Welcome to Norwegian Dawn

Ahoy there!

Tampa port and tourism officials were happy to recently welcome the cruise ship Norwegian Dawn to her new home port.  Lionheart had the opportunity yesterday to add her own welcome.  We met the huge ship as she made the turn from Sparkman Channel headed out to Tampa Bay.  It’s exciting to be so close on the water – but not too close – to such a massive vessel.  Read more

A Back Stage Pass to Olde World: A Tribute to the Elegance and Service of Another Time

Our goal for the Olde World Sailing Line is to provide our guests an experience they will long remember, and by so doing, that our guests will help us grow by sharing these memories with friends and family. To differentiate our company from the scores of other sailboat ride operations up and down the Gulf and Atlantic Coasts and to develop a product that truly exudes excellence and quality, Kathy and I decided from the design phase to create a sailing line that celebrated the romance and opulence of the Golden Age of Sea Travel as well as the era of the tall ships. The period is remembered for its over-the-top service, attention to every detail, and level of amenities long lost in today’s travel industry.  Read more


Sailing in Florida’s late summer is problematic at best – winds are generally extremely light and sometimes non-existent, with the days punctuated with often violent afternoon thunderstorms. It is an ideal time for haul-out and maintenance chores in preparation for the generally excellent conditions Florida waters offer sailors throughout most of the year.

For Kathy and I, this year’s routine maintenance has been magnified many times over. Lionheart is a new boat to us – the culmination of a year long search. We located her on Lake Michigan, near Chicago and had her shipped by semi-truck to a St. Petersburg shipyard for retrofitting. Even for a boat in excellent condition such as Lionheart, refitting is a time intensive and laborious undertaking. Installing new equipment, buffing and waxing the hull, and applying fresh anti-fouling paint to the bottom were only the beginnings the six-week retrofit.

Lionheart was finally “splashed” in mid-August 2012. The sight and sounds of our 35,000 pound, 44 foot-long treasure being deftly lifted from her shore side cradle to the water’s surface was nerve wracking. And I still feel guilty placing this iconic vessel that spent her lifetime in the cool clear fresh waters of Lake Michigan into Florida’s tropical briny seas.

But it was saltwater she was built for – right here in Tampa shipyards. Lionheart is a CSY 44 (Caribbean Sailing Yacht), designed and constructed specifically to commercially ply the waters of the Caribbean Sea. CSY yachts have always been known the world over for their classic “clipper ship” appearance and also famous for their extraordinary strength, bronze fittings, seaworthiness, and sailing prowess. Today CSY’s can be found cruising in every ocean of the world.

Following “splash day” and subsequent vessel rigging, Kathy and I were thrilled with the initial sea trials and the fall months that followed giving Lionheart a chance to stretch her legs and show us how best to squeeze every last knot of boat speed from the winds. She sails surprisingly well even in light air, but is particularly in her element as the winds pick up. Lionheart loves to sail, and her massive construction makes her an extremely comfortable and safe vessel.

From the outset of our business model for Olde World Sailing Line, our vision was to share the joy and adventure of sailing, while paying tribute to the elegance and amenities of the golden age of seafaring. We believe a sailing excursion should be a magnificent, luxurious event – reminiscent of the opulence and majesty of an early 20th Century ocean voyage. The trip should become a moment captured in a long-lived memory.

We believe Lionheart is the perfect setting for your special event. Kathy and I hope you will join us on a sail that may well become one of your most precious moments.

Come Sail with Us on an Ocean-Going Classic

tampa sailing chartersDo something worth remembering. Come sail with the iconic Lionheart, flagship of Olde World Sailing Line, as we pay tribute to the elegant, bygone era of First Class sea travel.

A sailing journey is a vivid tapestry for the senses… inhale the fragrance of the salt-tinged breeze, hear the sound a seashell makes, feel the gentle cadence of the sea, and experience the romantic siren sounds of sea shanties from one of the word’s most ancient instruments – performed live onboard by a renown orchestral concert master.

Whether a glorious afternoon at sea or a romantic voyage in celebration of the setting sun, your Lionheart seaborne adventure will creat memories to last a lifetime.