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Getting engaged in the Tampa, Clearwater, St Petersburg area in Florida


Planning the perfect romantic engagement? Looking for a great marriage proposal idea?

What could be more romantic than popping the question on a beautiful sailboat at sunset? Just you, your sweetie and your own private captain. You have the entire sailboat to yourselves.

We are in New Port Richey, just a short drive North of Tampa, Clearwater and St. Pete in the Tampa Bay area, Florida.

The sailboat departs  about 2 hours before sunset and once out of the channel, we hoist the sails, cut the engine and all you hear is the gentle sound of the wind in the sails and the waves lapping on the hull. All sailboats are equipped with powerful stereos and speakers up on deck so you can even bring your special song to play while you propose.

At Windsong Sailing Charters, we handle many engagements each month and are very experienced in helping you plan that perfect proposal. In all of our history, not ONCE have we ever had an engagement where she said NO, so your engagement is in very safe hands.

If you would prefer to get engaged on a romantic beach on a barrier island we can arrange that too! The sailboat can anchor off the island and the captain will run you ashore in a dinghy.

Detailed below are just some of the marriage proposal ideas we have seen in the past. Whatever new idea you have for proposing to your sweetheart, we can make it happen for you.

Rates start at $295


  • Make your proposal of marriage on the bow of the sailboat

  • Get engaged on a beach on a deserted island

  • We can hide champagne and roses on the boat and bring them out just when you need them

  • Pop the question while standing knee deep in warm crystal clear water on a beautiful beach

  • Propose marriage in writing in a bottle and we'll "pretend" to find it floating in the ocean

  • You can "find" the marriage proposal buried in a seashell on the island

  • Write your marriage proposal in the sand on the island beach

  • We can serve your champagne in the cockpit and sneak the engagement ring into a glass of champagne for you

  • Hire an airplane to fly past the sailboat with your marriage proposal written on a banner

Rates start at $295


Or you can treat yourself and your loved one to a luxury beach sunset BBQ on one of our beautiful islands.  It's intimate, fun, tasty and romantic. The perfect way to celebrate an engagement.

You own personal captain will drive you in a luxury pontoon boat out to the island while you sip on the complimentary champagne and soft drinks provided on the boat. The boat ride is about 45 minutes.

Your personal chef will cook a 4 course dinner and serve it on the beach. Watch the sunset as you cruise back to the dock.

 more info...


"Thanks for an awesome day! Dave was pretty much the best captain ever, couldn't ask for any better! Will definitely recommend to all my friends and family to go sailing at Windsong. And we kept the 100% yes rate :)"


"This is Yat Ming Ho, I took a sunrise cruise on the August 26th, 2013 and proposed to my beloved GF (now fiancee :) ). I want to thank you for making everything so smooth and perfect, and we couldn't ask for more!

Special thanks to Captain Wendy and Captain Mark, thank you for arranging everything, waiting and staying late for us! We will definitely recommend WindSongCharter to our friends and we are already thinking about another cruise with WindSongCharters. Thanks again and best of luck, hope to see you soon! Lastly, please enjoy a short video that I have created for our wonderful proposing trip. "

The Boats

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

Rates start at $295

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

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