About our various cruises and things that happen during them.

Uncharted Waters


Olde World Sailing Line Schedules

Dear Guests –

The Coronavirus has presented global challenges to us all unlike any in modern memory.   Challenges in personal life, business and community commerce, and professional interactions – truly uncharted waters for everyone.  Following the guidance of the respected health officials we will all get through this world disaster together.

Throughout the fall 2020 of the coronavirus infections has spread in most states.  Florida is a leading state in the rising rates of COVID-19 infections.

Olde World Sailing Line is doing our part to follow the guidelines established to curb this epidemic by personal self-distancing.  In respecting these guidelines Olde World Sailing will not be operating cruises until medical officials determine it is safe to do so.  Your safety has always been our primary concern throughout our eight-year history.  Although this safety concern is far different than we have ever faced before, our commitment to the well being of our guests remains our top priority.

When conditions improve and leading medical doctors inform us that it’s safe to resume operations, we look forward to welcoming you aboard again.  We look forward to again showing you the Tampa Bay Area from the sea.

God Bless You All,

Captain James McManus
Captain Kathryn McManus


Phase I Reopening Plan for Olde World Sailing Line


Olde World Sailing Line

Beginning March 1, Olde World Sailing Line discontinued sailing operations as prescribed by U.S. health experts.  After reopening briefly from August – October, we have suspended sails again due to the widespread surge in coronovirus cases in the U.S.

When health officials indicate it is safe to begin some business activities again, we will update our website and resume sails.  Following are our reopening guidelines when that time comes.

U.S. Health Official Guidelines for PHASE I business reopening:

                * Social Distancing –Remain at least 6 feet from other non-household people.

               * Wear masks or face coverings when outdoors and around other people

      * Avoid large groups of people, particularly in indoor spaces

For the safety of our guests and crew, Olde World Sailing Line has developed a

Phase I Reopening Plan:

  1. All sailing cruises will be private, with no more than two guests aboard.  Guests will verify they are not sick or feeling ill, and have not been in contact with any individuals known or suspected to be COVID-19 positive.
  2. Forehead temperatures will be taken for all guests and crew before boarding, and you will be asked to use provided hand sanitizer upon boarding.
  3. Guests will wear facemasks before entering the dock gate at the parking lot and continue to wear them until permitted to remove them once seated aboard the boat.
  4. Comfortable padded armchairs will be provided on the foredeck of the boat (lots of fresh air in private setting).  Guests will not leave the bow foredeck area.  If the restroom is needed, guests will wear masks when moving back to the bridge area and stairway below decks, and use the provided hand sanitizer after using the head.
  5. During the 3-Hour Sail no food will be served.  Guests are welcome to bring their own snacks or alcoholic beverages.  A cooler will be located on deck with water and soft drinks, as well as a place for your snacks as needed.
  6. Guests will wear masks when departing the vessel and dock area at the conclusion of the cruise.

Our Phase I Reopening Plan is temporary.  The Plan revises Olde World’s traditional business structure and practices, as business all over the world have had to do.  We look forward to the day when we can resume full operations.   Thank you for sailing with us.  We are committed to continuing to provide you with the TripAdvisor 5-Star service you have honored us with for the past eight years in Tampa Bay.

Exclusive Private Sailing Cruise

 $448 per Couple

A VIP Guest Experience – from 98Rock Baltimore

We were thrilled to welcome Sarah Fleischer aboard Lionheart this January.  She is an on-air personality at 98Rock from the Greater Baltimore area.  Check out her Blog at 98Rock Online.

Sarah at 98Rock Online Onboard Lionheart

Sarah at 98Rock Online – Aboard Lionheart

All Aboard Matties!

Just getting away from the “Polar Vortex” for 6 days to Clearwater,Florida was wonderful in itself but a real highlight of out little getaway has to be our half day sailing outing in Tampa Bay! We sailed the Lionheart, a 44 foot blue water yacht on Olde World Sailing Line. It’s not that the weather was spectacular for sailing-the day was overcast with very little wind but warm enough , 70 degrees or so.

It’s always the people that make the experience special .We set sail with our very dear friends who live in Tampa and were greeted by Captain Jim and his first mate, Kathy, a lovely couple with enough grace, charm and talent to woo a cranky pirate! They served yummy horderves, told great stories and even entertained us with Kathy’s accomplished and angelic harp playing. Jim’s a master at conch blowing and will invite you to try it out for yourself (very loud!!)

By the end of the day we felt like 6 chummy sailors out to sea for an afternoon adventure.What’s so unique about the voyage is that Captain Jim and Kathy pay special tribute to the grand age of seafaring and enjoy the experience as much as their patrons! They offer dinner cruises, half day, full day, sunset voyages and even engagement voyages. It’s a great time. Look them up the next time you’re in Tampa




Proposals on a Private Sailing Yacht

Beginning a brand new life together.

Beginning a Brand New Life Together

Spectacular sunset sailing, steady predictable winds, and comfortable temperatures – all the wonderful things we love about Tampa Bay and Gulf Coast sailing in the fall. Apparently Cupid has an affinity for the season as well. The past few months have been a great time for marriage proposals aboard Lionheart. Congratulations to these lucky couples as they begin a glorious new life together.

Engagement on deck of Lionheart

Engagement on deck of Lionheart

One of the most wonderful perks about operating Olde World Sailing Line is the opportunity to share time with such interesting and fun-loving couples. Lionheart is a “happy boat” and this is certainly a “happy” business. The smiles of our guests are always infectious and engaging. This is especially true when we are honored to be chosen as the venue for one of life’s most exciting and solemn moments – a marriage proposal! We take this honor very seriously and pull out all the stops to help make this occasion one of the lifelong hallmarks in the lives of these lucky couples.

Thank you all for choosing Olde World Sailing to host this first formal hallmark on your brand new life together. Congratulations and best wishes.

Update:  a new video sneak peek at many happy couples celebrating their love on SV Lionheart!


Tampa Bay Under Full Sail and Full Moon

Tampa Bay Sunset Sailing Cruise

Back at the Dock after Full Moon Cruise

In mid-June, Olde World Sailing Line will present one of its most unusual cruises, unique in all of west-central Florida. On Saturday, June 22, the sun will set at 8:24 pm, the second longest day of the year. At about the same time the sun is setting in the west, the full moon will be rising in the eastern sky – a fairly rare event.

As the sky turns from bright reds and oranges through deep shades of purple, the huge full moon will dominate the eastern skies. While close to the horizon, the full moon appears twice its normal size, painting ever-changing Monet-like reflections on the waters. It is a rare and spectacular sight to behold.

Lionheart will make other Full Moon Excursions on other days surrounding June 22nd. Friday’s sail is fully booked, but Sunday and Monday will also have a moon nearly as full as that of the 22nd, with moonrise only a little later.

Don’t miss this opportunity to experience this unique astronomical and maritime event. We’ll make memories you will treasure for a lifetime. Like all Olde World Sailing cruises, you will be treated to Tampa’s most luxurious sailing line, with extravagant hors d’oeuvres, live music, flowers, and First Cabin service from the moment you board.

Reserve Your Full Moon Sailing Cruise Today


Full Moon Sailing Cruise

Moonrise from Sea

Sunset Sailing Cruise

Chasing the Sun to the Horizon

Tampa Sailing Tours

Olde World Sailing Line

You haven’t seen the Tampa Bay Area until you’ve seen it from the sea. Get a preview from our video…

Make your reservation today…Click Here!

Elegant Dinner On Your Sunset Cruise from Tampa

Romantic Getaways Tampa

Hors d’oeuvres on Deck. First Class

Olde World Sailing Line has developed a reputation for providing the most luxurious day cruises from Tampa. Are you ready for a Tampa romantic getaway? Whether a beautiful Half Day Sail, Full Day Sail, or magnificent Sunset Cruise, we strive to make every sail a very special occasion for our guests. Each cruise features elegant hors d’oeuvres, fresh flowers, imported chocolates, live music, all aboard a 44’ world class sailing yacht.

Dinner at the Captain’s Table

It is on Olde World’s Sunset Dinner Cruises, however, that Lionheart pulls out all the stops. Dinner Cruises cast off from the Tampa River Walk docks a couple hours prior to sunset. After riding the winds toward the setting sun over Tampa Bay, your teak table is set with fine china, cloth napkins, and silverware. In the galley, your chef is preparing a full 3-course dinner that you selected prior to your cruise, catered from a downtown Tampa restaurant.

As the sun sets, Lionheart becomes your own private “waterfront restaurant”. Your meal is accompanied by the music of a Celtic harp, played by Kathryn, former Florida Orchestra principal harpist. Desserts, chocolates, and bubbly as you wish. Magnificent.

Sunset Cruise Tampa

Romantic Sunset Dinner Cruise

Tampa romantic getaways

Elegant Dinner Music

Truly the Premier Tampa Boat Trip

Then conclude your Tampa romantic getaway with a sail back toward civilization and to the spectacular colors of city’s waterfront after dark. You haven’t seen the Tampa Bay area until you’ve seen it from the sea. And you’ll have a completely different and magical impression, when you experience it after nightfall.


Make your reservations HERE for your Sunset Dinner Cruises from Tampa

Tampa Dockside following Sunset Cruise

Tampa Dockside following Sunset Cruise






2012 Sails Into the Sunset

Diamonds of light

Sunshine Skyway on the Faraway Horizon

The final sailings of 2012 were spectacular. The light itself on these short December days has a different quality than that of the warmer months. The air is more crisp and clear, seeming to move the visual horizon miles beyond the dog days of summer. The reflective shimmer on the waters is spell binding. Even the sounds of the gulls, diving pelicans, and broaching dolphins seem more intense. Winter sailing in Florida has a magic all its own.

One of our favorite places to ring in the New Year is the Vinoy Basin in St. Petersburg. This protected small anchorage is surrounded by one of the most vibrant waterfront communities in Florida. High-end shops line Beach Drive, beautiful parks with sculptures, sprawling banyan trees, and a rare kapok tree, world famous museums, and eclectic restaurants. And of course standing guard at the mouth of the harbor is the iconic St. Petersburg Pier – even more beautiful as seen from the water. A decades-old Florida landmark.

Few communities put on a better firework show to welcome the New Year than St. Pete. And no better place to be awed by them than from an anchored boat. Please enjoy and “like” our pix of our year-end sailing festivities – better yet, come and join us as we sail into 2013. And don’t forget to check out our higher res photos on Pinterest.

Last New Years for the St. Pete Pier

Last New Years for the St. Pete Pier

Can't be too careful about that December Florida sun.

Can’t be too careful about that December Florida sun.






Conch Horn Tribute to Day's End

Conch Horn Tribute to Day’s End



Rockets Red Glare

Please, just one.

Please, just one.

A Back Stage Pass to Olde World: A Tribute to the Elegance and Service of Another Time

Our goal for the Olde World Sailing Line is to provide our guests an experience they will long remember, and by so doing, that our guests will help us grow by sharing these memories with friends and family. To differentiate our company from the scores of other sailboat ride operations up and down the Gulf and Atlantic Coasts and to develop a product that truly exudes excellence and quality, Kathy and I decided from the design phase to create a sailing line that celebrated the romance and opulence of the Golden Age of Sea Travel as well as the era of the tall ships. The period is remembered for its over-the-top service, attention to every detail, and level of amenities long lost in today’s travel industry.  Read more

Come Sail with Us on an Ocean-Going Classic

tampa sailing chartersDo something worth remembering. Come sail with the iconic Lionheart, flagship of Olde World Sailing Line, as we pay tribute to the elegant, bygone era of First Class sea travel.

A sailing journey is a vivid tapestry for the senses… inhale the fragrance of the salt-tinged breeze, hear the sound a seashell makes, feel the gentle cadence of the sea, and experience the romantic siren sounds of sea shanties from one of the word’s most ancient instruments – performed live onboard by a renown orchestral concert master.

Whether a glorious afternoon at sea or a romantic voyage in celebration of the setting sun, your Lionheart seaborne adventure will creat memories to last a lifetime.