Havana via Avalon

Why be the first people to go to Cuba in a pontoon? WHY NOT?

At 15 miles out we are ready to celebrate, maybe have a beer. We have already been to Cuba and are on the run back, this leg from Key West to Marco Island. In other words, we are almost done. We are on a good clip to Marco Island when I see them coming: two large waves, back to back and very tightly stacked, one right behind the other, just 30 or 40 yards ahead. We are approaching them quickly, and I am trying to find a way out. I look left and then right — no safe place to turn. We are going to fall, I tell myself, now it’s just a matter of how hard.

“Hold on boys!” It is all I have time to yell.

The crewmembers — (l. to r.) Doug Haskell, Charlie Chiara, Travis Conners and Jim Wolf — are all smiles as they prepare to leave Florida and head for Cuba on their Avalon pontoon.

As we punch through the back of the first wave, the front door blows open and 1,500 gallons of water — we did the math — swamp us. The boat slows instantly, rolls to the right and actually starts backing up into the oncoming surf. We are being pulled, backwards, into the waves. As the water shifts to my side of the boat, it fills up to the bottom of my captain’s chair and is held in by the L-shaped seating at the rear.

Charlie grabs the drone and life raft before they float out the back, and Doug grabs someone’s jacket and a few floating yetis. The next wave is coming. I hear Travis yell, “Full throttle. Turn right!” As the 800 horses respond, the water shifts to the left side of the boat and starts pouring out of the rear door nearly as quickly as it had come in the front.


Doug Haskell, an Avalon dealer in Michigan, and I — hi, I’m Jim Wolf — the CEO of Avalon, have been making long-distance extreme pontoon excursions since November 2004, when we took our first trip, from Baltimore to Key West. Since then we have completed five other Extreme Pontoon Adventures:

  • Chicago to Mackinac Island
  • Fort Lauderdale to Bimini Island
  • Key West to the Dry Tortugas
  • The Mississippi River
  • Los Angeles to Catalina to San Diego

During our last trip, the 2015 Pacific Adventure, we pondered, “Where to next?”

“Cuba,” someone said, half joking.

But once we started looking at it, we thought, “Why couldn’t we? It’s supposed to be a pretty cool place to visit and sits only 100 miles from Key West.” Yes, but that is 100 miles of open ocean, Doug reminded me. And no support or chase boat. “No problem,” I said. This is how we do it in the Wolf family.

Once we knew we really wanted to go in 2017, the plan came together quickly — experience acting as our guide.


Within 30 seconds we are back underway and bouncing to and from each and every wave, still dodging the big ones. A quick check reveals one flip-flop and my new baby blue Yeti cup are missing — but they’re the only things missing. All in all, we have come out of it in great shape. But as we regroup and relive the moment, telling our versions of what had just happened, Doug says, “I smell burning.” Sure enough smoke is coming from under the seats.

“We have an electrical fire somewhere,” yells Travis Conners, an Avalon engineer.

I immediately pull back on the throttles, turn off the motors and reach for the fire extinguisher.

“Keep moving,” Travis shouts.

I try to start the engines but they won’t fire. Travis quickly goes to the back and flips on the emergency reserve battery. We are dead in the water. One engine fires and we start moving. Now underway, I get the other motor to start. Smoke is coming from the USB port where I have my phone plugged in. Smoke but no fire. Yet. We decide it’s a good idea to let the Coast Guard know of our position and situation, merely as a backup. We don’t want to lose power and be dead in the water in eight- to 10-foot waves. We keep moving while talking to the Coast Guard. We let them know there is no medical emergency but we did take on a lot of water and are experiencing electrical and burning issues due to all of the salt water.

Marco Island is getting closer and closer. As we pass the southern tip of Marco Island, the waves start to die down; we are in more protected waters. We see a Fire & Rescue boat close to shore. It’s heading south and looking for us. We are still underway and let dispatch know which boat we are. We quickly have a Sheriff’s boat in front of us and the Fire & Rescue boat trailing us. We ask for the name of an open marina that has a forklift to get us up out of the water. We need to assess the boat. They escort us into Marco Inlet and direct us to Rose Marine where a large forklift awaits us.

When the boat comes out of the water, I am extremely glad to see that our engineering efforts over the past two years have been paying off. The underside of the boat looks like it just rolled off the production floor. No damage at all to the front walls, the structure or the tubes. I think the crew got more beat up than the boat.


Cuba seems a long way away from the launch ramp in Clearwater, Fla. The first leg, Clearwater to Key West, with a fuel stop on Marco Island, was actually longer than the second leg, from Key West to Havana.


Searching the web for information about boating to Cuba resulted in a lot of conflicting information. I started making calls and finding boaters who knew the lay of the land and could explain the dos and the don’ts. An early contact named Wally provided some good info and pointed me in the right direction. He told me that we would have to fill out an application with the Coast Guard that would allow us to enter Cuban waters and that the process could take up to six weeks.

Through one of our suppliers, I met another person who proved to be invaluable. Ron Shelton, now retired, worked and lived in Cuba for more than 10 years and frequently visits Cuba by boat from his home in Florida. Shelton suggested we hire his friend George, a Cuban national and tour guide who speaks very good English. Shelton gave me pointers on how to find the customs office when entering Hemingway Marina, how to exchange money, and how much to tip the dockmaster and guards. Over the next several weeks I spent a lot of time on the phone with Shelton, asking questions and finalizing the plan.

He assured me that Cuba is an extremely safe place and has a rich culture, a deep history, awesome architecture, great music, mind-blowing old cars, great rum and even better cigars. He also informed me that the marine fuel in Cuba had not been reliable lately and recommended we carry enough to make the return trip too. The Avalon Ambassador comes standard with a 100-gallon fuel tank built into the center pontoon. I challenged my engineers to add a second 100-gallon tank, which became the only modification we made to our stock production boat. To err on the side of caution, and to observe the one-third rule — one-third out, one-third back and one-third in reserve — we also took eight five-gallon tanks, giving us a total supply of 240 gallons.

The last big unknown, as on any marine adventure, was the weather.


A forklift at Rose Marine on Marco Island prepares to lift the pontoon out of the water for an inspection, which shows no damage to the pontoons or underskin.


The morning weather report says it is going to be a nice day, and we are a go. This is it. We are pumped. Before leaving Key West, we fly the drone and get some video and then set a waypoint for Hemingway Marina, just west of Havana. A bearing of 215 degrees will take us on a straight line to Cuba. What will it feel like? What will we find in the middle of the ocean? Well? Not much, actually.

The 100-mile crossing is smooth under blue skies and without a care in the world. We crank the music and take in the vast beauty of the deep, blue, open ocean. We pass a lonely freighter. At the halfway point, we stop to contemplate our achievement. Epic. We fly the drone. We put in the fuel from the cans. And then, we go. Only 50 more miles to reach our goal of being the first people to take a pontoon boat to Cuba.

Hemingway Marina marked the end of a 100-mile open-ocean run for the four-man crew.

Under hazy skies we scan for the horizon. We are 20 miles out. Can you see it? The clouds are high and storms are looming as the Havana skyline comes into view. We stay on our course to Hemingway Marina, 12 miles to the west of Havana. As we enter the marina, a few locals wave to us from the breakwall. Soviet-style one-story buildings line the entranceway. This feels familiar, like going to the Bahamas. Very tropical. We take the first canal to the left, as Shelton had instructed, and see a very blue wall and a small building on our left. It looks like nothing but should be the Customs Office. And it is. We pull in and tie up.

The crew’s Cuban guide, George, helped the crew secure Cuban cigars, which Doug Haskell shows off.

The first officer comes out, but he doesn’t speak English and we struggle to communicate for 10 to 15 minutes. Charlie Chiara, Avalon’s media coordinator, lives in California, so I thought he knew some Spanish; it is very little and doesn’t really get us anywhere. Soon another officer appears. He speaks some English and we start making progress. They take us, two at a time, to fill out our visa documentation and take photos. They ask about things like SAT phones and drones, and we tell them we have both. They put special security tape on the drone and the satellite phone cases and instruct us not to use either while visiting Cuba. They will check the tape at the end of our trip.

They take us and our bags to another small room for screening. Finally, we are free to go but need to go to our designated docking location for a visit with the harbormaster and the doctor, who greet us when we arrive. They both speak English rather well. The dockmaster quickly dubs the Avalon the Sea Car, and everyone agrees. The doctor comes on board and asks us some questions — some very funny. Several locals mill around and check out the boat. Travis hands out hats, T-shirts, koozies and other memorabilia.

Fusterlandia is a converted train station that is now an art-filled area full of shops.

We secure the Avalon and hire a couple of the dockhands to be security for the next 48 hours. George (our guide) is there and helps us with our bags into his waiting 1952 Chevy Bel Air. All in all, a pretty easy experience. Now we are off and running, in Cuba.

Thanks to Shelton and George, we have a great rental house, in a nice neighborhood, with a pool and a staff who have prepared some amazing Cuban sandwiches for us. That is the first thing we do — have a Cubano and a swim. In Cuba. Excellent. The pool comes in especially handy, because the weather is hot and muggy. We barely have time to relax before George says we must go to dinner, at a local place where we can have some traditional Cuban food.

Driving into Old Havana, in the evening, is surreal. The sodium lights give everything a yellow hue and the buildings, though architecturally quite lovely, are well worn and look foreboding in the faded light. And the old American cars we always hear about? They are here, and they are everywhere. I feel like calling it Cuba-land. Very fun and curious. A great local dinner, Cuban cigars and rum complete the mood. We have made it.

Classic American cars were everywhere in Havana — a step back in time for the crew.


By mid-April we had coordinated schedules and picked dates, which is often the hardest part. Doug, Travis and Charlie are all seasoned boaters, so everyone quickly divided up tasks. Jim would work with the team in the factory to build a 27-foot Ambassador and outfit it with brand new, state-of-the-art twin 400 Mercury Verado outboards, Garmin GPS, a JL Audio stereo and Yeti coolers. Travis, our engineer, would arrange the necessary safety equipment, including EPIRBs, tracking beacons, strobe lights, flares, marine radios, Mustang life jackets and a satellite phone. Doug watched the weather, found a suitable, rentable, six-man provisioned lift raft, provisions and charts, while Charlie did background work on the requirements to visit Cuba and the various cameras we would take. The finished boat would be trailered down to Clearwater by Travis’s friend Harold and his fiancée, Amy, while the crew would fly to Tampa on Tuesday, June 13, and leave for Cuba the next morning. No one had to be back home for a week, so we had a good window in the event of weather delays.


George shows us a great time as we tour around Cuba. The people, the country, the music and the food are just as Shelton described. We spend the day visiting an old train station that has been converted into shops — the best tourist shopping, we are told. And then Charlie wants to get a high-elevation shot for the film we’re making of the trip, so George takes us up to a SkyBar where we have some excellent local beer called Cristal. Then it’s off to more shops and a local restaurant where they serve meats on a skewer — Who doesn’t like that? — and more beer.

After that, we go in search of cigars. And a weather report. We have to be aware of an approaching system in the gulf. Our plan is to spend three nights; however, the weather reports show deteriorating conditions, so it looks like we have to depart on Saturday morning if we want to make the crossing back to the U.S. before the weather turns.

The waves in the gulf stream are three to five feet as we leave Cuba behind us. But within 90 minutes the seas have calmed and we again have excellent conditions. At the halfway mark we stop to take a few more drone shots, and I enjoy a quick swim. Everyone else is chicken. With the sun beating down, the 78-degree water is cool and refreshing. Then off again. An easy 30 mph. At one point we pass a large sea turtle on the surface, but by the time we turn around to check it out, it is gone.

Arriving in Key West in midafternoon, we head to the fuel dock and fill up with 168 gallons of fuel. We have a nice reserve left over from the 200-plus-mile journey, and I feel a sense of pride that we made the trip without risking burning up the motors with potential bad fuel.

Walking into Sloppy Joe’s later, I immediately notice the back wall is covered by Ernest Hemingway memorabilia and pictures. I recently started reading “Hemingway’s Boat” by Paul Hendrickson, which describes Hemingway’s love of Cuba and his daily fishing excursions to the Gulf Stream on his boat, Pilar. As I look at the large pictures from afar, I notice one in the middle. It shows Hemingway sitting on the back of his boat. I glance around and ponder whether any of the other patrons have been to Cuba by boat — probably — and if any of them had ever done it on a pontoon. Not a chance. I smile and think about the fact that we are probably the only four people in the world who have ever been to Cuba on a pontoon.

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