• Tampa Sailing Tours

    Tampa Bay’s Most Luxurious Sailing Cruises  

    Join us on a luxury sailing cruise on beautiful Tampa Bay aboard the S.V. Lionheart, a classic 44’ ocean-going sailing yacht. From the moment you arrive dockside along Tampa’s Riverwalk, to when you’re piped aboard as honored VIP guests, you will understand that this is much more than an ordinary boat trip. From your first glimpse of Lionheart, you will understand this is not your typical sailboat. She seems part pirate ship, part Yankee clipper, and all luxurious sailing yacht fully capable of sailing every ocean of the globe in ultimate safety and comfort. Prepare to be pampered, whether you choose a romantic Sunset Cruise, a magnificent Half Day Sail, or an elegant 3-Course Dinner Cruise customized to best meet your needs and schedule.

    Sailing from the Tampa River Walk Docks

    The Lionheart departs by reservations from the River Walk docks in front of the Tampa Convention Center. Located in the heart of Tampa’s downtown waterfront with convenient parking, first class dining, and the city’s major attractions along the brand new River Walk. As we depart, you’ll see Tampa as you’ve never experienced it before as well as Florida’s largest port, the Port of Tampa.

    Sunset Dinner Cruise

    Tampa's Finest Dinner Cruise

    Experience the Best of the Bay – Sailing Elegance, Luxury, Ultimate Relaxation

    Every Olde World Tampa Bay Sailing Tour features elegant hors d’oeuvres, a wide range of refreshments, First Class service, and live harp sea shanties performed by a national award-winning orchestra musician. The choice will be yours – take the wheel, hoist a sail, or kick back in one of Lionheart’s easy chairs, put your feet up on the railing and relax.

    Half-Day Sail – Departure at 11:00 daily – Return mid-afternoon


    Sunset Sail – Departure 2-hours before sunset. Three hour cruise returning after dark.


    Sunset Dinner Cruise – Departure 2-hours before sunset. Elegant 3-Course Dinner