Sailing traditions, history and information.

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



This Year, A Real Pirate Ship at Tampa Bay’s Gasparilla Festival

Tampa Bay’s dirty little secret is that its famed annual Gasparilla celebration is a fake. Jose Gaspar, the fabled pirate for which our celebration is named, never lived – he’s a tall tale at best. And his famed pirate ship that leads the Tampa invasionisn’t even a ship – it’s an unpowered barge!

This year, however, city guests and residents alike will be treated to the real thing – a genuine pirate ship, under her own sails, straight out of history. At least that’s what the invading British called the Lynx and ships like her during the War of 1812. Lynx was one of the fastest of the “privateers”, extraordinary schooners that sailed circles around the massive Royal Navy and terrorized it’s merchant fleet. The privateers, owned and crewed by private citizens, sank many of the much larger British man-o-war ships and hundreds of their merchant ships along the Atlantic coast. The Royal Navy called the Fells Point area of Baltimore Harbor, where many of the privateers were constructed, a “Den of Pirates”.

 Decked Out for War . . . and Education

Lynx on Tampa Bay

Privateer Lynx

Today’s Lynx is of course not the original ship from the War of 1812 – only the Constitution survives today from that war. She’s a replica built in Rockport, Maine, and operated by the Lynx Educational Foundation as a living history museum to educate children and adults alike about American history through active sail training aboard a real wooden sailing ship. Lynx is armed with a functioning main battery of four six-pounder carronade and four swivel guns. In addition, a complementary stand of historic small arms, for demonstration and instructional purposes, is aboard, including muskets, pistols, cutlasses, boarding pikes and axes. To maintain the historic integrity of the onboard experience, the permanent crew of Lynx wears uniforms and operates the ship in keeping with the maritime traditions of early 19th Century America.

 Come Aboard in Tampa or St. Petersburg

The Lynx is visiting at the Tampa Convention Center docks, near Lionheart’s berth, through Wednesday, January 22nd, then departs Thursday for a short stay in St. Petersburg. The Lynx will join the Jose Gaspar and the Gasparilla fleet on January 25th as they invade Tampa – watch for those tall masts and majestic square-rigged sails! She will return to share the Tampa Convention Center docks with Lionheart for another ten days on February 17th. Then she’ll sail back to St. Petersburg, where she will remain until March 13.

On Deck Aboard Lynx

On Deck Aboard Lynx

Don’t miss this rare opportunity to walk the decks of this grand tall ship. Better yet, go aboard for a journey back in time as Lynx puts to sea in the beautiful waters of Tampa Bay. Numerous ship tours and sailings are scheduled during their Tampa and St. Pete visits. And plan a January or February cruise with Olde World Sailing Line aboard Lionheart, as she escorts Lynx throughout Tampa Bay. You’ll get unbelievable up-close pictures of Lynx under full sail.

 See a Great Video of the Lynx

Learn more about the Privateer Lynx and her schedule at


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

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






Golden Age of Sail to Come Full Circle? A Modern Tall Ship Cargo Vessel sans Engine!

Olde World Sailing Line is dedicated to paying tribute to the “Golden Age of Sail”.    A relaxing sail on a beautiful yacht like Lionheart , with its billowing sails,  peaceful sounds, long graceful lines, and gorgeous bow sprit, reminds us of the lost days when sail power ruled the world.   If some forward-thinking entrepreneurs are correct, the “Golden Age” may return to solve the some of the most pressing challenges of  21st Century world commerce.

Tall sailing ships of the 18th and 19th Centuries were Europe’s lifelines to the world.  Laden with wool, tobacco, spices, teas, chocolates, as well as gold, silver and human cargo, wind-powered vessels reached their peak during the 1800’s – a time that become known as the “Golden Age of Sail”.  Surpassed by the advent of steam-power, the great sailing ships were largely abandoned by commerce and the military.   As we move into the second decade of the 21st Century, around 90% of all world trade is conducted by commercial shipping.   This is why a recent threatened strike by longshoreman dock workers would have such devastating effects – nearly everything on the shelves at Walmart, Home Depot, Lowes, and countless other retailers arrives to us by ship.

The massive rate of global changes in economics, financing, energy, and effects of global warming make the current model of shipping unsustainable.  Many shipping companies are declaring bankruptcy due to the soaring costs of fuel (costs have risen 400% since 2000).   Added to high fuel costs are regulations that will require massive industry-wide changes and innovations. Shipyards will be compelled to produce more fuel-efficient vessels.  In January 2014 regulations from the International Maritime Organization will require shipping companies to cut carbon emissions by 20% over the next 7 years and by 50% in 2050. If the shipping industry were a country, it would be the 6th largest emitter of greenhouse gases on earth.  The current model is unsustainable.

Three Sailors With an Answer for Shipping

Cargo Sailing Ship

Tres Hombres Cargo Sailing Ship

Last fall (2012) the 96’ brigantine, Tres Hombres, set sail from Den Helder, Netherlands to the Caribbean on an 8-month voyage carrying ale, wine, rum, and chocolate – much like her 19th Century protegees.  Tres Hombres is “carbon neutral” – she has no engine and relies entirely on solar power for refrigeration and other electrics.   All the cargo is organic, making it eco-friendly.  Tres Hombres is an attempt to invent a green alternative to the fuel guzzling cargo vessels of the 21st Century and revolutionize world shipping.

The Dutch once ruled the global seas, and so it is fitting that three Netherlands friends (and thus the name of the ship) launched this grand experiment to rescue world shipping (Anreas Lackner, Jorne Langelaan, and Arjen van der Veen).  Co-Captain Van der Veen explained that “we chose a traditional rig because it’s a beautiful design and we wanted to show people sailing can still be effective”.

Speed is not critical for all forms of cargo.   There may be circumstances where time can be traded for environmental benefits and fuel savings.   Way to go “Hombres”!  God Speed.

What do you think?  Tell us about an opportunity you had to visit or sail on a tall ship? Post your pictures.

In a following blog post, we’ll discuss some other concepts and sailing ship designs that show much promise for solving these global challenges.

News & Photos from CNN, Main Sail

Check out video of life Aboard Tres Hombres

How to Talk Like a Sailor – You Already Do!

Ahoy, mates! In the spirit of Olde World Sailing Line’s dedication to the tribute of the Golden Age of Sea Travel, we’d like to pass along some unconscious salutes we all pay to our nautical history every day. Much of our everyday lexicon is steeped in our maritime legacy, from colorful sailors, pirates, and military seamen who sailed the oceans blue (see our “Blue Oceans Blues” board on Pinterest for another perspective). They all contributed to common English phrases


“Three Sheets to the Wind”?  How long since a friend said you’d reached this third level?

The term is derived from the days of sailing ships to describe the degree of intoxication of a particular sailor – perhaps as a prelude to “What Do You Do With a Drunken Sailor?”.

As on modern sailboats, “sheets” refer to the lines (never “ropes”) that control or “set” the sails (“halyards” pull the sails up the mast).  Sheets either tighten or loosen the sails to most efficiently match the existing wind conditions with the ship’s heading.

He's definitely reached the Third Sheet Level.

He’s definitely reached the Third Sheet Level.

On the old tall ships, there were three lines or chains used to secure each sail. If they were loose or sloppy, the ship’s track through the water became erratic. Being “three sheets to the wind” meant a pretty drunk sailor, while only one sheet to the wind might mean a sailor with a slight buzz but still maneuvering relatively well.


“Three Square Meals a Day”

Aboard tall ships of the 18th and 19th centuries, appliances and furniture were adapted to the rocking and rolling of the ship. Since china plates were far too delicate for these conditions, ship carpenters made square flat tray-like plates out of wood, simply by cutting planks straight across. They were durable, easy to stack and store and were almost indestructible with normal use. The crew would come down to the galley to eat, weather permitting, getting a square plate, which eventually led to the phrase a “square meal”. Captains would then use “three square meals a day” as a way to entice sailors to their crew with the promise of hot, substantial meals.

The USS Constitution (Old Ironsides) was one of America’s first naval ships, launched and commissioned on October 21, 1797.

"3 Squares a Day" - Serving plate on old sailing ships.

“3 Squares a Day” – Serving plate on old sailing ships.

After serving in the War of 1812, she is the oldest continuously commissioned warship in the world. Currently open to the public in Boston, samples of the navy’s wooden square dinnerware are on display in Constitution’s galley. Bon appetite.



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.