Day Trip to St Augustine: Gilded Age Architecture, Spanish History & Florida Fresh Food!

On my quest to visit…every single place in Florida (it’s going well ; ) I was bound to eventually end up in St. Augustine.

Founded in 1565 by the Spanish, St. Augustine is the oldest continuously occupied settlement in the US. Famous for its rich history (Pirates! The Fountain of Youth!) and Gilded Age architectural gems, St. Augustine’s maze of cobblestone streets is also home to one of Florida’s best local food scenes making it an absolute must on any Florida trip.

Voted “The South’s Best Small Town” in 2023 by Southern Living magazine, I had pretty high expectations. There are few curated travel recommendations I take more seriously than Southern Living. Their travel section is first rate, and honestly, it’s never steered me wrong.

So on my most recent trip to Florida where I visited several new to me spots on the Atlantic Coast, I made sure to carve out a few days for St. Augustine.

Well, long story short…I loved it. St. Augustine is soooo different from any other place I’ve been in Florida and it really does offer a distinctly unique cultural experience.

BUT…if you’re like me and you sometimes have trouble tearing yourself away from the theme parks or the white sand beaches and turquoise waters on the Gulf Coast, I do think it’s possible to see and do a LOT in St. Augustine as a day trip.

Can you spend several days in St. Augustine? Absolutely! But if for whatever reason you find yourself only having one day to explore the “Ancient City,” it’s absolutely worth it.

Day Trip to St. Augustine

St. Augustine is a super easy day trip from quite a few popular spots in Florida:

Orlando to St. Augustine: 107 miles (just over 1.5 hours)

Daytona Beach to St. Augustine: 55 miles (1 hour)

Jacksonville to St. Augustine: 40 miles (45 minutes)

Amelia Island to St. Augustine: 70 miles (1 hour and 15 minutes)

Wherever you’re coming from, here’s how I would spend one day in St. Augustine:

Breakfast at Blue Hen Cafe

Start with a cozy farm to table breakfast at the Blue Hen Cafe. This local neighborhood spot puts a fun Southern twist on breakfast with dishes like bbq pulled pork & grits, blue crab quiche, chicken biscuits, and King’s french toast.

We also really liked the breakfast sandwich with sweet potato home fries and the pumpkin pancakes.

It’s just a small neighborhood spot and it’s really popular with locals so either get there early or be prepared for a bit of a wait.

Flagler College Tour

After a yummy breakfast, head on over to St. Augustine’s downtown historic district to check out what I think is the big draw of St. Augustine: The Gilded Age hotels!

Henry Flagler (the railroad tycoon who was responsible for developing most of Florida), tried his absolute hardest to make St. Augustine a winter destination to rival Palm Beach.

The weather may not be as good year round as it is farther south, but St. Augustine is still home to three original hotels from the Gilded Age (although only one is still operating as a hotel).

The most impressive is Flagler College. Built in 1888, this historic institution (formerly the lavish Ponce de Leon Hotel) is a complete feast for the eyes with its Spanish Renaissance architecture.

You can walk through the outdoor courtyard and marvel at the great hall on your own, but if you want to go farther into the interior, you’ll need to sign up for a guided tour.

Definitely sign up in advance! I goofed around (I couldn’t get the tour to book on my phone and wasn’t super on top of it) and the tours ended up completely sold out for the day I was there. So we had to settle for just poking around outside and in the main hall.

You can book guided tours here. Tours are $17 per person and last one hour. They usually offer at least two tours a day but add quite a few more during busier tourist seasons.

The tour includes the courtyard and grand hall plus the dining room (where you’ll see the 79 Tiffany stained glass windows) and the Flagler Room (formerly the Women’s Grand Parlor). So with the guided tour you’ll get access to TWO rooms that you aren’t able to see if you just show up to poke around on your own.

I’m really bummed that I didn’t get to do the tour when I was here, but that just gives me a reason to go back!

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Casa Monica

When you finish up at Flagler College, head across the street to the Casa Monica.

Seamlessly blending Moorish Revival and Spanish Baroque styles, Franklin W. Smith originally opened the Casa Monica Hotel in 1888 but after some major financial struggle, Henry Flagler took over the hotel renaming it the Cordova Hotel.

The hotel operated under that name for several decades, but today it’s back open as the Casa Monica Hotel in partnership with Marriott Bonvoy (it was the first hotel to be added to Marriott’s Autograph Collection).

So of the three original Gilded Age hotels in St. Augustine, it’s the only one that still operates as a hotel and if you appreciate architecture and historic hotels, it’s a GEM.

Pop into the lobby for a quick peek to take in the ornate details and exquisite craftsmanship. It’s pure opulence with antique furnishings that seem more exotic than old world.

Lightner Museum

Next up, let’s finish off the trifecta at the Lightner Museum. Housed in the former Alcazar Hotel this place is like a time capsule of Victorian wonders.

Built by Henry Flagler in 1888, the Alcazar was originally the “recreation complex” for the Ponce de Leon Hotel across the street. Home to extensive spa and bath facilities as well as an extravagant indoor pool, the Alcazar eventually opened with guest rooms.

The museum showcases plenty of lavish collections (the glassworks collection is impressive) and architecture, but the collection of antique oddities is the most interesting.

While the spa and bath facilities were a big draw back in the day, they certainly weren’t luxurious like we think of spas today ; )

But by far the big draw of the Lightner Museum is the indoor swimming pool. The whole building seems like it’s built around the pool, and they’ve even opened a small cafe on the floor of the pool.

With a three story atrium unfolding over the pool, it’s pretty spectacular and I think it’s definitely a don’t miss in St. Augustine.

There’s also an entire floor of the museum that’s open to special exhibits. When I visited, they had a pretty extensive Art Nouveau exhibit on loan from the Chrysler Museum in Virginia.

Find more info about the Lightner Museum here.

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Lunch at The Floridian

For a classic Florida lunch spot in the historic downtown area, head to The Floridian.

It was recommended by Southern Living, so who am I to question, right?

Well when we settled in about 1 PM we were some of the only people in the restaurant but in just a few minutes the place was packed!

Everything about this place is “so Florida” but in the best way. The decor feels eclectically tropical and the menu is a take on Southern and Floridian favorites all made with fresh, local ingredients. Think: Fried green tomatoes, biscuits with pork belly, shrimp po boys, meatloaf sandwiches, Cuban sandwiches, and lots of fish, grits, and cornbread.

Castillo de San Marcos

After you’ve fueled up with lunch, you’ve got to experience St. Augustine’s #1 historic attraction: the Castillo de San Marcos.

Built in 1672 by the Spanish, the Castillo de San Marcos has seen it all – Its sturdy walls have weathered battles, sieges, and centuries, earning it the title of the oldest masonry fort in the US.

The Castillo is a fixture of St. Augustine’s profile from the Mantanzas River and even if you’re not super into the history, the upper deck has such great views of downtown St. Augustine and the river that you’ll definitely want to check it out.

Plus the Castillo de San Marcos is a National Monument operated by the National Park Service and you know I never miss a chance to get my passport stamped ; )

Shopping in Uptown

Okay, we’ve spent the day doing a lot of sightseeing, so let’s take a little break and check out some local shopping!

They say there’s really no better way to get to know a city than through it’s shopping, right? Right?!

Just north of the historic downtown, St. Augustine’s Uptown neighborhood is kind of getting to be the epicenter of new entrepreneurship in St. Augustine.

For a few blocks, San Marco Ave is lined with local boutiques and vintage shops.

My favorites were Declaration & Co, Cool and Collected, and Spinster Abbott’s (also a great place to stop for a drink).

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Have a Celebratory Dinner!

That’s a BIG DAY of sight seeing in St. Augustine! Cap it off at one of the city’s great restaurants/hang out spots:

River & Fort: Seafood and steaks with the best view of the Castillo de San Marcos.

Boat Drinks: Two story bar and seafood joint with retro tropical interiors, a world-class rum library, and a balcony overlooking St. George Street that’s Drywa’s go-to place for people-watching.

Casa Reina: Tacos and tequila in a 120-year-old Spanish Revival building. Their upper terrance has great views of the Bridge of Lions.

The Ice Plant: Farm to table food AND craft cocktails in an industrial park turned destination on the San Sebastian River.

Where to Stay in St. Augustine

Whether you want to make the most of a full day in St. Augustine and spend the night, or you’ve decided on a bit longer stay, I really liked staying at The Local.

This old roadside motel has been completely renovated and IT IS CUTE.

They’ve really leaned into the classic Florida, pink Flamingo theme and this is the perfect spot if you just need a basic place to sleep and shower (it’s super budget friendly), but you like a little style too.

Want to Read More Posts about Florida? I’ve got plenty!

Check out these destinations: Miami (Things to Do Besides Party & Where to Stay) // Key Biscayne // Sanibel & Captiva // Longboat Key & Anna Maria Island // Marco Island // 30a // St Augustine // Amelia Island // St Pete Beach // St Petersburg // Fort Myers // Dunedin // Crystal River & Weeki Wachee Springs // Honeymoon Island & Caladesi Island State Parks // Tarpon Springs // Matlacha & Pine Island // Apalachicola

Trying to narrow it down? Siesta Key vs Anna Maria Island // St Pete Beach vs Clearwater Beach // Sanibel vs Marco Island // Destin vs Panama City Beach // Destin vs 30a // Key Biscayne vs South Beach // Seaside vs Rosemary Beach

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