From the moment you arrive dockside, to when you’re piped aboard as honored VIP guests, you understand that this is much more than a boat ride. Even as you arrive at the docks and get your first glimpse of Lionheart , you know instinctually this is not your average sailboat. She seems part pirate ship, part Yankee clipper, and all blue water-capable of sailing every ocean of the globe.  Visit our video gallery for a taste of what you can expect aboard Lionheart.

Get ready to create memories and be pampered.

tampa romantic getaways

Experience the Romance of a Classic Sailing Yacht

Olde World Sailing Line cruises are a tribute to the glory days of our seafaring heritage. To that long past time when travel was a relaxing celebrated event marking significant highlights and treasured memories in the lives of most travelers.  Sea passages were the epitome of luxury and indulgent First Class service.

We recognize that you have a choice when it comes to how you spend your valuable recreational time.  When you choose Olde World Sailing Line whether chasing the setting sun on a Sunset Cruise, celebrating the Full Moon under canvas, or savoring one of most unique dinner experiences ever, you’ll be treated to the romance and pageantry of a bygone era when sea travel was a luxurious and very special event.

Each relaxing Lionheart Sail is a Tribute to the Luxury of a Bygone Era

Live Sea Shanties by Professional Harpist/First Mate Kathryn

Live Sea Shanties by Professional Harpist/First Mate Kathryn

Why shouldn’t your sail be a glorious First Class adventure aboard a grand sailing yacht, custom-designed by a world class marine architect, adorned with rich exotic woodwork and polished brass?  Why shouldn’t your “passage” include world-class professional entertainment, imported chocolates, and exquisite hors d’ouevers to tempt your pallet many steps beyond the typical peanuts and pretzels fare?  Why shouldn’t your next become one of your most treasured memories of gracious First Class service on a classic sailing yacht?

As honored guests of the sailing clipper Lionheart you will experience the relaxing grandeur of sailing the blue waters of Tampa Bay under her magnificent billowing sails.

Old World Sailing Line so much more than a boat ride!
A Tampa Bay Sail with Attitude

Book Your Passage Here