Caladesi Island

Trip Overview

In the beginning…

There was Caladesi Island. I had retired to Florida in 2016, and in 2017 scored two used Ocean Scrambler XTs for the bargain price of $425. A friend of mine in Safety Harbor alerted me to the fact that neighbors moving to California were selling them. And then the very next day I purchased an ultra-lightweight trailer from some guy up in Tarpon Springs.

As a transplant from Massachusetts, my aquatic orientation was salt water, with the exception of a 7 year love affair living on a fresh water lake outside of Boston.

In March of 2016 my wife and I settled into semi-retirement life in a lovely little neighborhood about 15 minutes from the Dunedin Causeway. I quickly discovered that the ultra-lightweight trailer could not exceed about 45 miles per hour without it, and my precious kayak cargo, going air born. I dove into kayaking without zero study or purpose. I had done random kayaking over the years prior to my move to Florida, but it was not a habitual activity. I was far too focused on career and making living to have given any real thought to hobbies or consistent, pleasurable non-work activities. I made myself be content with a paltry two week vacation a year.

My affinity for salt water, and the limited range of my kayak trailer, saw me return again and again to the Dunedin Causeway and trips to Caladesi Island too numerous to count. Although I was semi-retired, I still was working part-time at jobs that mostly allowed me to be outdoors and getting exercise. I valet parked cars at both Morton Plant and Meese Countryside Hospitals. I worked the service ramps and drove customers at Ferman BMW and Dimmitt Cadillac in Pinellas Park and Clearwater. My final gig before truly calling it quits on all forms of work was prepping cars and driving customers for Enterprise Car Rentals.

From 2017 to 2019 my wife and I did a ton of DIY projects to restore our 1949 house to its former glory. These projects plus my part-time outdoor jobs did not leave a ton of time for kayaking. Furthermore, my wife is not a big fan of open water kayaking, and I had not yet figured out that I could go off on solo ventures. I was content to go out maybe once a month, always returning to the waters around Caladesi and Honeymoon Islands.

My true descent into kayak junkie-ism began with COVID. Pinellas County shut down everything. I couldn’t launch my kayak from the Dunedin Causeway anymore. Honeymoon Island was closed. I wasn’t working a part-time job. I was like a caged beast. I needed to find a body of water where I could launch my kayak.

On May 11, 2020 I hit pay dirt! I discovered that Fred Howard Park in Tarpon Spring was still open and that there was a tiny, muddy kayak launch at the end of one of the mangrove trails. Fred Howard Park was in striking distance with my ultra-lightweight trailer. My wife and I were thrilled to be back on the water.

In my desperation to find places to launch during the COVID shutdown, I started doing more research on other nearby salt water locations. Rivers were not yet on my radar screen.

I vaguely recall thinking that my kayaking options were severely hampered by owning a trailer that could not exceed 45 m.p.h. My brain had already been traveling in the direction of, “we need extra kayaks for when friends come to visit us.” On May 28, 2020 I found a trailer, plus two kayaks, for sale in Mt. Dora.

Finding this 6-pack trailer was a slippery slope. I wasn’t thrilled with the two kayaks that came with it. They were older model sit-ins, a style of kayak I affectionately call bath tubs. I exclusively paddle sit on tops. I have friends that move easily between SOTs (Sit On Tops), sit ins and paddle boards (SUPs).

As the COVID shut down dragged on, I plunged myself into all things kayak research. I purchased books about Florida’s rivers, springs and State Parks.

On August 8, 2020 I sold my ultra lightweight trailer and the two sit in kayaks from the Mt. Dora purchase. On August 15 I purchased a red Ocean Scupper Classic kayak, on August 25 an older model Hobie Pursuit, on September 7 a bright yellow Necky Dolphin, on September 14 a grey Ocean Scupper Classic, on October 14 a teal Ocean Scupper Classic and on November 11 a Hobie Maui kayak.

It is important to note that all of the above kayaks are SOTs and no longer made by their respective manufacturers. The Necky company no longer exists. Within 4 months I assembled a bad ass collection of high performance, somewhat vintage kayaks. I have, more recently, added two Current Designs Kestrel 140 SOTs to my fleet.

During my kayak buying jag, the woman who sold me the grey Scupper Classic told me about an online kayak forum. I learned that there are tons of kayak forums on FB. Who knew? I had never thought to look. This small bit of advice accelerated the rate at which I became a kayak junkie. The kayak trip that permanently sealed my fate was my first paddle on a Florida river, an amazing mix of both black water paddling and crystal clear spring runs. I will post about that river. But first, I must honor my beginnings as a salt water paddler. There is much more to tell about my much beloved local island.

Caladesi Island

Launch: Dunedin Causeway – the last parking lot on the left, west of Sail Honeymoon Canoe & Kayak Rental, but before the second causeway bridge.

Paddle Time: A few hours or many more. This can be a full day excursion with many opportunities for exploring, hiking and swimming.

There are many ways to enjoy Caladesi Island. The seemingly most popular and shortest trip is to head south and slightly west from the causeway across St. Joseph Sound with your sight set on the white sand north tip of Caladesi Island. This route is a 15 to 30 minute paddle depending on type of kayak or SUP, your personal paddling strength, and the direction of the tide and wind. On a calm day this crossing is a cake walk. If the tide is against you and the winds are strong it can be a horror show. Do not bother with wind apps for this location. They are almost always wrong and there is nothing predictable about the winds in St. Joseph Sound. One can paddle out in the morning with still air and on water resembling glass. By the afternoon you can be hit with choppy seas and unrelenting wind, even though calm winds and water were the prediction du jour.

The waters here are generally shallow, and then even more shallow at low tide. There is a well-marked, dredged channel for motor boat traffic. Crossing it on a kayak, canoe or SUP can be a terrifying experience for the novice paddler. And it isn’t much fun for an experienced paddler either. However, the rewards are worth the risk to make this crossing. If you must go out on a weekend, go early in the morning and try to return in the early afternoon. Even though operating a motor boat or jet ski under the influence of alcohol or mind/mood altering substances is illegal, it very commonly occurs in the world of motor boating. Paddlers also indulge in booze and drugs while on the water, and they are mostly a danger to themselves. A motor boat or jet ski operator under the influence can inflict far more lethal damage to others at an alarmingly rapid pace.

Once you have crossed to the north end of Caladesi, you can swim and relax on the north/north east end of the island, or paddle around to the north/north west end of the island. Many paddlers and motor boaters beach here and it is generally party central. If you choose to paddle further along the west side of Caladesi to find a less populated area, hug the shoreline of the north end of the island until you are out of the insane currents in Hurricane Pass. Hurricane Pass is shallow at the edges, but the middle of the pass has been dredged to allow for motor boats and jet skis access to the Gulf. Motor vehicles blaze through this pass at high speeds. In addition to the wakes they create, Hurricane Pass has its own, ever present, washboard currents. When the tide is going out, I have seen paddlers who were stuck in the currents of the pass, unable to make any forward progress. Many have flipped their kayaks or fallen off SUPs. This is not a place where anyone should be bobbing around in the water. The danger from speeding boats is great.

The waters on the east side of Caladesi Island are shallow with an abundance of sea grass growing from the sandy bottom. As you paddle towards Caladesi Island and enter this grassy area, signs restricting combustion engine vessels are present. What this means to a paddler is that you can safely and quietly paddle south down the east side of the island without the annoyance of fast moving vessels. There is a specifically marked channel further offshore of Caladesi that is the designated motor boat route to the Caladesi Marina.

My favorite route and day trip to Caladesi is to immerse myself in the tranquility of the mangrove trails. It is roughly a 45 to 60 minute trip from the Dunedin Causeway to the Caladesi Marina. As with all open water paddling, the time it takes to make the trip is very much impacted by wind, tide and surf conditions.

The easiest way to locate the entrance to the marina is to paddle to the right of the motor boat channel markers (staying in the shallow protected waters) or to observe the direction of the easily identifiable Caladesi Ferry which shuttles people back and forth from the island every half hour. In low season the ferry runs hourly. Your paddling direction is on the east side of the island, heading south.

As you enter the marina, you will see a series of docks and boat berths along with the island concession facility. Stay close to the mangroves on the left side of the marina, continuing left until you see a sign for the entrance to the mangroves.

Unlike other mangrove systems, which are often unnavigable at low tide, the Caladesi mangroves are more easily paddled at low tide (with the exception of negative low tides in winter months). You still can paddle the mangroves at high tide, but your head will be in the mangrove canopy where you will be required to duck and weave to avoid the spider-web maze of mangrove branches. I do not recommend paddling this trail on a SUP.

The first section of mangrove trail begins at marker 1 in the marina and is a short run to marker 6. This section of trail will exit you back into St. Joseph sound. When you exit the mangrove trail, continue paddling south, hugging the mangrove forest which will be on your right. You will pass marker 7 and a mile marker post and after about 10 minutes you will arrive at marker 8 where you re-enter the mangrove trail. Paddling open waters during Florida’s summer months can be brutally hot. The shade of the mangrove canopy is a delightful relief from the punishing sun. However, make sure you have packed bug repellent for this journey. The dredged mangrove trails were misguided human intervention at controlling mosquito populations. These navigable channels rarely occur naturally.

The continuation of the mangrove trail begins at marker 8 and ends at marker 18. This section of the trail is slightly more difficult to follow. It appears that some of the marker signs have been slightly pushed askew by the force of tidal shifts and the directional arrows are not entirely accurate. There are only 2 or three turns where a paddle could venture off in the wrong direction. However, most of these wrong turns become quickly impassable and it is a short distance to reverse course and rejoin the official trail.

It is in this section of trail that one paddles back in history to the days of land ownership via homesteading. In 1888 an immigrant from Switzerland, Henry Scharrer “discovered” Hog Island and decided this would be a beautiful place to live. He became a U.S. citizen, put in his application for a homestead and in 1890 took up permanent residence on the southern 156 acres of Hog Island. Hog Island was severed in two in 1921 by a severe hurricane, creating North Hog Island and South Hog Island. We know these islands today as Caladesi and Honeymoon.

The ruins of the Scharrer Homestead are located approximately a half mile from the end of this section of mangrove trail. Your only clue to this portal back in time is a small, sandy slope break in the mangroves, not more than 6 feet wide. If you are not watching for it on the right side of the mangrove channel you could easily float right past it. This small landing is the only good place to get out of your kayak to take a break. This is not to say that you cannot get out of your boat in the paddling channel, but you may find that you sink up to your hips, or deeper, in the mushy bottom of the mangrove channel.

The Scharrer Homestead can also be reached on foot. There are hiking trails on Caladesi Island that lead to the homestead. There are two signs that provide a brief history of Hog Island and the Scharrer Homestead, the ruins of the Scharrer house and a picnic table for your dining convenience. There are no facilities or trash receptacles, so as with all kayaking adventures, be responsible and carry out whatever you carried in.

Leaving the site of the Scharrer Homestead and continuing south through the remainder of the mangrove trail, one can further explore the waters around Caladesi Island. You will exit the mangroves at trail marker 18. Turn right. You have the option of exploring the quiet, shallow waters in Scharrer Bayou or paddling further west into Dunedin Pass and locating a sandy cove on the east side of Bird Key. Access to Bird Key is an obscure break in the mangroves that leads to a sandy cove and beach. I found my way to it the first time by making a few wrong turns. You will know you have found the portage cove because there are two shelters on the Gulf side of this beach made from driftwood. The ocean often knocks them down and some 2 guys in a motor boat periodically return and rebuild them. From this cove on Bird Key you can walk the short distance across the sand to the Gulf side and take a refreshing swim. You can also portage your kayak and paddle the west, or Gulf side of Caladesi Island. Another option is to retrace your path back through the mangroves. You can also head through Scharrer Cut and island hop your way north back to the Dunedin Causeway. On calm water days my preferred route is to circumnavigate the island.

These small islands sprinkled around St. Joseph Sound are called spoil islands. They were created by human interference in the ecosystem. These man-made islands are a result of dredging in order to promote boating and commerce throughout Florida. Large boats would not be able to travel through St. Joseph Sound were it not for dredging. Motor boats keep to the marked channels for their navigation from the sound out into the Gulf of Mexico, giving kayakers safe paddling through the shallows.

Do not skimp on packing a sufficient supply of hydration options. I have seen people get seriously dehydrated on this journey.

On my really lucky paddling days I have had dolphin escorts, observed raccoons swimming across the mangrove channels and seen manatees mating.