Windsong Boat Charters of Tampa Bay - sunset cruises, snorkel trips, boat trips
Home Page - Windsong Sailing Charters of Tampa Bay, FL Sailing Lessons in Tampa, Florida - learn to sail! Picture galleries from our Sailing Charterers, Sunset Cruises and Beach Weddings All about the sailboats and crew at Windsong Sailing Charters Rates and packages for our sailing charters, sunset cruises and boat trips Make a reservation for your sailing charter or boat trip in Tampa.


Phone: 727.859.0213        Email Us

5015 U.S. Highway 19, New Port Richey, FL 34652


These folk will be your first line of contact, taking your reservations and setting you off on your trip.

About Captain Wendy

Capt. Wendy is a USCG Licensed Captain (scoring TOPS in her class!). She runs the office, co-ordinates charters & rentals, and handles reservations. Capt. Wendy is also Windsong's Wedding Planner and co-ordinates all of Windsong's wedding ceremonies (she's a hopeless romantic...or maybe just hopeless!).  Bright and bubbly, she will be most likely be your initial contact at Windsong.

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. 

When's she's not working (when's that?!!) Capt. Wendy loves to spend time with her babies (two rescued cats), her beloved hubby of over 18 years and travel.

About Captain 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!" 

When he's not running the docks, Capt. Bruce often doubles up as our island chef, preparing scrumptious feasts for clients who add our Beach BBQ package.  Apart from sailing, Capt. Bruce's interests  include cooking, music (he plays guitar and keyboards) and playing with computers.

About Susie

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 Susie 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. How can she do it all and be in so many places at once? Oh yeah, she's also going back to school to earn another degree! Whew! You go girl!


These are the guys that will take you out on the sailboats and make your sail fun, fun, fun!

About Captain 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 9 years.

About Captain 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.

Capt. Dave has also delivered boats all over the Caribbean and and Gulf of Mexico. He owns his own 23 foot Hunter sailboat as well as a power boat.

If Capt. Dave is your captain for the day, you'll most likely see his best buddy Moko (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 5 years.

About Captain Spencer

Capt. Spencer has been a charter boat captain for several years running 40+ feet sailboats in the Florida Keys for the Boy Scouts of America.

Capt. Spencer is also very handy and responsible for maintaining Windsong's boats. He loves sailing and has a great sense of humor.

Even though Capt. Spencer is the youngest captain in Windsong, he is also a Master Captain and has sailed with Windsong for over 3 years.

About Captain 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 owns his own classic '60's power boat and loves to play drums.

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


These guys are responsible for cleaning and prepping your boat as well as maintenance and repairs.

About Sten

Sten is Windsong's Assistant Operations Manager. He used to live in Chicago where he was some kind of computer networking 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 can generally  be found working on his own 37 foot sailboat moored at our marina which he is restoring.

About Evan

Evan is our weekend dock hand setting off kayaks and pontoon boats. He lived on the water for many years and grew up on boats.

Evan is currently attending Marchman Technical College learning how to become a marine mechanic.

He has just taken his captain's test with flying colors.

His hobbies include boating and riding his jet ski and motorcycle.

About Bud

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

Bud owns a power boat as well as a sailboat and can often be seen sailing his O'Day 23 in the Gulf.

Bud is also a certified HVAC and refrideration 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, boating and boating!

About Matt ("Mattman")

Matt is Bud's son (we like to keep it in the family) and works weekends. He is in charge of the kayaks and will assist you in launching and retrieving on your return.

Matt has just graduated high school and his favorite thing to do is going fishing!

He has passed his captain's test too!

About Meow

This is Meow, our dock cat. She lives at the marina moving from boat to boat but has her favorites.

She is feral cat but has adopted Windsong as her home. We provide her meals and she keeps an eye on the place for us when we are not there. Also, we have not seen a rat in the area since she moved in.

She also has the remarkable ability of pronouncing her own name exactly right!


Jeanneau 34 - Windsong

"Windsong"  our Jeanneau 34 Espace pilothouse sloop. The ultimate in luxury, styling and comfort. Apart from being sleek and modern, she has a large deck and cockpit.  She is very bright and airy inside the cabin because of her wrap-a-round windshield and interior steering.  There are only three of these beauties in the United States, making her a rare gem indeed!  More...


"Windy Day" our Elite 32  is sleek, stylish and FAST!  Consider her the little sister to the Jeanneau 34. Both possessing the innovation  of features and French styling, she is definitely a thing of beauty, poise and charm. She is deceptively roomy down below with twin private cabins, full galley and a luxurious salon!   More...


Elite 32 - Windy Day

Phone: 727.859.0213          Email Us

*Packages, Prices and Policies subject to change without notice and according to your attitude!

Rates exclude gratuities for captain.



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

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