Visit St. Augustine: Florida’s Jewel of a City

If you could design a Florida tourism brochure, what images would you choose? Maybe palm trees, beaches, art deco buildings and bikini-clad babes? Or perhaps a mouse with big ears, smiling kids and amusement rides? Those iconic images of South Beach and Disney have been so burned into our mind’s eye that we rarely think of what else is worth visiting here.  Maybe that’s because 16th century cities, fortresses and a rich maritime history just aren’t sexy enough for the average tourist.  But that’s exactly what you’ll find in St. Augustine, a jewel of a city on the northeast coast of Florida.

St. Augustine is the oldest European colonized city in the United States.  (There were “cities” in Florida before the white men arrived—communities of native Indians.) Before the pilgrims landed at Plymouth, Ponce de León was already exploring Florida’s northeast coast around 1513; there’s evidence that some Spanish slave traders were here even earlier.

Spaniard Pedro Menendez de Avilés founded St. Augustine in 1565, beginning what would be a complicated story as Florida—not yet a state—passed from Spanish, British and ultimately to American hands.  This history is beautifully preserved in the architecture and quaint streets of St. Augustine and that’s what makes it so interesting.

Little annoys me more than criticism from people who think of Florida as a place with no substance and no history.  And sure, we forget about Florida’s colonial past when we’re in Miami Beach and Disney.  But in St. Augustine, it’s all there, right before our eyes.  Florida was connected to the Caribbean, to trade, piracy and the settling of the New World. And while it was not originally colonized as aggressively as our neighboring islands in the Caribbean Sea—the peninsula had nothing to offer in terms of profit—Florida was more than just an afterthought:  so many ships passed by here on their way to Spain, their holds loaded with valuable cargo. With countless shipwrecks dotting the east coast, it’s no exaggeration to say that a good part of Florida’s past is underwater.

I recently visited St. Augustine and fell in love with it – so much so that I’m going back on a road trip later this month!  Here are a few tips and suggestions for visiting St. Augustine.

GETTING THERE

The flight from Miami International Airport is only one hour and 15 minutes. You land in Jacksonville, where shuttle services are available to St. Augustine, which is about 45 minutes away.  I strongly suggest you rent a car so you can explore beyond the old town.  Take note: I flew on an American Airlines small propeller plane and at MIA they herded us on a bus to the tarmac where we boarded the aircraft from its ladder.  Packing heavy is not a good idea.

The drive from Miami to St. Augustine is approximately six hours – less if you avoid rush hour traffic.  There’s also an Amtrak stop in Jacksonville.  You could get there by Miami-Dade Metrorail connecting to Tri-Rail (jump on the Amtrak train at Mangonia, Palm Beach) or just take Amtrak directly from Miami.

WHEN TO GO

I traveled to St. Augustine at the beginning of October. The weather was just right as light cold fronts trickled in from up north.  October is the tail end of the tourist season, so it’s a good time to visit to avoid the summer crowds.

From Miami, a weekend getaway is perfect, but three or four days are optimal for a relaxing trip.

WHERE TO STAY

Choose from many inns or bed and breakfast around old town.  St. George Inn on picturesque St. George Street, run by a former Miamian, is a beautiful and convenient spot.  Go for a second-story room facing the Castillo de San Marcos; a cozy wooden veranda wraps around the building, where you can sit at night and enjoy a bottle of wine.

The Carriage Way Bed and Breakfast, just a few blocks away, is also lovely, offering delicious full homemade breakfasts every morning.  Even if you don’t stay there, stop by and purchase a copy of their cookbook.

One of the buildings that comprise The St. George Inn. There’s a lovely courtyard behind this building with great little shops.

The veranda behind my room. St. George Street was quiet at night and utterly romantic.  The structure you see in the background is the old city wall.

Breakfast at the Carriage Way started with fruit and ended with a rich egg and bacon casserole dish.

STROLLING

St. Augustine is a walker’s paradise.  Because of the beautiful architecture, ambling about is a must do activity in and of itself.  You’ll feel as if you’re in movie set depicting an old Spanish town, except it’s never fake or kitschy.  (Take my word on this:  I’ve been to Spanish towns in Europe many times.)

Slow down your pace in the Spanish quarter.  It’s ok to dilly dally here. Meander on the cobblestone streets, many of which are pedestrian. Walk by the Matanzas river, the plaza and don’t miss the oldest street in the country – Avilés Street, which was recently given a little face lift. All electric wires are now underground and wider sidewalks make room for outdoor café seating.  Avilés Street features a handful of restaurants, shops and art galleries. Stop by Worley Faver’s pottery studio to meet the artist and see his incredible handiwork with clay.  Faver comes from a long line of St. Augustinians and is inspired by global spiritual traditions.

Beautiful Avilés Street on a rainy day.  That building in the background is the city’s tallest. No high-rises allowed in St. Augustine.

Red and yellow: the colors of Spain on Avilés Street.

This public art piece on Avilés Street represents a collaboration between local college students and their counterparts in the sister city of Avilés in Spain.

Worley Faver working his pottery magic in his Avilés Street studio and gallery.

HISTORIC SITES

No visit to St. Augustine is complete without setting foot on the Castillo de San Marcos National Monument, a fort completed in 1695 to protect Spain’s stronghold in the New World. The impressive structure, the oldest masonry star fort in the country made of coquina shells, was the site of many a waterfront battle in America’s colonial history.  Check out the canon firing reenactment; it’s a real treat.

It was a rainy day when I took this photo, which made the experience more dramatic.  A section of the fort.

The reenacters in costume.  All of them are volunteers except for the park ranger, leading the way. There’s actually an academy in St. Augustine where you can learn how to fire a cannon. And yes, if you think wearing wool in Florida is a crazy idea, you’re not far off the mark.  But the colonials knew about wicking, which pulls sweat away from the skin.

The St. Augustine Lighthouse and Museum is well worth the short drive to neighboring Anastasia Island.  Here you’ll find not only the lighthouse, which will reward you with a spectacular view after a climb up its spiral stairs, but also a permanent exhibit about the history of modern shrimping.  The worldwide shrimp industry as we know it today got its start in northeast Florida and was very important to St. Augustine’s maritime culture.  Next time you eat shrimp, wherever you are, thank the sea-faring Italian immigrants who made it happen.

The St. Augustine lighthouse, built in 1874.

This bare bones replica of a 1760 yawl, not yet completed, is part of a wood shipbuilding program at the lighthouse associated with its archaeological maritime program.  The yawl will participate in a cultural exchange event with Spain involving a transatlantic sail.

SIGHTSEEING TOURS

As soon as you unpack, take a tour by horse-drawn carriage with Country Carriages.  The driver will give you St. Augustine 101 to prep you for your own exploration of the city.  As well, enjoy culinary delights and additional history with Savory Faire, a two and half hour food tour that covers some of St. Augustine’s best spots.  Ghost tours abound, but if you want to do it on your own, Shivers and Awe offers a $4.99 iPhone app.

Familiarize yourself with St. Augustine by horse-drawn carriage.

A tour of Flagler College is a must.  The gorgeous building now houses a liberal arts college but was once the Ponce de Leon Hotel—during its hey day the most expensive luxury lodging in the world.  The hotel boasted electricity in all its rooms at a time when even the White House had minimal juice. The property is part of Henry Flagler’s railroad and hotel legacy, which shaped the history of Florida from St. Augustine to Key West with Palm Beach, Fort Lauderdale and Miami in between.  (Flagler’s Royal Palm Hotel was once at the mouth of the Miami River.)

There’s so much architectural detail here… and to think Flagler built this in less than two years, circa 1888.

Classy eats: the dining hall currently houses the college cafeteria. It features the largest collection of authentic Tiffany glass in the world outside of a museum.

If golf is your thing, you absolutely must drive to Ponte Vedra (about 40 minutes north) and visit the beautiful TPC Sawgrass Clubhouse (TPC stands for The Player’s Championship).  Call ahead and request a free tour by a “story teller” and if you can get Gus Stokes, you’ll be lucky – I knew nothing about golf and he made me a fan in minutes with his easy to understand explanation of the game.  Here you’ll learn about golf’s greatest players and moments. You’ll also see for yourself the most famous hole in golf history – the 17 played magnificently by Tiger Woods.  The clubhouse, which is otherwise very exclusive, is also where the champion gave his mea culpa speech to the press after his adultery scandal.

Gus Stokes, a veteran, scholar, family man and lifelong golfer, changed my mind about golf as a boring sport. Here he stands before a large painting depicting Tiger Wood’s 17th hole moment of glory.

PLACES TO EAT

St. Augustine is a foodie paradise and there are restaurants of all kinds, but you’ll want to focus on Spanish heritage here.  The Tasting Room puts a contemporary spin on tapas accompanied by Spanish wines.  Avilés Restaurant at the Hilton offers sumptuous Spanish-inspired dishes – try the Jerez Chicken (chicken in sherry sauce with piquillo peppers, onions and mushrooms) and see if you can taste the subtle paprika on your palate.

A typical Spanish appetizer at Avilés:  olives, piquillo peppers, serrano ham, roasted garlic and manchego cheese, served with fresh crusty bread and olive oil.

Further afield and well worth the drive north up a scenic section of A1A are two great spots where you can pay tribute to the area’s shrimping industry.  Cap’s on the Water in Vilano Beach offers great food and a gorgeous view of the intracoastal with outdoor seating under enormous live oaks and cedar trees bedecked with Spanish moss.  In Ponte Vedra, check out trendy Karma, owned by a former well-traveled Miamian. Although the menu features “global eats” it was the tasty shrimp and grits, with a properly spiced and aromatic tomato sauce, that satisfied my craving for some southern cuisine.

Cap’s on the Water is beautiful and so is the food.  They also have an oyster bar.

The Vilano signature appetizer at Cap’s: sautéed shrimp, tossed with olives in a spicy hot Thai chili garlic sauce over fried spinach with Asiago cheese.  Try the shrimp taco too. Seriously, it was some of the tenderest and most flavorful shrimp I’ve ever had and I’m totally spoiled on good shrimp.

BARS, TAVERNS & WATERING HOLES

There are plenty of watering holes in St. Augustine, but my favorite is La Taberna del Gallo (The Rooster Tavern), which was founded in 1734. Servers dressed in period costume pour refreshing red and white wine sangria, a popular drink in St. Augustine. Beer on tap is available for brew aficionados. While you’re there, notice that there’s no electricity in the authentically decorated and sparsely furnished room.  Real candles in antique lanterns provide illumination. Don’t be surprised if a performer from a local reenactment swaggers in through the door in full regalia after “work” – I had a husky pirate sitting next to me at the bar.  The experience was priceless and the reasonably priced $6 sangrias were even better.

Oops! This tavern wench was wiping off some red sangria someone had spilled on the wall the night before.

I’ve only scratched the surface of St. Augustine here.  There’s much more to see and do! For additional information about St. Augustine, visit their official travel and city websites. There’s more 411 at Visit Florida, too. Want to talk about the destination? Stop by our Miami Beach 411 travel forums.

Related Links: • Maria's Keys and Key West Adventure • A Weekend Trip to Cassadaga, FL Related Categories: Nearby Cities Miami: Travel News, Miami: Things to Do, About the Author: Maria de los Angeles is a freelance wordsmith who loves to write about all things travel in Florida and the Caribbean. She is also the author of the award-winning blog Sex and the Beach. See more articles by Maria de los Angeles. See more articles by Maria de los Angeles Was This Post Helpful? Please Share It With Others! Tweet

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