Sailing Tampa Bay in Class

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All aboard!


 “I must go down to the sea again, to the lonely sea and sky.

And all I ask is a tall ship and a star to steer her by.”
English poet, John Masefield, from his poem,
“Sea Fever”, 1902


S.V. Lionheart – A Sailor’s Sailboat 

Tampa Bay Sailing

Lionheart Ready to Cast Off

Your Tampa Bay sailboat cruise will make memories that will last a lifetime.  Admire the abundant rich teak and mahogany craftsmanship throughout, solid bronze portholes, accented with polished brass oil lamps and other fixtures – these will be your first impressions of the sailing vessel, Lionheart.

Sailing Tampa Bay in Class

day cruises from tampa

King of the World

The mission of Olde World Sailing Line is to provide each guest with the ultimate experience in sailing luxury, peaceful relaxation, and “First Cabin” service.  This “Olde World” experience begins with the sailboat itself.  Lionheart is a 44’ long Caribbean Sailing Yacht (CSY), weighing in at over 40,000 pounds.  Massively constructed right here Tampa’s famed shipyards, Lionheart’s stout design and heavy displacement make her extraordinarily comfortable at sea.  Her proud profile, from her elegantly carved bowsprit, carved mahogany belaying pins, and her gently up-curved gunwales make Lionheart seem as if she’s from of a long past era, reminiscent of the lines of a classic tall ship.  Go ahead – climb up to the bowsprit and do your best “Titanic, King of the World” pose!

Sailboat Safety, Comfort, Modern Conveniences 

“Olde World” charm aside, Lionheart is a truly state-of-the-art sailing vessel boasting modern heads (bathrooms, with electric flush toilets rather than the usual hand-pump designs found on most other sailboats), state-of-the-art navigation electronics (including radar, multiple satellite navigation systems, emergency satellite beacons, and more), as well as safety equipment exceeding Coast Guard regulatory requirements.  And at the helm is Captain James McManus, holding a U.S. Coast Guard Masters certification, with 25-years sailing experience in the Gulf of Mexico, Atlantic Ocean, and Great Lakes.  Assisting is Captain Kathy McManus, also U.S. Coast Guard licensed.

A Sailboat Designed for Speed as well as Comfort

Despite her stout construction, Lionheart’s architectural design and sail plan enable swift sailing in even the slightest of breezes.   This vessel loves to sail!  With three massive sails, this cutter-rigged design has won a surprisingly large number of sailboat regattas for a boat designed primarily as a cruiser rather than racer.   But it’s when the winds pick up and the waves roll, that Lionheart shows her pedigree.  You’ll always feel stable, secure, and comfortable on this sailing yacht.   She was designed for blue water sailing, and her shipyard sisters are currently cruising in nearly every ocean of the world.  You’ll have all the comforts and security of home on your “Olde World” Tampa Bay sailing cruise.

Your Olde World Tampa Bay Sailing Cruise –

 Choose A Romantic Sunset Sail, a Private Cruise for Just Two of You, or 3-Course Dinner Sunset Cruise    

Tampa Bay Sailing Cruise

Tampa Bay’s Most Luxurious Sailing Cruise

Billowing sails on towering mast, sea spray along her clipper bow, flags flying proudly at the spreaders and stays – it doesn’t get any better than this.  Sailing is undeniably romantic and has the ability to evoke a wide range of emotions. It provides a tremendous sense of freedom and relaxation and a way of re-connecting with ourselves. We consider ourselves very lucky to be able to share our passion for the sea, sky, and canvas with adventurous friends like you. Come take the helm and feel the wind in your grin-etched face.  Or lounge on Lionheart’s leather settee on her spacious foredeck as you count our dolphin escorts.  Experience the luxury and elegance of a classic blue water sailing yacht.



Book Your Tampa Bay Sailing Tour Here

Book Your Sail Today!