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






Flying "Olde" Glory - A Symbol of the Golden Age of Sailing

Flying Bold New Colors Over Tampa Bay – Sailing the “Olde” Way

Olde World Sailing Line provides the most luxurious sailboat cruises on Florida’s west coast.  Every one of our Tampa Bay sailing tours is a tribute to the Golden Age of Seafaring – a time when sea travel was the epitome of luxury and First Class service. As a “tip-of-the-hat” to this maritime heritage, Lionheart has always flown the Colonial American flag, sometimes called the “Betsy Ross” flag.

Our previous company was a hot air balloon operation called 18th Century Aviation, in honor of the world’s first aircraft flight in 1786. Our newest balloon was named “DaVinci’s Dream”, from which we flew the Colonial Flag, thousands of feet over the Tampa Bay area on bright early mornings. It seemed fitting that when Lionheart was put into service at Olde World Sailing Line, we crowned her with the original flag that flew on DaVinci’s Dream.

New Colonial Flag for Olde World Sailing Line

New Colonial Flag for Olde World Sailing Line

This flag was a good-sized flag, at 3×5 feet. However, when we saw an opportunity to acquire an even larger 5×8 feet flag, we couldn’t resist. Not until we brought the new flag to the dock alongside Lionheart, however, did we realize how very BIG an 8-ft. long flag really is.

Lionheart is a big girl, however, and once hoisted aloft high on the backstay, the new flag looked wonderful, and fully proportional to the sailboat’s 44’ length. What do you think? Do you like the circular star pattern of the Betsy Ross flag? Did you know that American historical flags are still considered “official” flags – American Flags remain officially authorized flags, even when newer designs are adopted?

Flying the Colors

Flying the Colors

The large new flag looks great, but we are bit saddened to replace our DaVinci’s Dream original flag – it brings many happy memories. However, any flag on a sailboat cruise takes a beating. We’ll relegate our beloved 18th Century Aviation’s flag to a safer indoor locale. And if you’re in the downtown Tampa area near the Convention Center or Bayshore Drive, see if you can spot the huge Betsy Ross flag flying from Lionheart. Give us a wave!


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

Bullet Proof

On March 1 Jeff Yates posted on our Face Book fan page about Lionheart, “Love these old CSY yachts, why because I helped build every one.”   CSY’s (Caribbean Sailing Yacht) were designed and constructed right here in Tampa throughout the ‘70’s and 80’s in a ship building facility near the Gandy Bridge.  The Tampa Bay Area was then home to more yacht producers than anywhere else in the U.S.

I continue to be amazed at how many people I run in to in the Tampa Bay Area who proudly proclaim that they worked at the CSY factory – and most for very long tenures.  All exude extraordinary pride in the craftsmanship that went in to every one of these beautiful yachts.

Launching Lionheart

Launching Lionheart

Though the CSY was one of scores of world-class sailing yachts built on Tampa Bay’s shores, its mission and product were very unique in the industry.  The CSY corporation did not have a retail dealer network like other boat manufacturers.  These ships were not built for the mass market, but were designed for CSY’s own commercial operations in the Caribbean.  And they were “overbuilt” in every way.  Strong, stout, heavy boats that could be safely and comfortably at home in any ocean in the world in most any weather.  Yet CSY’s were blessed with marine architectural designs that made them world-class sailing vessels, from the lightest winds to gale force blows.

More than one former CSY boatwright has described strength tests during which the hull was literally shot with a Remington 341 high-powered rifle.  It did not penetrate the thick hull!   CSY has a hull that is truly “bullet proof”.   Where most other boats of the class are fitted with plastic or aluminum portholes, CSY used only bronze.  Likewise, all the

The boatyard went through 5 sets of saw blades in the installation of Lionheart's bow thrusters.

The boatyard went through 5 sets of saw blades in the installation of Lionheart’s bow thrusters.

through-hull hose fittings are solid bronze – not brass or steel.    Some of the most identifiable features of CSY’s are the generous use of exotic woodwork and the fine craftsmanship displayed throughout and the hand-carved bowsprit, reminiscent of the grand sailing ships of the past.  You’ll find very little plastic or veneers on a CSY.

Lionheart has a very special history in that she spent most of her life in the fresh waters and short sailing season of the Great Lakes.  Time has treated her well.  She is an excellent example of the products of these world-class craftsmen (and women) and designers of CSY, as well as the business acumen of this corporation.   Thanks Mr. Yates for reminding us of this heritage – we look forward to putting you at the helm once again.






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.



Tall Ship, Lynx

One of the authentic and inspirational aspects of the craziness of Gasparilla this year was the surprising appearance of the tallship, Lynx. Unfortunately, not many Gasparilla viewers were able to see this great ship because her deep draft restricted her passage to the deeper waters of the Bay. During Saturday’s invasion, on January 26, she departed from St. Petersburg with a complement of very lucky passengers.

Lynx is a re-creation (completed in 2001) of an actual privateer named Lynx, built originally in 1812 in Fell’s Point, Maryland. During the War of 1812 she was among the first ships to defend American freedom from the invading British naval fleet which blockaded American ports.

At the outbreak of the War of 1812, the American Navy consisted of only 17 ships – the British Navy was the most powerful in the world. When America went to war, President Washington granted owners of private vessels special permissions, called “letters of marque,” to prey upon the enemy’s shipping – thus the name, “privateers.”

We took this opportunity to sail on the Lynx the day following the Gasparilla invasion. What a treat to see such a magnificent ship under sail!Lynx Lynx

The Lynx is owned and operated by the Lynx Educational Foundation, which is a non-profit, non-partisan, educational organization, dedicated to hands-on educational programs that teach the history of America’s struggle to preserve its independence.

Check out this excellent video about this majestic ship.  Also see additional photos of the invasion on our Pinterest page.

Lionheart Joins Gaspar’s Navy

The Gasparilla Pirate Fest is a mainstay of Tampa’s social calendar.  Held each year in late January (some years early February) since 1904, the Gasparilla pirate ship invasion and parades bring between $20M – $40M of booty into the city’s coffers, according to a 2007 study.   This year’s festival and pirate invasion on January 26 saw over 300,000 spectators according to official estimates.

Jose Gaspar, flagship of the fleet.

Jose Gaspar, flagship of the fleet.

Most people experience Gasparilla from the parade routes, watching the fabulous floats and gathering the sparkling booty.  Parade watchers, however, may miss the invading fleet of thousands of boats, lead by the pirate ship Jose Gaspar, as they storm Tampa’s waterfront and take possession of the Key to the City.   As the armada crosses Tampa Bay enroute to the channel along Davis and Harbor Islands, it is out of easy viewing range for most spectators.  This year the crew (“krewe”) of Olde World Sailing Line boarded the Lionheart to lend firepower to the Jose Gaspar and fleet.  Land bound crowds see only the final 20% or so of the spectacular convoy from the sea to city-center.   I hope you enjoy these photos of our up close and personal encounter with the floating hoards.  Check out the additional photos with on Olde World Sailing’s Facebook and Pinterest pages.  Also see the Gasparilla section on the Gallery on this website.  More to come . . .


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.

Sailing into the New Year

Camille says "...this isn't a seat - it's heaven!"

Camille says “…this isn’t a seat – it’s heaven!”

Sailing in Florida December waters is often a crapshoot. It can be gloriously sunny or a bit nippy and blustery. This beautiful late December day was both – with only three days left of 2012 we were treated to bright clear skies with moderate breezes and temperatures that made your jacket most welcome.

Lionheart’s huge bridge area can be enclosed on four sides for comfort in cooler weather. Throughout most of the year no windows are necessary, but after Christmas this year the front panels became a welcome addition to break the chilly breezes.

Good friends, fresh sea air, and following seas – what a glorious way to sail into the New Year.

Mindy - Master and Commander

Mindy – Master and Commander

Steady as she goes, Camille.

   Steady as she goes, Camille.


Sam and Mindy

Sam & Mindy

Sharon enjoyed the blanket.

Sharon enjoyed the blanket.

“Don’t feel sorry for me. I’ve fed tens of thousands”

Among the very special joys of sailing are the interesting places and fascinating people you often stumble upon when least expected.  Such was the case this weekend walking the extensive shoreline dock of Port Salerno, near Stuart, Florida.  The dock, which extends for what seemed like a half-mile or more, is on the west shore of an anchorage called Manatee Pocket.

Spanish mackerel, Fish of the Day

Dozens of sailboats of various descriptions anchored throughout the Pocket.  But it was the docks that drew my attention this day.  Several commercial fishermen were unloading catches from small net boats, filling the dock with large iced containers of Spanish mackerel and other fish. They were then quickly loaded onto commercial refrigeration trucks that were bound for local fish houses and restaurants.  Several friendly fishermen noticed our interest and offered us beautiful Spanish mackerel, but unfortunately we were unprepared to transport them.

Bruce Stiller


Further down the dock I met fisherman entrepreneur, Bruce Stiller, who was loading brand new netting onto his vessel with the help of his two crewmen.  Sharks destroyed a section of his old net, Bruce explained.  As delicate an operation as it appeared to be loading the fine netting from his truck onto the boat, I was surprised at his willingness to engage in conversation.

Bruce explained that several years ago he built his own dock, along with adjacent water well and electric, then donated it to the county as part of the larger public fishing docks so everyone can enjoy them.  In return he received a permanent irrevocable lease protecting his livelihood as future politicos come and go.

Bruce said the fishing populations are very well managed so the fish are plentiful and healthy.  Business is healthy.  Unfortunately, he explained, there is no regulatory protection for full time businessmen like himself from part timers who take off a couple weeks from work in the height of the seasonal fish run, throw out a net and then sell their catch to the same vendors he works with.  “With a $50 permit anyone can become a commercial fisherman.”

“I’ve been fishing these very waters since I was a kid”, he said.  Following in his family’s footsteps, Mr. Stillman now owns two boats that ply federal waters in search of Spanish mackerel, blue fish, and small sharks.  The near-shore deep water on Florida’s east coast, allow the netters to go out and return daily without the need for multi-day trips.

“Fishing is my heritage”, Bruce explained proudly.  He related that one day as he was scooping up the heavy nets a young guy told him he was going to get a good education so he wouldn’t have to work like that.  Bruce told the boy, “…don’t ever feel sorry for me.  I did go to college and I am doing exactly what I set out to do.  It is hard some days, and I don’t like every single job that needs to be done (like in every other profession), but I love being a fisherman and I can’t imagine doing anything else.  I have fed tens of thousands of people with my catches.”  Bruce is a very lucky man.  How many people can say the same about their job?

As recreational sailors who receive such joy from “messing around in boats”, it’s inspirational to reflect upon our “heritage” of those who make their living from the sea.

What interesting people have you encountered along our waterfronts?  Favorite places?  Bruce acknowledged that most regulations are two-sided coins, with pros and cons depending on your point-of-view.  Do you see other sides to these or other maritime regulations?