Situated along the shores of the Matanzas River, St. Augustine is so much more than just the oldest continuously occupied settlement in the United States. Along with its deep history, it has a great deal of natural beauty to appreciate as well. We spent a weekend in Saint Augustine to visit this historic city. Walking around town on the cobblestone streets makes it feel as if you are in another country.
Where to Stay:
Brenda and I stayed at The Casablanca Inn. This inn is a restored 1914 Mediterranean revival inn located just across the street from Matanzas Bay. The hotel’s location on the waterfront makes it an ideal destination for those wanting to spend a weekend and discover all that Saint Augustine has to offer. It will be our home base for our weekend in Saint Augustine.
Where to Eat:
The Oasis:
The World Famous Oasis is a Saint Augustine Beach staple through and through. This restaurant serves traditional hamburgers, sandwiches, munchies, seafood, and salads. It has a casual and comfortable beach vibe environment to be enjoyed. They even serve breakfast.
Harry’s Seafood
Harry’s Seafood offers New Orleans-inspired dishes, all of which are delicious, and I always recommend sitting outside. The lush greenery and string lights adorning the space added a beautiful and romantic feel to our experience. It must have worked because I later popped the question to Brenda on a carriage ride around the city. Harry’s has other locations in Florida. We visited downtown Gainesville and had dinner at that location too. Click the link for our visit to Historic Gainesville, Florida.
Columbia Restaurant:
The Columbia Restaurant is one of Saint Augustine’s most popular restaurants. The original Columbia Restaurant, in Tampa’s Ybor City, is Florida’s oldest restaurant. The restaurant serves lunch and dinner in dining rooms adorned with hundreds of hand-painted tiles and Spanish-style fountains. Make sure to get the sangria pitcher!
Raintree Restaurant:
The Raintree Restaurant is the perfect date night spot. It’s located in a beautiful Colonial Victorian-style home on San Marco with a large courtyard. You can enjoy the evening air outside or at an intimate table indoors while you dine on pasta, steak, and seafood.
Crucial Coffee Cafe:
For delicious baked goods and freshly brewed coffee, visit the Crucial Coffee Cafe in St. Augustine. This cute coffee shop is conveniently located in the heart of St. Augustine’s historic district. Crucial Coffee is a charming place to stop for a cup of coffee or refreshments.
What to do:
Take a Tour on the Old Town Trolley
From the Fountain of Youth to quaint St. George Street, the St. Augustine Old Town Trolley takes you to all the major neighborhoods and attractions. Old Town Trolley Tours has the largest fleet of trolleys in the city! So when you hop off, spend a few hours (or even just a few minutes) at any of the stops, you won’t have to wait too long for the next trolley. The tours are narrated, and you can learn a lot about the city. It’s a great way to get a feel for where everything is.
Visit Castillo de San Marcos National Monument
Built by the Spanish in St. Augustine to defend Florida and the Atlantic trade route, Castillo de San Marcos National Monument preserves the oldest masonry fort in the continental United States and the oldest structure in St. Augustine. The fort was constructed using native coquina stone. The fort is a national monument and you can step outside the walls of the fort, hear cannons fly, and be part of reenactments.
Take some time to wander around this massive fort that overlooks the sea on the St. Augustine coast. Walkthrough the numerous rooms that were once home to war soldiers and prisoners.
Out on the large interior courtyard, you’ll see the gun deck and enjoy magnificent views of the city. On Fridays, Saturdays, and Sundays, there are often historic weapon demonstrations, though you’ll want to check in advance before you go for times. Park Rangers and Volunteers in period dress are happy to answer your questions and share stories about the life of the colonists who once lived here. The fort is a National Monument and part of the National Park Service. Stay for a canon and weapons demonstration at the top of the fort. You will hear the cannonballs fly and be a part of reenactments.
Ripley’s Believe It or Not Museum
Experience the bizarre, explore the mysterious, and enjoy the weirdest place in St. Augustine. That’s right, we went to the Ripley’s Believe it or Not Museum.
From shrunken heads to some incredible artwork, the odditorium left us amazed.
Matanzas Bay
If you want to get a unique view of the city and to see the main historical landmarks from a different perspective, a cruise around Matanzas Bay is the ideal way to explore St. Augustine.
Flagler College
Flagler College, which is located in what was once one of Henry Flagler’s most opulent Gilded Age hotels in St. Augustine, is a private four-year college. The college draws students from all over the world to study liberal and fine arts. It’s a beautiful campus that features Tiffany stained glass windows that decorate the dining hall and is a magnificent setting in the nation’s oldest city.
Ghost Tour:
I’d also recommend going on a ghost tour. St. Augustine is the oldest city in the country and much of what you see now was built on Spanish soldier graves so there have been ghost sightings all throughout the city. We took Ripley’s “Spine-Chilling Train Adventure” and made stops at some of the spookiest spots in the City. It makes for a really fun evening listening to the stories. They even take you back to the museum and turn the lights out for a walk around. SPOOKY!
St. Augustine Lighthouse & Maritime Museum
This iconic St. Augustine lighthouse, completed in 1874, offers amazing panoramic views—once you climb all 219 steps of the 165-foot tower, that is. The museum has some fascinating displays that include maritime artifacts and some recent archaeological discoveries.
Visitors to the St. Augustine lighthouse can enjoy some of the best views of the city, learn more about the Nation’s oldest port, and learn how this incredible monument to history played a pivotal role in St. Augustine’s maritime history. The lighthouse stands tall above the beautiful shores of Anastasia Island.
ENJOY A COCKTAIL
There are so many things to enjoy about Saint Augustine. The food and drink scene is one of them! The Casablanca Inn where we stayed had the Tiny Martini Bar. This was a great place to grab a cocktail and people-watch. It is located just across the street from the bay. We sat on the front veranda and enjoyed bay breezes before heading to dinner.
SHOPPING ON ST. GEORGE STREET
St. George Street is the most popular street in the city. Walking through the cobblestone streets and shopping in little locally-owned shops with art, jewelry, and clothing available for purchase!
Saint Augustine is a great choice for a short weekend getaway in Florida. There is so much amazing history here, so much to explore, and so many restaurants to try. Spending the weekend here was just enough to get a feel for the city, but there is so much to see and do here. When we return, we can pick up where we left off and still not see the same place twice.
Have you ever been to St. Augustine? What are some of your favorites!? We would love to hear from you!
