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.

When sails resume we will be offering our . . .


Exclusive Private Sailing Cruise

$448 per Couple

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Sailing Cruises

Private Concierge Class Sunset for Two • $448 per couple

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. Relax 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.
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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”!

A 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.

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Cancellation Policy
If personal reasons require you to reschedule or cancel, 24 hour notice before your cruise enables us to adjust our plans.  If you need to cancel within less than 24 hours  (or do not arrive at the time of your sail), refunds cannot be accommodated.

While we always try to give customers as much notice as possible regarding schedule changes, Olde World Sailing reserves the right to cancel any sail at any time.

Contact Us for Reservations or Questions

To reserve your cruise, please complete this email booking request form below.  Please include your 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 Capt. Kathy