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.



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. 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. 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



JImmy is the Assistant Dock Managers at Windsong and is also responsible for boat maintenance. He wants to learn the business from the ground up so one day he can run his own outfit.



Andre recently graduated college as a registerred nurse and works the docks at Windsong on weekends during the summer..



Isaac is currently in college and works for Windsong during the summer. He He is interested in engines and is studying to become an engineer.

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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