Itinerary: 24 Hours in the USA’s Oldest City, St. Augustine, Florida

St. Augustine is a small city on Florida’s northeast Atlantic Coast. Founded in 1565 (yes, a whopping 200 years before the USA was founded!), St. Augustine’s claims to be the United States’ oldest city and is loaded with early American history. Today, the town is quite charming, offering visitors a walkable old town, gorgeous Spanish Architecture, including a castle(!), and tranquil beaches. St. Augustine makes a fun weekend getaway or a stop on a longer Florida itinerary. One could easily spend several days in and around St. Augustine, but if you only have 24 hours, this itinerary is for you!  Based off my recent weekend in St. Augustine, this post explains how you can make the most of St. Augustine in 24 hours!

The group at Flagler College’s Dining Hall during our 24 hours in St. Augustine. And that is, indeed, Tiffany stained glass behind us!

WALKING ST. AUGUSTINE’S OLD STREETS

Begin your time in St. Augustine on Aviles Street, aka the city’s oldest street, preferably in the morning to avoid the crowds of tourists and get the best pictures (without said tourists). There is nothing you really must “do” on Aviles except walk and take in the old timey sites (Aviles Street really leans into its status as “oldest street”). When you reach Plaza de la Constitución, what I would describe as one of St. Augustine’s main squares, walk up to the water to view the Medici Lion Marble Statutes (copies of the real Italian ones) guarding the draw bridge and then circle back to Plaza de la Constitución to view its gorgeous Oak Trees with Spanish Moss and the Cathedral Basilica of St. Augustine, which is a very beautiful and old Catholic Church. It still holds mass every Sunday if you are interested.

St. Augustine – the oldest city in the USA.

Turn right just past the Cathedral onto St. George Street and stroll down this pedestrian-only street (much of it anyway). St. George Street is the place to find lots of tourist shops (some pretty trashy honestly), some local boutiques, loads of restaurants, coffee shops and bars, and, frequently, buskers playing live music. Like Aviles Street, there is nothing really to “see” on St. George Street until you reach the opposite end, where you will find the U.S.’s Oldest Wooden Schoolhouse. And just as its named, this building claims to be the oldest wooden schoolhouse in the U.S. The schoolhouse is still standing and you can go inside for about $7 USD. We just walked by the exterior, but lots of people were going inside. You can spend as little or as much time on St. George Street as you desire. It is more tranquil in the morning, getting more crowded as the day goes on and a bit rowdy at night.

The start of St. George Street (near Plaza de la Constitución).

LUNCH BREAK AT THE FLORIDIAN

After a morning stroll, you will likely have worked up an appetite and while there are a hundred restaurants in and around St. George Street, I suggest The Floridian. The Floridian is only a 3 minute walk from St. George Street, but feels further away in that its quiet and local. The Floridian offers indoor and outdoor seating, serves local food, and features a lot of alligator-inspired decor in the restaurant – very Florida in the best way. I enjoyed a delicious Pimento Cheese BLT with house-made tortilla chips and an incredible Strawberry and Sour Cream Pie (this pie was a highlight of the entire weekend!).

One of the many alligator portraits at The Floridian. 

My Pimento Cheese BLT at The Floridian.

The Strawberry and Sour Cream Pie.

FLAGLER COLLEGE HISTORIC TOUR

Pre-book tickets for the Flagler College Historic Tour in the afternoon. And no, this is not a “college tour” that you would take in high school before selecting a college. Rather, this is an art, history and architecture tour. Flagler College is a college in the historic center of St. Augustine, founded by businessman Henry Flagler, located inside the former grand Hotel Ponce de Leon. This tour is limited to 10 people, lasts a little over an hour, and gives visitors a detailed glimpse into this historic college, largely focused on the history and architecture from when the college was the Hotel Ponce de Leon. The highlight of the tour are the incredible Tiffany stained-glass windows and chandeliers. You can only see most of the stained glass and chandeliers on the tour.

One of the Tiffany stained glass windows at Flagler College. This is one of the few that the public can view without a tour, located at 74 King Street (in the walkway between Cordova Street and the West Lawn).

More stained glass on the Flagler College historic tour.

The Dining Hall at Flagler College.

The famed rotunda at Hotel Ponce de Leon (now Flagler College).

The former Hotel Ponce de Leon.

The Frog Fountain at the former Hotel Ponce de Leon. The middle represents a Spanish sword in a rock.

LATE AFTERNOON WATER ACTIVITIES

Spend the late afternoon enjoying St. Augustine’s seaside location. There are numerous options, including a sunset cruise, a beach stroll, or actually getting in the water.

Boats in St. Augustine. The famous drawbridge is in the background.

DINNER AND DRINKS IN HISTORIC ST. AUGUSTINE

Have dinner at St. Augustine Fish Camp in the historic center. Fish camp is a small Northern Florida chain, with this location opening in 2020. The menu is heavy on seafood, serving “old favorite entrees with creative, new twists.” We dined here, and the food was excellent. The Pimento Cheese was incredible, as was the Deviled Crab and the desserts. Reservations highly recommended.

The Spicy Pimento Cheese Spread at Fish Camp.

Cool wine glasses at Fish Camp.

And if you are not a fan of seafood, have dinner instead at the Meehan’s Irish Pub & Seafood Restaurant. Meehan’s is an adorable Irish Pub on the water very close to the Castillo San Marcos. I only had Guinness here, which was wonderful, but the food smelled delicious and the menu offers much more than seafood. Meehan’s also quite popular. I suggest a reservation.

Meehan’s Irish Pub.

The cute interior of Meehan’s Irish Pub.

A pint of Guinness at Meehan’s Irish Pub.

SECOND MORNING AT THE OAK CANOPY (AND POSSIBLY THE FOUNTAIN OF YOUTH IF YOU’RE FEELING TOURISTY)

Start your second morning at the St. Augustine Oak Canopy on Magnolia Street, which is simply stunning. By far, my favorite thing about St. Augustine. Go as early as possible for pictures without the crowds. I would also note that this is about a 15 minute walk outside of St. Augustine’s historic center. Most people will want to take a car or the green tourist train, which stops here regularly.

St. Augustine Oak Canopy.

I would also note that the St. Augustine Oak Canopy is located just outside the Fountain of Youth Archeological Park. We intended to go inside the Park and view the Fountain of Youth but the exterior resembled a D-list Disney, advertised “real” Sangria (always a red flag) and cost $30 USD to enter. We opted to skip it.

Fountain of Youth Park.

The “Classic Sangria” advertisement.

CASTILLO DI SAN MARCOS

After the Oak Canopy, venture back to St. Augustine’s historic center (via foot, car or tourist train) to tour the Castillo di San Marcos National Monument. Castillo di San Marcos is a 1600s-era fortress built by the Spanish in 1672. While it is just a fort without much on the inside, the upper level offers great views of the surrounding area and the Matanzas River. We only spent about 20 minutes in the Castillo (we were in a hurry), but we easily could have stayed for an hour. They also shoot off real canons at 10 AM on Sunday (and maybe other days!).

The Castillo di San Marcos from the outside.

Entering the Castillo.

ST. AUGUSTINE PIRATE & TREASURE MUSEUM

Next, literally walk across the street to the St. Augustine Pirate & Treasure Museum. Now, this museum sounds like a bit of a tourist trap AND a bit of a child-friendly attraction (neither my style), but, it is home to one of only two (or possibly three) remaining Jolly Roger flags. My inner Pirates of the Caribbean personality just had to see it. Entrance costs $19 per person, and the museum is surprisingly great! And while it is totally family friendly, the museum is also super interesting and had loads of real pirate artifacts and that Jolly Roger flag. I would note that the museum may be a bit scary for younger guests.  Plan at least an hour for this museum.  Highly recommend for those interested in pirate lore, or those in need of AC after the Castillo!

A real Jolly Roger flag!

ST. AUGUSTINE DISTILLERY

End your St. Augustine tour with a visit to the St. Augustine Distillery, which makes its own vodka, whiskey, rum and mixers. St. Augustine Distillery offers a few for-pay tours and classes, but the most common visit is the self-guided tour, complete with four sample cocktails. I was iffy on the self-guided part before our visit, but it ended up begin very easy to navigate and the four sample cocktails were on the route. Very fun! I highly recommend this tour for drinkers in St. Augustine.

St Augustine Distillery!

St. Augustine Distillery’s rum.

LATE LUNCH AT THE ICE PLANT BAR

End your St. Augustine stay with lunch at the Ice Plant Bar, which is attached to the St. Augustine Distillery (despite the two not being associated aside from sharing a building) . We enjoyed cocktails and brunch here. The menu was local American fare. I definitely mis-ordered with the Mortadella Eggs Benny (it was bologna – NOT mortadella) but everyone else loved their fish sandwich.

Pimento Cheese spread at the Ice Plant Bar.

Eggs Benedict at the Ice Plant Bar.

WHAT WE MISSED IN ST. AUGUSTINE

First, we missed the Fountain of Youth. Actually, as discussed above…

Second, we missed the Lightner Museum, which we would have love to have visited if time permitted. The Lightner Museum is across the street from Flagler College and is equally beautiful

WHERE WE STAYED IN ST. AUGUSTINE

We stayed at the Spark by Hilton in the Historic Center of St. Augustine. This decision was an easy one, as we had a promo with Hilton and this was the least expensive Hilton in the area. The location was great – within walking distance to everything in historic St. Augustine – but checkin was not until 4 and the staff was not super welcoming. Our room was nice and due to our Diamond status, we were upgraded to a room with a small balcony. The hotel also has a small pool on site that we did not use.

View of St. Augustine from the Spark by Hilton.

Going back, I would LOVE to stay at Casa Monica, but rates were insane during our visit (which may have spanned Spring Break).

GETTING TO AND AROUND ST. AUGUSTINE

St. Augustine is right off I-95, making it easily reachable by car. The closest airports are Daytona Beach (very small, Breeze flies there), Jacksonville (45 minutes by car) and Orlando (2 hours).

Once in St. Augustine, most everything in the historic center is walkable. A tourist train runs between the sites for those not wanting to walk, and Uber is readily available. For-pay parking is available in the historic center of town.

STEAL THIS ITINERARY

The Floridian: 72 Spanish St #3638, St. Augustine. Closed Tuesday. Open Wednesday – Monday 11 – 9 (until 10 on Friday and Saturday). Casual. Reservations recommended.

Flagler College Historic Tour: 74 King St B, St. Augustine. Tours are at 10 and 2 daily. $14 USD per person. Recommend buying tickets in advance. $23 USD per person.

Fountain of Youth Archaeological Park : 11 Magnolia Ave, St. Augustine. Open daily 9 – 5.

Castillo de San Marco: 11 S Castillo Dr, St. Augustine. Open daily 9 – 5. $15 USD per person. This reminded me a lot of the Spanish forts we have seen in Puerto Rico!

St. Augustine Pirate & Treasure Museum: 12 S Castillo Dr, St. Augustine. Open daily 10 – 7. $19 USD per person (discounts available for seniors, children, etc.).

Fish Camp St. Augustine: 142 Riberia St, St. Augustine, FL 32084. Open Tuesday – Sunday 11:00 – 9:00 (until 10:00 Friday and Saturday). Open Monday 4:00 – 9:00. Reservations suggested.

Meehan’s Irish Pub & Seafood House: 20 Avenida Menendez, St. Augustine. Open daily 11 – 11 (until 12:30 on Friday and 1:30 on Saturday).

St. Augustine Distillery: 112 Riberia St, St. Augustine. Free self-guided tour and tasting.

The Ice Plant Bar: 110 Riberia St, St. Augustine. Open daily 11:30 (opens at 10 on Saturday & Sunday) – 12 (until 2 on Friday & Saturday).

Spark by Hilton St. Augustine Historic Center: 42 San Marco Ave, St. Augustine.

2 thoughts on “Itinerary: 24 Hours in the USA’s Oldest City, St. Augustine, Florida

  1. I really enjoyed this travel blog. When I lived in Daytona Beach we would do day trips to St Augustine, 1976, Fountain of Youth park was free

    • LOL, not free anymore! Dan’s Nonni lived in Daytona Beach for years – she loved it! St. Augustine is a nice little town. I enjoyed it a lot.

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