Boat Rental FAQs, Tampa

About Windsong Charters in Tampa Bay Area, FL

Windsong began in 2002 with just one sailboat. Now we are the largest pontoon boat rental company in Tampa Bay! Here is some information about the staff who will serve you. 



Capt. Wendy

Capt. Wendy is a USCG Licensed Captain (scoring TOPS in her class!). She manages the office, co-ordinates charters & rentals, and handles the bookings. Capt. Wendy is also Windsong's Wedding Planner and co-ordinates most all of Windsong's wedding ceremonies (she's a hopeless romantic...or maybe just hopeless!). 

Wendy has many years boating and sailing experience and originally hails from Upstate New York; she's also lived in Maine, California, Arizona, Texas and finally Florida is home. Capt. Wendy loves to spend time with her babies (three rescued cats), her beloved hubby of over 19 years and traveling.


Capt. Bruce

Capt. Bruce is a USCG Licensed Captain and manages the operations at Windsong. Originally from South Africa, you'll be delighted by his quaint English type accent (you say toe-may-to and he says toe-mah-to). He has sailed many thousands of miles in the Gulf of Mexico and knows these waters like the back of his hand. He says: "I know every rock and shoal in this area because I've run into them!"

Capt. Bruce owns his own powerboat and jet ski which he takes out when ever he can. Apart from sailing, Capt. Bruce's interests include cooking, music (he plays guitar and keyboards) and playing with computers.



Suzie is a State Commissioned Notary and has been with Windsong for several years as a wedding officiate. She also works the office and phones when we are busy and is Windsong's accountant. She is the proud mother of two or maybe that's three if you include their dog Riley!

We're convinced Suzi is cloned - she's ether at a Girl Scout function for her daughter, an awards banquet for her straight A, "into every activity under the sun" son, performing weddings for Windsong, working at her tax/booking keeping business or on the island enjoying the sun.



In addition to being the dock manager, Bud is also Windsong's Executive Chef and you will meet him on the island if you book our Beach BBQ package.

Bud owns a power boat as well as two jet skis. Bud is also a certified HVAC and refrigeration mechanic and keeps Windsong's ice machine, freezers and fridges in top shape.

Bud has several children who often turn up at work to help him clean and prepare boats! Bud's hobbies are boating, grilling and jet ski trail riding!



Evan has lived on the water for many years and grew up on boats. There is nothing in the water he cannot drive. Evan is our office manager taking reservations and checking in customers. He is your first point of contact when you make a reservation.

Evan's hobbies include boating, diving and spear fishing. He also loves riding his motorcycle.

Our Captains


Capt. Dave

Capt. Dave has been a charter captain for many, many years. He has run large sailing boats in the Florida Keys as well as Clearwater Beach. He has captained schooners and powerboats and can sail just about anything on the water. He is a well known fisherman in our local waters.

He owns his own 20 foot power boat. If Capt. Dave is your captain for the day, you'll most likely see his best buddy Moco (a mix of something here and there - woof woof!) hangin' out at the marina. Capt. Dave is also a 100 ton Master Captain and has sailed with Windsong for over 10 years.


Capt. Roland

Captain Roland, who holds a 100 Ton Master's license, has been a part time charter captain for over 30 years. Roland has recently retired after over 30 years teaching Math at Middle School! In addition to being a captain for Windsong he has a keen interest in growing organic vegetables.

Captain Roland skippers his own Hunter 30 and is an ASA certified instructor from basic keelboating through offshore passage making. His stories, personality, and humor will add countless memories in providing your perfect day!
Captain Roland has been with Windsong for over 10 years.


Capt. Ed

Capt. Ed moved to Florida for the laid back lifestyle - he is the epitome of Jimmy Buffet. Ed started with Windsong as a part time dock hand over 10 years ago but moved on to get his captain's license and now is a professional charter boat captain.

Ed is originally from Long Island, NY and has driven big rigs most of his life.


Capt. Roy

Capt. Roy handles all of Windsong's fishing charters. He has been a charter boat captain for many years and even owned his own fishing charter company before retiring and deciding to work part time for Windsong.

He owns a cat fising boat as well as a flats fishing boat and is an expert fisherman.


Capt. Larry

Capt. Larry hs spent most of his life on the water running everything from a big tourist boat to para-sailing boats.

On The Dock



Sten used to live in Chicago where he was some kind of computer IT Guru. In 2006 he decided to give up the dark and dingy computer room for bright and sunny Florida!

While he used to being called "Stan" instead of Sten, his family originates from Sweden where Sten is a common name. Exchanging computers for boats was a pleasure for Sten and he owns a 37 foot sailboat. He is a certified diver and likes to dive Florida's rivers looking for relics.



Andre is currently in college and works the docks at Windsong during the summer..



JImmy works the docks at Windsong and is responsible for maintenance. He wants to learn the business from the ground up so one day he can run his own outfit.



Isaac is currently in college and works for Windsong during the summer. He switches between running the office and working the docks.



Matt has worked part time for Windsong every since he was still in high school! Now he still fills in on busy days whever he is available. He is a fanatical fisherman.

Areas our New Port Richey location is near to in the Greater Tampa Bay Area

We are about a 2 hour drive from Orlando, Disney World and Universal

Clearwater Beach
St. Petersburg
St. Pete Beach

Palm Harbor
Tarpon Springs
New Port Richey

Port Richey
Spring Hill
Hernando Beach
Weeki Watchee

Hillsborough County
Pinellas County
Pasco County
Hernando County

PHONE - 727-859-0213

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Windsong Sailing Charters is located near to Clearwater & Clearwater Beach, St. Pete Beach and St. Petersburg in Tampa Bay, FL

We DO NOT force you to share the sailboat with anyone other than those in your own party. Our rates are for THE WHOLE SAILBOAT - you may bring up to 6 people, all for the same price.

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