November 27, 2023

Cruising the Florida Keys in a 40-ft Trawler Cat

Katie and Gene Hamilton

Bring Binocular News

Boating from Miami to Marathon in the funky and fragile FL Keys

We left Miami airport and traffic congestion behind as we stepped aboard a new Endeavour 40-foot trawler cat.  Bob Vincent, designer and builder of the trawler cat line, and his wife Alice, had invited us to cruise the Keys with them after the Miami boat show. We had never cruised the Florida Keys from Miami to Marathon in a cruising cat so were quick to step aboard. Join us on a 40-foot power cat cruise from Miami to Marathon in the funky and fragile Florida Keys.

Following the lead of local cruisers

We came aboard, stowed our gear, and in no time were underway leaving the dock at Key Biscayne.  We wound our way through a maze of eye-popping waterfront canal homes leading to the Intracoastal Waterway aka the ICW and rendezvoused with Peter and Anna de Sisto aboard Oceania, a 38-foot Endeavour.  They would lead us to Boca Chita, a picture postcard harbor that’s one of their favorites on the Florida Bay side of the Keys, to spend the night.  A picturesque stone lighthouse welcomes boaters into the harbor that’s part of Biscayne National Park. We followed Oceania down the channel into a basin and tied up for the night. Only a few boats were there enjoying the quiet and protected harbor, usually filled to capacity on weekends.

Boca Chita in Biscayne National Park

We arrived in time for a short walk to the sandy beach on the ocean side of the island and saw a red dive flag flying off a blue kayak in a small cove. Soon we spotted a diver looking to snare a lobster in the calm waters.  On our way back to the boat we followed a walking trail around the island through dense mangroves, dropped $15 in the pay box (honor system), and chatted with the other boaters. It was hard to believe just hours earlier we were fumbling through airport security at BWI which seemed a lifetime away.

Dining in style at Boca Chita

The feast began with Anna swirling a tablecloth on the picnic table at the pavilion, Peter lighting charcoals on the grill and Bob uncorking wine. We noshed on grilled brushetta topped with an olive tapenade, then with a spectacular sunset as a backdrop, enjoyed baked potatoes and steaks sizzling to perfection.   

The next morning a tour boat arrived complete with park ranger and we tagged along to learn the history of the small island, so close, yet so far, from Miami. In the early 1900’s when the Upper Florida Keys had several wealthy owners Boca Chita was bought by Indianan Mark Honeywell of thermostat fame, who wintered in Miami Beach. He bought the island as a rural vacation retreat to entertain friends.  Today some of the limestone buildings remain, but the coral rock lighthouse is the most notable and striking structure. Just 70-some steps up and there’s a panoramic view in any direction. 

Heading south down the Keys

The day warmed to 70 with gusty southeast winds for a 30-plus mile run from Boca Chita to Blackwater Sound where we anchored.  We noticed our first signs of civilization at Jewfish Creek, a land cut and bridge over US Highway 1, the main and only artery to Key West. We waited for an opening as traffic rumbled across the bridge while dolphins teased and amused us. Today a high bridge spans the waterway. Two marinas, often busy with boat traffic were near empty and several boats swung quietly at anchor nearby. 

Eye candy for cruisers

We were fully immersed in cruising, our land lives and responsibilities receded, replaced by the more ethereal.  Spotting a white heron on the shoreline or a lumbering turtle or manatee consumed us. A few days in the Keys was like being part of a travel video. The shades of water intrigued us. We used the water color to help read its depth.  The paler the blue or brown bottom, the shallower the water. The marked channel had a bottom of deep blue with sand or brown grassy patches. 

Cat cruising at its finest

Sometimes it takes a while to become accustomed to the new surroundings of a boat, but the design and cruising comforts of the 40-footer made us feel right at home. The sturdy triple lifeline stanchions around the perimeter of the bridge provide a firm grip to move about and the wide side decks and molded steps make getting around easy, especially those off the stern hulls to get on and off the boat. On the wide bridge there’s more than enough space to entertain a crowd and plenty of seating area while underway.

A beautiful evening in the Florida Keys

 The open and airy expanse of the interior saloon resembles a traditional single hull design and the two staterooms forward were spacious and comfortable. We particularly liked being at the helm in the pilothouse with its good seating and visibility.

Anchoring in the Keys

We anchored for the night in Blackwater Sound near the entrance to Dusenbury Creek with protection from low lying mangroves filled with sea birds.  When Anna and Peter left after dinner their outboard coughed a few gasps and stopped and they began to drift toward Bush Point.  About the same time a custom rigged fishing boat skimmed across the sound and approached us to admire the cat.  When they saw the dinghy adrift they went to retrieve them. As fast as they appeared they were gone. 

At anchor in shallow waters

The next morning the buzz of early bird anglers gave us a wake up call; we quickly concluded we were anchored in good fishing grounds by the number of the skiffs and rigs around us. We discussed the outboard malfunction over coffee and the diagnosis was unanimous: water in the tank from condensation. 

TIP  Our firsthand experience using binoculars on a boat: Binoculars are vulnerable on a boat. An unexpected roll from a passing boat wake can send binocs onto a hard deck surface or worse, bouncing off the boat. To protect binoculars, stow them near the helm so they’re readily available but tucked in a safe cubby that prevents them from being damaged.

On to Islamorada

We had a short run to Islamorada so we were slow to get going, evidence of our laid back Keysie frame of mind. Clearly we were relaxed and brain cells not functioning because we misread the GPS callout for high tide at Little Basin. Wanting to enter the skinny waters of Bayside Marina at World Wide Sportsman at almost high tide we had miscalculated and mistakenly planned our arrival for Greenwich Mean, instead of Florida Keys time.  Fortunately, Peter and Anna had it right so we pulled anchors and left for the day.  It was another heavenly 70 degrees day, but the wind was blustery and blowing 15-20 mph covering the sparkling new hull with a whitewash of saltwater spray. At the helm station in the pilothouse we took advantage of the dutch doors and closed the bottom half leaving the top open for fresh air.  We noted that on other boats in the Keys snagging a lobster pot in its shallow waters was always a concern.  The Endeavour had tunnels molded into the hulls that housed the running gear so it was protected, a notable feature for us Chesapeake Bay cruisers accustomed to dodging crab pots.

Cruising through mangrove lined Dusenbury channel

We took the snakey turns and twists of the mangrove-lined Dusenbury channel in stride noting there wasn’t much traffic for such a nice weekend afternoon. But we enjoyed the company of playful dolphins and spotted large turtles and manatees along the way. 

New cruising friends aboard a 40-ft Endeavor power cat

We spotted the bright blue Conch Republic flag flying from a boat reminding us that a gang of Keys’ residents made the nightly news when they “temporarily” seceded from the U.S. in the 1980’s.  We laughed about the minute-long rebellion followed by their surrender and demand for one billion dollars in foreign aid reminiscent of the satire “The Mouse That Roared”.  The waterway zigs and zags through seagrasses and hardwood hammocks, then takes a sharp left; then goes starboard approaching the red markers at Tavernier’s Community Harbor.

Clear waters at a safe harbor in Florida Keys

We arrived at Little Basin late in the day and eased our way slowly down the channel with Oceania in our wake.  Neither of us touched bottom but we did disturb it. We rafted onto two more Endeavour friends, Ralph and Bonnie Jean on AmmyBoo and Dean and Linda on Seagull, both 44-footers who winter in the Keys. In the summer Ralph and Bonnie head up the Tennessee Tombigbee while Dean and Linda are bound for the Chesapeake Bay. We enjoyed drinks and dinner aboard our host boats and felt the strong bond between Endeavour owners catching up with family and cruising news. Anyone who has ever toured one of their show boats has met some of these enthusiastic owners who act as display boats showing their custom interior layouts.   

The charter fleet and anglers were out early the next morning in search of grouper, yellowtail and tarpon.  The marina complex is a hub of all things fishing with a large charter fleet and retail center on the water.  Black and white photos of the smiling faces of fishermen, including a host of presidents and celebrities, line the walls of the two-story building that sells everything from the latest fishing equipment to artwork and clothing. Upstairs the Zane Grey Long Key Lounge offers an enticing menu and panoramic view of the water. We laughed how fishing-mania permeates the complex, even the parking lot. Neat rows of white fish shapes add a whimsical touch to mark off parking spaces replacing the more traditional straight lines. 

Finding our way to iconic institutions in the FL Keys

We walked north on U.S. Hwy. 1 to Mangrove Mike’s and enjoyed a hearty breakfast. On our slow walk back to the boat we strolled through an impressive exhibit of the Florida Keys Art Guild displaying their work in clusters of white tents staked in a patch of sand on the roadside. We wound our way past a lemon tree ready to burst with bright yellow fruit and through a maze of dazzling artwork – watercolors, oils, pastels and pottery, wood and ceramics pieces – with a steel drums group playing soft Bama music in the background.

Lorelai, a Keysie favorite for years

Some of us took an afternoon stroll to Lorelei’s, a Keys’ institution that was devastated by Hurricane Wilma and recently reopened. While locals mourn the passing of the eccentric ‘50s atmosphere there’s no denying the smell of new wood decking and fresh paint permeated the air; a family of cats meandering about added to the charm. It was beer o’clock and people were arriving by boat, bike, car and on foot to find a good spot to celebrate the sunset and listen to Rock and Reggae music. It was easy to see how the Keys inspired Jimmy Buffett’s many songs about being Key-wasted. 

Others went to Robbie’s, another popular Keys’ attraction with a pool of tarpon who frequent the docks, along with resident pelicans, waiting for visitors to toss them a bucketful of baitfish. The tree-lined shore is lined with kayaks and fishing boats for rent.  A restaurant and small shops dot the landscape creating a laid back Keysie atmosphere in a pristine setting.

Bahia Honda State Park

The morning greyish blue skies hinted at rain but developed into white pillow clouds and blue skies for a run to Bahia Honda, a Florida state park just beyond Moser Channel. The boat’s integrated Raymarine chartplotter helped Bob pilot the boat through the red and greens through Bowlegs Cut.  We brought along a handheld Garmin GPSMAP 76Cx that was handy to use and provided a nice backup if needed.  We passed by Channel Five where some boats were heading to Hawks Channel on the oceanside.  Kayakers paddled along the shoreline and jet skis buzzed around us, but we noticed boat traffic was never a concern.

We were on the bayside of Marathon paralleling the impressive 7-mile bridge spanning Moser Channel when we passed Pidgeon Key, a five-acre island that’s on the National Register of Historic Places.  Originally settled in the 1900’s for workers from Henry Flagler’s Overseas Railroad project, the tiny island today features the restored conch style cottages and dormitories and a research center for the University of Miami and a site for the U.S. Coast Guard. 

Turquoise waters and white sandy beach at Bahia Honda State Park

Bahia Honda, known for its long sandy beaches and clear deep waters for swimming and snorkeling, is a 524-acres state park.  We turned down the channel and went under the bridge to find a protected anchorage from all but northeasterly winds. You can explore the beach, peek into tidepools and be close to nature just minutes from your boat. A narrow cut leads inside the basin where boats can tie up and a concessions building rents kayaks, snorkeling gear and sells necessities. The harbor is busy with campers and park visitors going to the beach and riding along bike trails. Boaters and fishermen come and go and dive boats full of snorkelers head out daily. While we were there volunteers from the University of Florida were helping de-litter the beaches and paint some of the bathhouses. 

Signs along the nature trails identify the unique and rare subtropical plants brought here by birds, hurricane winds and ocean waves from the West Indies and Caribbean Sea. Park rangers tell visitors about the history and wildlife in this unusual pristine setting. It’s a gardener’s paradise where silver palm and yellow satinwood trees flourish and lush crops of sea lavender and Jamaican morning glory thrive.


It’s a short run into Boot Key Harbor on Vaca Key, the heart of Marathon.  We turned to go under the 7 Mile Bridge, the longest segmented bridge in the world, into the Atlantic and then headed northeast to enter the harbor channel and calmer water.  We took on fuel, went under the bridge and followed the markers into the basin through a maze of boats on moorings. We had plans with George and Suely Brandes aboard Journey, a 44-footer to meet for lunch and later celebrate our last sunset outside the harbor.     

Marathon is the center of the Keys and clearly the melting pot where boats of all size and description are tied in slips, hang on moorings or anchor in the protected harbor lined with homes and condos.  The water taxi Smorgasboat, a city pump out boat, and dinghies made up the harbor traffic.  We tied up on new floating docks at the city-operated marina and walked the grounds counting 80-some tenders and kayaks at the dinghy dock. The marina is ideally situated in a lovely community park with field hockey, skate park, bocce ball and tennis courts and basketball and baseball fields.

We dinghied out to Journey and enjoyed a delicious lunch, then later both boats anchored off the shore to see yet another perfect sunset. We toasted our hosts who introduced us to many new friends and showed us a side of the Keys we’d never forget.  The next day we woke early to the buzz of outboards ferrying worker-bees ashore.  We took the On Time taxi to pick up a rental car and leave for Miami Airport, while Bob and Alice headed to the west coast and George and Suely were Bahama-bound.

No question about it, cruising the Florida Keys in a trawler cat was a delightful passage that makes boating from Miami to Marathon, a very special cruising grounds,

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Gene and Katie Hamilton are veteran sail and power boaters and award winning boating writers. They are authors of Coastal Cruising Under Power and Practical Boating Skills. They are members of the Outdoor Writers Association of America.
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