Exploring the Charms of Saint Augustine : A Complete Travel Guide
Welcome to the enchanting city of Saint Augustine, Florida, where history comes alive amidst cobblestone streets, colonial architecture, and stunning coastal beauty. As the oldest continuously inhabited European settlement in the United States, this picturesque destination offers a unique blend of historical significance, cultural treasures, and natural wonders (aka: beach). My best friend, Carla, and I both turn 30 this year and decided to take a girl’s trip to celebrate our slide into a new decade. We both wanted something semi-tropical where we could relax and enjoy the sunshine, while exploring a new city for the both of us.
After doing some research, Florida seemed like the best option (duh, beaches) and Saint Augustine had recently been voted one of the cutest small towns in America by Southern Living. So, of course, we decided to make our destination official. Our weekend in Saint Augustine was charming! Although we spent most of our time lounging and relaxing at our hotel, I felt like we were still able to explore quite a bit.
A few notes (and shocks?) from your gals, Hope & Carla:
Saint Augustine is as beautiful as it is touristy. Expect both. Gorgeously renovated southern homes with 30-foot palm trees and lush courtyards co-existing with fanny packs and orthopedic sneakers. I’m sure you’re thinking, “But Hope … more touristy than Savannah or Charleston?” Maybe not; however, the square footage area of the city is smaller which makes it feel more crowded with tourists. To combat feeling crowded, I’d HIGHLY recommend prioritizing your hotel/accommodations. We stayed at a historical boutique hotel a block south of the Lightner Museum and it felt like an oasis.
This city can SLING a mocktail. I was officially halfway through my pregnancy when making this trip (so no cocktails for meeeeee), and I was SHOCKED at how many delicious mocktails I was able to get my hands on. The Well (our hotel bar), The Floridian and Catch 27 all had fabulous drinks, which makes me excited to visit again when I can enjoy an adult beverage.
The city is very walkable! We were just a few blocks from the Plaza de la Constitucion, Saint George Street and the harbor. Be sure to pack a solid pair of sandals to walk around in. Heels might be a tad tricky with the cobblestone streets.
Saint George Street can be a total tourist trap (“good people watching” as our concierge politely put it). However, you will find some hidden gems down that well-worn way! It’s also home to some fun live music. We spent one evening walking off dinner and wandering around listening to all the live music acts we could find. The band playing oldies at The Trade Winds Lounge was 10/10!
Where to Stay: The Collector Inn - A Luxury Boutique Hotel
For an unforgettable stay in Saint Augustine, look no further than The Collector Inn. This luxury boutique hotel beautifully combines historic charm with modern comforts. Located in the heart of the city's historic district, The Collector Inn offers elegantly appointed rooms, each showcasing unique décor and an inviting ambiance. The hotel is aptly named as it is situated on the site of the former Dow Museum of Historic Houses and features a collection of restored historic buildings (we’re talking 500 years old). The property has a bar on site called The Well, where I had one of my favorite mocktails (The Florida Sling) as well as a pool, fire pits and shaded verandas. Breakfast is included in your stay, and Carla and I thoroughly enjoyed our slow mornings in the lush courtyard, sipping on a cup of coffee. We LOVED staying here.
Sightseeing and Attractions:
Castillo de San Marcos: Begin your exploration of Saint Augustine with a visit to the majestic Castillo de San Marcos. This 17th-century fortress, built by the Spanish, is an impressive structure made of coquina stone. Take a guided tour to learn about its intriguing history, enjoy panoramic views of the city and the Matanzas River, and witness reenactments of historical events.
St. George Street: Albeit touristy, you’d be amiss to miss. Stroll along the vibrant St. George Street, the city's pedestrian-only thoroughfare. Lined with charming shops, art galleries, and delightful cafes, this street offers a glimpse into Saint Augustine's lively atmosphere and provides ample opportunities for unique souvenirs and culinary delights.
Aviles Street: The oldest street in the nation! The cobblestoned streets are lined with sidewalk cafes and local art galleries. We enjoyed popping in and out of galleries while stopping to read all of the historical markers.
Lightner Museum: Housed in the former Alcazar Hotel, the Lightner Museum is a treasure trove of art, history, and curiosities. Marvel at the extensive collection of Gilded Age artifacts, including Victorian art, antique musical instruments, and stained glass pieces. We didn’t actually tour the museum, but we did enjoy wandering through their courtyard and watching staff set up for different rehearsal dinners and weddings. It’s a popular venue and for good reason! The building is gorgeous.
Flagler College: Admire the architectural splendor of Flagler College, a masterpiece of Spanish Renaissance Revival design. Once a luxurious hotel, it now serves as a prestigious liberal arts college. There is an option to take a guided tour to appreciate the grandeur of the Ponce de Leon Hall, with its breathtaking rotunda and Tiffany stained-glass windows (WOWZA). OR. You could also admire the architecture from outside while you walk to Mayday Ice-Cream.
Vilano Beach: Carla and I are both land-locked girlies, so we made a mad dash for the beach on Saturday morning. Vilano Beach is just ~15 minutes away from downtown Saint Augustine and an easy drive. There are public beach access spots where you can park and settle in. We arrived early enough to snag a good parking spot and spend enough time in the sun for Carla to earn her inaugural summer sunburn. Be sure to look for colorful seashells!
food & drink:
Columbia: Indulge in a culinary journey at Columbia, a legendary restaurant that has been serving Spanish and Cuban cuisine since 1905. Located on St. George Street, Columbia delights diners with a vibrant ambiance, live flamenco dancing, and an extensive menu featuring signature dishes like paella and 1905 Salad (the star dish of our meal).
Catch 27: For a taste of fresh seafood and farm-to-table delights, head to Catch 27. This cozy eatery sources ingredients locally, ensuring the highest quality and supporting the region's sustainable food movement. Savor dishes like shrimp and grits (Carla’s favorite meal of the trip) and be sure to order their deviled eggs with fried oysters (MY favorite dish of the trip). Be sure to request patio seating to really enjoy the atmosphere.
The Floridian: Trendy tiki bar meets Florida beach fresh food and a killer outdoor patio = The Floridian. Carla and I stopped in here for a light lunch after spending our morning at the beach. It was the perfect afternoon meal on a warm Florida day.
Mayday Ice-Cream: Hand-crafted ice-cream located in the heart of downtown Saint Augustine, this parlor was recommended to us by multiple locals for a sweet afternoon treat. Their inventive flavors were fun (and delicious!) to taste test. We would highly recommend.
Ice-Plant Bar: A trendy farm to table restaurant and bar featuring an inventive and fresh menu, craft cocktails & mocktails was at the top of our brunch list. Our hotel concierge HIGHLY recommended this spot for any meal as a local insider. We ended up pivoting on Sunday brunch plans and just enjoying a slow breakfast and cup of coffee at the hotel. However, it will be my first stop when I return to visit.
For more on our Saint Augustine adventures, check out these videos!
Saint Augustine Day One // Girl’s Trip
Saint Augustine Saturday // Girl’s Trip
Happy trails!
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