2-Day St. Augustine Itinerary

2 days in st augustine

The Best Way To Spend Two Days in St. Augustine

Are you looking for things to do in St. Augustine this weekend? With just two days in St. Augustine, you can experience a seamless blend of historical wonders and contemporary thrills that are bound to make your weekend unforgettable. As the sun rises over the city, embark on a journey that takes you from the evocative echoes of the past on the historic cobblestone streets to the delectable flavors of the present at local eateries. Don’t miss out on the interactive exhibits at the city’s museums, or the chance to enjoy waterfront views on a scenic boat tour. Your two days in St. Augustine will be a whirlwind of exploration, whether you’re discovering hidden gems in the Historic District or savoring artisan spirits at the local distillery. Pack light, but expect to leave with a heavy heart, filled with memories of a lifetime spent in America’s oldest and most captivating city.

St. Augustine Itinerary

Day 1

Old Jail St. Augustine

What To See/Things To Do

Embark on a captivating tour led by knowledgeable jailers at the St. Augustine Old Jail Museum. Traverse the stony corridors into the prisoners’ cells, echoing eerie tales of yesteryear, making it an ideal part of any St. Augustine weekend getaway. Feel the chill as you approach the maximum-security gallows, where condemned criminals met their end. Walk through the sheriff’s quarters, preserved in their original form. Marvel at the fascinating collection of historical weapons and artifacts on display. This family-friendly tour offers a visceral glimpse into a tumultuous past, ensuring an unforgettable historical exploration during your weekend in St. Augustine.

Old Town Trolley
Ray Charles wax figure
City Gate St. Augustine
St. George Street St. augustine

What To See/Things To Do

St. George Street, a historic artery of St. Augustine, is home to many must-see attractions, perfect for those planning a St. Augustine weekend getaway or seeking exciting things to do in St. Augustine this weekend. Marvel at the Peña-Peck House, a splendid relic from the First Spanish Period. Visit the Oldest Wooden School House, an emblem of early education, and experience a shiver at the Medieval Torture Museum’s eerie exhibits. Explore the Colonial Quarter’s vivid depiction of the city’s past, and unleash your inner explorer at the Pirate & Treasure Museum. Each twist and turn on this street guarantees a captivating glimpse into history, making it a significant locale on any St. Augustine tour itinerary.

Where to Eat:

The Columbia Restaurant

Nestled in the heart of St. Augustine, the Columbia Restaurant, Florida’s oldest eatery, established in 1905, offers an exquisite culinary adventure. Its historic charm and delectable Spanish-Cuban cuisine provide the perfect lunchtime retreat. Nearby, Mojo’s Tacos offers a burst of Mexican flavor, while Crave satisfies health-conscious cravings. These gastronomic gems, set amid the city’s rich history, make your St. Augustine visit a feast for the senses.

Hop Back on the Trolley

Hop back on the trolley and let your journey take you to the historic churches of St. Augustine. Be struck by the awe-inspiring architecture of the Cathedral Basilica, a captivating fusion of Spanish mission and neoclassical styles that pays homage to the city’s history. Just a short ride away lies the Grace United Methodist Church, a testament to Henry Flagler’s vision, uniquely characterized by its poured concrete technique. Each church visit offers a serene respite amid the bustling city tour, wrapping you in a blanket of peace and tranquility.

Visit Churches of St. Augustine

Cathedral Basilica

Things To Do at the Cathedral Basilica

The Cathedral Basilica of St. Augustine mesmerizes with its deep red ceiling, cross-beamed and adorned with gold-leaf Lindenwood statues, making it a must-see attraction for those planning a two-day St. Augustine visit. A custom-built pipe organ resonates with history. Murals portray seminal events such as the first Mass, the Minorcans’ arrival, and stories of missionaries and Native Americans. Intricately designed stained-glass windows illustrate the life of Saint Augustine of Hippo. Don’t miss the richly detailed altar, a testament to architectural ingenuity, and the captivating bell tower on your visit.

Baptist Church

Things To Do at Ancient City Baptist Church

Venture into the history room at the Ancient City Baptist Church to delve into its past, with a display of early records and memorabilia. Take a guided tour led by informed church members who will enrich your understanding of its unique Romanesque Revival architecture and significant historical connections, providing an enriching experience for those on a St. Augustine weekend getaway. The tour offers beautiful stained-glass windows, a three-story tower, and a Norman tower for your exploration, a fascinating journey through St. Augustine’s architectural history.

San Sebastian Winery St. Augustine

Things To Do at the San Sebastian Winery

Discover the magic of winemaking at the San Sebastian Winery, where you can embark on a guided tour through the production facility, making it an essential addition to any St. Augustine weekend getaway. This exploration includes a captivating short film, unveiling the secrets of barreling to bottling, and a walk around the winery’s heart, providing an insightful glimpse into the full wine-crafting process. Complementing this rich learning experience are tastings of award-winning wines. The winery also features an extensive gift shop and a rooftop bar, ensuring a memorable visit for every wine enthusiast.

St. Augustine Itinerary

Day 2

Anastasia State Park

Anastasia State Park Things To Do

Hang out on the beaches

Bask in the untouched beauty of Anastasia State Park’s four miles of pristine beaches, a haven for nature enthusiasts and an essential destination for a St. Augustine weekend getaway. The park outshines other local beaches like Crescent Beach and St. Augustine Beach with its undisturbed natural allure. Spend your day sunbathing or strolling along the coast in search of intriguing seashells. A visit to this idyllic park promises a unique blend of relaxation and adventure.

Go for a hike or a bike ride

Experience a thrilling exploration of Anastasia State Park’s diverse landscape on the Ancient Dunes Nature Trail. This trail winds through maritime hammocks of blooming southern magnolias, leading to ancient dunes that offer breathtaking views. Extend your adventure by renting bicycles from Island Joe’s Camp Store to navigate the park’s extensive roads, including a scenic ride along the expansive beach to the bustling tidal salt marsh, a hot spot for local shorebirds. Whether on foot or on wheels, Anastasia State Park offers an unforgettable adventure, brimming with natural beauty and abundant wildlife.

Hit the waterways on a kayak

Venture into the aquatic world of Anastasia State Park with Anastasia Watersports’ kayak rentals. Paddle along the serene Salt Run, a tidal marsh teeming with dolphins, manatees, and sea turtles. You’ll be entranced by the abundance of avian life along the Marsh Trail, home to wood storks, great blue herons, and roseate spoonbills. The journey offers mesmerizing views of the tranquil salt flat shimmering under the sun. Kayaking in this unique marine ecosystem is an unforgettable experience that provides a different perspective of the park’s beauty.

Go wildlife viewing

Journey on a wildlife adventure through Anastasia State Park, an integral part of the Great Florida Birding and Wildlife Trail. While exploring the park’s protected lands, you’ll discover a haven for diverse wildlife. Positioned along a migratory route, the park offers abundant bird-watching opportunities, with water birds like the graceful tricolor heron and majestic osprey often spotted soaring above the tranquil waters of Salt Run. On the park’s dry land, you’ll encounter an array of shorebirds, including laughing gulls and elegant black skimmers. Beyond bird-watching, keep an eye out for charming gopher turtles, scuttling crabs, and the elusive Anastasia Island beach mouse, adding to the park’s rich biodiversity. Whether you’re a seasoned birder or a nature enthusiast, Anastasia State Park promises an unforgettable wildlife viewing experience.

Where to Eat: (LUNCH)

The Conch House

Savor lunch at The Conch House, an upscale restaurant in St. Augustine, renowned for its fresh seafood and classic American dishes. The restaurant’s enchanting marina setting offers panoramic views of the Salt Run channel and Anastasia State Park. Remember to try their signature conch chowder, and don’t miss the chance to unwind at their unique marina lounge, featuring grass-thatched dining huts over the water.

A guide to the Alligator Farm & Zoological Park

Things To Do at the Alligator Farm Zoological Park

When visiting the Alligator Farm Zoological Park, there are a plethora of activities to engage in and sights to behold. Guests can immerse themselves in the captivating Wildlife Show, where they’ll witness the mesmerizing behaviors of various animal species. For thrill-seekers, the zipline offers an exhilarating journey through the zoo, providing a unique perspective of the park’s expansive grounds. Explore the diverse exhibits, including the rare albino alligators and the immersive “Birds of Africa” exhibit, which transports visitors to the heart of the African wilderness. Delve into the tranquil surroundings of the Wading Bird Rookery, where the majesty of nature unfolds before your eyes. Discover the endearing sloths at Sloth Landing and marvel at their gentle movements and charming personalities. For those seeking unforgettable animal encounters, the Alligator Farm Zoological Park offers a range of immersive experiences, allowing guests to connect with wildlife in meaningful ways. Join in on one of the park’s fun Zoological Park Events to further enrich your visit and create lasting memories with family and friends.

historical sites in St. Augustine

Things To Do at Castillo de San Marcos

During your two days in St. Augustine getaway, immerse yourself in the captivating experiences offered at the Castillo de San Marcos. Explore the soldier quarters, prisoner cells, and expansive interior courtyard, each corner steeped in history. Ascend to the gun deck for panoramic city views or engage in the fascinating daily programs and ranger-led tours, gaining insight into the fort’s past. Don’t miss the riveting cannon firings and weaponry demonstrations, which bring the fortress to life with the echoes of its military past. With its intricate masonry, historic exhibits, and timeless allure, the Castillo de San Marcos promises a memorable and enriching visit for all.

Youth Archaeological Park

Things To Do at the Fountain of Youth

During your two-day St. Augustine getaway, immerse yourself in the wonders of the Fountain of Youth Archaeological Park. Step into the Planetarium and gaze at the stars, or visit the Native Timucua Village to learn about indigenous culture. Watch a cannon firing demonstration and marvel at Spanish exploration on the two-story high Discovery Globe. Discover the significance of the 1565 birthplace of European America and enjoy a leisurely picnic under the oak trees or at the snack bar. Take in panoramic views from the 600 ft long observation platform over the marsh and quench your curiosity by drinking from the legendary waters at the Spring House. Explore the Native Christian Burial Ground and delve into the archaeology exhibit to deepen your understanding of this historic site.

Where to Eat: (Dinner)

The Columbia Restaurant

The Columbia Restaurant, Florida’s oldest eatery, is nestled in the heart of St. Augustine, a city steeped in history since 1565. Known for its authentic Spanish cuisine, Columbia offers an unforgettable dining experience. While visiting, don’t miss indulging in Mojo’s Tacos for a Mexican flair or opting for a healthy dinner at Crave. These culinary experiences, paired with the historical charm of St. Augustine, make for an enriching visit.

The Raintree Restaurant

The Raintree Restaurant, nestled in the heart of historic St. Augustine, is renowned for its intimate dining experience. It serves American cuisine with a touch of international flair presented in a Victorian-era setting that is both elegant and romantic. Visitors can indulge in a fine selection of steaks, seafood, and poultry dishes accompanied by an impressive collection of wines. The restaurant’s charming ambiance, accentuated by its lush garden and soft candlelight, makes it an ideal location for a memorable evening. Don’t forget to explore the beautiful artwork adorning the walls, adding to the overall charm of this exceptional dining experience.

Lighthouse in St. Augustine

Things To Do at the St. Augustine Lighthouse

The St. Augustine Lighthouse, an iconic brick structure, offers an exhilarating self-guided climb up its 219-step spiral staircase leading to breathtaking vistas. Visitors can also partake in guided tours, including the eerie Dark of the Moon ghost tour or the informative Lighthouse Keeper’s tour. The on-site Heritage Boatworks museum showcases boatmaking traditions through engaging demonstrations, making it a perfect addition to your St. Augustine weekend getaway. Diverse daily programs educate about maritime navigation, lighthouse operations, shipwreck tales, and underwater archaeology. Not to be missed is the monthly Sunset Moonrise tour, presenting a stunning celestial transition as the sun sets and the full moon rises over the Atlantic. Get ready to immerse yourself in a captivating blend of history, science, and nature at this notable landmark in St. Augustine.


How can I spend two days in St. Augustine?

For a two-day trip in St. Augustine, start with a visit to the iconic St. Augustine Lighthouse, where you can experience breathtaking city views from its 219-step spiral staircase and explore the maritime exhibits in the Keeper’s House. Then, head to the Fountain of Youth Park to delve into the city’s rich history. On day two, enjoy a meal at the Columbia Restaurant, Florida’s oldest eatery, known for its authentic Spanish cuisine. Later, unwind at the Raintree Restaurant with its intimate dining experience. Make sure to fit in a visit to Potter’s Wax Museum and hop on the Old Town Trolley Tour.

What is the most famous street in St. Augustine?

The most famous street in St. Augustine is St. George Street. A pedestrian-only thoroughfare in the heart of the Historic District, St. George Street is lined with original and reconstructed colonial buildings housing a variety of shops, restaurants, and museums. It’s a bustling hub of activity and offers a unique blend of history and modern amenities, making it an essential destination to explore in St. Augustine.

Is Downtown St. Augustine walkable?

Yes, Downtown St. Augustine is highly walkable. The city’s layout, particularly in the Historic District, is compact and pedestrian-friendly. The most famous street, St. George Street, is a pedestrian-only thoroughfare lined with shops, restaurants, and museums. Additionally, many significant landmarks are within convenient walking distance. Walking also allows visitors to truly absorb the city’s rich history, architectural charm, and atmosphere. However, for those who prefer not to walk, there are several other transportation options available, including trolleys and horse-drawn carriages.

What is the main shopping street in St. Augustine?

The main shopping street in St. Augustine is St. George Street. It’s a pedestrian-only thoroughfare in the heart of the city’s Historic District. This bustling hub of activity is lined with a mix of original and reconstructed colonial buildings, which house a wide variety of shops, boutiques, galleries, and restaurants. Whether you’re searching for unique souvenirs, artisan crafts, or stylish fashion, you’ll find it on St. George Street. St. Augustine’s fusion of historical significance, cultural diversity, and contemporary conveniences positions it as an enticing destination for shopping enthusiasts in the area.

Does Crescent Beach have clear water?

Yes, Crescent Beach in St. Augustine is renowned for its crystal-clear waters. This natural beauty is complemented by the beach’s soft white sand, making it an ideal spot for swimming, sunbathing, and beachcombing. As with any beach, clarity can be affected by weather and tidal conditions, but typically, the water at Crescent Beach is clear and inviting.


Potter’s studio is where the magic happens! Every part of the process except for fiberglassing the body is done here. Figures are sculpted, painted, dressed, and detailed in view of guests.


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