Things to Do in St. Augustine Florida on a Rainy Day

Ya know how I’m always saying there’s sooooo much of Florida I’ve yet to explore? Here’s another case in point.

I just visited Jacksonville and St. Augustine for the first time this past weekend – after three years and nine months of living in the Sunshine State!

My friend Kelly recently moved to Jacksonville and invited me up for the weekend. She’s a fellow adventurer, so Saturday we drove to St. Augustine for a day of exploring. Both newbies to St. A, we ditched a plan for a more spontaneous approach. Winging it worked in our favor, because…

Saturday was rainy. One of those days when the rain perpetually alternates between drizzle and downpour, and no amount of waterproof gear will keep you dry. Did that phase us? Nope. Armed and footed with umbrellas and rain boots, we embraced the elements – including wind that challenged the life out of our umbrellas!


On the drive to St. Augustine, the rain let up long enough for us to pit stop at Ponte Vedra Beach. As much as I love a blue sky, I’m also a sucker for a moody beach—which is honestly more fitting for what I consider to be the wild Atlantic coastline. (And, is it just me, or does that sand look like fur on a calico cat?? Just me? Okay.)

Stormy beach on the Atlantic Ocean in Florida


Down the road from the beach, we drove past this seriously Irish-looking castle peeking out over the treetops. Whaaaaat?? Curious, we Googled. Turns out, this place—Castle Otttis (no typo)—was modeled after an Irish castle. It’s privately owned and available by appointment only. Huh!

Castle Otttis near St. Augustine Florida


Anywho. Drizzle mode was in full effect when we reached St. Augustine’s Old Town. That giant “Fountain of Youth” sign immediately lured us in. Buuuut, after parking we couldn’t justify the admission fee and instead wandered around Magnolia Ave, which runs adjacent to the park. Spanish moss my heart!

Street lined with Spanish moss trees
Feet walking along a curb with dried leaves


Next stop: Castillo de San Marcos. Sort of. Parking was a struggle, but we finally found a FREE spot on Sevilla Street, near Flagler College. (Kelly is a parallel parking wizard!) Umbrellas up, we tromped through shop-lined streets to the waterfront. There, those umbrellas managed to survive gale force winds while we up-close viewed the Castillo de San Marcos. Just the exterior, though. We agreed to save the tour for a sunnier day. (And no photos thanks to wind. Boo.)


Real quick yo. We popped into this shop called the Red Pineapple Boutique on St. George Street. Because we basically wanted ALL the stuff inside.

Ceramic husband and wife coffee mugs
Wooden wall signs with quotes


I said we didn’t have a plan, but we did reach out to our Instagram friends for recommendations. One rec we received was Pizza Time, voted America’s #2 pizza joint on TripAdvisor. SOLD. We shared garlic knots and two slices of pie. One slice—the thin crust Margherita Pizza—was delicious, no doubt. But, the other—Grandma’s Pizza—was the standout. That combination of thick, toasty-chewy crust, a not-too-thick-not-too-thin layer of asiago cheese, and Grandma’s special, slightly sweet sauce… I’m STILL drooling! The other varieties looked just as enticing, so do eat here if you love pizza. (Basically everyone eat here.)

Pizza Time sign "Ranked 2nd best pizza in the United State
Tray with slices of pizza and garlic bread with sauce


Braving the downpour, we scooted out the back door toward Flagler College. But first, coffee. Kelly was jonesin’ for a cup of joe and we spotted Relampago Coffee Lab right behind Pizza Time. Perfect! What happened next was life-changing. You see, I loathe coffee. Loathe. And that is such a struggle this time of year because pumpkin spice lattes!! I’ve never had one, but they tempt me so. Relampago’s PSL was no exception, and THAT’S when Kelly changed my life. She suggested I order it as a steamer, sans the coffee. I had NO idea I could do that—with any flavored coffee!—so I did. I ordered a pumpkin spice steamed milk and it was everything this coffee-hater wanted a PSL to be!! Like I said. LIFE CHANGED. I’m still too frugal to indulge all the time, but still. Watch out Starbucks!


We purposely passed Flagler College on our way back to the car—even though the rain was reeeeaaaallly coming down when we exited the coffee shop, full cups in-hand. I couldn’t help but snap a shot of my sweet pumpkin nectar drink. After a few photo op stops, we hopped back into the car for a quick dry while heading to our final destination of the day.

Cup of coffee in front of Flagler College in the rain
Flagler College sign
Ornate church in St. Augustine Florida


Did you know the St. Augustine Distillery offers FREE tours?? Yes, free. Rainy day activity win! (And we weren’t alone in that thinking because the parking lot was packed.) After reserving our spot in the 4:10 tour, we passed the time browsing the museum and gift shop. The tour itself was quick, but informative, and ended with a taste test of four signature spirits—a mixer, a rum, a bourbon, and a gin. I’m not much for bourbon, but the rest earned thumbs up! Ooooh. And check out the restroom. It’s SO vintage chic.

St. Augustine Distillery
St. Augustine Distillery barrels
St. Augustine Distillery bottles of Vodka and Florida Mule MIxer
St. Augustine Distillery vintage style bathroom

Overall, I think the rain was kind of a blessing. It added to the adventure, and didn’t keep us from enjoying our day. Instead, it forced us to get creative, be more spontaneous, and just live in the moment. It was good for the soul (like that pizza and pumpkin spice steamer)!

So, that was our day. Are you a rainy day adventurer? What would you do on a drizzly, downpour day in St. Augustine?

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