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19 Things to Do in St. Augustine: Romantic and Fun

Welcome to the charming city of St. Augustine, where romance and history intertwine to create the perfect setting for a memorable getaway.

Whether you are planning a romantic date night or a fun-filled adventure with your loved one, St. Augustine offers an array of experiences to suit every taste. Here are 19 must-do activities to make the most of your time in this historic gem!

A lifeguard tower stands on a sandy beach with calm waves in the background. There are signs on the tower that read "No Lifeguard on Duty" in English and Spanish.

1. Enjoy Live Music at Various Bars and Lounges in St. Augustine

In St. Augustine, music enthusiasts can revel in live performances from blues and Caribbean tunes to bluegrass and country melodies.

Bars and lounges like Mill Top Tavern and Listening Room, Trade Winds Lounge, and Harry's Seafood, Bar & Grille provide the perfect ambiance for soulful tunes while savoring delicious meals and craft cocktails. 

Additionally, the city hosts various music festivals throughout the year, such as the Gamble Rogers Folk Festival, Music by the Sea Concert Series, and Unidos a La Musica: A Latin American Festival, adding to the vibrant musical tapestry of this historic city.

2. Indulge in a Romantic Dinner

Bar area of Prohibition Kitchen

Indulge in a romantic dinner at one of St. Augustine's charming eateries, where you can savor a delicious meal crafted to perfection.

From the historic ambiance of the Columbia Restaurant to the laid-back charm of Prohibition Kitchen, these romantic restaurants offer a culinary journey filled with delectable flavors and exquisite presentations. 

Whether you are in the mood for fresh seafood at St. Augustine Seafood Company or an elegant fine dining experience at Cordova, you will find yourself immersed in a world of culinary delights.

Sip on expertly crafted craft cocktails as you toast to love and romance in the heart of the historic district, creating memories that will last a lifetime.

3. Take a Carriage Ride

2 white horses that are dirty with feather hats on puling a carriage

Step back in time with a romantic carriage ride through the heart of the historic district. Snuggle up with your loved one as you trot along cobblestone streets in an old-fashioned horse-drawn carriage, taking in the sights and sounds of this enchanting city.

Some great carriage companies to check out while visiting St. Augustine include Country Carriages, Coastal Carriages, and St. Augustine Horse & Carriage.

4. Explore Historic Downtown

Lightner Museum is located in this building in St. Augustine, Florida.
Lightner Museum

Explore historic downtown St. Augustine hand in hand, immersing yourselves in the enchanting ambiance of cobblestone streets and centuries-old architecture.

Wander along the iconic St. George Street, where charming shops and historic landmarks beckon you to discover their stories. 

As the heart of the historic district, Downtown St. Augustine offers plenty of attractions and tours to uncover the city's rich history, including the opportunity to join a St. Augustine Historic Walking Tour.

For a unique perspective, rent bikes and pedal through downtown and its surrounding areas, embracing the timeless beauty of this historic cityscape.

5. Climb to the Top of the Lighthouse at the St. Augustine Lighthouse & Maritime Museum

A white lighthouse with a black lantern room at the top pokes through the branches of green trees. There is a blue sky in the background. The lighthouse is located at the St. Augustine Lighthouse & Maritime Museum.

Embark on an exhilarating journey to the summit of the St. Augustine Lighthouse, where panoramic views of the Atlantic Ocean, Matanzas Bay, and the city's skyline await.

Ascend the historic structure hand in hand, cherishing the opportunity to make memories together at one of the city's most iconic landmarks. 

Included in your admission are immersive experiences such as exploring exhibits in historical buildings, attending daily demonstrations on lighthouses and maritime archaeology, and marveling at conserved shipwreck artifacts.

After your climb, take a stroll along the nature trails surrounding the lighthouse, soaking in the lush vegetation and coastal beauty that surrounds this historic site.

6. Embark on a Sunset Sail

A harbor full of colorful boats bobbing on the water. In the foreground are houses with colorful facades. This image may be of St. Augustine, Florida, which is known for its colorful architecture and historic harbor.

Experience the magic of the city's maritime heritage aboard various boat tours, including sunset sails with Cruisin Tikis St. Augustine Sunset Cruises & Tiki Hut Bar Boat Tours, where you can enjoy breathtaking views of Anastasia Island and Matanzas Bay.

Alternatively, embark on a memorable voyage with Florida Water Tours, offering sunset cruises alongside brunch and bottlenose dolphin viewing experiences. 

For a majestic sailing adventure, climb aboard the Schooner Freedom, the tallest ship in the city, and set sail on a romantic sunset sail or day excursion along the historic waters of St. Augustine.

Whether you seek a serene escape or an exhilarating voyage, St. Augustine sailing offers the perfect opportunity to unwind and create unforgettable memories with your loved one.

7. Partake in one of St. Augustine's Guided Tour

People sitting around a table eating, drinking, and socializing

Embark on a captivating guided tour through the historic streets of St. Augustine, where you will uncover the secrets of its storied past and explore iconic landmarks such as the Castillo de San Marcos and the Lightner Museum.

With options like the Old Town Trolley Tours offering hop-on and off privileges at 22 stops, you will have the freedom to delve into the city's rich history at your own pace. 

For a culinary adventure, join The Tasting Tours on a romantic food tour, where you can indulge in delectable treats and local specialties while strolling hand in hand with your loved one.

Do not forget to add a touch of mystery to your exploration with one of St. Augustine's ghost tours, where the nation's oldest city reveals its eerie tales and haunted history around every corner.

Whether craving history, gastronomy, or a thrill, guided tours in St. Augustine offer the perfect way to immerse yourself in the city's enchanting atmosphere and create unforgettable memories.

8. Relax on Vilano Beach

An aerial view of Vilano Beach in St. Augustine, Florida with white sand and turquoise water.

Escape to the serene shores of Vilano Beach, a tranquil oasis nestled just north of downtown's historic district. Embrace the casual atmosphere and quiet ambiance as you bask in the sun and enjoy the vibrant waves, perfect for swimming and water sports.

Its sandy Atlantic shoreline and picturesque fishing pier adorned with the iconic Bluebird of Happiness statue offer a peaceful retreat for locals and visitors alike.

Explore the surrounding area, dotted with casual beach grills, pizza places, and a marina, or stroll along the Vilano Beach Nature Boardwalk, where mosaic art celebrates the beauty of local wildlife.

Compared to bustling St. Augustine Beach, Vilano Beach promises a more secluded and intimate experience, making it ideal for a relaxing day by the sea.

9. Plant a Kiss under the Love Tree

Someone holding up heart hands with tree branches as the background

In St. Augustine, Florida, the legend of the love tree unfolds with the intertwining of two distinct trees - a palm and an oak - planted by two lovers, eventually merging into a symbol of eternal love. Today, the city boasts seven love trees steeped in romance and folklore.

According to local tradition, couples who exchange a kiss beneath these arbors are blessed with a love that withstands the test of time.

It is a cherished tradition that many return to the love trees on their anniversary, seeking to renew the magical bond sealed with a kiss beneath their branches.

10. Stroll Across the Bridge of Lions

A photo of the Bridge of Lions at night. The bridge is lit up with yellow lights and its reflection shimmers on the dark water below. Located in St. Augustine, Florida.

Embark on a picturesque stroll across the Bridge of Lions, a historic landmark named after its majestic white marble lion statues adorning the west side.

This scenic route offers a one-mile walk, perfect for a scenic hill workout, and unparalleled views of downtown St. Augustine and Matanzas Bay from the bridge's summit. 

As you traverse the bridge connecting downtown to Anastasia Island, pause to admire the iconic lion statues and capture the ultimate photo opportunity overlooking the tranquil waters on both sides.

A green bridge with ornate railings stretches across a waterway. The water is a dark blue and there are small sailboats in the distance. This is the Bridge of Lions, a historic landmark in St. Augustine, Florida.

With its blend of architectural grandeur and natural beauty, a leisurely stroll across the Bridge of Lions promises an unforgettable experience in the heart of St. Augustine.

11. Rejuvenate at the Fountain of Youth

Embark on a journey of exploration at Ponce de Leon's Fountain of Youth Archaeological Park, where the legendary fountain awaits to bestow its mythical powers upon you.

Sip from the sacred waters and embrace the timeless allure of eternal youth as you wander through the park's verdant gardens and engaging exhibits. 

Take delight in the diverse array of activities offered within the park, from visiting the Timucua Indian Village to delving into the site's rich archaeological history.

Experience the wonders of the cosmos at the planetarium, stroll along the Founders' Observation Riverwalk, and be captivated by the roar of Spanish cannons echoing through the air. 

12. Indulge in Sweet Romance at Whetstone Chocolate Factory

A pile of chopped chocolate sits on a wooden cutting board. The chocolate pieces are various shapes and sizes, and there are crumbs scattered around the pile. The chocolate appears to be milk chocolate or semi-sweet chocolate.

Indulge in a chocolate lover's dream at the Whetstone Chocolate Factory in St. Augustine. Embark on the "Original Chocolate Tour" to uncover the secrets behind the art of chocolate making and delight in a four-tiered tasting experience led by Whetstone Chocolatiers.

As you journey through the factory, learn about the finer characteristics of dark, milk, and white chocolate, cocoa nibs, and more, igniting your senses with sweetness and love. 

With delicious samples, fascinating knowledge, and coupons toward your next purchase, this tour promises a decadent experience for chocoholics with discerning palates. Book your tour today and gain a deeper appreciation for the chocolate you adore.

13. Explore History at the Oldest Masonry Fort

Marvel at the historic landmark of Castillo de San Marcos in St. Augustine, Florida, the oldest masonry fort in the continental United States, built in 1695.

A large, weathered brick wall of a fort, surrounded by green grass and brown dirt. In the distance, there is a round, moss-covered lookout tower. This image is from Castillo de San Marcos National Monument in St. Augustine, Florida. Castillo de San Marcos is the oldest masonry fort in the United States.

This remarkable fortress, constructed from coquina, a semi-rare type of limestone, stands as a testament to Spanish military engineering and resilience.

With its unique architecture and strategic advantage of coquina walls that absorbed or deflected enemy projectiles, the Castillo de San Marcos is a symbol of the city's rich history and enduring legacy.

14. Visit Lightner Museum

Immerse yourself in the splendor of the Lightner Museum, an iconic building in the heart of historic St. Augustine. Housed within the former Hotel Alcazar, a Spanish Renaissance Revival gem constructed in 1887, this museum of antiques offers a captivating journey through art, architecture, history, and design. 

Delve into the opulence of the American Gilded Age with its impressive collection of artifacts, providing a glimpse into a bygone era of elegance and grandeur. Beyond its cultural significance, the Lightner Museum is a popular wedding venue, adding an extra layer of romance to its storied halls.

15. Escape to Nature at Anastasia State Park

Anastasia State Park

Escape to the tranquil beauty of Anastasia State Park, a serene haven just across Matanzas Bay from downtown St. Augustine. From its unspoiled beaches stretching four miles along the coast to its lush vegetation teeming with wildlife, the park offers a romantic retreat immersed in nature's embrace. 

Delve into the park's rich history, exploring Spanish Coquina Quarries that played a vital role in shaping 17th-century St. Augustine. With plenty of activities, including bicycling, birding, and surfing, Anastasia State Park provides the perfect backdrop for creating cherished memories together amidst the splendor of the great outdoors.

16. Relish Sunset Views and Savor Wine at San Sebastian Winery

2 wine bottles on a barrel with vineyards in the back

Step into the world of wine at San Sebastian Winery, housed in one of Henry Flagler's historic East Coast Railway buildings since its founding in 1996.

Embark on a complimentary self-guided tour and wine-tasting experience, where you can sample a selection of their finest wines and delve into the art of winemaking with a short audio-visual presentation. 

At The Cellar Upstairs Bar and Restaurant, indulge in live music performances ranging from Jazz to R&B and Blues while savoring light appetizers perfectly paired with your favorite San Sebastian bottle of wine.

Relax on the open-air deck, take in the spectacular views, and unwind to the rhythm of live music without any cover charge, creating the perfect ambiance for a romantic evening in the heart of St. Augustine.

17. Explore the Saint Augustine Distillery

A row of wooden barrels stacked vertically in a warehouse. The barrels are stained a dark brown color and have metal bands around their middles. There is text stenciled on the sides of the barrels, including “St. Augustine Distillery” and “Handmade in the Nations.” Some of the barrels are stacked on pallets.

Embark on a journey of flavor and history at the Saint Augustine Distillery, a locally-owned craft distillery housed in a meticulously restored ice plant from 1917.

As one of the most visited craft distilleries in the United States, it boasts a diverse range of award-winning spirits, including rum, gin, vodka, and bourbon whiskey, crafted from local and regional agricultural products. 

Explore the distillery's fascinating heritage with free self-guided tours and tastings, or book a one-hour guided tour to delve deeper into the history of bourbon and the legacy of the St. Augustine Distillery, offering a unique glimpse into both the art of distillation and the storied past of this vibrant city.

18. Spot Bald Eagles in Ponte Vedra

The torso and head of a bald eagle

Experience the majesty of nature as you spot bald eagles soaring and nesting in Ponte Vedra, Florida. Head to the Visitor Center and gaze through the telescope to catch a glimpse of a bald eagle's nest, or venture to the GTM Environmental Education Center, where you can observe these magnificent birds in their natural habitat. 

19. Experience the Magic of Nights of Lights - Seasonal Experience 

Experience the wonder of the Nights of Lights festival in downtown St. Augustine, Florida, where millions of twinkling white lights adorn the cityscape from November 23, 2024, through January 31, 2025. This enchanting display creates a romantic ambiance reminiscent of a hallmark love story, transforming the streets into a magical wonderland.

With lights illuminating the city daily from 5:30 pm until past 2 am, immerse yourself in the breathtaking beauty of this whimsical festival, making it the perfect choice for a memorable winter date night with your loved one.

Romance Awaits!

A fiery red sun peeks above the horizon, casting a golden glow over the rippling waves of the ocean in St. Augustine, Florida

St. Augustine has so many romantic and fun activities for couples to enjoy! From exploring the historic downtown streets and climbing to the top of the iconic lighthouse to indulging in delicious meals at romantic restaurants and embarking on sunset sails, there is something for every pair to cherish.

So why wait? Plan your romantic getaway to the nation's oldest city and embark on an unforgettable journey filled with love, laughter, and adventure!
Have you visited St. Augustine, Florida? Let me know in the comments below! Share this article with the person or people you want to go on your next adventure with! Also, be sure to SUBSCRIBE below to learn about other places you should add to your "To Visit" List! Ready? Okay, vamos. Time to have fun!

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