Windsong Sailing 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.


Sunset Cruises &  Sailing Charters Tampa, Beach Weddings & Fishing Charters

Phone: 727.859.0213        Email Us

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



Windsong Sailing Charters of Tampa Bay offers half day, full day, sunset cruises and beach and sailboat wedding packages.  We are located in beautiful New Port Richey, Florida. Only a few miles north of Tampa / St.Pete / Clearwater and a short 2 hour drive from Disney and Universal Studios in Orlando. Explore white sandy beach islands, experience our secret snorkel spot or just R & R! 


Sailing Tampa Charters

Half Day Sailing Cruise Approximately 4 hours morning and afternoon sailing departures. Good chance of seeing dolphins! From $295 for 6 people. more info...

Full Day Sailing Cruise Your sailing charter leaves in the morning and sails the entire day on the Gulf of Mexico, snorkel and explore the islands or  beaches, look for shells on the beach, dolphin watch...whatever YOU want! From $395 for 6 people. more info...

Sunset Sailing Cruise Sail out into the Gulf of Mexico and watch one of Florida's famous sunsets as the sun dips into the sea. From $295 for 6 people. more info...


Fishing Charters Tampa

Let Capt. Dave show you some of the best back bay and near shore fishing in Florida. Catch Tarpon, Snook, Redfish, Mackerel, Trout and so much more in the waters of Anclote Key State Preserve, north of Tampa and Clearwater Beach.

Whether you are an avid fisherman or a family with kids, Capt. Dave has a fishing charter experience for all.

Rates are based on 1-2 anglers. Add $50 each additional angler. Four people MAXIMUM.

4 hours - $295 (departs at 9AM or 1.30PM)

6 Hours - $395 (departs at 10AM)

8 Hours - $495 (departs at 9AM)

More info on our fishing charters


Rent a self drive pontoon boat or hire a captain to drive it for you.

You can visit many different and unique islands all less than one hour boat ride from our dock. Sugary white sand beaches, crystal clear emerald water, palm trees and dolphin sightings almost every day! Enjoy mangroves, manatees, birds and other wildlife.

We also rent kayaks, canoes and stand up paddle boards. Explore a multitude of residential channels with beautiful homes, or paddle your kayak into a protected bay on the Gulf surrounded by mangroves and wildlife.

We have single seat kayaks, double seat tandem kayaks, stand up paddle boards and 3 seat canoes for rent.

Click here to visit our Boat and Kayak Rental website


Windsong Boat Rentals offers eco jet ski / waverunner tours from our marina in beautiful Gulf Harbors, New Port Richey - just a short drive North of Clearwater and Tampa.

Windsong Boat & Jet Ski Rentals is the best place for eco jet ski rental tours in Tampa. Our area abounds with mangroves, islands and beaches where you can view birds, fish, manatee, dolphin, turtles and more.

Explore a multitude of Florida wetlands with beautiful mangroves, offshore fish houses, or ride your rental jet ski out to beautiful beaches on offshore islands in the Gulf of Mexico.

4 hours - $250 (departs at 9AM or 1.30PM)

More info on our Jet Ski Tours


Overnight Sailoing Tampa

Spend the night on a sailboat anchored off a beautiful island. Go for a walk on the beach, watch the sunset then return to the sailboat to enjoy a BBQ dinner cooked for you by your captain. Sleep to the sound of the water gently lapping against the side of the boat.

One Day, One Night  - leave before sunset returning the next day at 4PM. Rates from $695. more info...

Two Day, One Night Cruise - would leave at 10AM and enjoy sailing our local waters before anchoring for the evening at one of the islands with a full day sail the next day. Rates from $1195. more info...

3 days and 2 nights - leave at 10AM, three days sailing and 2 nights returning at 4PM on the 3rd day. Rates from $1595. more info...


Beach Island Boat Trips Tampa

Treat yourself to a beach BBQ on one of our beautiful islands - a great addition to your full day charter. You are taken out to the island on one of our sailboats (sailboat charter fee applies), then shuttled to the island by dinghy (or swim!). 

Your personal area on the beach will already be set up by our island crew - beach chairs, shade cover, sun umbrellas, table, cooler stocked with sodas and water - all ready and waiting for you to arrive.

Our chef will cook your BBQ meal right in front of you on the beach. 4 menus to choose from - starting at $225 for 6 people. more info...


Sailing Lessons Tampa

Intro to sailing - 4 hour class designed for those who have never been sailing before and are wondering if this is for you. You will get a feel for how a sailboat handles and learn the very basic points of sail. $350 for 4 people. more info...

Beginners Class - 8 hour class covering the basics of sailing. If you are SURE you want to learn how to sail then this is the class where you begin. $475 for 4 people. more info...

Intermediate to Advanced Class - 8 hour custom designed class for the more experienced sailor. You tell us what you want to learn and we customize the class just for you. $495 for 4 people. more info...


Beach Weddings Tampa

Did you know that Windsong performs over 100 weddings a year? And we have a 100% "YES" record on our engagement cruises!

Treat yourself to a Florida wedding on a sailboat, or a Florida beach wedding on an island. It's intimate, romantic and affordable.

Windsong has a dream Florida beach or boat wedding for every budget.  We offer several wedding packages - on your choice of sailboats or on an island beach.

Perhaps you want to get married on an island and relax on the beach while our chef prepares a luscious BBQ dinner for you and your guests. Wedding packages from $395 for 6 people. more info...


Ash Scatterings Tampa

Windsong Charters guarantees you a professional, affordable memorial service and burial at sea for your loved one.

Your captain and crew conduct a dignified, caring, memorial ash scattering service at sea, approximately 5 miles offshore in the Gulf of Mexico, just north of Tampa.

The services may be attended or unattended. A commemorative nautical certificate stating your loved one's name, date, and exact latitude and longitude of the ash scattering ceremony can be provided for just $10. We also offer ash scattering services or burial at sea for pets. Services from $275. more info...


Snorkeling Trips Tampa

Visit our favorite local snorkel spot by captained pontoon boat. Perhaps not as pretty as the Caribbean, you will see coral, sponges and colorful fish. Maximum 6 people, $350 includes boat, captain and snorkel gear. You may have already booked some of the Orlando hotels at or came here wanting to experience a great vacation, do so with one of our private charter snorkel trips.

After snorkeling it is a short boat ride out to our favorite island which has pristine white beaches, clear water and great shelling.


Add a wine tasting package to your Private Charter!  Celebrate a specific occasion, an individual, a couple or a holiday - we can tailor any wine tasting for your personal needs.

Sit back, relax, and sip wine with a professional wine steward while enjoying the views as you pass effortlessly through the waters of the Gulf of Mexico.

Wine tasting cruises are offered on sailboats or pontoon boats. more info...


Corporate Events Tampa

Your staff can participate in sailing the boat as a team building exercise and the sailboats can even race each other under supervision of the captain.

Sailboats are limited to 6 passengers per boat and we can provide 2 sailboats for a maximum of 12 guests. If you have more, we can transport many more people on pontoon boats.

We can also arrange a full beach BBQ company picnic for your organization. We will transport your office party out to a beautiful island where a chef will be waiting to cook a scrumptious meal on the beach. We provide beach chairs, shade tents and soft drinks on arrival at the island.

Sailing Clearwater Beach, FL


We are the largest and oldest sailing charter company and boat rental company in Pasco County.

We have been in business for over 12 years and won Business of the Year award in 2010.

We are the ONLY sailing charter company licensed to take passengers to Anclote Island State Park.

We are the closest boat rental company to the popular North Anclote Sandbar beach.

Visit our photo and video gallery of past sailing trips. Or take a virtual tour of our boats and meet your captain.

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.

You can get directions of where to find us on Florida's West Coast or purchase a sailing cruise gift certificate for a loved one.

Buy a "What HAPPENS on the boat STAYS on the Boat" Windsong T-shirt for only $12.00!

Phone: 727.859.0213        Email Us

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



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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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