Take a weekend getaway to St. Augustine, Florida to explore history from Colonial days to the Gilded Age in first United States city on the East Coast.
Weekend Getaway in St. Augustine
Despite a keen interest in history, and multiple ventures to Florida, I have somehow missed the opportunity to visit the city of St. Augustine. Working with VISIT FLORIDA, I had the opportunity to experience this historic location, and go back to the beginning in the first United States city on the East Coast.
While many of us may have the 1620 landing at Plymouth Rock implanted in our memories as the first settlement, St. Augustine takes the record as the oldest continuously European-established settlement within the borders of the contiguous United States. It was founded in 1565 by Spanish admiral and Florida’s first governor Pedro Menéndez de Avilés.
My weekend plan was to take in two definitive time periods of St. Augustine’s history. One day would be dedicated to the colonial period, when the Spanish, English, French, Americans and pirates battled for the land of “La Florida.” The second day would focus on the major wave of development that shaped the city’s architecture in the late 1800’s Gilded Age by Florida developer and Industrialist Henry Flagler.
Day 1: Arrival in St. Augustine
Anastasia Island – St. Augustine Lighthouse
On my way into town, I stopped off at Anastasia Island to see the black and white swirl of the St. Augustine Lighthouse. The climb to the top of the lighthouse for a birds-eye view of the Matanzas Bay is a highlight. The lighthouse museum also showcases the structure’s history, a lighthouse keeper daily life, an archaeological program for historic maritime shipwrecks, boat building displays, and World War II artifacts focusing on the history of the US Coast Guard.
Onward to St. Augustine, I took another chance for a sea-focused view of this historical city with an evening sail on the “Freedom” Schooner. The crew was delightful, making sure we all had refreshments and cocktails, and answering questions. I was impressed at their enthusiasm and ability to keeping on-deck conversations lively with stories of their experiences in St. Augustine as home-born locals and fervent, post-college transplants.
We passed under the Bridge of Lions to sail alongside St. Augustine’s 300-year-old Castillo de San Marcos fort. It looked both small compared to the defense structures of today and yet imposing for the low profile landscape of St. Augustine. What a night to see the sunset, with a double treat of a harvest moon rise and cool breezes on the Matanzas Bay.
This is the view of St. Augustine as we came back to dock, framed by the beautiful skyline with the late 1800’s architecture of Flagler buildings.
Day 2: The Colonial Era
I devoted this day to traveling back to the beginning of St. Augustine’s history, by exploring the historic center.
Throughout the day, as I walked the narrow and sometimes cobblestoned streets, I peeked into some of America’s oldest history. The first house. The first schoolhouse. The Greek Orthodox Shrine dedicated to the first Greeks to come to America in 1768. There seemed to be a “first” for every interest, all adding up to an education on the variety of cultures that have lent their influence.
St. George Street
St. George Street is the main pedestrian walkway through the city. Look past the tourist kitsch shops unless you fancy a pirate eye patch, and take in the main colonial thoroughfare — a rather narrow street with quaint two-story buildings.
To learn the history of St. Augustine, this should be your first stop. Our charismatic guide, Ella, was quite the storyteller, entertaining and informing us with 300 years of history on an hour-long walk around the compound.
The European history all started when Juan Ponce de Leon claimed “La Florida” in 1513. Spanish explorers, with shiploads of gold and silver from Mexico, sailed up the “La Florida” coast to catch the Gulf Stream back to Spain. This trade route had several threats, including raiding pirates and the French, who had a foothold at Fort Caroline just 40 miles north of St. Augustine. King Philip II of Spain sent Pedro Menéndez de Avilés and 700 soldiers and colonists to create a Spanish settlement and mission system on the East Coast, 100 years before the mission system on America’s West Coast.
The next 300 years saw nine different flags fly over St. Augustine as the European powers fought for control. The time span also witnessed an influx of immigrants of all stripes, who expanded the cultural diversity of the area.
This historical tour had the group of 20 adults engaged and enthralled as we watched the guide run the kids through musket drills and did some fancy metal-bending blacksmithing, complete with fire tricks.
St. Augustine Pirate & Treasure Museum
I love pirates. So there was not a chance I would miss taking a stroll through this extensive museum. Owner Pat Croce, a passionate collector of pirate memorabilia, created his original pirate museum in Key West, and moved it to St. Augustine in 2005.
St. Augustine was raided by pirates and burned twice. Sir Francis Drake, a privateer turned English admiral, was knighted by Queen Elizabeth I. But he remained a pirate – El Draque — and villain to the Spanish who put a bounty on his head equivalent to $6.5 million today for capture. Drake burned down Spanish St. Augustine in 1586.
St. Augustine was the victim of the pirates again in1668. Robert Searles, also known as John Davis, sacked the city in response to a Spanish attack of the English settlement in the Bahamas. This last plundering prompted the Spanish queen to order the building of the stone fort, Castillo de San Marcos, in 1672.
The city has countless tales of pirate encounters and you can see the lines blurred between hero for their country, privateer for their own monetary interests, and villainous pirate dependent on the point of view of the European powers fighting over the new lands of the Americas
When you think about the life of a pirate, it’s amazing anything really survived. The collection includes one of Blackbeard’s “blunderbuss” firearms and gold from his Queen Anne’s Revenge ship, Thomas Tew’s original treasure chest with an intricate lock system that is the only known authentic one in the world, and a real Jolly Roger pirate flag. My favorite piece was a hand-written logbook with watercolors of the all the flags used at sea. That book could (and does) tell amazing swashbuckling adventures.
Castillo de San Marcos Fort
First comes the colony with gold and riches, then come the pirates to sack and pillage. The result is a BIG FORT.
This is history you can walk right on up to and see in St. Augustine at any time of day. The diminutive outline from the sea on the sailboat the previous night was an imposing wall of coquina shell concrete from land. The fort survived attacks because the coquina shell that makes up the mortar could absorb the impact of cannon balls. It’s both incredibly strong but also fragile after hundreds of years of wear and tear.
With my admission ticket, I walked the drawbridge into the fort — only one way in and one way out. The fort is a rather simple structure made to withstand sieges with the Plaza de Armas, a hollow square surrounded by four diamond-shaped bastions on each corner.
Several historical displays are in the storerooms under the fort, with park rangers available for demonstrations and questions. The most interesting feature for me was the 300 years of graffiti etched into the coquina walls by soldiers, inmates, and townspeople.
Spanish troops guarded St. Augustine through the turbulent colonial era, so I made sure to catch the firing of the cannon in a structured Spanish drill. Many boats, including ones with pirate flags, zipped about the bay, demonstrating how an attack would have looked. It was both an interesting and LOUD demonstration with a thrill of seeing and hearing a canon fired from a fort. There was even a photo-seeking girl with a mermaid tail flitting under the fort – though this is not a scheduled part of the Fort demonstrations, just good timing and further proof of charm of St. Augustine residents.
The fort still has its outline of a dry moat. The moat was kept dry and stocked with animals if attacked by sea and flooded if attacked from land.
You can see more traces of history in the Cubo and Rosario Lines. After the British burned St. Augustine during the siege of 1702, the Spanish surrounded the town with a wall made of earth and palm logs and a wide, shallow moat with the only entrance the City Gate.
You can find 18 different tour companies, each with its own version of local ghost stories, running night tours in St. Augustine. While less factually historical than other city attractions, it is highly entertaining dependent on the storytelling guide who takes you through areas of the city including Old Drug Store and the Old Jail and under mossy trees for a chilling scene.
Day 3 – The Gilded Age
Today’s historical time jump was only 100 years back to the Gilded Age, in another section of St. Augustine main city center.
The Gilded Age, an era from 1870 to 1900, was coined by Mark Twain to describe how gold gilding covered up underlying social corruption. The American post Civil War era of industrial growth saw the rise of “robber barons” including J.P. Morgan, Andrew Carnegie, Andrew W. Mellon, John D. Rockefeller and Henry Flagler. These industrialists became rich almost overnight from finance, mining and industry and expanded their wealth as the railroads started to crisscross America.
Henry Flagler, the founder of Standard Oil, was one of the wealthy to develop the marshy state of Florida. His vision included luxury hotels along the east coast in St. Augustine, West Palm Beach and Key West, with his new railroad connecting them all.
Ponce de Leon Hotel • Flagler College
The first of Flagler’s hotels in Florida was the Ponce de Leon Hotel, opened in 1888. With no expense spared, this hotel featured all the latest technology for the time including steam, one of the first poured-concrete structures using the same durable coquina aggregate used in the fort, and two large towers for fresh water. This hotel was one of the first with electricity thanks to Flagler’s friend, Thomas Edison. The Spanish architecture hotel was designed and decorated by some of the leading artisans of the day including Carrère & Hastings, who studied in France and went on to build the New York Public Library.
The hotel was the height of luxury for hotel guests during the “season,” with guests paying today’s equivalent of $100,000 in lump sum for a three-month stay at the all-inclusive hotel. Post-World War II, the hotel changed hands until it finally transitioned to Flagler College in 1968.
I started my one-hour tour in the hotel lobby that looked like it was straight out of the Titanic movie. Carved wooden goddesses flanked the 68-foot domed octagon with symbolic mosaics in the ceiling highlighting all the virtues in mythology. Beyond the lobby, the tour takes you through the two key public rooms of the former hotel, the dining hall and the grand parlor.
Can you imagine dining at your college bathed in light of 79 Tiffany windows under a ceiling of 100-year-old mosaics? These liberal art students do so daily in the extravagant dining hall. All that glitters IS gold in this hotel.
“All that glitters IS gold in St. Augustine’s Ponce de Leon Hotel.“
The last room I saw was the Women’s Grand Parlor with Austrian crystal chandeliers and one of the few remaining Edison clocks embedded in white onyx.
Tip: Take the tour to discover hidden details about the symbolism in the murals and to find the secret face hidden in the tiles.
Alcazar Hotel • Lightner Museum
A short walk across the street is Flagler’s second hotel, the Alcazar. The hotel is in the Spanish Renaissance Revival Style and has the same pedigree of famed artisans and architects as the Ponce. This slightly less luxurious hotel was built for the overflow of guests wanting to stay at the Ponce de Leon Hotel, which is to say those slightly out of the main circle of Henry Flagler.
Today, the Alcazar Hotel is utilized as both the City Hall, shops and the Lighnter Museum. After the hotel closed in 1932, Chicago publisher Otto C. Lightner purchased it in 1947 to house his extensive collection of Victoria Era collections.
Otto was a serious collector. As you walk through the floors you’ll find a variety of everyday and exotic objects more than 100 years old.
- Victorian cameras, typewriter, hats, toys – at least 50
- Victorian cut glass – sets in every color
- Victorian curiosities – shrunken heads, Egyptian mummies, stuffed animals.
- Victorian music – Victorolas, sheet music, pianos
- Victorian glass – Dozens more examples for Louis Comfort Tiffany’s glass works
One of the more interesting areas to demonstrate how those of this era lived and played are the Turkish saunas, and the gallery overlooking the pool. This drained pool is now a café where you can dine in the deep end after walking down the sloping shallows.
Check out some of the independent antique shops in the courtyard of the Lightner Museum for some Gilded Age era finds.
One block over from the two historic hotels sits the fantasy home of hotelier Franklin W. Smith, inspired by the Spain’s Alhambra Palace. Smith also takes his place in history for introducing Henry Flagler to Florida. The home has been preserved and still houses Smith’s eccentric collection of Victorian curiosities.
I have a fondness for these eccentric old “museum” homes. These guys always seem to collect from their extensive travels, filling their homes with stories and symbolism while mish-mashing all the cultural finds into a unique collection. The interior Court of Lions, for example, feels to me like a cross between the Alhambra and the central salon of “Downton Abbey.”
Cathedral Basilica of St. Augustine
The historic center of the town still maintains the traditional grid plan of Spanish colonies. Around the main square sit the Governor’s house and the Cathedral Basilica of St. Augustine. Founded in 1565 and rebuilt in 1797, the Cathedral is the oldest church in Florida. The 1797 exterior has a classic mission style while the interior was refurbished in the late 1800’s after a fire with funding by Henry Flagler and more traces of the gilded age and Spanish Revival.
Next to the church, you’ll find the only skyscraper in St. Augustine. This former bank building, built in 1926, has the same Spanish architecture and demonstrates the prosperity of the city during this time period.
Bridge of Lions
At the far end of the square is the Bridge of Lions that I sailed beneath on my first night in St. Augustine. The 1927 bridge was financed but the two Italian Carrara marble lions are an adornment gifted to the city from Gilded Age benefactors. The lions are copies of the Medici lions found in the Loggia dei Lanzi in Florence, Italy. They’ve been replicated several times, with smaller versions at Flagler’s Markland House, located near the former Ponce de Lion Hotel, and in the Throne Room in the Royal Palace of Madrid. They are rather stunning, the white marble shining under the spotlights and framed by the blue sky at dusk.
St. Augustine exceeded my expectations thanks to the warmth of its residents, who embrace every moment of their long history. I recommend a visit post Labor Day after the main tourist season for great weather, good eats, and lots of history.
Where to Stay
Case Monica was my choice during my stay in St. Augustine. Villa Zorayda’s Franklin W. Smith built this hotel in 1888 in the same Spanish Revival style seen in the other Gilded Age buildings in the area. Through several transformations over several decades, it was refurbished and reopened in 1999 as part of the Kessler Collection and the Marriott Autograph Collection.
The building has Moorish influences and decoration throughout the bar, restaurants and pool. The quality of the architecture is matched by the service of Marriott Autograph collection and the location is deal for walking to the St. Augustine historical sites.
Casa Monica Resort & Spa, Autograph Collection
95 Cordova St.
St Augustine, Fla., 32084
Where to Eat
Maple Street Biscuit Company
39 Cordova St
Saint Augustine, Fla., 32084
Recommendation: The Five – The fresh biscuits, maple back and sausage gravy are no joke! Saturation of flavors at their best.
121 St. George St
St. Augustine, Fla., 32084
Recommendation: St. George Street diner for Cinnamon rolls or a traditional breakfast.
A1A Ale Works
1 King St.
Saint Augustine, Fla, 32084
This seemed to be every local’s go-to recommendation for lunch with a view.
Recommendation: Shrimp & Lobster Tacos
72 Spanish St
Saint Augustine, Fla., 32084
Decorated in Florida kitsch, this restaurant uses local, seasonal and sustainable ingredients
Recommendation: Spicy Melt with Blackened Fish on a whole grain hoagie with tasty fresh vegetables.
Harry’s Seafood Bar & Grille
46 Avenida Menendez
Saint Augustine, FL 32084
This New Orleans-inspired restaurant has a great patio with live music for evening dining.
Recommendation: Fill up on seafood with Calamari appetizer and Shrimp & Scallop Orleans.
Caps on the Water
4325 Myrtle St
St Augustine, FL 32084
This restaurant is on one of the islands and was a local recommendation for sunset views. Get here early on a weekend; it’s busy.
Recommendation: Lump Crap Cake or the Shrimp Vilano
24 Cathedral Pl
St. Augustine, FL 32084
Recommendation: Great stop for iced coffee!
The historic St. Augustine center is very walkable.
Sites including the Lighthouse and island dinner recommendations will require a car.
- For more information on St. Augustine: visitstaug.com
- For more information on Florida: VISITFLORIDA.com
BlueSkyTraveler traveled solo to St. Augustine and worked with with VISIT FLORIDA to develop this sponsored conversation, however all opinions, itinerary recommendations and adventures are my own.
Is St. Augustine, Florida on your bucket list?
If you have been, tell us your tips and favorite adventures.
Travel • Dream • Adventure
Never Stop Exploring!