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Castillo to Colonial Streets in Historic St. Augustine

By: TLP's Partners

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A Two-Day Itinerary in Historic St. Augustine, Florida

Discover the captivating charm of historic St. Augustine, Florida, the oldest city in the United States. With its cobblestone streets, centuries-old architecture, and rich cultural heritage, this coastal gem offers a unique blend of history and relaxation. From exploring ancient forts to indulging in culinary delights, St. Augustine promises an unforgettable vacation experience.

Tasting and Touring Your Way Through Historic St. Augustine

Day 1

Start your day at The Kookaburra, a cozy coffee shop and bakery. Grab a fresh-brewed coffee, tea, or a hot chocolate to pair with one of their famous pastries or breakfast sandwiches. After fueling up for the day, visit the St. Augustine Lighthouse and Maritime Museum for a unique and interactive experience. Climb to the top of the lighthouse, explore the museum’s exhibits, and learn about the city’s maritime history.

After exploring, head to The Floridian for lunch. This farm-to-table restaurant offers Southern-inspired fare using locally sourced ingredients. Try their famous datil pepper chicken wings, shrimp and grits, or vegetarian black bean cakes for a satisfying meal. In the afternoon, spend some time exploring the Flagler College campus. Take a tour with a student guide and learn about the history of this former luxury hotel. Admire the Spanish Renaissance architecture and the ornate details of the buildings.

After your tour, wander down to Michael’s for an upscale dining experience, where you can enjoy authentic Spanish tapas, fine wines, and craft cocktails. Savor dishes like the stuffed squid, steak tartare, or their famous paella. End your day with a leisurely stroll down St. George Street, a pedestrian-only street filled with charming shops, restaurants, and historic buildings.

Day 2

Kick off the day at The Blue Hen Café, where the emphasis is placed on hearty breakfasts made with locally sourced ingredients. Try their banana bread French toast, biscuits and gravy, or egg and bacon sandwich for a satisfying start to your day. Afterward, visit the Lightner Museum and explore the collection of fine and decorative arts, including Victorian-era artifacts, Tiffany stained glass, and musical instruments while admiring the grandeur and architectural beauty of the building.

For lunch, head to Back 40 Urban Cafe, a specialty sandwich and pizza shop with a laid-back ambiance. Try their namesake, the Back 40, a goat cheese and pesto sandwich, or their vegan spinach pizza for a divinely flavorful break. Next, take a guided tour of the Old Jail, a preserved 19th-century jail that offers a glimpse into the harsh conditions of the past. Learn about the criminals who were once held here and hear stories of their daring escapes.

Cap off your trip with a garden-to-table dinner at The Raintree Restaurant. The restaurant is housed in a beautiful historic building with a cozy ambiance and a serene garden, making it the perfect setting to enjoy a nice steak dinner or pasta dish. After dinner, set out on a ghost tour to explore the haunted past of America’s oldest city. Take a nighttime walking tour of the Old City with an experienced guide embellishing historic facts with chilling stories of the city’s paranormal visitors.

Plan your visit to St. Augustine