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There’s something special about the serene waterways and small-town vibe synonymous with St. Augustine. Even the first explorers were enchanted by the rich flora and boundless fauna. Because of this vibrancy, and sailors finding this location on Easter Sunday, the area was named La Florida by Spanish Conquistador Juan Ponce de Leon.
But it wasn’t until 1565 that St. Augustine was settled by Pedro Menendez de Aviles, affording it the honor of the oldest, continuously inhabited settlement in the United States.
Since those fledgling days, St. Augustine has continued to charm and welcome visitors with its unmatched Southern hospitality and captivating Spanish influence. The city’s distinct and warm personality is why it remains a popular travel destination, especially for families. Yet, there’s more than history in this former Spanish foothold. St. Augustine has abundance hiding in every inch of its quarters. Here’s what this old town offers the adventurous tourist:
Take a Trolley Ride
The best way to get acquainted with the Oldest City in America and immerse yourself in its layered history is to take a trolley tour. Two trolley trains circle the historic district; Ripley’s Red Train Tour and Old Town Trolley Tours, the green and orange train. The latter is also a hop-on and hop-off ride. Both are equally informative.
You’ll be dazzled with the anecdotes of the history that formed this community, starting with the Spaniards and indigenous people, the Timucua. From unimaginable tales like learning what a dead ringer means to the shrewd tendencies of Henry Flagler, these train tours are full of fun and furious facts.
Tour the Castillo de San Marcos
Step into history when you visit this iconic site. The Castillo de San Marcos is technically a castle. It’s also been an integral part of the city’s history and success as a settlement. After the Spanish settled in this area, the town was burnt down. Twice. (Thanks to the damned English).
Because of these raids, the fort was commissioned, and constructed from native and durable coquina, a mixture of shell fragments and quartz granules. Nestled on the banks of the Tolomato River, sightseers will be able to spot the glitter of the Atlantic, a calculated placement to halt impending threats. Canons linger, marking the battles it has endured in its centuries of existence.
The bastion design was a strategic plan and has contributed to the fort’s longevity and success as a stronghold. Today, it is the oldest masonry fortress in the U.S.A., serving as a reminder of resilience as well as hope. Fun fact: During invasions, livestock was sheltered in the moat around the building to keep them safe.
Meader Down St. George Street
With retail shops, ice cream parlors, and restaurants, this pedestrian walkway showcases the charm that is the heartbeat of the Ancient City. With its modern-day food establishments nestled into vintage storefronts, retail treasures line the street and are neighbors to gems of the past.
Take a journey to see what education was like in the 18th century at the Oldest Wooden Schoolhouse. Then sample some fine wines and nibbles at Casa de Vino 57 before you’re awed by street musicians. There is a fun surprise awaiting at every turn and delicious ways to pass the time.
Take a Boat Cruise
No boat, no problem. The marina’s scenic waters are accessible to adventure seekers. From romantic sunset cruises and sipping sails to sailboat outings and squash-buckling pirate experiences, there are countless ways to have a water adventure.
Learn about the river dolphins, who have adapted to the brackish waters, or indulge in a wine cruise. These waters were made for exploring, so wherever your preference is, there’s an excursion to get you excited.
Visit the Beach
Home to some of the top beaches in Florida, inviting sandy shorelines are just steps away. If you’re situated downtown, there are several options to bask in the glory of the sun’s rays. Vilano and Porpoise Point Beaches are a five-minute drive from the town square. Take the Francis and Mary Usina Bridge and you’ll catch the stellar view of the ocean and the boats cruising through.
You can even walk or bike over the river. Just south, you’ll find St. Augustine Pier and beach, with a splash pad that is great for littles or an easy way to rinse off a salty day. For all the best beaches in St. Augustine, see this article and discover more ways to take advantage of the Northeast Florida sun.
Tour the Flagler Memorial Presbyterian Church
This congregation, the first in Florida, was established in 1824. A Shrewd businessman who built the Florida railway, Henry Flagler was a lifelong member of the Presbyterian Church. The current place of worship was dedicated to the congregation in honor of his daughter, as well as his granddaughter and first wife.
Henry Flagler is laid to rest here with his family and, as with many of the other buildings commissioned by Flagler, the Presbyterian Church is indulgently ornate. Though it is different in style, reminiscent of the Venetian Renaissance, outside details include gold finishings and white terracotta.
The dome itself was crafted in Italy and much of the construction of the building is the poured and sturdy coquina. The church is open for tours daily at 11 a.m. and holds church services each Sunday at 8:30a.m and 11 a.m.
Take a Food Tour
Not sure where to go for a great bite? Perhaps you’re overwhelmed by options. Why not, try them all? Taking a food tour in St. Augustine is a great way to dive into the dynamic fusion of flavors that embody the city.
You’ll be carted around the town on a street-legal golf cart to sample the savory and sweet delights of the town, each paired with a signature beverage. Book a group or make new friends when you join a party. Either way, the memories you make will last.
See a Concert at the Amphitheatre
Tucked into the natural landscape, is an epic concert venue, the St. Augustine Amphitheatre, affectionately referred to as The Amp. With nearly 5,000 seats in an open-air forum, this stage highlights some legendary talent and fresh up-and-coming faces.
The venue is situated on Anastasia Island, over the Bridge of Lions and a half mile from the ocean, sheltered by the foliage of Anastasia State Park. Adjacent stages include The Backyard; an intimate stage behind the main arena for smaller, more personal performances with artists.
These shows are general admission and standing room only. The Front Porch is utilized for Market Nights and the weekly Farmers Market. It’s the perfect place to have a snack and tap your foot to a local groove. Concert aficionados won’t want to miss this unique entertainment space.
Indulge in Local Spirits at the St. Augustine Distillery
Several families in the St. Augustine area collaborated to start this distillery. Their collective mission was simple: craft world-renowned spirits and leave St. Augustine better for future generations. Preserving the town’s dynamic history was also imperative. As such, the selected space, the former power and ice plant initially built in 1907, has been restored to operate the distillery.
The gin, vodka, rum, and various bourbons are made through locally sourced products. The distillery is open daily for self-guided tours and guests can schedule more robust guided experiences. Sample the various liquors in the retail shop or try your favorite spirit in a hand-crafted cocktail at the Ice Plant Bar. Both the shop and bar are conveniently located in the same historic building.
Sample Wines at San Sebastian Winery
In 1996, the Family-run San Sebastian Winery opened its doors and has flourished ever since. Today it can bottle 15,000 units of wine daily and can store up to 40,000 gallons. The winery produces popular varietals like Chardonnay, Pinot Grigio, Petite Sirah, and Cabernet. It also sells several Muscadine options as well as a sparkling wine. For a perfect finale, sample the distinct Cream Sherry or Port.
Take your time as you wander through the winery swirling, sipping, and tantalizing your palate during this self-guided tour. You’ll soon understand why San Sebastian has earned over 650 accolades. Once you finish and find a bottle or two to pack away, settle on the top floor for an al fresco experience. Pair with live music and skyline scenes with your new favorite glass.
Visit the Basilica
As a Spanish settlement, Catholicism played an integral role in the city’s development and culture. While the Catholic faith may have diminished during the British hold of Florida, when the territory was relinquished back to Spain in 1784, the Spanish rule insisted on a new Church.
Thus, the Basilica was constructed. Years later, to honor St. Augustine’s quadricentennial, the Basilica was renovated and eventually raised to minor basilica status by Pope Paul VI. While the Church still holds weekly Mass services, tourists can elect to walk through the space, taking in the imagery during a private or self-guided tour.
Tour Flagler College
What was once the most expensive hotel, known as the Ponce De Leon Hotel, is now an educational institution. From its inception, this artistic marvel was designed to be technologically advanced with the inclusion of electricity.
Now, this former hospitality paradise is named for its creator, Henry Flagler, a man pivotal to Florida’s history and growth. Flagler had a vision to build a decadent destination resort for the elite. The hotel was only open three months a year. And it was a success, receiving guests like Babe Ruth, Mark Twain, and even President Theodore Roosevelt.
Tourism declined in the 1910s and 20s due to Flagler’s expansion of the Florida Railway system as well as the Great Depression. Yet, his development efforts are credited for the blossoming of other cities like Miami.
During World War II, the hotel was used as a Coast Guard Training center until it was decommissioned in 1945. The hotel began receiving guests again but was closed in 1967 and ultimately turned into the college that exists today. Even now, you can experience the bountiful, lush gardens and stand in wonder as the Tiffany & Co. stained glass windows reflect onto the magnificent hand-painted murals. Schedule your tour to see this stunning work of art for yourself.
Be awed by the St Augustine Lighthouse
Climb the 219 wrought-iron stairs and learn about the vital role these structures have in history as well as the rigorous daily responsibilities of the keepers. With sweeping 360-degree views of the landscape, the trek up the steps is worth the effort. The lighthouse complex is home to Heritage Boatworks, an organization dedicated to crafting boats by hand from wood as it was done centuries ago.
The grounds host a play yard for kids as well as trails to explore and a butterfly garden for welcoming these delicate winged insects. Grab a refreshment from the Tin Pickle, a World War II-themed eatery with specialty snacks and local brews. Fun Fact: Florida has 30 lighthouses still standing today.
Explore the St. Augustine Pirate Museum
Florida’s coastal waters have devoured countless passing vessels. St. Augustine’s shores were not spared from unsavory situations as pirates were a constant threat. These escapades, as well as the history and culture of these craggy characters, have been chronicled at the museum.
From historical significance to present-day pop culture, the museum is home to over 800 artifacts and stories including tales of Sir Francis Drake to the Pirates of the Caribbean memorabilia. Interactive multimedia games share the struggles and surprises of life on the rough and ragged seas while informing about these real-life–and fictional–legacies. The Pirate Museum is open daily for tours.
Float Through the River on a Tiki Boat Cruise
You’ll experience St. Augustine in a way like no other on this river cruise. Bring your favorite beverages as your captain guides you through the Matanzas River. Chose to drift along the waters as you learn about the buildings that dot the skyline or take in the last glimmer of the sun’s rays on a sunset outing.
Opt for the longer sail and jump into the refreshing waters at hidden sandbars. All ages are welcome on board. It’s an excursion you won’t want to miss.
Bike Through the Historic Downtown
Lease some wheels and put the pedal on the pavement. Navigate the cobblestone streets with your itinerary, or schedule a guided group tour to get familiar with the beat of the city. Fun Rentals offers all sorts of wheels to get your adventure rolling.
Snap Photos on the Most Beautiful Street in America
Scenic Magnolia Avenue hosts dozens of Live Oak Trees, each draped in Spanish moss. It’s an unparalleled snapshot with tourists constantly vying for their vantage point to capture the serene mystique of these towering trees. It’s easy to see the allure of this road and why it’s regularly voted one of the most beautiful streets.
Meet the “Old Senator”
Not quite the politician you’d expect. It’s an unmatched tenure as this Live Oak is the oldest tree in St. Augustine. With more than 600 of life, this steadfast hero stands proud in the courtyard of 1565 Villa, just north of the Fountain of Youth and Magnolia Ave. Be sure to keep a watchful eye for the magical Love Trees.
These distinct arbors feature two tree species: a palm tree growing out of a Live Oak tree. While practically says seeds were dropped in the oaks thus producing fragmented palm trees, local legend says if two lovers smooch under one of these timbers, they will be blessed with enduring love. Kiss carefully.
Find the Secret to Longevity at the Fountain of Youth
When the Spaniards landed and began a settlement, they were struck by the staggering height and youthful appearance of the indigenous population, the Timucua. The Spanish were desperate to know their secret and were convinced it was the natural spring that gave the local people their vitality (which is still gurgling at the Spring House on site).
For various reasons, a rift ensued between the Natives and the Spanish, but the mystery of their health and vitality remained. The Fountain of Youth is the site of these first encounters, and more importantly, the center of the Timucua village, Seloy.
Today, the grounds have served as an archaeological site, paying homage to the Timucua people as well as the first Spanish settlers. Artillery history and astronomy navigation of the time are highlights of the park. Local tip: Be mindful of the resident peacocks milling about. They are slow-moving but beautiful to watch!
Dine on the Water for Views on Views on Views
Whether you’re at the beach, parked on Anastasia Island, or bopping down the main A1A strip, St. Augustine has a plethora of water views. On the island, relax at the Conch House on their deck with a beverage and enjoy some sultry tones as you sip the night away.
Take in the river views from Harry’s Seafood Bar & Grill balcony, one of the two deck tiers at River and Fort, or get lucky to snag a pub table at Meehan’s Irish Pub, each centrally located front with perfect water views. Across the Usina Bridge, chill at Beach’s Restaurant on the outdoor patio while watching the ships sail across the glass water.
Further up A1A, find tranquility on the expansive decks of Cap’s on the Water or get to The Reef Restaurant early to catch a glimpse of the Atlantic waves crashing to shore. Wherever you choose to unwind, the perspective will be picture-perfect.
Learn to Surf
St. Augustine is a surfers’ paradise and the waves are ideal for all levels. Snag a surf session for a one-of-a-kind day in the water. Happy Waves has private lessons available on Anastasia Island while Surf Station allows individual or group lessons with their instructors and provides rentals and sales. St. Augustine Surf School offers rentals as well as individual or private group sessions.
Graze, Shop, and Be Entertained at the Farmers Market
Held weekly each Saturday at the Amphitheater, experience the local artisans of St. Augustine. From farm fresh produce to handcrafted honey, the market is a great way to experience Florida’s diverse climate, creativity, and abundance.
Food trucks sprinkle the path to keep you satiated while to pursue the tents. Ready for a sit-down? The Front Porch always has a relaxing vibe to enjoy a food find or refreshment. Treat yourself and sway to some sweet tunes from a local band.
Bike or Run the Guana Reserve
This conservation area, which covers over 76,000 acres of land, is research in action. The center holds educational opportunities for all ages, regularly organizing beach cleanups, nature walks and community events to share the research efforts for the facility.
Trek the paths to see the serenity of nature, on your feet or by bike. It’s a great natural resource to escape the concrete walkways and get close to nature. Vehicles cost $3 for access, while cyclists and pedestrians are $1.
Go Fishing
Whether you prefer the calm of the river or the ripple of the waves, fishing excursions are a great way to enjoy this water-centric town. Steer into the ocean for some deep sea catches like mahi-mahi, red snapper, kingfish, and tuna.
But don’t forget there are surly river creatures to behold like redfish, sea trout, and snapper, you may even hook a shark! There may seem to be many boats ready for renting, but spots fill up fast, especially in the summer. So don’t hesitate if fishing is your favorite.
If the water makes you wobbly, keep your feet steady on the St. Augustine pier as you cast a line. Or fish right from the beach. You’re certain to capture a delicious prize.
Rent a ScootCoupe To Tour the Town
Sort of a golf cart, sort of a tricycle, these eye-catching vehicles are a snazzy way to know more about the town and pop from place to place. Local note: Pay close attention to buildings. Some still hold cannonballs and secrets of the battles in days gone by.
Cool Off With the Hyppo Ice Pop
A superb spin on a classic treat, these popsicles are handcrafted with fresh fruits and seasonal produce. They are crafted in crazy flavors like Datil Honeydew and Prosecco Pear Mascarpone to give a powerful punch to your tastebuds.
Don’t worry, there’s simple chocolate and vanilla too. This town favorite started with a popsicle mold and an idea for a clean, refreshing snack. Now, these boundless flavors will keep your tongue tricked and your brain cool after a day in this busy Sunshine State town.
Be Intrigued by the Marvels of Ripley’s Believe it or Not
Jump into a weird and wacky world at the odditorium. From animal anomalies to one-of-a-kind human traits to just crazy facts, Ripley’s Believe it or Not began as a cartoon. Robert Ripley coined the column and traveled to find oddities across the globe.
As the stories and findings grew more popular, due to the paper being syndicated, he enlisted the support of a full-time research assistant to ensure his stories and findings were factual. The cartoon grew into a radio program and eventually, the mayhem museums we know today. With 14 themed rooms, St. Augustine Ripley’s is full of unfathomable things to keep your mind intrigued.
Schedule Some Self-care at the Poseidon Spa
All this travel and touring may require some pampering. The Poseidon Spa, located in the Casa Monica Resort and Spa (a Marriott Hotel), offers a full-service repertoire of indulgent amenities. Melt away the stress of travel with an aromatherapy massage, then relax your toes with a pedicure.
Hydrate your skin after a day in the sun with a custom facial. This gem of a spot will help you recover from your daily adventures. Once finished, continue your pampering at the Casa Brava hotel bar. Whether it’s bubble water or Champagne, this bar will keep your vacation mode activated.
Learn About Sea Life at the St. Augustine Aquarium
This home-grown spot has various species of aquatic life and knowledgeable staff who are eager to engage your curiosities. Great for families and kids who like to get hands-on.
Feed a ray and touch a starfish in a family-owned environment, dedicated to conservation and education. Feeling daring? Sweep over the grounds on the zipline to see the animals from the sky.
Score Some Deals at the St. Augustine Outlet Mall
Who doesn’t enjoy a good buy? Just 15 minutes from downtown, you’ll find an abundance of stores all with steals to up your travel wardrobe. Find super cool kicks at Adidas, New Balance, and Clarks. Look sharp with attire from Brooks Brothers and Cole Haan. And don’t forget the shades from Sunglass Hut. Got too much? Get extra luggage for all your purchases from Samsonite.
Go Back in Time With the Colonial Quarter
The adage, “Back in my day,” has a whole new meaning when touring the Colonial Quarter. Here, discover a house that’s 270 years old. Then, watch trained professionals demonstrate how muskets were operated and maintained. Witness the demanding labor process of a Blacksmith’s work.
This site shows the true experience of life in the Ancient City’s colonial times. The space also hosts intimate concerts and theater events. A magical way to observe life’s nuances at that time and the intense workload experienced by the settlers of the First Coast.
Discover the Sacred Grounds of Our Lady of la Leche at Mission Nombre de Dios
Where the devout Catholic Spaniards first set foot in the new world, this site is known as the Sacred Acre, believed by some to be the holiest site in North America. Today, the shrine reflects on the faith and foundations of the inaugural settlers.
The new main Church serves the community through its commitment to honoring its historical beginnings and its religious mission. Catholic or not, this area holds the key to Florida’s beginnings and its beauty is spellbinding.
Get Creeped Out at the Alligator Farm
Ok, not really, but these creatures sure are crazy impressive and robust, not to mention fast. The Alligator Farm is globally recognized for reptilian education and conservation. It was also the final home of the popular crocodile, Gomek, measuring nearly 18 feet in length and weighing approximately 2,000 pounds.
It’s currently home to the most crocodilian species in the world. You’ll also find Galapagos turtles, lemurs and sloths, and many other creatures hanging around. Be sure to ask when the next feeding is happening; watching the gators move for food is an unreal sight.
Visit Aquatic Life at Marineland
Thirty minutes south of the city’s heart, you’ll find the world’s oldest oceanarium. From the first aquarium to having dolphins born into human care to hosting an array of film crews, Marineland has a plethora of history situated on the sunkissed backdrop of the Atlantic Ocean.
The grounds provide a home to tortoises, sharks, dolphins, and other marine life. Dive into the zoo’s history and conservation efforts or splash into the waters as a trainer for the day.
Kayak Through the Mangroves and Estuaries With an Eco-Tour
In these guided tours, you’ll learn about the converging aquatic life of the river and salt waters, as well as the flora and fauna that surrounds Northeast Florida and its vital importance to our local environment.
See the Coquina Watchtower of Fort Matanzas National Park
This national monument was erected in 1742 as a means of thwarting invasions to the southern city border. It remains today as a symbol of history surrounded by 300 acres of protected lands. As a national park, this area has trails and nature to explore. But note, there is only one way to get to the fort: by ferry. So, be sure to reserve your spot in advance.
Go Paddleboarding
Stand-up paddleboards are a great way to see the city skylines and enjoy the wavy waters, all while powering through a great workout. Whether you schedule a group tour or a private outing, spoon through the ripples as you marvel at the land sites from your water view. Want to test your strength and balance? Try SUP yoga for a true challenge.
Swing into the World Golf Hall of Fame
About 15 minutes north of the city limits, you’ll find a golfer’s paradise. The Hall of Fame is poised with golf’s history, showcasing memorabilia from famous faces on the greens. The Hall also highlights the groundbreaking influences of African Americans in this sport’s history. Try your swinging skills with the complimentary challenge hole, a 132-yard green all guests can attempt to master.
Try a Handmade Treat From Whetstone Chocolates
The Willie Wonka of St. Augustine was founded by lifelong Florida residents, Henry and Ester Whetstone. They began with an ice cream parlor on St. George’s Street, which is still in operation today, and expanded their enterprise with the addition of homemade fudge.
Eventually, the pair perfected hand-dipped chocolates and added these options to the menu. Experience their tasty beginnings and try a few of their renowned chocolates on a scrumptious tasting tour.
Experience The Lightner Museum
This museum finds its home in another former hotel, the Alcazar Hotel. Commissioned by Henry Flagler, the initial design was meant to be an entertainment annex to his luxurious Ponce de Leon Hotel. Plans were revised to make it a separate establishment. The hotel boasted a bath house, indoor swimming pool, tennis and croquet courts as well as a casino.
After the Great Depression stormed the country, the Alcazar closed its doors and was eventually purchased by Otto Lightner to preserve and showcase his extensive art collection. Today, the Lightner Museum hosts various rotating exhibitions and makes for an exquisite space for weddings and celebrations.
Discover Medicinal Practices of the Day at the Spanish Military Hospital Museum
A fully guided tour that revisits the beginnings of medicine. See how surgeries were performed and the role the apothecary played in revitalizing the ill and injured. Think you can stomach some disturbing truths? Take the hospital’s night tour and uncover the treatments that led to lethal outcomes. The museum is open daily for tours, except for certain holidays. Group tours are available with advanced notice.