Tampa Bay Sailing Tours


Call (888) 989-SAIL (7245) or
BOOK NOW via email

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 SeaTell him or her how much you love them!   Come aboard now with our video sneak peek of Lionheart Romantic Cruises!  The perfect gift for any special occasion – or just “because”!

book now ticketA pampered cruise on Tampa Bay aboard one of the west coast’s most beautiful sailing yachts.

Gift certificates are redeemable anytime for 6 months from issue.


Spectacular Sunset Sail • $109 per person

Sunset sailing Tampa Bay

Spectacular Sunset Cruise

book now ticketChase 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 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 approximately 90 minutes prior to sunset.


Dinner at the Captain’s Table for Two – The Ultimate Sunset Dinner Cruise Under Sail • $474 per couple

Ask about pricing for additional guests

Sunset Dinner Cruise

Tampa’s Finest Dinner 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 4-course dinner under the light of a polished ship’s oil lamp.  Then return to Tampa 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.


Private Concierge Class Sunset for Two • $364 per couple

book now ticketThere 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 upgraded hors d’oeuvres in your deck chairs while enjoying the magnificent sunset.  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.


Custom Photo Package • $29


Gift certificates available.book now ticket

Contact Us for Reservations or Questions

To reserve your cruise, please complete this email booking below and indicate your selected Cruise Package (Sunset, Full Moon, Dinner at Sea, or Concierge) in the space provided.  Please include the number of people in your party, preferred date or date range, and any special requests in the message.  We’ll confirm by phone and email.  You’re going to love your Lionheart sail.

Capt. Mac and Kathryn