of Florida). Up-to-date trail information can also be obtained by calling or visiting local outfitters.  Whether you are planning to paddle an hour or a week or more, seeing the keys by kayak offers many rewards.


1: John Pennekamp Coral Reef State Park to Tavernier, 12 miles

        John Pennekamp Coral Reef State Park is an appropriate beginning point for the Keys trail. Dedicated in 1960 and named after the late John D. Pennekamp, a Miami newspaper editor and strong supporter of establishing the park, this was the first undersea park in the United States. While the famed coral reefs are considered too far offshore for a kayak, the park offers several types of tours in which to safely view the reefs and rich marine life. Call 305-451-6300 for more information on these tours. The park also boasts a large aquarium and visitor’s center, two nature trails, full facility camping, and 2.5 miles of marked mangrove wilderness trails for canoes or kayaks. Approximately 100 feet offshore from Pennekamp’s Cannon Beach, you can snorkel or glide over the remnants of an early Spanish shipwreck.      


You can begin this section at Pennekamp’s kayak and canoe launch along Largo Sound. Be watchful of boat traffic as you make you way to the Atlantic along the park’s canoe and kayak trail, heading south along a tidal creek through the mangroves. Paddle along Key Largo to Tavernier. Many paddlers camp on Tavernier Key, but this island is private and formal approval for camping has not been granted.


Tavernier Creek can take you to the bay side, if so desired. Accessible motels along the bayside include Coconut Palm (305-852-3017), Island Bay (305-852-4087) and Lookout Lodge (305-852-9915). See map for GPS points. During the peak spring season, some of these motels may require a two or three night minimum stay.


2: Tavernier to Islamorada, 9 miles


In his History of Tavernier, found on www.keyshistory.org , Jerry Wilkinson writes, “In early writings, the harbor between Tavernier Key and Key Largo is mentioned as a rendezvous area for Bahamian wreckers. It offered a haven from Atlantic gales and a good view of the Upper Keys reefs. In the early 1820s it is believed that slaves were gathered on Key Tavernier to be smuggled into the Bahamas by wreckers, but this has never been documented. It was used as a relay point for some escaped slaves enroute to the Bahamas.”


The Keys history website, along with several good books, can inform you more about fascinating aspects of Keys history such as the wrecking industry, sponging, early native inhabitants, Flagler’s railroad, devastating hurricanes and more. 


Leaving historic Tavernier Key, it is a fairly straight shot along Plantation Key, once the site of a large Native American village. A huge Indian mound that stood on the island for centuries was leveled for construction in 1958.


 When you reach the town of Islamorada, you can arrange for Islamorada Lodging at one of several resorts and motels. Waterfront motels that are considered kayak friendly include: Conch On Inn Motel (mm 89.5) 305 852-9309; Lookout Lodge (mm 88) 305-852-9915; Coconut Cove Motel (mm85) 305 664-0123; and the Hampton Inn and Suites (mm 80) 1-800 426-7866. The Whale Harbor Channel in Islamorada is a link to the bay side. Islamorada has often been called the fishing capital of the world.


3: Islamorada to Long Key State Park, 15 miles


The first of many long bridges separate Upper and Lower Matecumbe Keys in this section. On the Atlantic side of the bridge is Indian Key, famous for a Seminole raid in 1838 on the family of Dr. Henry Perrine. Perrine and several others were killed, though many family members successfully hid in a turtle kraal beneath the house. The island is now a state park and can be visited seven days a week from 8 AM to 5 PM. Tours are available at 9 AM and 1 PM Thursday through Monday.

Just to the southwest of the park is the San Pedro Underwater Archeological Preserve State Park. In good weather, you can glide over or snorkel the remains of a 1733 Spanish treasure ship, which lies in 18 feet of water. Look for the five white mooring buoys marking the site approximately 1.25 miles south of Indian Key. You can tie your kayak to these while snorkeling.


On the other side of the bridge is Lignumvitae Key, famed for harboring now rare lignum vitae trees. Meaning “wood of life” in Latin, the tree was used to treat diseases ranging from syphilis to gout, and its dense wood was used for submarine propeller shafts and other specific uses. Rare orchids, tree cacti and an historic homestead can also be seen on this state botanical area. Note that the park is also open from Thursday through Monday, from 8 AM to 5 PM. Tours are available at 10 AM and 2 PM.


Surrounding the island is the Lignumvitae Key Aquatic Preserve and the Lignumvitae Key Management Area.  Encompassing 10,000 acres of seagrass meadows, deep-water channels and hard-bottom communities, look for tarpon, bonefish, permit, sea turtles, lobster and other marine creatures in the clear waters. Most of the seagrass areas are zoned off limits to combustion engines.


Past Lower Matecumbe Key, Long Key sticks out like a huge boot. Early Spaniards called it “Cayo Vivora,” which means Viper Key because its shape is said to resemble a snake with open jaws. On Long Key, you’ll see remains of coral reefs formed 100,000 years ago, when sea level was 20 to 300 feet higher than today. When sea levels dropped during the last Ice Age, the reefs died and formed the islands of the keys. The highest point in the Keys is 18 feet above sea level, while the average is less than 10 feet above sea level, a main reason why the Keys are so vulnerable to hurricanes.


Long Key is famous for Henry Flagler’s Long Key Fishing Club, which attracted such notables as western author Zane Grey. Grey summed up his time spent on Long Key: “Into my memory had been burned indelibly a picture of a sunlit, cloud-mirroring, green and gold bordered cove, above the center of which shone a glorious fish-creature in the air.” The original fishing resort was destroyed in the 1935 hurricane.


Camping is on the Atlantic side in Long Key State Park where you can reserve one of the park’s 60 scenic campsites in the campground (all bordering the Atlantic Ocean) or camp in one of the park’s six primitive campsites open to paddlers. You must reserve through Reserve America for the campground, or you can call the park headquarters up to 24 hours in advance to check on availability of the primitive sites: (305) 664-4815. The park also offers nature trails, an observation tower, and ranger led interpretative programs.



4. Long Key State Park to Curry Hammock State Park, 13 miles


In this section, you’ll pass several small islands and cross a long section of open water. Duck Key, which was bypassed by both the railroad and overseas highway, is the first large island you’ll encounter. In the early 1800s, Charles Howe utilized the tidal creeks and pools of Duck Key for making salt. At that time, salt was the main element used in preserving meat.


You have the option of paddling to the inside (along the Overseas Highway) or outside of Duck Key to Tom’s Harbor Keys and Grassy Key. Just past Grassy Key is Little Crawl Key and Curry Hammock State Park. Use Reserve America to reserve a site in advance at Curry Hammock State Park or call the park at least 24 hours in advance to check walk-in availability (305) 394-3330. Take a walk through the hardwood hammocks and view one of the largest populations of thatch palms in the United States.

5. Curry Hammock State Park to Molasses Key, 15 miles


Take your time paddling through this section. First, you can take a break at Sombrero Beach in Marathon. Make sure to use the kayak launch site on the west side of the swimming beach.


As a side trip, you can take Sister’s Creek (just west of Sombrero Beach) and then paddle through a labyrinth of shallow mangrove tunnels that wind through Boot Key, but be careful not to become lost! Once on the trail again, you’ll cruise alongside a famous Keys landmark—the Seven Mile Bridge just past Marathon. You can view the new bridge, built in 1982, as well as the longest surviving bridge segment of Flagler’s railroad. Imagine the work that went into the original bridge. Top quality cement was imported from Europe. Huge floating concrete mixers had to be used. Dams were built around each column to keep out water, as workers labored to bridge the span. Several hurricanes dealt serious blows to men and machines during the overall project. The fact that the bridge remains is a testament to the quality of workmanship and materials. The new bridge is also acclaimed as a major architectural and engineering achievement.


A little over two miles down the old bridge from Knight’s Key, you can stop at Pigeon Key Marine Science Center and tour through a restored village and museum. Pigeon Key originally housed workers for the Flagler Railroad. What survives are eight restored Flagler-era buildings. Be sure to land on the beach on the north side of Pigeon Key. There is an entrance fee.


Primitive camping is on Molasses Key, a private island just over half way down the Seven Mile Bridge on the Atlantic side, but far enough away from the highway to avoid most of the traffic noise. Be mindful of swift currents and the potential for strong winds when crossing these open spans of water.


As an alternate overnight stop, you can camp at the privately-owned Knights Key Resort & Marina just before the Seven Mile Bridge. It can be accessed by either Sister’s Creek (just west of Sombrero Beach) or by taking the Atlantic side around Boot Key. There is spacious tent camping in the center of the campground and restaurants are within easy walking distance. Like most private Keys campgrounds, in can be pricey in the winter months. You must call ahead to reserve a spot and land at the manager’s campsite, which is site #9 (see gps coordinates on map). Access can be muddy and rocky at low tide. Call (800) 348-2267.


6. Molasses Key to Bahia Honda State Park, 7 miles


Some places just seem more graced with beauty than others.  Bahia Honda State Park is one of them. Arching palms frame sandy beaches and coves alongside sparkling clear water. An old section of the Flagler railroad bridge (the only trestle bridge along the route) across the Bahia Honda Channel gives the park an historic flavor.

This is a very popular state park, considered one of the top beaches in the world, so reserve campsites early. Prime tent sites along the Atlantic are in the Sandspur Camping Area. Non-electric beachside sites are 49 through 56. The more expensive electric sites are 64 through 72. There is also camping near the bridge in the Buttonwood Camping Area (sites 12 through 25 are electric sites along the water) and eight non-electric sites (cheaper) along Florida Bay in the Bayside Camping Area. You may want to access the park on the north side of the abandoned railroad bridge along the west end of the key if the surf is strong along the Atlantic beaches.


Campsite #80 on the bay side is available to paddlers on a first-come, first-serve basis. Paddlers must first register at the park’s ranger station. If you plan to use the site, call the park at (305) 872-2353 on the morning of your planned arrival to ensure that the site will not be released for use by the general public. The site is held by the park until 3 p.m. each day to allow for paddlers to get a first shot.


At the far end of Sandspur Beach, don’t miss the nature trail that follows the shore of a tidal lagoon. Here, you can see two national champion trees: the silver palm, a threatened species, and the yellow satinwood. The endangered lily thorn can also be seen. The park boasts one of the largest stands of silver palms in the United States.


If Bahia Honda is booked, try camping at the Big Pine Key Fishing Lodge just across the Bahia Honda Channel (305 872-2351). You can land at the boat ramp via the inlet parallel to U.S. 1. Sites 10 through 14 and 40 through 46 are tent sites right on the water. The campground has a convenience store, pool, and laundry. Bicycles can often be rented if one wants to ride the two or so miles to restaurants and a larger grocery store in Big Pine.


Be on the lookout for endangered key deer, which roam freely on Big Pine Key. The Key deer is the smallest subspecies of the Virginia white-tailed deer, having become isolated in the middle keys about 4,000 to 10,000 years ago when sea levels rose. Big Pine Key also contains a high level of biodiversity, with 466 documented plant species.


If you stay at Big Pine Key Fishing Lodge, you can cut about 3.5 miles off your next day’s paddle to Sugarloaf Creek.


7. Bahia Honda State Park to Sugarloaf Key KOA, 17 miles


Part of the beauty of paddling this stretch is that once you pass Spanish Harbor, you can paddle alongside several remote islands more than two miles from the main highway, so traffic noise is minimized. You’ll also cruise through the 6,000-acre Coupon Bight Aquatic Preserve, located on both sides of Newfound Harbor Keys. On the Atlantic side of the keys, look for circular domed formations which are living coral patch reefs. By snorkeling, you can spot brightly-colored tropical fish along with larger grouper, snapper, snook and barracuda. Besides providing necessary habitat for marine life, patch reefs such as these baffle wave energy, thus helping to provide storm protection for the islands.


Coupon Bight itself is a shallow tropical lagoon where you can spot numerous wading birds and possibly key deer along the shore. Sea turtles nest on the preserve’s beaches. These waters are known for harboring large numbers of tarpon in the spring.

Camping is at the Sugarloaf Key KOA, 305-745-3549. This full facility commercial campground is located on the Atlantic side of Sugarloaf Key along a well-marked channel. GPS on map is for the boat ramp. Kayakers can stay in a spacious primitive tent area for less than the regular fee. Some paddlers stay at an unauthorized campsite near a collapsed bridge along Tarpon Creek.


8. Sugarloaf Key KOA to Geiger Key Marina, 13 miles


On your way to Geiger Key, you’ll paddle along Sugarloaf Key. An 1850 census reveals only three males residing on Sugarloaf Key. One was known as “Happy Jack.” Believed to have a fondness for whiskey, he survived by trapping deer and raising fruit. Other colorful Keys hermits of the time included Paddy Whack, Jolly Whack, Red Jim and Lame Bill.


Sugarloaf Key is better known for a 35-foot tower that remained unoccupied. In 1929, trying to control the hefty mosquito population, R.C. Perky called in outside help to build a giant bat house. Stocked with imported bats, the bats promptly flew away and the tower failed to attract new bats. Nevertheless, tourists continue to flock to this national historic landmark. The tower is located on the west side of Sugarloaf Sound on the bayside.


A good rest stop and launch site is a small parcel of public land on the east side of Sugarloaf Creek (see map) where there are picnic tables and a pavilion.


Geiger Key Marinais located on the east side of Geiger Key just inside Saddlehill Key. It offers several amenities such as tent camping, showers, water, Laundromat and a restaurant. For more information or to make reservations, call (305) 296-3553.


9. Geiger Key Marina to Boyd’s Key West Campground, 7-8 miles


Paddle alongside Boca Chica Key through the Western Sambo Ecological Reserve, believed to contain the greatest habitat diversity in the Lower Keys. Nearshore patch reefs are accessible to kayakers while bank reefs and other coral formations may be too far offshore. Learn about fishing and snorkeling regulations in Western Sambos Ecological Reserve .


Proceed to Key West, the largest of the Keys’ towns and one that boasts a culture all its own. The campground is located on the east side of Stock Island about a half-mile south of the main highway. It boasts several waterfront tent sites along with a heated pool, laundry facilities, game room and convenience store.  You can reserve a site by e-mail (www.boydscampground.com) or, if you are planning to arrive within seven days, you can call directly at (305) 294-1465. Reservations between December 25 and January 1 are not accepted (first come, first serve). There are also several oceanside resorts and motels in Key West.


The old part of Key West is about five miles west of Boyd’s Campground. Buses or taxis, or your own two feet, can take you to numerous museums, restaurants and other attractions. Don’t miss the sunset celebration at Mallory Square, where people-watching is an added bonus.


10. Boyd’s Key West Campground to Fort Zachary Taylor Historic State Park, Key West, 7 miles


Cruise along several scenic beaches, such as the renowned Smathers Beach.  You may want to stop for a photo at the southernmost point in the continental United States, identified by a huge red-topped metal marker just past South Beach. The end of this segment is Fort Zachary Taylor Historic State Park. You can land at a kayak launch spot on the eastern end of the park’s beach near a kayak concessionaire. You need to check in at the admissions gate before using the park and touring the fort.


Construction of Fort Taylor began in 1845. Union forces occupied it during the Civil War to control blockade-running ships. This helped Key West to prosper during the war since numerous ships from several nations were seized and brought into Key West’s harbor for disposition. The fort was used again during the Spanish-American War. Today, Fort Taylor is noted for containing the largest buried arsenal of Civil War cannons in the United States.


You can end (or begin) your journey here, or turn around and head back to Boyd’s Campground. Another option is to circumnavigate Key West, but beware of large ships (such as cruise liners) entering or leaving Key West harbor just past the fort. Taking this route will add three to four miles to your return trip to Boyd’s Campground.


Note: if you are doing the entire circumnavigational trail in one swoop, you are welcome to shuttle back to the point where you entered the Keys. No need to paddle the same water twice. 



Segment 15 Maps:


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Last updated: January 07, 2015

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