This article shares what to do during your weekend getaway to St. Augustine, FL.

castillo de san marcos lit up at night weekend getaway to st augustine

Castillo de San Marcos encourages you to gather in its shadows every evening to enjoy the last light of each day by the waters edge.  ©Dawn Damico

A weekend getaway to St. Augustine will captivate your imagination the moment you step onto Aviles Street, the oldest street in the United States. Founded in 1565, St. Augustine predates Jamestown by 42 years and the landing at Plymouth Rock by 55 years.

Florida’s Ancient City immerses you in generations of stories. Explore the coquina stone fort, a gilded-age-era hotel turned college, the legendary Fountain of Youth, and a mass graveyard. It’s a city with a past, a future, and plenty of things to do right now.

The goal for my weekend getaway to St. Augustine during the Festival of Lights was to get a taste of history, sample the breweries and culinary scene, and of course, visit the beach.

Although the streets were livelier than usual because of the holidays, it didn’t take away from the charm of the continent’s oldest continuously occupied city.

In this article, I’ll share my recommendation for where to eat and what to do in St. Augustine. But first, let’s take a look at some of the iconic places you will see during your weekend getaway to St. Augustine.

Overview of St. Augustine

Flagler college with fountain in foreground weekend getaway to st augustine

After almost 80 years of entertaining winter guests, Ponce de Leon Hotel closed its doors to well-to-do snowbirds in 1967, only to be reborn as the centerpiece for Flagler college ©Dawn Damico

You can’t talk about St. Augustine without talking about Henry Flagler. His vision of transforming St. Augustine into a major tourist resort is alive and well, sort of. While the “resort” vibe may be more prevalent in nearby Ponte Vedra, St. Augustine exudes timeless beauty. Flagler’s architectural influence helped shape the city you see today.

Tip: Discover where to eat in Ponte Vedra

St. Augustine is a family-friendly tourist destination and college town. It’s long on history and charm, with the opulence from the Gilded Age existing side-by-side with the Spanish colonies’ humble beginnings.

Though you will find a few “touristy”attractions, such as the Ripley’s Believe it Or Not Museum, Red Train and trolly tours, the oldest wax museum in the country, an alligator farm, and pirate ship cruises, don’t let that stop you from planning a trip to the Historic Coast.

Beyond the family-friendly facade is a tapestry of history, architectural beauty, and great culinary finds. In addition, an iconic lighthouse, outdoor adventures, stories concealed by every brick and wall, and pristine beaches keep you interested. Plan a weekend getaway to St. Augustine and you’ll discover why it has remained a Florida bucket list destination for centuries.

View of matanzas river

St. Augustine is surrounded by water on three sides, including the Matanzas River seen here from the wall by Castillo de San Marcos. ©Dawn Damico

Iconic Landmarks

St. Augustine is nestled on a peninsula between the Matanzas and St. Sebastian Rivers, two miles from the ocean. As you walk St. Augustine’s historic streets, you’ll appreciate the city’s efforts to restore many of the colonial structures to their original glory after devastating fires in 1887 and 1914. A sense of the past touches everything. Old coexists with new. And the result is a charming college town on the water that celebrates its heritage even as it reaches to define itself in the next generation.

Still, while St. Augustine’s charm lies in its ability to transport you through time, many people would agree that it has several iconic symbols. When you think of St. Augustine, you think of these. I’ll list a few of them here as a touchstone for your weekend getaway.

Bridge of Lions

The Bridge of Lions arches over the Matanzas River, connecting downtown St. Augustine to Anastasia Island. During our visit, this section of town had active construction, a testiment to continued investment in the city. The bridge itself got a much-needed makeover when it closed in 2006 to undergo an $82 million upgrade. The project was completed in 2010 and successfully preserved its heritage while embracing modern upgrades and enhancements.

City Gates

The City Gates were once the only entrance to St. Augustine. They serve as a vivid reminder of the city’s turbulent pass. Because St. Augustine is surrounded by water on three sides, the north side was deemed the most vulnerable to invasion. This prompted the construction of three lines of defense:

  • Fort Moosa on the Matanzas River;
  • A second line near present-day Myrtle Avenue;
  • The inner and final line running from Castillo de San Marcos (previously known as Fort Marion) to the San Sebastian River and the City Gates.

In addition, tight rows of Palmetto trees planted closely together were a natural line of defense. Sharp leaves provided an impenetrable barrier against pirates, native tribes, and foreign powers seeking to add New World land to their real estate and economic portfolios. St. Augustine had to fight for its survival, literally.

It’s enduring presence as the oldest continuously inhabited city in the United States is impressive. A testament to the resilience and determination of the peoples who fought to safeguard its rich heritage.

Castillo de San Marcos

Castillo de san marcos with oak tree in foreground weekend getaway to st augustine

Castillo de San Marcos has four triangular-shaped corners, called bastions, once known as St. Peter, St. Paul, St. Augustine, and St. Charles ©Dawn Damico

Castillo de San Marcos is an imposing presence. Located along the Matanzas River, it welcomes visitors throughout the day encouraging you to gather in its shadows every evening.

Originally constructed in 1695 to ward off pirates and foreign powers vying for control over Spain’s military outpost, it now welcomes travelers and history enthusiasts from around the world. It is an historic gem in the heart of downtown St. Augustine.

This architectural marvel has stood the test of time, tragedy, and great storms. You can’t help but be transported back to the age of struggle and hope when man dared to dream what riches (real and imaginary) could be found in this strange land.

Did You Know

  • Three signers of the Declaration of Independence were held prisoner here during the Revolutionary War.
  • When Florida became a United States Territory in 1821, it was renamed Fort Marion in honor of General Frances Marion, a patriot from the Carolinas. It wasn’t until almost 20 years after becoming a national monument in 1924 that Congress restored its original Spanish name, Castillo de San Marcos.
  • The four triangular-shaped corners, called bastions, were known as St. Peter, St. Paul, St. Augustine, and St. Charles. The four connecting walls were called curtains.

Towers of Flagler College

The towers of Flagler College are an architectural masterpiece and a testament to Henry Flagler’s ambition. Once the opulent Ponce de Leon Hotel, this incredible structure has been recognized by the American Institute as one of the nation’s 100 most important buildings.

Henry Flagler, the Empire Builder who dreamed of transforming Florida into an American Riviera, started by building lavish hotels. His hotels catered to wealthy Northerners seeking a winter retreat in perpetual sunshine. However, after realizing the need for efficient transportation, he purchased and built a railroad. This allowed him to deliver construction materials for the hotels, and then provide transportation for his future clientele.

As a side note: Read the book Last Train to Paradise: Henry Flagler and the Specular Rise and Fall of the Railroad the Crossed an Ocean. You’ll recognize how the poured concrete technique was was instrumental in his projects, and understand more about what drove the man who built Florida.

The Ponce de Leon Hotel Opens

The Ponce de Leon Hotel opened its doors in 1888. Early guests included President Grover Cleveland and his wife Frances Folsom Cleveland. Lyndon B. Johnson visited in 1965. A slew of writers found inspiration within its walls, including Samuel Clements, Stephen Vincent Benet, Edna Ferber, John Dos Passos, Ernest Hemingway, Henry James, Sinclair Lewis, Somerset Maugham, and Thornton Wilder.

After almost 80 years of entertaining winter guests, the luxury hotel closed its doors to well-to-do snowbirds in 1967, only to be reborn as the centerpiece for Flagler college.

Today, the towers of Flagler College are seen from anywhere in the city. They are the reminder of Henry Flagler’s visionary spirit and the ingenuity that shaped St. Augustine into a world-class destination.

Beacon from the St. Augustine Lighthouse

The St. Augustine Lighthouse towers 164 feet over Anastasia Island, casting light many leagues over the sea.

A short drive from historic downtown, you can spend several hours exploring the lush grounds. Immerse yourself in the area’s rich history at the Maritime Museum, or climb to the top of the lighthouse for panoramic views. You can even bring a picnic and enjoy it on the grounds.

black and white striped lighthouse weekend getaway to st augustine

Guided and self-guided tours are available at the Lighthouse which includes four historic structures and the maritime Education Center.  ©Dawn Damico

Magnolia Street and the Fountain of Youth

I’m told the water from the Fountain of Youth tastes eerily like rotten eggs, which is why I prefer the water poured from the local Distillery (more on that later). The pursuit of eternal youth led Ponce de Leon to the shores of Florida; however, the treasures he uncovered here span the ages.

You are greeted by a canopy of majestic Live Oaks lining the street when you visit Ponce de Leon’s Fountain of Youth Archaeological Park on Magnolia Street. As the story goes, the street was originally planted with rows of Magnolia trees. However, the trees froze and died after an unexpectedly harsh winter. Rather than replace them with more Magnolia trees, the hardy and majestic oaks were put in their place.

St. Augustine has hundreds of years of history to discover. However, these iconic locations serve as a touchstone for your journey. Now, let’s take a look at what you can do during a weekend getaway to St. Augustine.

Day 1: Weekend Getaway to St. Augustine…Dinner and Nighttime Stroll

Day 1: Weekend Getaway to St. Augustine

bougenvilla growing by yellow wooden doors

Before closing its doors during the Great Depression, the Hotel Alcazar (now the Lightner Museum) was one of the most opulent resort hotels in America.   ©Dawn Damico

We visited during the annual Nights of Lights. This popular holiday event transforms St. Augustine into a twinkling wonderland from mid-November through the end of January. Streets and buildings light up with millions of lights. It’s quite a sight!

We missed the opportunity to enjoy a sailing cruise to see the sparkling city from the water. However, you can stroll along the Bridge of Lions and look back at the city from that vantage point. Stunning at any time of year; magical during the festival.

Be sure to check out their full line-up of events if you visit during winter. As an example, Nights of Pints showcases the city’s breweries. Keep in mind this is one of the world’s top ten holiday light displays, according to National Geographic. Expect higher foot and car traffic than usual.

A large parking area by Castillo de San Marcos National Monument, a parking garage on Cordova Street between W. Castillo Drive and Orange Street (near the Visitor Center), and several places to park along the streets are availalbe and then you can walk into the city.

Dinner at The Press

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soup shot from above

Voted the Best Burger two years in a row by the people of St. Augustine, The Press is a must-visit for burger aficionados and craft beer enthusiasts. You’ll love the freshly baked bread made in-house daily. My pictures don’t do it justice! Towering burgers are stacked high and the beef is cooked to order.

I started with a small cup of potato soup flavored with cheddar cheese, roasted garlic and caramelized onions. The flavor stumped me; I had to ask, “Oh my gosh…what is the flavoring in this soup, it’s delicious!” Roasted garlic, of course! It’s the little things that matter!

The burger was stacked high with delicious meat and served on their signature homemade buns. I was only able to finish half a burger because there’s a lot of meat (delicious meat!).

In addition to great burgers, they serve wine and craft beers, including local favorites from Dog Rose brewing company and Ancient City Brewing.

Location: 525 State Road 16 Unite 101, Saint Augustine, FL 32084

View Castillo de San Marco at Night

castillo de san marcos lit up at night weekend getaway to st augustine

The fort’s iconic silhouette is bathed in light each night, creating a hauntingly beautiful scene that begs you to delve into the city’s ghostly tales. ©Dawn Damico

The holiday spirit in downtown St. Augustine was palpable. The mood was festive as crowds gathered along the ancient stone walls and large grassy area along the water at Castillo de San Marco. Somehow, moments of hushed anticipation penetrated the energy as the sky changed colors and the final light of day faded to the west. The moon rose in the east, casting a gentle glow over the water.

Spanning over 20 acres, the National Monument has plenty of room to explore its storied past. Originally, its main purpose was fortification for St. Augustine. However, the grounds have hosted everything from golf games to grazing livestock and chickens in the moat.

The fort’s iconic silhouette is bathed in light each night, creating a hauntingly beautiful scene that begs you to delve into the city’s ghostly tales. And yes, they have a ghost tour for that!

During the day, a nominal fee gets you inside Castillo de San Marco. Explore the interior rooms at your own pace with brochures and maps provided onsite, or download the Castillo Park app. Rangers and volunteers are there to answer questions, musket or cannon demonstrations take place on most weekends, and you can interact with people dressed in period clothing.

Rooftop Drinks at River and Fort

rooftop view of city lights weekend getaway to st augustine

The view opposite the water shows historic buildings and a tall spire that at first glance I thought was part of the college. However, I believe it is the Grace United Methodist Church.  ©Dawn Damico

Enjoy stunning views of the Matanzas River and Castillo de San Marco from the rooftop of the River and Fort Restaurant. Watch the bustling crowds below as you sip on your favorite wine or craft cocktail. And if you’re lucky, you may get to watch the moon’s light dance across the water setting a romantic mood.

spanish style restaurant front river and fort

River and Fort has two rooftop areas. One on the second floor and another on the third, which is where we sat. The view opposite the water shows historic buildings and a tall spire that at first glance I thought was part of the college. However, I believe it is Grace United Methodist Church.

It gets busy up on the roof so be patient. The anticipation of the special rooftop menu coupled with breathtaking views and craft cocktails is well worth the wait.

Location: 12 Avenida Menendez, St. Augustine, FL 32084

Day 2: Explore the City, Lighthouse, and Distillery

empty historic street weekend getaway to st augustine

As you walk St. Augustine’s historic streets, you’ll appreciate the city’s efforts to restore many colonial structures to their original glory after devastating fires in 1887 and 1914.
 ©Dawn Damico

I love to embrace the early morning hours when I’m visiting a new city, and St. Augustine is no exception. You’ll feel as if you have the city to yourself as you stroll mostly empty streets and imagine what life was like in St. Augustine way back when. Because my plan was to take pictures and enjoy the historic building without navigating a crowd, getting up early was worth it.

Walk down Old St. George street with its overhanging balconies. What I loved about this street is that while the storefronts were simple and seemed small, it was an illusion. They hid expansive interiors and some had really fun outdoor eating areas and cafes. Many shops and restaurants open later in the morning, so if you are there very early, like I was, most things will still be closed.

While I waited, I wandered the sleepy lanes which are like a passage through time. From the oldest narrow streets lined with modest homes, developed as early as the 1600s, to the glamor and glitz of Henry Flagler’s Gilded Age hotels. Read the signs along the road; you’re walking in the footsteps of history. Peoples of many shapes, sizes, cultures, colors, and backgrounds traveled these same roads.

Self-Guided Walking Tours

historic st augustine plaza with street lamp and intersecting sidewalks

The obelisk in St. Augustine plaza commorated Spain’s first constitution. When Spain repealed the constitution and ordered these commemorative monuments to be removed and the plazas renamed, St. Augustine didn’t comply. The monument  in the Plaza de la Constitucion may be the only original, unaltered monument to the Constitucion in the Western Hemisphere.   ©Dawn Damico

Download the Then and Now Walking Tour that guides you through the city and showcases the actual spots that inspired the paintings you find in the Lightner Museum

The Touch St. Augustine Braille Trail guides people of all abilities through Plaza de la Constitucion. According to its website, seven sculptures around the historic square are highlighted on the tour. They represent people and images important to the city’s growth. Everyone can access the audio tour with stories to enrich your St. Augustine experience.

Lightner Museum

lightner museum historic spanish revival building exterior weekend getaway to st augustine

The Alcazar’s architectural style mirrors that of the Ponce de Leon Hotel, yet with distinct details that set it apart. Originally, it was designed to provide amusement and accommodations for visitors of the Ponce de Leon.  ©Dawn Damico

Most people know the Lightner Museum is located in the former Hotel Alcazar. The Hotel was part of Henry Flagler’s vision for St. Augustine so as you can expect, every last detail was carefully designed.

Before closing its doors during the Great Depression, the Hotel Alcazar was one of the most opulent resort hotels in America. Guests enjoyed an incredible indoor swimming pool, tennis grounds, club rooms, and world-class Turkish and Russian baths. Bicycle excursions were available too, including lessons on how to ride! There was an arcade of shops opening onto the plaza and a tropical garden with a rustic bridge. Some of this remains today.

The Alcazar’s architectural style mirrors that of the Ponce de Leon Hotel, yet with distinct details that set it apart. Originally, it was designed to provide amusement and accommodations for visitors of the Ponce de Leon. Today, as the Lightner Museum, named after professional hobbyist Otto C. Lightner, the building and its collection stands as a testament to St. Augustine’s history.

Fun Facts: The Gilded-Age “Dream Team” responsible for many historic downtown buildings, including the Ponce de Leon Hotel and Alcazar Hotel, was architects Carrère and Hastings and builders McGuire & McDonald.

Flagler College

Flagler College with fountain in foreground weekend getaway to st. augustine

 It has been said that from every point of view, the Ponce de Leon design (now Flagler College) was irreproachable. An architectural masterpiece that was utterly captivating, a testament to the meticulous attention to detail that was the priority during construction. ©Dawn Damico

You cannot mistake the former Ponce de Leon Hotel, now home to Flagler College. It has been said that from every point of view, the Ponce de Leon was irreproachable. An architectural masterpiece that was utterly captivating, a testament to the meticulous attention to detail that was the priority during construction. Cost was no object in the pursuit of perfection. Every element was crafted with uncompromising precision.

An early publication produced by the contracting firm, created for architects around the world, noted that the interior plans and decor were even more magnificent than the breathtaking exterior. In their opinion, the crown jewel of the Hotel was the magnificent dining room, where “…the coloring of the decorations in general carries out the Renaissance spirit that appears everywhere else in the building.”

Stained glass windows illustrated allegorical subjects, bathing the space in a warm, ethereal glow, while a gallery for musicians, fresh flowers, and beautiful paintings adorned every corner, elevating the art of dining to new heights.

Beyond the grand dining hall, the former hotel boasted an array of luxurious amenities, including a huge indoor swimming pool and casino.

Flagler College Historic Tours are available, departing from the Rotunda.
Note: They are undergoing renovations. According to their website, tours will be suspended from May 2024 to August 2024. They anticipate continued work through 2025 so check the website before your visit for the most recent information. 

Memorial Presbyterian Church

Henry Flagler dedicated the Memorial Presbyterian Church to the memory of his daughter who died as a result of complications from childbirth. The building is stunning, as you would expect from Flagler. Inside this sacred space, Henry Flagler, his first wife Mary, his daughter Jenny Louise, and granddaughter Marjorie are entombed at the Flagler family mausoleum.

Take a tour of the church on Fridays between 11:00am and 3:30pm. According to their website, as long as there is not a wedding or funeral scheduled, docents are available to answer questions and provide history and background information.

City Perks Coffee

arches in historic fort pickens places to visit in pensacola

Nestled in the heart of downtown, City Perks has a small dininginside with views of the water or step out back through the wine shop onto the cozy courtyard.  ©Dawn Damico

City Perks Coffee is a delightful stop for both coffee and wine enthusiasts. Nestled in the heart of downtown, this is a cozy cafe and a wine shop with several entrances. Enjoy your morning cup of coffee and a breakfast sandwich. A small dining area is available inside with views of the water or step out back through the wine shop onto the cozy courtyard.

Location: 15 St George St Unit B, St. Augustine, FL 32084

VIC: The Visitor Center You Shouldn’t Miss

arches in historic fort pickens places to visit in pensacola

VIC is a clever fusion of museum, boutique tour guide company, and comprehensive resource dedicated to ensuring your weekend getaway to St. Augustine and the Historic Coast is both memorable and meaningful. ©Dawn Damico

The St. Augustine and St. Johns County Visitor Information Center, aka VIC, is more than a bunch of pamphlets on a rack (although they have those too!). Think of it as a clever fusion of museum, boutique tour guide company, and comprehensive resource dedicated to ensuring your weekend getaway to St. Augustine and the Historic Coast is memorable and meaningful.

Face it, when you navigate any city around the world with centuries of history, it’s easy to feel overwhelmed. You can easily miss the significance of what you’re seeing. The VIC aims to provide context, offering insights into the city’s past, present, and future. They offer curated information and experiences you can tailor to your interests. Whether you’re interested in history, outdoor adventures, pristine beaches, or the local culinary scene, the VIC is a valuable resource.

They also have clean bathroom facilities and a large parking structure!

tall clock in front of visitor center weekend getaway to st. augustine

Before you leave, look at the graveyard just outside the VIC between the clock and the river. I overheard a tour guide telling his group the site has an unusual amount of ghost activity. Each headstone represents about 25 bodies, making it a mass grave site. While nothing sinister caused this (it was a result of the flu epidemic)  it’s a reminder of harder days and the city’s resilience in the face of adversity.

 

Anastasia State Park during your Weekend Getaway to St. Augustine

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Imagine standing on a boardwalk near the crest of a sand dune, crisp salty air blowing gently through your hair, as you gaze across miles of pristine coastline, the sun’s rays dancing on the water…   ©Dawn Damico

If you love the beach, and love hiking, then Anastasia State Park is a coastal paradise that will speak to your soul.

Imagine standing on a boardwalk near the crest of a sand dune, crisp salty air blowing gently through your hair, as you gaze across miles of pristine coastline, the sun’s rays dancing on the water.

Stepping onto the soft white sand, you feel grounded as the gentle warmth envelopes your toes. The brilliant blue-green waters beckon you to take a refreshing dip. Instinctively, you inhale, filling your lungs, then let it out completely. If you’re like me, there is a part of you that feels like you are home.

This is the breathtaking scene that greets you at Anastasia State Beach.

There is nothing quite like an east coast beach. As you stroll along the shore, shorebirds like sandpipers and willets scurry across the sand, their little legs moving at lightning speeds. If you’re lucky, playful dolphins may put on a show as they glide through the waves offshore.

No matter how you beach, be it sunbathing, beach combing, building sandcastles, or just relaxing with a good book, take the time to visit the beach during your weekend getaway to St. Augustine.

arches in historic fort pickens places to visit in pensacola

This is a sign from the Lighthouse Trail; however, you’ll experience the same type of plants and terrain on the trails at Anastasia State Park…   ©Dawn Damico

But Anastasia State Park is more than a breathtaking beach. We ventured away from the sea to walk our dog along one of the nature trails that wind through maritime hammocks which, according to the trail signs, were formed as the coast line receded and created stabilized beach dunes that allow for larger growth trees.

The Ancient Dunes Trail, a 4-mile loop, takes you through a forest of towering sand dunes covered in lush vegetation. Along the way, you might even stumble upon coquina rock formations crafted by nature over thousands of years.

Beyond hiking, you can enjoy camping, bicycling, fishing, kayaking, and more. Anastasia State Park is a coastal gem that captures the magic of Florida’s natural landscapes.

St. Augustine Lighthouse and Maritime Museum

view out a lighthouse window weekend getaway to st. augustine

 Imagine the lightkeeper’s task of carrying a 20-pound bucket of oil up 219 cast iron steps to the top of the tower. ©Dawn Damico

Visiting St. Augustine Lighthouse is an experience that should not be missed; definitely worth the price of admission! It offers a blend of history, panoramic views of the St. Augustine coastline, and immersive educational opportunities.

Climb to the top of the lighthouse if you can. Along the way, you’ll learn about lighthouse living from the stencils and pictures painted on the interior walls.

For example, imagine the lightkeeper’s task of carrying a 20-pound bucket of oil up 219 cast iron steps to the top of the tower. Now imagine that you are a woman doing that. Specifically, Kate Harn, who became the Second Assistant Keeper in 1889, earning a salary of $400 per year.

Getting hungry? If you were living at the lighthouse you might dine on a bird that hit the lighthouse glass and died. Or, if you were the mischievous son of the lightkeeper you may test the law of gravity by attaching a parachute to your sister’s cat and toss him off the top of the lighthouse.

For that story, not only did the law of gravity prevail, the little boy also proved that cats do, indeed, have nine lives!

Beyond the lighthouse itself, the complex is full of history and education. There are four historic structures and the Maritime Education Center. Little ones will enjoy the hands-on activities, and interactive exhibits, while history enthusiasts will enjoy maritime history and a tour of the lightkeeper’s living quarters.

arches in historic fort pickens places to visit in pensacola

A view from the top of the Lighthouse, the complex has exhibits in the Keepers House, which includes Northeast Florida Shrimping and the Lighthouse’s role during the major wars;  Heritage Boatworks, Outdoor exploration for the kids,  Nature Trails, and WW11-era structures. ©Dawn Damico

In addition, witness the art of wooden boat building and participate in ongoing demonstrations and interpretive programs. Guided and self-guided tours are available, allowing you to explore at your own pace or with the assistance of a knowledgeable guide.

Trails wind through the property, great for a little hike, and a playground lets kids be kids. Dogs are welcomed on the grounds, but not in the lighthouse and only service animals may enter the historic buildings.

You can easily spend a few hours here exploring everything. Kids will love it! I was really impressed by how the property was set up, the learning opportunities that felt more like play, and the number of exhibits and hands-on activities available. There were several families taking their time and enjoying the property, planning ahead and enjoying a packed lunch picnic. What a great idea.

Drive on St. Augustine Beach

Drive on designated stretches of St. Augustine Bea if your vehicle can handle it! The first time we did this was on the Carolina Coast and there is just something so cool about it. A cruise along the sun-drenched shoreline is a throwback to the early 1940s when beach racing was a thing at St. Augustine Beach and Vilano Beach.

Beach driving is practical for hauling beach essentials like toys, surfboards, and coolers. You’ll drive along the top side of the beach where the sand was mostly hard-packed when we were there.

Love cars? If you are a car enthusiast, check out the Classic Car Museum of St. Augustine.

Distillery Tour

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What truly sets St. Augustine Distillery apart is its commitment to sustainable practices. From restoring the historic 1917-era ice plant (rather than demolishing it) to implementing water conservation measures, sourcing local ingredients, and harnessing solar power, the Distillery walks the walk with mindful business practices.  ©Dawn Damico

While I didn’t partake in the promise of Ponce de Leon’s youthful water; I thoroughly enjoyed the intoxicating elixir flowing at the St. Augustine Distillery. Despite the holiday crowds, the free self-guided tour and tasting were run like a fine-oiled machine, offering a glimpse into the art of craft distilling. They offer guided experiences too, which I would love to experience on a return trip to St. Augustine.

St. Augustine Distillery has been recognized as the Best Craft Gin Distillery by USA Today. They made headlines with their Port Finished Bourbon aged in barrels from San Sebastian Winery which is located just up the road. They offer bourbon, rum, gin, and vodka along the craft cocktail mixers to make it easier to replicate their cocktail recipes at home.

The Distillery is located in a repurposed Ice House. The vibe is cool. Displays detail the distilling process and tasting stations invite you to enjoy their premium spirits. The sight of rows of wooden barrels stacked inside a cavernous warehouse space evokes a sense of appreciation for the craft.

Sustainable Spirits

What truly sets St. Augustine Distillery apart is its commitment to sustainable practices. From restoring the historic 1917-era ice plant (rather than demolishing it) to implementing water conservation measures, sourcing local ingredients, and harnessing solar power, the Distillery walks the walk. Mindful business and creation practices resonate with their values and make a statement about what is important to the founders.

Purchase your favorite mixer or spirit at the Distillery store. Trust me, you’re going to want to take something home with you!

Ice Plant Bar

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Sit at the bar and watch the mixologists create their masterpieces at Ice Plant Bar, located around back from the Distillery.  ©Dawn Damico

After your tour, head around back and up the stairs for a little pre-dinner cocktail at Ice Plant Bar.

In addition to Farm-To-Table offerings like grass fed beef and local seafood, the bar upstairs mixes craft cocktails to enjoy in an open, industrial-chic setting with lots of metal and wood accents. Everything around you pays homage the history of the building. Sit at the bar and watch the mixologists create their masterpieces. I enjoyed an espresso martini and an appetizer of Blue Crab Beignets. I know, it’s an interesting combination but still very delicious!

Dinner at St. Augustine Fish Camp

arches in historic fort pickens places to visit in pensacola

Situated directly on the water with an iconic fishing boat docked right out the back door, it’s easy to imagine that the fish served on your plate was swimming in local waters just a few hours earlier.    ©Dawn Damico

After your Distillery tour and pre-dinner cocktails, it’s time for dinner. Be sure to make reservations and then walk from the Ice Plant Bar to the St. Augustine Fish Camp where the catch of the day is as fresh as it gets

Situated directly on the water with an iconic fishing boat docked right off the back deck, it’s easy to imagine that the fish served on your plate was swimming in local waters just a few hours earlier. Known for their exceptional seafood and oysters, the Fish House offers a variety of preparation styles to suit every palate, from crispy fried, to open-flame grilled, or blackened.

The dining area feels like a warm and welcoming Southern home; the deck beckons al fresco dining on those perfect Florida evenings. This is the perfect nightcap to a full day of exploring St. Augustine.

 Location: 142 Riberia St, St. Augustine, FL 32084

Day 3: Weekend Getaway to St. Augustine

View of the tower at Robinson Preserve looking from across the water

The area all around The Distillery and Fish House is part of a greater effort to restore this neighborhood. I’m looking forward to see what’s new in the coming months!   ©Dawn Damico

After an action-packed day, it’s time to slow it down a little on day three. We’ll start with breakfast, then head outdoors, enjoy sips of brews and vino, then enjoy lunch overlooking the water. Let’s get started.

Breakfast

There are several popular breakfast restaurants in and around downtown St. Augustine. I’m sharing a few of the top-rated ones to start your day before you head outdoors. I didn’t try these because I wasn’t hungry and just had a cup of coffee; however, they are on my list to try the next time I’m in St. Augustine for a weekend getaway.

The Blue Hen Cafe for Southern comfort food (think biscuits baby!)
Location: 117 Martin Luther King Ave., St. Augustine, FL 32084

The West Egg for breakfast burritos, biscuits and much more. Diners say this is the place for “breakfast done right!”
Location: 233b W King St, St. Augustine, FL 32084
*No website

The Kookaburra Downtown for traditional Aussie breakfast pies, vegan donuts, and delicious coffee.
Location: 24 Cathedral Pl, St. Augustine, FL 32084

St. Augustine Eco Tours

While early settlers clamored to the shores of St. Augustine for strategic reasons, I can’t help but think they stayed because of its natural beauty. You can experience that beauty with a St. Augustine Eco Tour.

If you have your own boat, kayak, or paddleboard, there are several launches throughout the Historic Coast. Or, you can choose a guided eco boat tour, catamaran sailing, or paddle tour on the rivers surrounding the city. When the beach is more to your liking, consider a beachcombing tour and see the coastline as you’ve never seen it before.

St. Augustine Breweries

The local breweries held a special event to coincide with the Nights of Lights. Nights of Pints was an opportunity to get a punch card and create your own pub crawl and get a commemorative t-shirt. We enjoyed two locations located in downtown St. Augustine.

Ancient City Brewing Downtown Taproom

View of the tower at Robinson Preserve looking from across the water

Ancient City Brewing is near the Bridge of Lions and is a great spot to duck into off the street when you’re ready for a break!   ©Dawn Damico

Just steps from the Bridge of Lions and Plaza de la Constitucion, the Ancient City Brewing downtown taproom is ready to welcome you. We enjoyed a flight and I love that their website includes recipes so you can cook with beer. I can imagine how the flavors in the beer would enhance your favorite meal – in the glass, or as part of the recipe.
Location: 18 Cathedral Place, St. Augustine, FL 32084

Note: You can also visit the original location, Ancient City Brew House, where they have live music, a patio, and rotating food trucks.
Location: 3420 Agricultural Center Drive, Suite 8, St. Augustine, FL

Dog Rose Brewing

View of the tower at Robinson Preserve looking from across the water

The interior space at Dog Rose Brewing has room to play…  ©Dawn Damico

The tap room is 5000 square feet, painted a rich hue of blue, highlighted with a handcrafted maple bar, with space for live music and a game of shuffleboard. Located in the historic Lincolnville neighborhood, Dog Rose Brewing is a refreshing stop as you explore downtown St. Augustine. In fact, when we were there a couple getting their engagement photos taken across the street took a break for a cool, craft beer at Dog Rose.

Location: 77 Bridge Street, St. Augustine, FL

San Sebastian Winery Tour

street lined with historic buildings places to visit in pensacola

While I prefer less-sweet wines, I love the health benefits of Muscadine grapes, including one of the highest antioxidant levels among fruits.  ©Dawn Damico

It’s the second largest winery in Florida (Lakeridge Winery in Clermont is the first). San Sebastian Winery is located in an 18th-century East Coast Railway building. They have used the 18,000 square feet space wisely, providing tastings, tours, a gourmet gift shop, and rooftop bar with live music on the weekends. Be sure to stop by the little theater upstairs where they present a film about the winemaking process and history of San Sebastian. You can take your tasting with you, sit down, and learn something new!

Did you know that one ton of sweet Muscadine grapes makes about 165 gallons of juice? After that juice goes through fermentation, racking, filtering and bottling, it transforms into about 4,000 glasses of wine. Sweet Muscadine grapes are readily available throughout the South. While most of San Sebastian wines are made with Muscadine grapes, like their Vintners White and Vintners Red, they also have some delicious Cabernet Sauvignon and Petite Sirah varietals.

Health Benefits of Muscadine Grapes

While I prefer less-sweet wines, I love the health benefits of Muscadine grapes. As noted one a sign at the winery, the National Cancer Society wrote about this grape, saying:

“Studies conducted by the National Cancer Institute, the University of Florida, and the Nutraceutical Research Laboratories at the University of Georgia found the Muscadine grape possesses one of the highest antioxidant levels among fruits. Antioxidants play a key role in the maintenance of a healthy immune system. Their findings also showed the Muscadine holds anti-inflammatory properties, the ability to lower bad (LDL) cholesterol while raising good (HDL) cholesterol, and inhibit the growth of prostate and breast cancer cells…”

Tasting, Tours, and Rooftop Respite

Again, because we were there during the holidays, the place was packed. I asked how many guests they had and their count was at least five times normal. Still, the self-guided tours and complimentary tastings were efficient and I didn’t feel like we were being rushed.

In addition to the free tastings, they had a paid tasting option near the theater upstairs (which may have been special for the holidays). We enjoyed additional wine options, a little slower pace, and kept the wine glasses used for the tasting as souvenirs of our experience. The fee was nominal and well worth it.

After your tasting room experience, head to The Cellar Upstairs Bar and Restaurant. It is a beautiful place to relax with a glass of wine and take in the view of the San Sebastian River and downtown. They serve craft beer too!

Lunch at Casa Reina

street lined with historic buildings places to visit in pensacola

Casa Reina, a taqueria and tequila bar that honors the tradition of hospitality and history with a menu that blends seafood from the Florida Coast with your favorite Mexican and Latin American flavors.  ©Dawn Damico

The Spanish Revival building was a home, a hotel, an office building, and headquarters for the American Legion Post #37. Today, it’s Casa Reina, a taqueria and tequila bar that honors the tradition of hospitality and history with a menu that blends seafood from the Florida Coast with your favorite Mexican and Latin American flavors.

There is seating inside and out of this approachable, upscale restaurant overlooking the water and Bridge of Lions. We enjoyed some Chips with Guacamole topped with Pepitas, the Chicken Quesadillas, and Grilled Shrimp Salad.

Where to Stay in St. Augustine, FL

downtown Bradenton FL

There are many places to stay in and around St. Augustine, from luxury hotes, to unique “hotel clusters” and camping…choose your type of travel accomocations. ©Dawn Damico

There are several places to stay around during your weekend getaway to St. Augustine. Here are some historic and unique options.

Renaissance St. Augustine Historic Downtown

Renaissance St. Augustine Historic Downtown Hotel pays tribute to Hotel San Marco, the iconic lodging that inspired Henry Flagler to build Hotel Ponce de Leon.

Hotel San Marco was constructed of wood in 1885, rose five stories high with grand towers and a wrap-around porch, and defined St. Augustine’s skyline from miles away. It was known as a first-class resort, although it was not considered elegant. When Henry Flagler stayed there during one of his discovery trips to St. Augustine he was convinced of two things: One, St. Augustine had potential as a tourist destination, and Two, he could build a better hotel.

Fast forward to today, and you’ll find Marriott’s Renaissance St. Augustine Historic Downtown Hotel. The design is a blend of inspiration: The original Hotel San Marco, the Barcelona Hotel, and the Spear Mansion Hotel. It looks like a community of Victorian-style homes, which fits perfectly into historic downtown St. Augustine.

Location: 6 West Castillo Drive, St. Augustine, FL 32084

Camping: Anastasia State Park

Camp under the stars with the sound of the ocean soothing you to sleep at Anastasia State Park. The campground accommodates tents and RVs. We walked by the campground the day we hung out at the beach and it looked nice, had a great location, and serves as the perfect home base for RV travelers exploring the Historic Coast.

The Collector Inn

When you’re looking for a unique stay in a historic location, check out The Collector Inn. Nine historic homes are “collected” on one square block in downtown St. Augustine. The Inn welcomes adults 16 and up. It was originally the Dow Museum of Historic Houses and is now a storied hotel that blends the heritage of the past with a modern high-end experience.

 

You Will Fall in Love During your Weekend Getaway to St. Augustine, Florida

gulf coast sunset with palm trees in foreground. a day outdoors in Bradenton Florida and Gulf Islands

Rangers and volunteers are available at Castillo de San Marcos to answer questions, musket or cannon demonstrations take place on most weekends, and you can interact with people dressed in period clothing.  ©Dawn Damico

Whether you lose yourself in the Gilded-Era architecture, the rich history spanning hundreds of years, the local cuisine and libations, or the natural side of Florida, St. Augustine is certain to inspire a return trip. Transformations, some in process, and others in the planning stages, will continue to honor the city’s history and embrace the vision for its future. I’m excited to experience another weekend getaway to St. Augustine as the people who call this city home turn their visions into the next era of Florida’s Historic Coast legacy.

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Read More: Food Lovers Guide to St Augustine in May

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