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.

Having Fun Sailing Picture Gallery

Click on any picture to enlarge - hit back to return - scroll to bottom for videos

You can also visit our exclusively SUNSET picture gallery

Phone: 727.859.0213        Email Us

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

Arriving at our dock Loading up the sailboat Leaving the dock And you're off!!
Oh, I am so happy to be out at sea on a gorgeous sailboat Even sulky teenagers have fun Captain Dave surround by girls! or sitting with your toes hanging over the side of the boat
There are other comfortable places to sit too! One happy family - we love the ocean Sailing is romantic, too! Another happy customer

Cheers! Another happy day out on the water.

Dang, that there sailboat is heeling over - but no body cares because that's what it is designed to do! Just hang out where ever you want - it's no problem, mon. Nothing like a charter with an engagement thrown in! "Hi! Our sunset cruise with Captain Dave was great! I proposed to my girlfriend and she said yes!" from Andrew
 Thank you soooooo much for the beautiful sailing.  I couldn't picture a more perfect day for the proposal. The future Mr. & Mrs. Oren, New York
We had a great time and passed the word on what a wonderful excursion it is. Thank you for everything. The Keal Family,  Missouri Thank you for a wonderful time! We know it was memorable for us-due to the quickly changing weather. Keith has had a smile ever since!!  Next Florida trip we will be back!  Keith & Kay, Oklahoma We had a wonderful time.  Thank you so much for making my Husband's 60th
Birthday a very special and memorable one.

Dinghy to the island

Another great day sailing! Sandra & Richard, Monterrey CA Serve me up!
dolphin in gulf
Another dolphin show!!


You're always welcome behind the helm!

Capt. Wendy watch out! You have competition!  You're not the only chick cap'n in these here parts!

a fun excursion
You can dangle your feet over the side, but don't fall in! Step aside, we have a new helmsman! Smoking is allowed on deck

Everyone has fun on Windsong Charter's sailboats!!

Check out the rainbow! Enjoy a nice dip in the water. Dolphins playing in the bow.

The water is AWESOME!

Jeri and Don, Hudson, FL - VIRGIN SAILORS!

Deep in the heart of...SAILING

The Cummings Family, Abilene, Texas

Windsong Sailing Charters....ROCKS! The Collins family, Indianapolis, IN

Future Captain's of America!


Hey!  Don't tip the boat over! Playing footsie! Who's steering?  The autopilot!
snorkel adventure


Happy Anniversary!

My tan is better than yours!

Our secret snorkel spot!

relax and enjoy sailing

Everyday is a perfect for sailing!

You guys are the best!  Hubby and I had such a wonderful day!  Pete & Julie, England

Jump off the sailboat. (Only while anchored PLEASE!)

Smiles everyone! Smiles!

Landlubbers don't know what they're missing!

Ashlee & Mark from Minnesota - check out their blog here. Romantic for any couple (celebrating 20 years of bliss!)

Another beautiful sunset on the island. More sunsets here.

More dolphins!

Rainy days and Sundays NEVER get us down!

Three heads are better than one!

Even cloudy days are fun!

Even more dolphins!!


R & R in the bow

Capt. Mark and his new first mates!  They LOVED sailing!

Dolphins, mommy and baby!


What are you waiting for?


Read testimonials from from previous charters!


Windy Day Sailing

Our Elite 32 "Windy Day" with full sails out sailing over crystal clear water - this could be YOU!

Dolphin Video

Yip, you got it! Footage of dolphins swimming in the bow of the sailboat, which they love to do.

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Phone: 727.859.0213        Email Us

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

Rates DO NOT include gratuities for captain or crew.



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

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