Tampa’s Most Luxurious Sailing Cruise

Sailing Cruise

Lionheart at Tampa Convention Center Docks

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Immerse yourself in the romance and relaxation of the sea and the luxury of a fine ocean sailing yacht.  Your voyages aboard Lionheart will be among your most precious memories. Our promise is that it will be so much more than a boat rideCall or email now for immediate reservations.

Sailing Cruises

Gift Certificate

Give the gift of elegant, luxurious relaxation

Romance at Sea - Sailing Cruise

Tell him or her how much you love them!   Come aboard now with our video sneak peek of Lionheart Romantic Cruises!  The perfect Valentine’s Day or birthday gift, or for any special occasion!

book now ticket - Sailing CruiseA pampered three-hour cruise on Tampa Bay aboard one of the west coast’s most beautiful sailing yachts.


Gift certificates are redeemable anytime for six months from issue.


Half-Day Sail • $89.00

Romantic Getaways Tampa - Sailing Cruise

Hors d’oeuvres on Deck. First Class

book now ticket - Sailing Cruise

Casting off the Tampa River Walk docks at 11 a.m. daily for three luxurious hours under Lionheart’s billowing sails. Enjoy exquisite hors d’oeuvres, imported chocolates, live musical entertainment, and the companionship of pods of Tampa Bay’s dolphins.  Relaxation at its finest!


Spectacular Sunset Sail • $89

Sunset sailing Tampa Bay - Sailing Cruise

Spectacular Sunset Cruise

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Chase the sun to the horizon under full sail and watch the heavens and the seas change colors by the minute as dusk approaches.  Celebrate the glorious day’s end in style with live harp music, hors d’ouevers, a sip of the bubbly, sinfully delicious imported chocolates, and Lionheart’s special sunset cruise surprise. Then return after dark to experience the brilliant lights of Tampa’s waterfront from the sea.  Your Tampa Bay Sunset Sail will make treasured memories that will last a lifetime. Departures two hours prior to sunset.


Private Concierge Class Sunset for Two • $289

Promo Shot - Sailing Cruise

book now ticket - Sailing Cruise

There are occasions in life that demand the ultimate celebration.   Consider a Concierge Class Sunset Sailing Cruise with Olde World Sailing Line.

Treat yourself to a cruise on a private yacht aboard the S.V. Lionheart, where lavish amenities and pampered personalized services will create your own sanctuary at sea, where you can share elegant intimate moments far away from the crowds and congestion of everyday life.  Immerse yourself into the magic of a tropical sunset on the deep blue waters of western Florida.

On Olde World Sailing Line’s Concierge Class Sunset Cruises, you and your companion will be the only guests aboard the 44’ sailing yacht, Lionheart.  Enjoy service that is richly personalized, where every need is discretely anticipated and promptly delivered.  You’ll be served elegant hot hors d’oeuvres in your deck chairs while enjoying live entertainment.  Private yacht cruising is all about freedom.  It’s about private moments.  We make it all about you –  whether to create that very special occasion or knowing when to simply stay out of the way.  That’s one of the reasons Olde World Sailing Line was awarded the “Best of the Bay” by Tampa Bay Magazine.

Make your Concierge Class reservations today.  We’ll ready the ship for your departure.  Bon Voyage.


Dinner at the Captain’s Table for Two –
The Ultimate Sunset Dinner Cruise
Under Sail • $

Ask about pricing for additional guests

Sunset Dinner Cruise - Sailing Cruise

Tampa’s Finest Dinner Cruise

Sailing Cruise

It’s just the two of you dining aboard the elegant yacht, Lionheart.  After a beautiful sunset cruise, your solid teak dinner table set under sail – your own personal “waterfront restaurant”.  You will be served a delectable 3-course dinner under the light of a polished ship’s oil lamp and serenaded by the heavenly harp of Lionheart’s own mermaid.  Then return to Tampa’s River Walk docks after dark – a magical treat.  Select from the Olde World Sailing menu prior to your sailing cruise.  Invite additional friends for a modest additional fare. Call us to create your most special memory.


Full Moon Soiree • $109

tampa sailing charters - Sailing Cruise

Full Moon Soiree Ready for Boarding

book now ticket - Sailing Cruise

Celebrate a glorious sunset at sea, then sail on into the night under a beautiful Tampa Bay Moon. Some say during our Full Moon Soiree as the moonlight strikes her sails, Lionheart raises her bow and roars like the sounds of distant thunder (others say it’s the rum). The waters turn a magical silver and shine as brightly as the moonlit sky. Don’t miss this very rare and exotic cruise.

Sailing dates vary with the lunar calendar – call for specific dates. Depart Tampa Convention Center Docks one hour before sunset for 3-hour cruise.


Gift certificates available.

Contact Us for Reservations or Questions

To reserve your cruise, please complete this email booking below and write your selected Cruise Package (Half Day; Full Day; Sunset; Full Moon; Dinner at Sea; or Special) in the space provided.  We’ll confirm by phone and email.  You’re going to love your Lionheart sail.

Capt. Mac and Kathryn