Cruising Monohull Cruise in Tampa, Florida

Cruising Monohull
44 ft
6 Guests

About This Boat

Enjoy cruising in Tampa, Florida onboard 44ft Caribbean Sailing Yacht. Rent for as low as $89 per person (minimum 3 hours). 


  • Lionheart Romantic Cruises - $89 per person
  • Half-Day Sail - $89 per person
  • Spectacular Sunset Sail -$89 per person
  • Private Concierge Class Sunset for Two- $289
  • Dinner at the Captain’s Table for Two – The Ultimate Sunset Dinner Cruise Under Sail - $389
  • Full Moon Soiree- $109 (3-hours)

What You Can Expect:

S.V. Lionheart – A Sailor’s Sailboat :

Your Tampa Bay sailboat cruise will make memories that will last a lifetime. Embarking from the Tampa River Walk docks in front of the Convention Center, you’ll be piped aboard the S.V. Lionheart with an authentic Royal Navy boson’s whistle. Flowers greet you on the spacious bridge, abundant rich teak and mahogany craftsmanship throughout, solid bronze portholes, accented with polished brass oil lamps and other fixtures – these will be your first impressions of the sailing vessel, Lionheart.

Sailboat Safety, Comfort, Modern Conveniences:

A truly state-of-the-art sailing vessel boasting modern heads (bathrooms, with electric flush toilets rather than the usual hand-pump designs found on most other sailboats), state-of-the-art navigation electronics (including radar, multiple satellite navigation systems, emergency satellite beacons, and more), as well as safety equipment exceeding Coast Guard regulatory requirements. 

A Sailboat Designed for Speed as well as Comfort:

Despite her stout construction, Lionheart’s architectural design and sail plan enable swift sailing in even the slightest of breezes.  This vessel loves to sail!  With three massive sails, this cutter-rigged design has won a surprisingly large number of sailboat regattas for a boat designed primarily as a cruiser rather than racer.  

But it’s when the winds pick up and the waves roll, that Lionheart shows her pedigree. You’ll always feel stable, secure, and comfortable on this sailing yacht. She was designed for blue water sailing, and her shipyard sisters are currently cruising in nearly every ocean of the world. You’ll have all the comforts and security of home on your “Olde World” Tampa Bay sailing cruise.

What To Expect Onboard:

Lionheart Romantic Cruises

A pampered three-hour cruise on Tampa Bay aboard one of the west coast’s most beautiful sailing yachts.

Half-Day Sail

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

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

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.

Dinner at the Captain’s Table

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. 

Full Moon Soiree

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 – contact us for specific dates. Depart Tampa Convention Center Docks one hour before sunset for 3-hour cruise.


  • Type: Cruising Monohull
  • Capacity: 6 People
  • Make Model: Caribbean Sailing Yacht
  • Rental Minimum: 1 day
  • Length: 44 ft
  • Cancellation: Full Refund 1 Day Prior

Rental Requirements

FAQ – About Sailing on Lionheart

Q: How are this cruise different from sailboat rides provided by other companies?

A: Each cruise honors the golden age of sea travel, with its elegance, gracious service, and First Class entertainment aboard an authentic blue water sailing yacht. These are the qualities that make us unique as we work hard to forge long-lived memories for each of our VIP guests.  Your voyage aboard Lionheart will be an extraordinary experience.   We love seeing how many times our guests say “Wow”!

Q: Is there music aboard?

A: Not only music – there be live music! And a state-of-the-art sound system. From the tall ships of centuries past, music played a pivitol onboard role on most ships, for work, crew morale, and pure pleasure. Sea shanties have been passed down for generations and have become an important part of our maritime heritage. Lionheart embraces and brings to life this legacy and the grand musical traditions of early 20th Century ocean liners.  Kathryn is the past principal harpist of the Florida Orchestra and brings her Celtic Harp aboard each sailing – she’s the siren of the sea!

Q: Is food available?

A: On most of our competitor’s single-day sailing trips, customers are offered a bag of chips and soft drinks – if they’re offered anything at all! Aboard Lionheart you will be served surprise culinary delights that are beyond the ordinary. While only our special dinner cruises serve full 3-course meals with china, silverwear, and fine linens, remember that our mission is to pay tribute to the grand traditions of elegant sea travel… expect to be pampered. You won’t go away hungry here!

Q:  Is tipping appropriate?  Expected?

A: If you feel you had a fantastic cruise and the service was extraordinary, then tips are graciously appreciated.   You should feel no obligation to tip, however.

Q: Will I get seasick?

A: As an aircraft pilot as well as sea captain with decades of experience in tropical waters, closely monitoring weather conditions is second nature to us. In addition to aviation and NOAA weather resources, Lionheart has onboard electronics providing live wave and wind data from sea buoys throughout the area. She is a heavily constructed, stout vessel that is extremely comfortable in most all sea conditions. Our goal is to provide you with extraordinary memories that will last a lifetime. Your pale green face wouldn’t fit this guest experience profile – so you can be sure if the water and weather isn’t picture-perfect – we don’t go and you don’t pay!

Q: How many guests will fit on Lionheart?

A: Lionheart has one of the largest bridge decks of any sailing vessel of her class. Covered with a hard roof, this area could comfortably seat 8 people under deep shade from the Florida sun. More could be accommodated on the spacious fore-deck area and aft deck. But that’s not our goal – you are our VIP guests and deserve roomy accommodations.  Lionheart never sails with more than a half dozen guests.   And unlike other sailing companies that require minimum passenger loads, Lionheart will happily sail with only you and your special someone if others haven’t booked for your cruise – your own private yacht!  And for a small additional fare, you can guarantee a private sail.

Q: What should we bring and what should we wear?

A: Be sure to bring your still and/or video camera – you haven’t seen the Suncoast until you’ve experienced it from the sea! Sunscreen and a hat for daytime sails and light jacket during the cooler months are usually wise.  Lionheart carries cozy custom blankets for cool nights on deck.  Please wear only soft-soled shoes aboard (teak decks scuff easily), unless you’d rather wear no shoes at all – many do. Feel free to bring your favorite adult beverages – we will proudly pour them for you with class and flair.

Q: What sea life are we likely to encounter?

A: Dolphins visit Lionheart on most every cruise throughout the year. They love to play in our bow wake while under sail. We see manatees quite often as they come and go from the warmer power plant waters of the area. In the winter months, entire flocks of the shy White Pelicans are a common site. Their all white bodies contrast starkly with their black-feathered under-wings. Most Florida visitors, and many residents, have never seen the white pelican as they don’t hang out at the docks like Brown Pelicans. On our special Full Moon Cruises, you’ll often see one the most spectacular sights of all – the luminescence of the sea (Sea Fire), caused by millions of plankton suspended in the water. It’s another pure magic of the sea!

Q: What kind of safety equipment and procedures do you have?

A: Olde World Sailing Line takes safety extremely seriously. We regularly conduct various emergency drills and conduct passenger safety briefings before each cruise. Your crew holds current certifications in CPR and First Aid, and there is a comprehensive first aid kit onboard at all times. Captain Mac holds a U.S. Coast Guard Master Captain’s License, which requires many more years of experience than a standard Captain’s License as well as additional education. This training includes emergency procedures, man-over-board protocol, fire prevention, and much more. Lionheart exceeds U.S. Coast Guard Regulations minimum safety equipment requirements, to include multiple satellite navigation systems, marine radios, man-overboard equipment, flares, and E.P.I.R.P. Ensuring your safety and comfort is our most important mission.

Q: Can I take the helm?

A: Absolutely! We taught sailing for over six years (Basic, Advanced, Piloting and Navigation, and Heavy Weather Sailing) and is passionate about sharing “the ropes” of seamanship with all who are interested. And you’re most welcome to take the helm, not just for a quick photo op moment, but to stand watch for a significant time, if you like. You’ll be saying, “Aarrrgh!” to everyone you meet in no time. Be careful, though, this stuff is contagious!

Q: Anything else we should know?

A: Yes – make sure you ask. Remember this is your personal retreat and our goal is to make your adventure as pleasurable, decadent, and enjoyable as you’d like. If there are special things you’d like to see, places you’d like to go, experiences you prefer – please let us know. We’ll do our best to accommodate you.

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Member Since May 2016

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