What It’s Like to be a Charter Boat Captain

, What It’s Like to be a Charter Boat Captain

I’m always getting asked, “What’s it like to be a charter boat captain?” So, here’s a a typical day running a couple hour charter on a sailboat. I’m usually sailing out of St. Augustine on a 22 to 45 foot sailboat, on the Intracoastal Waterway, Tolomato River, Salt Run, St. Augustine Inlet, and offshore St. Augustine.

, What It’s Like to be a Charter Boat Captain


To start, a day in advance, I re-confirm the time and what boat I will be on so I can mentally prepare. And then… I check the weather and tides.

My sailing backpack, an Osprey Revo, stays ready to go. Sometimes I need to adjust from season to season. In the Winter, I have an extra top layer and warm gloves. In any rainy season, I have a full spare set of clothes. In Summer, I add in a bathing suit. I always have sunscreen and a rain jacket. You are going to need one or the other nearly every day in Florida!

My everyday sailing backpack is by Osprey, and has about a dozen pockets inside. The list of what is inside would astound you! Outside is easier – anything I need to get my hands on quickly is kept in the outside pockets.

I keep my sunscreen on the side pocket for easy access. I only use Stream2Sea due to the reef-safe concerns and container biodegrade-ability. As an ambassador for our outdoors salt and sealife, I absolutely must lead by good example and use only sunscreen that is safe for humans and coral larvae. You are welcome to use my code “KimW” to save a bit when you select your own ecoconscious sunscreen from Stream2Sea.

Also, the American Sailing Association log book stays readily accessible in one side pocket, along with the Code of Federal Requirement for Recreational Vessels.

I get to the boat at least a half hour in advance. This is so I can check the oil, cooling water, the bilge pump, the anchor windlass… Here’s what I check every day: Pre-Sail Checklist for Sailing.

Then I get out the winch handles, horn, throwable cushion, cockpit cushions, ignition key, and the American flag.

, What It’s Like to be a Charter Boat Captain

Assessing the Passenger Interests

When the passengers arrive, I ask them where they would like to go. I can suggest we go North on the Intracoastal Waterway to see what Florida used to look like. Another alternative is to head offshore and experience a bit of the Atlantic Ocean. Yet another option is to take a trip into town to see the fort and the bridge and the historic bayfront. Or, we can turn south and pass by the lighthouse and St. Augustine Yacht Club.

In two hours, I can make it to one of those places and back.

In three hours, I can generally make it to two of those spots. In more hours, I can definitely make it to put in a run offshore.

On a longer trip, we can make it to a couple of those choices, and even add a stop at one of the restaurants along the Tolomato River. There’s Cap’s on the Water for lunch on the weekend, or dinner after 4:00 p.m. Another option is a quick stop at Aunt Kates, a restaurant with roots over 100 years old. Right next to the Vilano Bridge with its own beach is Beaches at Vilano, open for lunch and dinner daily.

The Conch House is another destination, down Salt Run and near the St. Augustine Yacht Club and the St. Augustine Lighthouse. I like having a destination in mind; it gives us a purpose for sailing along.

We’ve had weddings and funerals on board, thankfully no birthings, and I’ve even had the request to just go barhopping! We have had some unusual charters over the years – enough material for several other articles.

, What It’s Like to be a Charter Boat Captain

Once on Board

As they are boarding, I make note of the age and ability of my charterers, and I plan the amount of sail I will carry accordingly. If the sail is more of a social event, with champagne, hors’d’oeuvers and things requiring small pointy sharp knives, I will be conservative sails-wise.

Once everyone is on board, I go through the safety briefing. There are a few things I pay attention to before I back out of the slip. I run through those checks, then we head out of the marina. We operate as St. Augustine Sailing out of Camachee Cove Marina.

, What It’s Like to be a Charter Boat Captain

What They Do While I Sail

If it’s an enthusiastic fit group, I might have them pitch in with raising and lowering and trimming the sails and even operating the boat, depending on their interest.

Sometimes the passengers just want to lounge and absorb the ambiance of the environment. Other times, they are full of questions and want to know about the area or sailing or boating in general. You just never know what mix you might get!

, What It’s Like to be a Charter Boat Captain

Stopping for Lunch or Swimming

Sometimes we have requests for swimming offshore, or swimming inland. There are several safety checks and procedures that I like to follow for this.

Sometimes, we stop somewhere for lunch at one of the waterfront restaurants mentioned above. It’s always fun to have someone else cook, and, of course, the most fun of all is arriving anywhere by boat! Plus, sometimes parking is tight at popular restaurants, and there’s usually more room at the dock.

, What It’s Like to be a Charter Boat Captain

What We Are Likely to See

While we are out, a lot of times people ask if we are going to see dolphins. Dolphins are wild animals, so you cannot promise a dolphin sighting. I’ve had some pretty funny moments when someone who is not used to seeing dolphins, and I have not prepared them that we might possibly see dolphins, suddenly sees them and screams “dolphins!!!!”

What we have seen over the years is right whales, sharks, Cobia, turtles, mating sea turtles, jellyfish, dolphins, manatees, varieties of birds, and all sorts of fish as well. In our area, we have a waterway, the ocean, bridges, and inlet, islands, uninhabited marshlands, and the historical bayfront.

We are likely to see fishing trawlers, shrimp boats, power boats, dredges, towboats, paddlewheelers, sailboats, row boats, sail boards, kayaks, pontoon boats, dinghys, sea planes, helicopters, surfers, personal watercraft, kayakers, canoes… We never know what we might see!

As far as weather, we have seen water spouts, lightning, torrential rain, hail, meteor showers, satellite launches, eclipses, and every kind of cloud imaginable.

, What It’s Like to be a Charter Boat Captain

Back at the Dock

After the sale, when we get back to the dock, I get the boat tied up and then help the passengers carry coolers and belongings. I always triple – check or left behind so friends, cameras, jackets. So far, no one has forgotten any children on the boat.

After the charter, it takes about a half hour to put all the cushions in when channels and other items stowed away.If the passengers were eating Oreos of Chito’s, I’m definitely scrapping the boat with soap and water. If we got salt spray on the boat, I also need soap, assault kit and up a little greasy and slippery for the next crew.

, What It’s Like to be a Charter Boat Captain

Next Day Setup

If the boats fuel needs topping off, this is a good time to do that. Our sale but between 1/3 of a gallon and a gal in an hour, and if we are sailing, we are not using the engine very much, so there’s usually no need.

After I clean the boat up, I swing by the office to check in, and log into the maintenance log any issues that need addressing before the next trip. After I clean the boat up, I swing by the office to check in, and log into the maintenance log any issues that need addressing before the next trip.

I checked the calendar for the next day, leave an invoice, lock up and go.If the weather turns horrible and everyone gets soaking wet, we offer them however much time they lost toward a future charter.

, What It’s Like to be a Charter Boat Captain

Scheduling and Turnarounds

Sometimes, charter boat departure times are like golfing teen times. Sometimes we will run several charters for the day, with anywhere from 10 to 30 minutes between them.

That means that if someone is late, we might not be able to extend their charter for the amount of time from when they met us. If there is no charter after the current charter, and they are running 30 minutes late, it’s generally up to the captains discretion if they want to extend the end of the charter that 30 minutes.

Sometimes the captains have an appointment that they cannot miss, so they have to get back to the dock on time.

After docking, I perform a quick sweep below decks, wipe the cabin soul, scrub and flush the toilet, wipe out the sink, and clear out the refrigerator of anything left behind.

That’s the day of a charter boat captain! Fun-filled, and even when you operate in the exact same area day after day; every day is new, brings new experiences and sights, weather, conditions, and learning. Let’s go sailing!!!

What to Read Next: 5 Things to Check Before Backing Your Boat Out of a Slip

Updated May 15, 2020.

, What It’s Like to be a Charter Boat Captain


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