One of my favorite paddle trips was a round trip from Pine Island to Cabbage Key in mid-February, 2008. I was renting kayaks from John Paeno, a Calusa interpreter I had kayaked with the year before. This year I discovered he lived across the road from our rented condo in Bokeelia, at the north end of Pine Island.
After picking up a kayak, I called him for his advice as to winds, tides, etc. and reached him on his cell phone as he was fishing in the bay at nearby Patricio Island. I learned that he had snagged a small shark, and the winds were fine for paddling in Pine Island Sound. I loaded the kayak atop the car and took off for Pineville.
I put in at the small beach at Pineville, just south of the marina. The Hurricane Santee 116 I had rented was one of my favorites: lightweight, stable and maneuverable. I put in at 12:30 in the afternoon, avoided the jetty that extended out from the marina and began paddling up the western side of Pine Island.
It was a bright and sunny Saturday � nice weather, but not the best day to be paddling, with weekend powerboats throwing up big wakes in the channels. I kept to the shallows, and managed to keep out of their way, although I would cross the main channels at least four times in the course of the afternoon paddle. Numerous birds were fishing in the sound, including cormorants, herons, and ospreys as I passed Part Island, the largest of the mangrove islands, and continued northward.
Eyeing Patricio in the distance, I paddled toward it, hoping to find a put-in in the bay and do some exploring. I found the bay, identified on a local marina chart as "Old Tom Bayou." I found a small opening in the background of green, then paddled around the perimeter of the bay, but there were no put-ins. Coming out, I headed west, and found a small beach on the southwest side of the island, where I stopped to take a short break. There was little chance of exploring Patricio, which is densely filled with mangroves, but I found what looked like a pig skull and the remains of a fairly large horseshoe crab.
Looking to the southwest, I noticed Useppa Island, lying maybe two or three miles in the distance. From experience, I knew Cabbage Key was just behind it to the west, hidden from my view, but certainly within paddling range. It was 1:30, I had been out an hour, and I figured I had plenty of time to get to Cabbage Key, have lunch and return to Pineville before sunset.
I paddled west, keeping Useppa in view to my left. There was a marina full of large and luxurious boats: catamaran and traditional sailboats, inboard and double-outboard powerboats, and everything else, from runabouts to yachts.
Useppa is a corporately owned barrier island � a private club for the ultra-rich, built on the site of a large Calusa settlement. In 1989, a large burial mound yielded the remains of a Calusa man who died in 600 A.D., making the island an archaeological prize, and it was added to the U.S. National Register of Historic Places in 1996.
Between the Calusa and later corporate owners, a Spanish rancher, who was later evicted in 1835 by the Seminoles during the Second Seminole War, occupied Useppa in the 18th century. The U.S. built a fort on the island in 1850, but soon abandoned it. Then the island became a haven for Union sympathizers, who used it as a staging area for guerrilla attacks on Confederate assets. Barron Collier, owner of Collier's Magazine, built a hotel on the island in 1911, but a 1935 hurricane destroyed it. As if Useppa needed more history, it was used briefly in 1980 as a training base for the ill-fated Bay of Pigs invasion.
As soon as I passed Useppa, Cabbage Key came into view to the south, identifiable by the large water tower in the center of the island. My wife and I had visited Cabbage Key the previous year on a tourist boat, and I was anxious to see it under my own paddle-power.
My approach to Cabbage Key (about a half-mile from Useppa) went well. A dolphin briefly surfaced in front of my kayak, as if to provide a welcoming party. As I neared the island, I paused to allow a sailboat to enter the docking area. Then I paddled to the south end of the dock, where a beach area provided a good put-in.
As I said, it was Saturday, and the place was crowded. The dock was full of pleasure boats, and the restaurant, built on an old Calusa mound at the center of the island, was full of pleasure-seekers. I was directed to a seat at the bar, where I ordered a cheeseburger and a beer.
My order took awhile, which gave me a chance to soak in the ambiance and history of the place. Cabbage Key was once the home of Mary Roberts Rinehart, a noted mystery novelist of the early 1900s. She bought the 100-acre island as a wedding present for her son, who built the main house in 1938. The island contains a small inn and seven one-room guesthouses, where overnighters are literally a stone's throw from Pine Island Sound.
The walls and ceilings of the restaurant are covered with autographed dollar bills, many from celebrities. One celebrity was Jimmy Buffett, whose cheeseburger lunch inspired his classic "Cheeseburger in Paradise," according to local legend. There is a signed picture of Buffett in the bar. The menu these days is more varied, and pricier, especially the drinks; the popular margaritas set you back $7.
The place was packed. College-age guys crowded the bar to order drinks, handing them to well-tanned coeds in towel-draped bikinis as I munched my cheeseburger and drank my beer.
I left the restaurant, walked to the beach, and launched my kayak. A small crowd had gathered at the dock as I began paddling off. "Well," I said casually, "I gotta get back to Pine Island." A young guy in the crowd gave me a surprised look. "You came all the way from Pine Island in that?" It really made my day.
As good as I felt, it was after 3 p.m. and I had a couple of hours' worth of paddling ahead of me. The hardest part was staying out of the way of powerboats, which were thick as mullet in the channels. Two fast jet-ski craft, trailing plumes of watery "rooster tails," were easy to avoid. But the heavier boats left deep wakes that needed to be taken seriously.
I crossed the main channel and headed north, passed Useppa, and pushed toward Pine Island, this time steering closer to Part Island. On the way I met the Tropic Star, an open-window, single-deck tourist hauler, making its last scheduled round-trip of the day to Cayo Costa, just north of Cabbage Key.
After about an hour of paddling, I saw a mangrove rookery ahead, black with maybe a thousand cormorants nesting in the branches. Not wanting to disturb the birds, I paddled within some 100 feet of the rookery, and rested my paddle.
What happened next may have been caused by my paddle making a small "click" against the kayak. Within seconds, one of the birds at the edge of the mangroves spooked, sending at least half of the crowd into an explosion of flight. They left the rookery in all directions, flying just a few feet off the water, their beaks pushed forward and their wings flapping furiously. I had to duck or at least a couple would have collided with me. Feeling sheepish, I backed away and resumed my paddle toward Pineland, as the rest of the flock settled back on the mangroves.
I paddled back to my starting point, steered around the jetty, and eased into the shallow beach at Pineland. I stepped out of the kayak around 5:30, after an estimated 11-mile paddle.
The small beach has no amenities and few parking spaces.
Pineland is at the far west end of Pineland Road, which intersects with Stringfellow Road about 3.5 miles south of Bokeelia.
Charts are available at local marinas. Also, the Standard Mapping aerial photo map F108 showing Sanibel/Pine Island is excellent.
- Trip Duration: 2-3 Day Trip
- Sport/Activity: Kayaking
- Skill Level: Beginner
- Water Type: Open Water/Ocean