More Than History, America's Oldest City Abounds With Dining, Shopping, Entertainment & Culture

Jeff Walker, Travel Writer

Founded by the Spaniards in 1565 St. Augustine, Florida is widely accepted as the oldest city in America, offering rich history, European-style architecture, and numerous tourist attractions including the Fountain of Youth, Castillo de San Marcos, St. George Street, and the Lightner Museum, among a dozen more notable landmarks. Just over the causeway Anastasia Island and St. Augustine Beach, home to the areas iconic St. Johns County Ocean Pier offers two miles of glistening white sand facing the Atlantic Ocean. 

Four and a half centuries later the historic points of interest remain surrounded by a with a hint of the modern world, making St. Augustine an ideal vacation destination for families, couples, seniors, and kids of all ages. While the city boasts a population around 16K, St. Augustine regularly rolls out the welcome mat to over 2.5 million visitors yearly.

Let's begin with the city's rich history which is evident in its well-preserved Spanish colonial architecture and the Castillo de San Marcos. Located on the western shore of Matanzas Bay, Castillo de San Marcos is the oldest masonry fort in the continental United States and one of Florida's recognized national monuments.

Although there are rangers and volunteers (dressed in period attire) walking about, the fort is designed for self-directed tours. However the workers and other volunteers are happy to answer questions, take pictures, and pose for pictures. There are numerous exhibits including musket and cannon demonstrations (weekends only), with the gun deck providing one of the best views of St. Augustine. To experience where 'America Really Begins' visit https://www.nps.gov/casa/index.htm

The Fountain of Youth Archaeological Park named for Spanish explorer Juan Ponce de Leon (circa 1513) is situated nicely on intracoastal waterway in a section called Hospital Creek. The famed attraction contains a well, claimed to be a freshwater source, with ancient myths asserting that drinking or bathing in its waters can recapture youth or grant immortality. 

But more than just the noted spring, the 15 acre park describes in detail the triumphs and tragedies endured by the Timucuan civilization, as well as the amazing story of Pedro Menendez de Aviles and the settling of St. Augustine. Restore your sense of history and maybe take a few years off at https://www.fountainofyouthflorida.com/

The St. Augustine Lighthouse on Anastasia Island and accompanying maritime museum have become a tourist beacon (pun intended) for years. Legend has it during the 16th century the Spanish built a series of wooden watchtowers as lookouts with one eventually becoming the St. Augustine Lighthouse, which provided navigational support for ships coming to the Continental United States. Follow the shining light to https://www.staugustinelighthouse.org/

Without question the best way to see historic St. Augustine up close and personal is by riding the Old Town Trolley, where riders can hop on and off from 9am until 5pm daily. Making 22 stops, the trolley provides over 100 points of interest including stops at the Old Jail, Potter’s Wax Museum, Castillo de San Marco, St. Augustine Distillery, Lightner Museum, and the Old Drug Store.

Surprisingly, St. Augustine has a rich African American heritage which includes several visits from the late Dr. Martin Luther King. Check out the churches he preached in and the homes he stayed at during the trolley tour. The trolley provides info on St. Augustine's Black Catholic Church as well as several other protestant denominations. 

Should you decide to stay on the tour for all 22 stops it would take roughly 90 minutes and provide you more than enough info on what you might want to go back and visit in depth. Check their website for more including Ghosts & Gravestones Fright-seeing Tour and Old Jail After Dark. Make your first online tour stop at https://www.trolleytours.com/st-augustine

When mother nature allows another way to explore America's oldest city is from the water. Offering over a dozen separate shared and private sailing experiences, St. Augustine Sailing is the city's preferred water charter. With a fleet of boats ranging in size from 21 to 45 feet including three Jeanneau Sun Odyssey 349s known for their sleek design, St. Augustine Sailing provides sailings for water lovers of all ages.

Whether you want to meet new friends or enjoy personal time with family, St. Augustine Sailing offers 'Brunch Sails', 'Sip & Sails', 'Sunset Cruises', and 'Dolphin Delights'. Among their premier sailings include the 'Sunset Tasting Cruise', a sumptuous two hour dinner tour featuring fine wine paired with a four course gourmet meal. Sail along St. Augustine's scenic coastline while indulging in the lap of luxury. 

Owned and operated by Rose Ann and Chuck Points, St. Augustine Sailing is like no other experience in St. Augustine. Private charters are completely customizable for groups up to six. If you're celebrating a birthday, anniversary, getting engaged, or observing any special occasion, no doubt spending time with loved ones on the water with St. Augustine Sailing will make it a memory no one will forget. Charter your own course and gain a new perspective of St. Augustine at https://www.sta-sail.com/

Two separate histories make up St. Augustine. There's the first 300 years including the journeys of Spanish conquistador Pedro Menéndez de Avilés and Ponce de Leon, as well as fellow Spaniards. That same period covers French and British invasions, colonization, religious outreaches through the Mission of Nombre de Dios, and the city's role in the Revolutionary and Civil Wars. The last 150 years, aka the modernization of St. Augustine can be attributed to American industrialist Henry Morrison Flagler (1830-1913).

Flagler made his fortune from Standard Oil and railroads. Visiting St. Augustine in the late 1870's to deal with wife's bout with tuberculosis, Flagler fell in love with the city and realized it needed much help. Soon he was building hotels, churches, railroads, and bridges. Founded in 1968, Flagler College a private liberal arts school was named in his honor. Historians and locals would be hard pressed to imagine what St. Augustine might look like without the generosity and vision of Henry Flagler.

Another St. Augustine landmark with a Flagler connection is the Lightner Museum. Housed in the former Hotel Alcazar, this Gilded Age resort now showcases a diverse collection including Tiffany lamps, vintage typewriters, American brilliant cut glass, and natural history specimens. 

Visitors can explore exhibits on fine and decorative arts, witness the architecture of the historic buildings, and enjoy the Spanish Renaissance Revival courtyard with a koi pond. Explore the history of art and architecture at https://lightnermuseum.org/

Two of the biggest festivals celebrated yearly in St. Augustine take place in the after Labor Day. Produced by SJC Cultural Events in partnership with the Live Wildly Foundation, St. Johns County Tourist Development Council, City of St. Augustine, and area businesses, 'Sing Out Loud' takes place over four weekends during the month of September, showcasing diverse music from over 200 artists.

Marquee events take place at various locations including Francis Field in downtown St. Augustine, Markland House at Flagler College, and the Ponte Vedra Concert Hall. Celebrating local, regional, and national recording acts, 'Sing Out Loud' now in its ninth year has become one of the premier music festivals in the state of Florida. Sing loud and proud at https://www.singoutloudfestival.com/

The second festival kickstarts the Christmas season in the ancient city. Beginning mid November through the second week of January 'St. Augustine's Nights of Lights' dazzles America's oldest city with over three million (you read that right, three million) lights, as the downtown area celebrates the season by staying open later for shopping and dining. 

The trains and trolleys offer special seasonal tours that take you through the most lighted areas. The City of St. Augustine offers a Free Park and Ride Shuttle service for Nights of Lights beginning on Light Up Night, November 15, and continuing on select days through the end of December. Holiday music abounds during the festival. The entire city joins in this festive celebration. A brilliant spectacle like no other. Get lit at https://www.visitstaugustine.com/event/nights-lights

Do you love to shop? Do you love to dine? St. Augustine has you more than covered. St. George Street in the historic district is easily the most trafficked shopping and dining area of St. Augustine. This pedestrian-only street in the heart of downtown is known for its boutiques, restaurants, art galleries, and historic sites, including the Oldest Wooden Schoolhouse and Cathedral Basilica. 

Whether you crave seafood, pasta, steak, burgers, pizza, Latin, or Cuban inspired food, you can find it all along this three quarter mile trek that runs from the City Gate and ends at Plaza de la Constitución (oldest public space in America). A handful of hospitality groups own several flavors of eateries along St. George.

Prohibition Kitchen (PK) invites guests to take a rendezvous back in time, dining in the same location Bartolo Genovar (prominent St. Augustine figure) created 'Genovar Theater', the social epicenter of Flagler’s prohibition era. PK carries a yesteryear speakeasy vibe, offering up a dozen signature burgers and or sandwiches, as well as a braised short-rib and an 13oz ribeye.

You can build your own burger or trust their PK Burger teeming with a blend of short rib, brisket, sirloin, and smoked bacon. Heaven for meat lovers. Want to put your teeth and gums around something sinfully delicious and off the wall? I highly recommend their Short Rib & Grilled Cheese sandwich overflowing with 24 hour braised beef smothered in cheddar cheese, sofrito (seasoned tomatoes, onions, & bell peppers) and garlic aioli on sourdough bread. 

I feel certain no one in St. Augustine pours up more bourbon, whiskey, rum, tequila, mezcal, and specialty cocktails as does PK. Another dozen select wines from California and European regions. Their draft beer selection is off the charts, with as many as 40 at any given time, including local, regional, and brews from around the state. Safe to say their drink menu is unrivaled in St. Augustine. Where taste, good times, and tradition merge, meet at https://pkstaug.com/

PK's sister restaurants are equally alluring. Sitting right next door at 121 St. George Street you'll discover the Roosevelt Room (RR), an upscale brunch only eatery offering up a varied menu with flair. Enjoy signature omelettes, Brulée French Toast, Fish & Grits, or Corned Beef & Potatoes alongside 'Sandwiches & What Not' and 'This & That' (they're on the menu).

All their entrees go well with bubbly, sangria, mimosas, sweet tea or nine coffee drinks including a Cortadito (Cuban espresso). An ideal setting for private occasions. RR is where locals and visitors come for another type of R&R aka 'refreshments & reflection'. To experience a dining destination that tantalizes your taste buds and captures the heart of St. Augustine visit https://rrstaug.com/

I did mention two. With it's main entrance at 60 Charlotte St. and a second entrance at 117 George St., Pizzalley's Chianti Room sits comfortably in a courtyard between both streets. Designed for the true Italian food connoisseur, Pizzalley provides an extensive bar and wine list to accompany made from scratch old country dishes.

Truly unique, their Pasta-bilities allows you to create your own pasta or order any of their nine signature Italian entrees that come with homemade breadstick and soup du jour or salad. Carnivores might opt for the 12 oz. Weekend Rib-eye. Furthermore you can craft your own pizza from their 'Pizza al Forno a Legna' aka wood fired oven pizza. Delicioso leads to mangia mangia at https://pizzalleyschiantiroom.com/

However if seafood is reeling (pun intended) you in, then I recommend casting your appetite at the Fish Camp. Located on the far side of town on backside of the Matanzas River, Fish Camp is a family and pet-friendly restaurant serving lunch and dinner with sides of atmosphere and ambiance, and excellent outdoor seating with spectacular scenic water views.

Owned by Ben and Liza Groshell, this modern eatery which serves up a healthy dose of southern hospitality alongside fresh seafood entrees complete with fries, hushpuppies, and slaw all under $30. We're talking dishes such as grilled salmon, blue crab cakes, Iron Skillet Fried Brook Trout, and Salt & Pepper Seared Tuna. 

Not feeling fishy, maybe order the Grilled Pork Chop with Bacon Molasses BBQ & parsley potatoes, or their Pan Fried Chicken, complete with collard greens, and tasso ham gravy. Their distinct plates go well with their ample drink menu that includes craft beers, extensive wine list, and smooth glasses of Hennessy VS and Courvoisier VSOP, (two upscale cognacs). Let your taste bud go wild at https://staugustinefishcamp.com/

You can't have an awesome city without have magnificent locally owned coffee houses. St. Augustine is host to more than a dozen caffeinated shops, several with multiple locations. One that I can fully endorse is City Perks Coffee at 15 St George St. near the Pirate Museum and directly across from Castillo de San Marcos. Set in cozy atmosphere full of ambiance, City Perks serve up your favorite coffees including nitro brews, lattes, and cappuccinos, alongside hot chocolate, with hot and iced teas to boot.

They all go great with a White Chocolate Raspberry scone or a Apple Cinnamon Pecan. Just two of the many sweet treats that accompany several bagels and croissants. Here's a twist. Maybe your not craving beer and or wine at 8am (hopefully not), but pop in City Perks later in the day and enjoy seven rotating local craft beers on tap or a subtle glass of wine. A must visit spot pouring your favorite beverages all day long in St. Augustine. Find them on Facebook at https://www.facebook.com/cityperkscoffeeco/

The ladies will especially love shopping at J.R. Benet Handcrafted Jewelry & Gifts. St. Augustine native and Flagler graduate Marla Pennington has a keen eye for gathering unique antiques and one-of-a-kind gifts and jewelry pieces, created by artists from around the world. If you fancy Mermaids & Merman, as well as great deals on pearls, and jewelry crafted from Atocha Shipwreck Coins then it's best to pop in Marla's shop at 62 St. George Street. Shop for brilliance at  https://jrbenet.com/

Reflecting the city's Spanish colonial heritage, St. George Street is busy morning, noon, and night offering up a vibrant mix of native culture and entertainment, surrounded by the city's premier restaurants and locally owned boutiques.

Don't leave St. Augustine without having strolled along St. George Street. It's one of those historic streets that has something for everyone, including some really cool pubs, including the Milltop Tavern & Listening Room, where it's five o'clock no matter what time you pop in. Enjoy some of the city's best pub food, craft cocktails, cold beer, and live music in this treehouse-style casual eatery. Their second story balcony provides a great view of St. George. Drink up the vibe at https://www.milltoptavern.com/

While the noted thoroughfare is considered the hotspot for shopping in the historic district, locals and tourists could consider the half mile stretch of San Marco Ave. as 'uptown St. Augustine', where chic, unique, and antique all merge. Cool and Collected Vintage & Antiques is the epitome of uptown, focusing on fun, funky and vintage attire, home decor, knickknacks, old LPs, and a whole lot of very cool yesteryear stuff. Facebook @ https://www.facebook.com/coolandcollectedvintage

Several others to take note of include the 360 Boutique and Materialistic Uptown. Searching for a trendy beach shop, then look no further than Soho Bohemian, where they specialize in hand crocheted tops, bottoms, and dresses, as well as selling a line of reversible bikinis. Be yourself at https://sohobohemianstore.com/

Maybe check out at The Painted Lady at 72 San Marco Ave where they carry an eclectic mix of vintage and antique art, jewelry, and one of a kind home decor pieces. In the fall usually beginning in October Uptown St. Augustine host Uptown Friday Night, a once a month end of the week block party featuring shopping, delectable food, live music, and exciting activities. Join the party at  https://stauguptown.com/

Got a sweet tooth. There are two specific tours I propose. Fruit of the vine lovers, especially those of the muscadine variety might want to tour San Sebastian Winery at 157 King St. (former home of Flagler's east coast railway building). Open 10-6pm Mon-Sat and 11-6pm Sun, San Sebastian Winery offer 45 minute guided tours every half hour, culminating in a tasting where guests can sample no less than six wines at their welcoming lounge inside the gift shop. 

Want more reason to visit San Sebastian Winery. Their niche third floor restaurant 'La Cocina at the Cellar Upstairs' is one of St. Augustine's most respected food & beverage destinations. Open at 11am they are known for the charcuterie boards, Honey Butter Shrimp, and Short Rib sliders. Dine on exceptional dishes complementing craft beers, specialty cocktails, and a wine list that includes more than just muscadine grapes. Follow the sparkle at https://www.sansebastianwinery.com/

Just across the street from the winery is one of St. Augustine's most beloved businesses. Lifelong northeast Florida residents Henry and Esther Whetstone had a vision back in the mid 1960's to open a small store and offer locals the best darn ice cream imaginable. The couple succeeded, but their passion soon turned to making chocolates, and before the decade ended they were selling 13 different flavors of fudge and hand-dipped chocolates. 

Fast forward into the 1990's and Whetstone Chocolate's operation (139 King St) has become one of the city's most sought after attractions, offering chocolate making tours on a daily basis. While in their factory you will taste 4 different flavors of chocolate and learn the ingredients used to make them. A definite family fun activity.

Chocolate lovers don't leave without taking this 25 minute tour (currently $4). Finished, consider purchasing a variety of their artisan creations in the adjacent gift shop. Two additional retail stores available on St. George St. and Anastasia Island. Visit the place that will 'make your mouth happy' at https://www.whetstonechocolates.com/

Live music fans might want to check out the St. Augustine Amphitheatre when they're visiting. Known locally as 'the Amp', this 4800 seat venue is rated among the Top 50 amphitheaters worldwide by Pollstar Magazine, and is often listed as the second best amphitheater in the country. 

Dating back to 1965 with huge renovations over 20 years ago, the St. Augustine Amphitheatre is a state of the art facility, attracting some of the biggest names in the entertainment industry. The 40 acre site on Anastasia Island less than 10 minutes from the historic district offers four concession stands, a large plaza and an elaborate arboretum with walking trails. Get 'Amped Up' at https://www.theamp.com/

There are several hotels dotted along Avenida Menendez Street paralleling the seawall and Matanzas Bay, with all providing epic sunrises. During my stay in St. Augustine I stayed at the Hilton Bayfront at 32 Avenida Menendez which is within walking distance of everything you could possibly want to do in America's oldest city, and just a stones throw from Lions Bridge, which transports you to Anastasia Island and St. Augustine Beach.

Their back door provides easy access (one block over) to St. George Street. With 72 rooms in colorful cottage-style buildings, Bayfront Hilton is currently the smallest hotel in their chain. However, don't let their size fool you. They are big on hospitality and amenities. Your stay includes concierge and room service, an outdoor pool, fitness center, free wifi, 24hr. snack shop, and streaming entertainment. 

While their lobby and Aviles Restaurant & Lounge are currently undergoing renovations through the end of October, they offer limited dinner menu, and a full breakfast on the second floor from 7-10am daily. Enjoy luxury and convenience at https://www.hilton.com/en/hotels/usthdhf-hilton-st-augustine-historic-bayfront/

If you're an early morning person, the kind that loves to walk the dog, take a nice run then St. Augustine is an awesome way to jumpstart your day. It's especially enjoyable if you walk and run along the sea wall in the bay front area, where you're greeted by some of the best sunrises along the east coast when mother nature allows.

There is tons of history in America's first city. You can't stroll or tour around St. Augustine without hearing the word Flagler or the word oldest offered up several times a day. Not only is it the oldest city in the country, but it has the oldest house, the oldest churches, and the oldest street, i.e. Aviles Street. St. 

Augustine, Florida might be a small city, but it hosts like a big city without all the big city hassle. St. Augustine is pristine, historic, accessible, and easy to navigate for visitors. Get the 'all you need to know before you go' at https://www.floridashistoriccoast.com/

Parting shots:

Approximately 30 minutes north of St. Augustine, just outside Jacksonville is where you'll find the Ponte Vedra Concert Hall. Operated by SJC Cultural Events, the same group who run 'the Amp', the intimate concert hall (built on a foundation of a former Baptist church) hosts over over 140 concerts and events yearly, bringing in music legends as well as top tier stand-up comedians. For an inspirational time be sure to check out https://www.pvconcerthall.com/

Love a good fright? Check out St. Augustine after dark aboard a Ghosts & Gravestones Tour. Discover the secrets of the Tolomato Cemetery and the apparition seen playing on the sacred grounds after dark. Could it be the spirit of five-year-old James or is it the Ghost Bride, still waiting for her walk down the aisle. Join your Ghost Host on this 90 minute narrated tour that includes stops at Potter’s Wax Museum’s Chamber of Horrors, and Cromwell's Parlour of Paranormal Curiosities. For a scary good time visit https://www.ghostsandgravestones.com/st-augustine#tours

Want to wrap your brain around the bizarre? Discover hundreds of rare and unusual artifacts at Ripley's Believe It or Not. Explore a three-story castle built in 1887, the very building that stole Robert Ripley’s heart, inspiring his dream of opening the world’s first permanent Ripley’s collection. Apparently there are a lot of firsts in St. Augustine. Experience extraordinary at  https://www.ripleys.com/attractions/ripleys-believe-it-or-not-st-augustine

Believe it or not (pun intended), Ripley's own the Bayfront Mini-Golf at 111 Avenida Menendez. Not only do you get an awesome view of the intracoastal, but you learn a lot of really cool facts along the way. Ripley's offer group and multiple attraction discounts. Learn more at https://www.ripleys.com/attractions/ripleys-bayfront-mini-golf-st-augustine

Remember I mentioned the Whetstone's first started out with ice cream. While they found their mark in chocolate they didn't abandon their first love. Tedi’s Olde Tyme Ice Cream (family nickname) is prominently located at 65 St. George Street, serving up everything from coffee, lattes, and fresh lemonade, to chocolates and of course their signature scoops of their ice cream cones. Cool and refresh at https://tedisicecream.godaddysites.com/

Being a former northerner (New Jersey), I'm often seeking out the best NY style thin crust pizza when I'm travelling. For my money Carmelo's Marketplace Pizzeria located at 146 W King St is by far the most authentic. It all started nearly a century ago when Carmelo Tringali left Sicily to shrimp in St. Augustine. 

Thankfully he (the grandfather) soon turned to what he and his family do best, serving up real NY style pizza, pasta, calzones, salads, Italian sandwiches and subs. Decades later the family still run the pizzeria. Hell yes they serve pizza by the slice. Here's a twist. Have a craving and it's after 10pm. Carmelo's is joined at the business hip by a Shell gas station, where the Carmelo's wrap single slices left available and place them for sale in the convenience store. Taste old school quality at https://www.carmelosmarketplace.com/