$20 for $50 Toward Boat Charters, Kayak Rentals, Sailing Lessons, & More at Windsong Charters

New Port Richey

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$50 60% $30
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In a Nutshell

  • Choose from any service or activity offered
  • Private sailing charters, pontoon boat rentals, kayaks
  • Weddings, team-building exercises, island BBQs
  • Licensed boat captains and expert fishermen are available

The Fine Print

Promotional value expires Jun 28, 2010. Amount paid never expires. Reservations subject to availability. Chartered sailing requires 24-hour notice. Not valid holidays. No cash back, must redeem in 1 visit. Not valid with other offers. Limit 1 per product/activity. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Jump to: Reviews | Beyond Cookies and Milk

Celebrate the sea on an oceanic romp aboard some sort of masted or unmasted thrilling masterboat of seathrills. For $20, today's Groupon gets you $50 toward any activity or service offered at Windsong Charters, just a few miles north of the Tampa area in New Port Richey.

Options are as diverse as ocean life, with none of the tear-like salinity. Services range from sailing school to full-day charters, and you can choose from a beguiling sailboat, pontoon boat, or kayak. If you apply your Groupon toward a kayak or canoe rental, you'll be exploring an area rich in marine life and salt-water eye candy. Paddle through residential channels in a search of lovely real estate, or rent snorkel gear ($7) to peek into a bay full of watery creatures and mangroves. Catch a glimpse of manatees, dolphins, and discarded tubes of cryogenically-sealed novelty Sea-Monkeys. Green Key Beach and Durney Key are a quick paddle away. Single-seat kayaks are $50 for the day, while two-person tandems cost $65.

Book a pontoon; Windsong has sizes ranging from two-seaters ($85/day) to 14-seaters ($350/day). You can add a local fisherman and spend the above the sea reeling in undersea residents for $120 a day, plus gratuity. Relying on years of maritime experience, Wingsong's fisherman will show you the hottest spots to catch toothsome beasts of the brine. Those without boat-piloting experience can opt for a full-day charter led by a licensed captain. (Boats hold up to six people and are $375 to $395 for the day.)

You may add extra packages, such as an island BBQ party. Windsong will host a private, personalized feast for you and your shipmates for an additional $175 to $295, depending on your menu of choice. Or see the sea for team building, wedding packages, and ash scattering services.

Weekends are busy; reservations are recommended and sometimes required depending on the activity. This Groupon is not valid on holidays.


Users on Merchant Circle give Windsong Charters four stars, and a 10Best user gives it five stars:

  • Wendy and her crew are fabulous! They take care of all of the details, so you just enjoy your day sailing and lounging around on the island. I'm really looking forward to my next cruise in June. – Eventful Connections, LLC, Merchant Circle
  • AWESOME! The most fun I have had sailing ever! The captains are top notch and let you get behind the wheel. The next day I rented a kayak and explored the area. These guys are fantastic! – Kate5, 10Best

Windsong Charters & Boat Rentals

"We've got more canoes, kayaks and SUPs than fingers and toes to count them," Captain Wendy explains. "Also, two sailboats, eleven pontoons––all rentable. The funny thing is, this business came from a big accident." She's referring to the company’s inception in 2002, when a devastating hurricane led a friend to sign his company’s single sailboat over to Wendy and her husband, Bruce. "We were in marketing––then, suddenly, we were in boating." More than 12 years later, Windsong Charters & Boat Rentals has flourished under the duo’s stewardship. The company now performs 200 weddings each year and equips a wide range of patrons to revel in the breathless joy of cutting through playful zephyrs and out across the water. Wendy and Bruce encourage fishing and bringing pets on boating voyages, and the two share stories to delight guests or calm champagne bottles propped next to brand-new yachts. As propellers hum to life and paddles make a gentle kissing sound against the surf, visitors scan the horizon for the variety of wildlife that slips along just below the surf's surface or comes wheeling out of tufts of cumulonimbus. "I wish the animals would give us their schedules,” Wendy says, “but, on a given day, you could see manatees, dolphins, stingrays, and lots of birds."

Customer Reviews

We had a great experience with Windsong Charters! The staff was very helpful and accommodating! I would highly recommend to anyone wanting a great day on the water!!
Steven G. · January 2, 2017
We have lived here all of my now adult (early 30's) children's lives, but never kyaked down the main north channel and surrounding estuaries. My son, daughter and I had a blast! The day was gorgeous, sunny upper 60's when we left. While it was harder than it looked when others kyaked we were able to go about 4 miles in two hours. With the sea breeze and outgoing tide working against us we defintely used out muscles. Great fun and helpful staff.
Mary A. · November 23, 2016
This was our FIRST time in a kayak and the staff were most helpful.....we thoroughly enjoyed it and going back...staff kept and eye on us which was a comfort to us both....
Janie P. · August 19, 2016
Merchant Location Map
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    New Port Richey

    4927 Us Highway 19

    New Port Richey, Florida 34652

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