Must-See Gems When Visiting 450 Year Old St. Augustine, Florida

St Augustine, Florida, Photo Courtesy of

Photo Courtesy of

At dusk a row of cars are at a stand-still as the drawbridge on the Bridge of Lions slowly splits upward to allow passage of tall, majestic sailboats. The forced delay, rather than causing grumbling from impatient motorists, inspires another reaction. Car doors open and people get out. A young woman hops onto the low concrete ledge and captures a selfie with the pink-lavender-orange of the setting sun illuminating the Matanzas River behind her. Everyone flocks to the edge of the bridge, leaning over to catch this bird’s eye view of the boats sailing soundlessly below. It’s mesmerizing. It’s St. Augustine, Florida.

St. Augustine a small picturesque seaside town between Jacksonville and Daytona, was founded in 1565 by Spanish conquistador Pedro Menendez de Aviles, making it the oldest continuously occupied city in what is now the United States. This year the Nation’s Oldest City is celebrating its 450th anniversary with festivals, fireworks and historic hoopla, especially during Founder’s Day weekend Sept. 4-8, 2015. But if you can’t get there in time to help blow out all those candles on the “birthday cake,” don’t worry. The happy truth is this city will be just as alluring in its 451st year, and beyond.

History is inescapable in this European-style town. With more than 60 significant historic sites and attractions situated around the small city center, you could be dropped from a helicopter blind-folded and still find the “tourist attractions” completely on your own. You can’t miss the must-see sites like the St. Augustine Lighthouse, Cathedral Basilica, Castillo de San Marcos National Monument and the Fountain of Youth Archaeological Park, so I will concentrate instead on the not-so-obvious local favorite places to eat, drink and be very happy you are in St. Augustine.

Here we go…

Stay in Swanky, Historic Hotels

First, you’re going to need a place to stay. The swankiest option is the historic Casa Monica Hotel, circa 1888, on the corner of Cordova and King St. While there get a massage at the Poseidon Spa (discounts available mid-week) and enjoy being in the center of it all downtown: the Plaza de la Constitution, the grandiose Hotel Ponce de Leon (now Flagler College); the Lightner Museum and City Hall (formerly the Hotel Alcazar), and the oldest street in the country, Aviles Street. Or stay in one of St. Augustine’s 30 historic Bed & Breakfast Inns. They’re all off-the-charts charming in that old-world style.

Amazing Breakfast Options + 18th Century Homes (and More)

The appealing little Blue Hen Café, 117 Martin Luther King Ave, sits humbly amidst homes and working shrimping docks in the historic, eclectic neighborhood of Lincolnville. Have the peach butter and biscuits, or the pumpkin pancakes and then walk off your full belly by strolling through the neighborhood. Lincolnville has more 18th century homes than anywhere else in town and also has many of the ACCORD Freedom Trail’s 31 historic sites, as it was the epicenter of action during the 1960s Civil Rights movement.

Another great option is the Metro Diner, 1000 S. Ponce de Leon. It’s new, so what it lacks in historic charm, it makes up for in unbelievably good food and creative specials. Get the half-order of chicken and waffles, drizzled with an unexpected mix of hot sauce and syrup. So yummy.

Learn about the 450 years of St. Augustine’s History

Head to the Visitor Information Center, to visit the “Tapestry: The Cultural Threads of First America” exhibition. This comprehensive exhibit is like taking a crash course in St. Augustine’s 450 years of fascinating multicultural history. Also, pick up a Passport mapping out 35 important historic sites, programs and exhibitions to get stamped during your stay.

Know Where the Locals Lunch

While downtown, lunch at the Floridian, 39 Cordova St. This engaging place boasts all the healthy adjectives – local, seasonal, sustainable and organic – so you might think it’s strictly vegetarian. But no! They have the most scrumptious “Not Your Mama’s Meatloaf Sandwich,” imaginable. Also, try the savory fried green tomato bruschetta.

Just outside the historic district, is The Bistro, 9 S. Dixie Hwy. You truly wouldn’t find this tiny place on your own, so you can thank me later. Established by the catering company, Culinary Outfitters, it’s only open for lunch on weekdays. Have their Famous Crab Bisque or go on Wednesday for their outrageously zesty ribs.

The next three local favorites put the sand in sandwich (well, not literally…) and will lead you to explore different local beaches. The South Beach Grill, 45 Cubbedge Rd. is on sugar-sand Crescent Beach. I mean, right on it. It’s the best place for a huge platter of juicy local oysters all set up with horse-radish, cocktail sauce and crackers.

On St. Augustine Beach, go to A1A Burrito Works, 671 A1A Beach Blvd. Get the UFO burrito with shrimp, a crazy-good pressed burrito big enough to share. After checking one of the country’s best beaches, take a walk on the pier or go to Anastasia State Park (north end of the beach) and rent a kayak or stand-up paddle board in Salt Run. On Wednesday mornings, take in the festive local Farmer’s Market at the pier. On Wednesday nights boogie to the great live bands at the free Music By The Sea concerts.

Just north of St. Augustine, you’ll also love the toes-in-the-sand atmosphere of Beaches at Vilano Beach. It is the perfect place to nosh on fried gator tail or fish tacos while gazing at the water and dreaming of just sailing away. On weekend afternoons, they have lively bands that inspire you to dance like nobody is watching.

Get St. Augustine Snacks

Snack options start with The Hyppo, 48 Charlotte St. and 70 St. George Street. Refreshing and tantalizing, these handmade gourmet ice pops are made with all real fruit in whimsically creative flavors. Their funny name comes from the town’s patron saint; St. Augustine of Hippo as well as their cross-street, Hypolita. Locals pronounce it “hi-pahl-eh-tuh,”and not “hippo-lee-ta.” Try the Datil Strawberry pop – sweet with a kick of hotness. Datil peppers are a local flavor not to be missed.

For true decadence, indulge at Cousteau’s Waffle and Milkshake Bar, 15 Hypolita St. Get the waffles topped with candied bacon and/or marshmallow fluff and a key lime milkshake and then wander blissfully with that milkshake mustache gracing your smiling face.

When chocolate cravings hit, find Whetstone Chocolate Factory, 139 King St. Pick out something tempting in the shop, then take the factory tour. Sure, the highlight is the tasting part, but it’s also fascinating watching the machines and the chocolatiers in action. They do make you wear a hairnet on the tour, but for this kind of artisan, gourmet chocolate, it’s well worth it.

Drink with the Locals

Whether you’re day-drinking, happy-houring or into late-night frivolity, you have options. Many, many options. A fun one is Matanzas Inlet Restaurant, 8805 A1A South. Located on the Matanzas Inlet, it’s common to see dolphins playing, boats sailing, fishermen casting, and frolickers frolicking from your comfortable seat with a beer in one hand and local steamed shrimp in the other.

The ideal happy hour spot is the ultra-hip Ice Plant Bar. Start first, though, at the St. Augustine Distillery, 112 Riberia St. Take the distillery tour that demonstrates how they make small batch vodka, rum, gin and whiskey and then lets you taste what a phenomenal job they do. Afterwards, go next door to the Ice Plant Bar and order a Florida Mule or their rather unique style of gin and tonic and the Devils on Horseback appetizer. Trust me on that one.

Wine drinkers may prefer the San Sebastian Winery, 157 King St. After the free wine-tasting tour, enjoy live music on the roof venue, the Cellar Upstairs. Pair your local wine with the cheese plate with extra hot stuffed peppers.

Another one-of-a-kind spot is the Conch House Restaurant, 57 Comares Ave. Sit at a tiki hut table and order your favorite libation and the calamari, drenched in a delectable banana-pepper sauce. Drink in the ambiance of the lively Marina, where you can watch the deep-sea fishing charters return. If you like a lively island-style party atmosphere, come for Reggae Sunday.

Anytime is the right time to stumble in to the Tradewinds Lounge, 124 Charlotte St. This is a smoke-gets-in-your-eyes dive bar downtown near the Bayfront that is both historic and really rocks. They have concert-worthy live music basically all day and night, including their house band, Matanzas.

Dine for Dinner

For elegant waterside dining in the Vilano Beach area, visit Cap’s On the Water, 4325 Myrtle St. Sit on the back dock along the Intracoastal, savor the She-Crab Soup and say, “life is good,” a lot. Sigh…

O’Steen’s Restaurant, 205 Anastasia Blvd., is a classic, homey family-run establishment. They have a varied menu, but it’s the fried shrimp and signature sauce that makes them so locally famous. They don’t serve alcohol, but it’s okay – you’ll want all your senses sharp to fully savor this appetizing experience. While in the neighborhood, visit the historic St. Augustine Alligator Farm & Zoological Park, too.

Creekside Dinery, 160 Nix Boat Yard Rd., is another place you’d likely not find on your own. Nestled by a tributary creek of the San Sebastian River, this place has so many huge old oak trees dripping with Spanish moss that when it rains on the deck you barely feel it. Order the Shrimp St. Johns and save some tidbits for the raccoon family that lives just off the deck. Great live music venue, too.

An enchanting choice is Catch 27, 17 Hypolita St. Order the catch-of-the-day or the Minorcan Gumbo. The Minorcans are a group of people from the one of the Balearic Islands of Spain who settled in St. Augustine in 1777 and have since beautifully influenced everything here, from festivals to food to the fishing/shrimping industry. Make a reservation — this inviting but tiny restaurant only has about six tables.

To taste the rich Spanish heritage inherent in this town, dine at the city’s oldest restaurant, the Columbia, 98 St. George St. Get their award-winning, trademarked signature 1905 Salad. It’s made table-side and the garlic dressing pulls it all together. Open noon to 8 p.m.

O.C. White’s Restaurant, 118 Avenida Menendez, is a­­nother locally-owned favorite just across from the main marina. Sit outside on the lush, garden patio to enjoy nightly live music. Order Chatty’s Home-made Blue Crab Cakes – named after the talkative owner – and ask about the building’s ghosts. At the marina, take the Freedom Schooner sunset cruise, an experience so sublime the locals can’t wait for someone to visit so they can go again.

As they like to say it there, “Life is short; make it wide.”


Thanks for the guest post Sue Bjorkman!


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