Preparing for Your Dream Vacation in St. Augustine

Welcome to St. Augustine, Florida—a city where history whispers from every corner and the ocean breeze rejuvenates your spirit. As the oldest city in the United States, St. Augustine isn't just a vacation destination; it's a vibrant, living museum with a stunning array of historical sites, breathtaking beaches, and a warm local culture. Here's what you need to know to prepare for a vacation that feels like stepping into another world, yet feels right at home.

Section 1: Understanding St. Augustine's Rich History

St. Augustine is a treasure trove of history, established in 1565 and rich with stories of the past. Key landmarks include:

Castillo de San Marcos: An impressive 17th-century fort offering panoramic views and a deep dive into colonial history.

Flagler College: Originally built as a luxury hotel by railroad magnate Henry Flagler, this stunning campus blends educational pursuits with architectural beauty.

Lightner Museum: Housed in the former Alcazar Hotel, this museum showcases collections of fine and decorative 19th-century art.

Tips for History Buffs: Join guided historical tours or reenactment events to fully immerse yourself in the old-world charm of St. Augustine. Early mornings or late afternoons offer a more personal experience at popular sites in the historic district.

Section 2: Discovering the Natural Beauty

The natural scenery in St. Augustine is as rich in beauty as the city is in history. Not-to-be-missed beaches include:

St. Augustine Beach: Located just four miles from St. Augustine's historic downtown, St. Augustine Beach is celebrated as the 17th best beach in the U.S. by Tripadvisor's 2023 Traveler's Choice Awards. Notable activities include enjoying tropical drinks at beachfront restaurants, various water sports, and exploring the excellent surf breaks near the St. Johns County Ocean & Fishing Pier. This main hub offers extensive amenities like free parking, a splash park, and picnic areas, plus it hosts a weekly farmer’s market and summer evening concerts. The pier and A Street serve as key access points to the beach, with additional walk-only paths available from other streets in the area.

Anastasia State Park: Anastasia State Park is a pristine preserve that offers a rich blend of natural beauty and recreational activities. This state park spans over 1,600 acres and boasts four miles of spectacular sandy beaches, making it a perfect destination for swimming, sunbathing, and beachcombing. It is also home to a diverse array of wildlife and offers numerous activities such as bird watching, hiking, and kayaking. Visitors can explore the ancient sand dunes, bike along the park's multi-use trails, or fish in the salt marshes. The park’s full-facility campground provides an excellent opportunity for those looking to stay overnight. Ideal for families and nature enthusiasts alike, Anastasia State Park serves as a peaceful escape into Florida’s coastal wilderness.

Vilano Beach: Vilano Beach, located at the confluence of the Tolomato River and the Atlantic Ocean in Northern St. Augustine, is known for its Art Deco charm, steep surf, and strong currents, making it a prime spot for surfing near 2725 Anahma Drive. The area extends to Porpoise Point, popular for fishing, sunbathing, and water sports, offering views of the St. Augustine Lighthouse and the historic downtown skyline. Nearby, the Vilano Beach Pier serves as a fishing and event locale, with amenities like a floating dock for boats and the St. Augustine Water Shuttle connecting to historic downtown. The vicinity also features fine dining, a large grocery store, and shops for essentials.

Outdoor Adventures: Try kayaking through the mangroves, paddle boarding along the Intracoastal Waterway, or joining an eco-tour to explore local wildlife. The best times to visit for ideal weather are spring (March to May) and fall (September to November).

For information on other local beaches, you can check them out here.

Section 3: Navigating Your Stay

Choosing the right accommodations can enhance your vacation experience:

Beachfront Resorts: Offer stunning ocean views and easy beach access.

Historic Inns: Located downtown, these inns provide a cozy, intimate setting.

Vacation Rentals: Looking for more privacy and an at-home atmosphere for your vacation? St. Augustine has a myriad of short term vacation rentals throughout the historic district and near the beach, which can be found through a simple search on Airbnb or Vrbo.  

Booking Tips: Plan and book your stay well in advance, especially if you're visiting during peak seasons (summer and major holidays). For transportation, renting a car provides the most flexibility, but biking is a great way to soak in the local scenery. Rideshare services like Uber and Lift are also available. 

Section 4: Culinary Delights and Shopping

St. Augustine’s culinary scene is a delightful mix of old-world tastes and modern flavors. Be sure to visit:

Columbia Restaurant: The Columbia Restaurant in downtown St. Augustine stands out as a historic gem celebrated as "One of Florida's Top Restaurants" since 1967. Nestled in the heart of the historic district, this esteemed establishment is renowned for its rich culinary heritage and authentic Spanish cuisine. As the oldest restaurant in Florida, Columbia has captivated diners with its charming ambiance and traditional dishes that echo the flavors of Spain. The restaurant's commitment to excellence is showcased in its meticulous service and a menu that offers a taste of history with every dish served. Visitors to Columbia Restaurant are not just dining; they are partaking in a storied tradition that continues to be a cornerstone of Florida's culinary scene.

St. George Street: St. George Street, nestled in the heart of historic St. Augustine, offers a charming glimpse into the past, making it a must-visit destination for both history enthusiasts and casual explorers. This pedestrian-only thoroughfare is lined with a mixture of original and reconstructed buildings dating back to the Spanish colonial era, each telling a unique story of the oldest European-established city in the United States. Visitors can stroll leisurely along the cobblestone paths, browsing through quaint shops that offer everything from handmade crafts to boutique fashion. Along the way, numerous cafes, restaurants, and historical sites such as the Oldest Wooden Schoolhouse enrich the journey, providing a picturesque and educational experience that captures the essence of St. Augustine's rich heritage.

Seafood Dining Options: In St. Augustine, FL, seafood lovers can revel in a variety of top-notch dining options. The St. Augustine Fish House & Oyster Co. offers a cozy, casual atmosphere where diners can indulge in freshly shucked oysters and traditional seafood dishes. For those looking for a more upscale experience, Collage Restaurant presents an array of gourmet seafood entrees, complemented by a fine wine selection. Another must-visit is the Blackfly Restaurant, known for its creative cuisine and artful presentations, providing a modern twist on classic seafood fare. All of these establishments are celebrated for their quality dishes, unique flavors, and delightful dining atmospheres, making them prime destinations for seafood enthusiasts visiting this historic city. For other seafood restaurants, you can check out the seafood restaurant directory of St. Augustine for the full list.

Shopping and Souvenirs: Explore Aviles Street for art galleries and local crafts, and don't miss the St. Augustine Outlet Mall for great deals. Aside from these locations, there are other dining selections that would fit your every palate.

Section 5: Planning Your Itinerary

Creating a balanced itinerary that suits your travel style is key to a memorable vacation. Consider these ideas:

Family Fun: St. Augustine offers a delightful array of family-friendly activities that cater to both fun and educational experiences. Explore the historic Castillo de San Marcos, where children can marvel at the old fort and learn about the city’s past. The St. Augustine Alligator Farm Zoological Park provides an exciting adventure among various species of alligators and other wildlife. For a more interactive experience, the Pirate and Treasure Museum offers a glimpse into the age of piracy with hands-on exhibits. Families can also enjoy the scenic beauty of Anastasia State Park, perfect for a relaxing day of swimming, kayaking, and picnicking. Each of these destinations provides a unique opportunity to create lasting memories with your family in the charming setting of St. Augustine. For more family-oriented activities, you can check out our list here.

Romantic Getaway: St. Augustine is brimming with romantic spots and activities that make for a perfect date night. Couples can stroll along the picturesque beaches at sunset, explore the historic streets of the Old City, or enjoy a leisurely boat ride along the Matanzas River. For a taste of local culture, visiting the Lightner Museum, housed in the former Alcazar Hotel, offers an elegant backdrop of art and history. Dining by candlelight in one of the city’s charming restaurants, such as Collage or Michael's St. Augustine, adds a touch of romance to the evening. To cap off the night, couples can take a ghost tour through ancient streets, adding a thrill to their romantic escape in this enchanting city. Check out our list of local date night recommendations to enjoy St. Augustine more.

Cultural Deep Dive: St. Augustine, the oldest city in the United States, offers a rich tapestry of cultural experiences, blending historical depth with vibrant artistic expressions. Visitors can explore iconic historical sites.  Art lovers will appreciate the numerous local art galleries that dot the city, showcasing both contemporary works and traditional pieces. The city's cultural festivals are a highlight as well, like the St. Augustine Music Festival or Nights of Lights , which transforms the city into a luminous wonderland every winter. These elements make St. Augustine not just a hub for history enthusiasts, but a dynamic locale where art and culture flourish. If you want to maximize your trip, you can visit hidden gems in St. Augustine that not too many people are aware of.

Event Planning: Check out our events page for festivals, concerts and other special events that could highlight your visit.

Conclusion

St. Augustine is more than just a place to visit; it's an experience to be lived. With careful planning and a spirit of adventure, you can uncover the authentic charm of this historic city. Whether you're basking in the sunlit shores or walking through ancient halls, St. Augustine promises a journey not just into the past, but into new memories you'll cherish forever.