Today we’d like to introduce you to John Blenker.
Hi John, thanks for joining us today. We’d love for you to start by introducing yourself.
My story began in law enforcement, where I spent nearly 30 years serving as a deputy sheriff with two agencies in California. During that career, I worked a variety of assignments, including eight years in marine law enforcement. I was proud of the badge and the work, but it came with a price—sleepless nights, two knee surgeries, high blood pressure, and the accumulated weight of things you cannot simply forget when your shift ends.
Even while I was still in law enforcement, the water was always calling me. I earned my U.S. Coast Guard Master Captain’s license and began imagining what life might look like beyond the badge. When retirement finally arrived, my wife, Kerri, and I made a major leap of faith. We left California and moved to Florida, settling near the waters of Tampa Bay.
Starting over was humbling. After decades of experience in one profession, I suddenly found myself a rookie again. My first opportunity in Florida was captaining a tour boat around Anna Maria Island. I learned the local waters, studied the wildlife and history of the area, and discovered how much I enjoyed showing families a side of Florida they could never experience from shore.
In 2014, I started Five O’Clock Charlie Boat Tours & Charters. I began with a Hurricane deck boat, a captain’s license, and a willingness to work. There was no guaranteed paycheck and no instruction manual for building a charter business. I had to learn everything from marketing and customer service to changing weather patterns, tides, fishing seasons, boat maintenance, and the realities of being responsible for people on the water.
The road was not always smooth. The business survived hurricanes, red tide, COVID-19, mechanical problems, rising expenses, and plenty of lessons learned the hard way. But it also gave me experiences I never could have anticipated: helping children catch their first fish, watching dolphins swim beside the boat, taking families to historic Egmont Key, scattering loved ones’ ashes at sea, hosting marriage proposals and vow renewals, and supporting trips for disabled veterans and Gold Star families.
Today, I operate my business aboard a Parker center-console boat on Tampa Bay. I still personally answer the calls, book the trips, captain the boat, and do my best to make every guest feel as though they are spending the day with an old friend. My first mate is Sammie, my mini Goldendoodle, who seems convinced that the dolphins are talking directly to her.
This journey also inspired me to write a memoir, *Trading My Badge for a Boat: Finding Peace, Purpose, and a Second Career on the Waters of Tampa Bay*. The book tells the honest story of leaving behind a career that had defined me, starting again from the bottom, and finding a different kind of service on the water. Book is currently at a Publisher and due for release 12/26.
I once wore a badge and carried the responsibility that came with it. Today, I carry a captain’s license and the responsibility of bringing people safely home from a memorable day on Tampa Bay. The uniform changed, but the desire to serve never did.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It has not been a smooth road, but I believe the rough water is what makes the story worth telling.
Leaving law enforcement after nearly 30 years was more difficult than I expected. The career had taken a physical and emotional toll—two knee surgeries, high blood pressure, sleepless nights, and memories that did not disappear when I retired. When you have worn a badge for most of your adult life, retirement is not simply changing jobs. It means letting go of an identity, a routine, and the people who stood beside you during some very difficult situations.
Moving from California to Florida brought another major adjustment. I left behind a profession in which I had decades of experience and became a rookie again. I had to learn unfamiliar waters, local weather patterns, tides, fishing techniques, wildlife, and the business side of operating a charter company. I also had to earn the trust of customers who had many established captains to choose from.
Financially, the early years were challenging. Boats are expensive to operate and maintain, and something always seems to need fuel, repair, or replacement. Early in the business, I used Groupon to fill the calendar. It brought customers aboard, but the discounted rates left very little profit and put tremendous hours on the boat and motor. It was one of several lessons I learned the hard way.
Then came challenges that no business owner could control. Red tide hurt tourism and fishing. Hurricanes disrupted operations and damaged communities. COVID-19 brought uncertainty and cancellations. More recently, Hurricanes Helene and Milton devastated parts of our coastal area. During those times, the charter business became secondary to helping neighbors and supporting the community.
There were certainly moments when I questioned whether I had made the right decision. However, every struggle taught me something about patience, preparation, humility, and perseverance. Law enforcement taught me how to remain calm when plans fall apart, and that lesson has served me well on the water and in business.
The road has been rough at times, but I would make the journey again. The challenges helped me appreciate what I have built and reminded me that success is not always measured in money. Sometimes it is measured in the child holding up a first fish, the veteran smiling at the end of a day on the bay, or a family leaving the boat with a memory they will carry for years.
Thanks – so what else should our readers know about your work and what you’re currently focused on?
I own and operate Five O’Clock Charlie Boat Tours & Charters, serving the waters around Tampa Bay, Palmetto, Bradenton, Anna Maria Island, the Manatee River, and Egmont Key. I hold a U.S. Coast Guard 50-ton Master Captain’s license and specialize in private fishing charters, dolphin and wildlife tours, Egmont Key excursions, sightseeing trips, and ash scatterings at sea.
One of the things I enjoy most is that no two trips are ever quite the same. On one charter, I may be teaching a child how to catch their first fish. On the next, I may be showing a family dolphins, manatees, sea turtles, rays, ospreys, or bald eagles. Other trips carry more emotional meaning, such as helping a family honor a loved one by scattering their ashes on the Gulf. Whatever brings someone aboard, my goal is to provide a safe, personal, and memorable experience.
I am probably best known for treating customers like guests rather than numbers. When someone calls Five O’Clock Charlie, they speak directly with me. I answer the questions, make the reservation, prepare the boat, and captain the trip. I do not hand customers off to a booking center and then place them with a captain they have never spoken to. I want people to know exactly who will be responsible for their family once we leave the dock.
My background in law enforcement also sets me apart. Nearly 30 years of public service taught me to remain calm, pay attention to details, anticipate problems, and place people’s safety first. A day on the water should be fun and relaxed, but I never forget that I am responsible for everyone aboard. I monitor the weather, maintain my equipment, carry the appropriate safety gear, and adjust the trip when conditions require it.
I also believe a good captain should be a storyteller, teacher, and host. I enjoy sharing the history of Tampa Bay and Egmont Key, explaining the local ecosystem, and helping guests understand the wildlife they encounter. You do not need any boating or fishing experience to come aboard. I provide the equipment, instruction, and patience, along with a little dockside humor.
What I am most proud of is my involvement in taking disabled veterans and Gold Star families out on the water. My eldest son, Jacob, is a combat-disabled Army veteran, so that work is deeply personal to me. Providing these families with a peaceful day on Tampa Bay is not simply another charter—it is an opportunity to continue serving in a different way.
After more than a decade in business, I am proud that many customers return year after year and have become friends. Some send me a text saying they are coming back to Florida and want to get on the calendar. That trust means more to me than any advertisement or award.
What sets Five O’Clock Charlie apart is simple: when you step aboard, you are not just hiring a boat. You are spending the day with a local captain who genuinely cares about your safety, your experience, and the memories you take home.
What quality or characteristic do you feel is most important to your success?
The quality most important to my success has been perseverance. I have learned that success rarely comes from one big break. It comes from continuing to show up, especially when things are not going according to plan.
My law-enforcement career taught me to stay calm under pressure, adapt quickly, and finish the job even when circumstances became difficult. Those lessons followed me into retirement and helped me build Five O’Clock Charlie Boat Tours & Charters. Starting over in Florida meant becoming a rookie again, learning unfamiliar waters, earning customers’ trust, and accepting that I would sometimes make mistakes along the way.
There have been plenty of reasons to quit—mechanical failures, hurricanes, red tide, COVID-19, rising operating costs, and days when the phone simply did not ring. Perseverance meant repairing the boat, learning from the setback, and being ready to leave the dock again the next morning.
I also believe perseverance must be paired with integrity. Customers place their families and their safety in my hands. I try to do what I say I will do, treat people fairly, and give every guest my full attention. After more than a decade in business, many customers have returned year after year and become friends. To me, that is the best evidence that persistence, honesty, and genuine care for people still matter.
Pricing:
- Five O’Clock Charlie offers private fishing charters, dolphin and wildlife tours, Egmont Key excursions, and customized trips on Tampa Bay. Pricing varies depending on the type and length of the trip. I work hard to keep my rates affordable for families while maintaining high standards for safety, service, and equipment. Guests can contact me directly to discuss their group, interests, and budget. Current pricing and trip information are available at www.fiveoclockcharlietours.com.
Contact Info:
- Website: Business: Five O’Clock Charlie Boat Tours & Charters Website: fiveoclockcharlietours.com Book page: Trading My Badge for a Boat Captain’s Corner blog: fiveoclockcharlietours.com/blog Contact and booking page: Contact Captain John Tripadvisor: Five O’Clock Charlie Boat Tours Email: captainjohn.blenker@icloud.com Call or text: (941) 527-8008
- Instagram: Five O’Clock Charlie Tours Instagram: @Fiveoclockcharlietours
- Facebook: @FiveOclockcharlietours
- LinkedIn: CaptainJohn Blenker
- Twitter: Fiveoclolckcharlietours
- Other: Trip Advisor Five.oclockcharlietours
