A Quick Weekend in St. Augustine
Less than an hour south of Jacksonville, Florida sits St. Augustine, nestled between swamp, golf courses, and beaches opening onto the Atlantic. The oldest city in the United States, St. Augustine retains a Spanish charm inherited from the original settlement on the city by Pedro Menendez de Aviles in 1565. For those interested in living forever, St. Augustine is also a prime destination, having originally been discovered by Europeans by Ponce de Leon during his search for the Fountain of Youth.
Although St. Augustine’s Fountain of Youth is just myth, visitors today can enjoy good eats, weather, and fountains of amazing cocktails. Oh, and while the downtown of the city feels a little like a tourist trap, it’s still delightfully charming and easily worth a weekend. We ventured down here for a friend’s birthday, and found it was the perfect quick getaway destination for an easy celebration.
Day One
Flagler College
A private liberal arts college close to the center of St. Augustine, be sure to visit Flagler College’s centerpiece, which was originally the Ponce de Leon Hotel. Built in 1888, the hotel boasts stunning architecture and grounds in an old Spanish style befitting the hotel’s original luxury use.
St. George Street
Cutting through the center of the city is St. George street, which is filled with most of your one stop needs — from torture museums to cigar shops, this place has it all!
For the more gruesomely-inclined history buffs, the Medieval Torture Museum features stomach-turning displays on what life was like for anyone unfortunate to have been alive during the medieval period. While we didn’t stay for a tour, it’s safe to say that this place is best seen before lunch.
For those looking for a less bloody and more suave stay in St. Augustine, Old City Cigars is half a block away and offers a wide variety of smokeables paired with great customer service — extremely helpful for wannabes like us with no actual knowledge whatsoever of what we wanted to smoke, beyond it being a cool activity for a birthday celebration.
Lavender lovers should also be sure to check out Pelindaba Lavender, which features all sorts of lavender-infused products.
To fully experience St. George, though, it’s best to embrace the Florida air, block off some time, and simply stroll. A large stretch of the street is fully pedestrianized, so take advantage and enjoy the wide range of quirks you’re bound to see.
Lunch at Floridian
You’ve been strolling, potentially smoking cigars, vomiting from the torture museum, and — what do you know? — you’re hungry! If that’s the case, head over for a lunch and cocktail at the Floridian. A quick hop away from St. George, the restaurant boasts a wide selection of locally sourced Southern cooking. With a large outdoor dining section, and a pleasantly kitschy interior, it’s easy to while away the afternoon.
Bridge of Lions
Crossing the Matanzas River in St. Augustine is the Bridge of Lions. A drawbridge originally built in 1927 adorned with marble lion statues, the bridge provides pictaresque views of the river and the city’s waterfront.
St. Augustine Beach
On the south eastern side of the city, St. Augustine Beach abuts the Atlantic Ocean. Featuring miles of pristine, soft sand and clear water, the beaches are quintessential Florida.
The Night out
Despite its small size, St. Augustine boasts a robust nightlife. Starting it off right, we pre-gamed with some wine, post-beach naps, and cigars from Old City Cigars on our Airbnb’s back porch. Next stop? Hitting up Sangrias Wine and Tapas bar for some live music, cozy atmosphere, and shared dishes.
After the meal, it was time to hit the streets. We had considerable success at Prohibition Kitchen, Scarlett O’Hara’s, and Dos Gatos. Prohibition Kitchen was a spacious gastropub which served top-knotch cocktails and a wide variety of beers — a perfect starting point before heading to Scarlett O’Hara’s which had a more classic dive bar atmosphere with beer-shot combos. Dos Gatos makes for a good final spot, with is lively dance floor and spinning DJ.
After the three bar tour, be sure to hit up Pizza Time for some classic New York-style slices to calm your drunchees and get you ready to sleep peacefully the rest of the night,
day two
Breakfast
Our friend loves Dunkin’ Donuts, and it was his birthday trip, so we splurged on some Dunkin’ for him. Had this been a normal trip, or had our friend had less specific tastes, we would have gone to the Metro Diner (which we did go to the next day anyway before catching out flight). The diner features a huge menu, befitting its diner status, all of which was delicious — and gigantic.
Most importantly, Metro Diner was featured in Diners, Drive-Ins, and Dives. All you Guy Fieri fans better prepare yourselves.
Anastasia state park
Now that you’re well fed, head over to Anastasia State Park. A beautiful park featuring swimming areas, trails, fishing spots, and most importantly canoe and kayak rentals, you could easily spend a day exploring here. We opted to go kayaking in the Salt Run with Anastasia Watersports. A tidal inlet, the water provides an opportunity to see a wide variety of animal life while taking in the scenery — we’re pretty sure we saw dolphins (Jen’s note: It was dope.)!
The Conch House Restaurant
To keep the good vibes and good time outside going, head over to the Conch House Restaurant. Overlooking Salt Run on the water’s edge, the Conch House is a Caribbean-style joint with plenty of outdoor seating, a wide variety of seafood dishes, and of course delicious cocktails (are you sensing a theme?). The restaurant also features a bar and lounge for those planning on spending longer there than just lunch.
Castillo de San Marcos
The oldest masonry fort in the US, the Castillo de San Marcos’ construction began in 1672. The fort, which has undergone significant changes over its nearly 400 year history, offers the chances for self-guided walking tours, as well as views of the Matanzas River.
Dinner
By this point, all the sight-seeing, sun, and alcohol had gotten to us; we were beat. Meaning, unfortunately, we splurged for Wendy’s for dinner. Had we done it again, we would have mustered up our energy and gone to the Ice Plant — a bar and locally-sourced eatery located inside a former, historic ice factory. Next door to the Ice Plant, technically within the same building, is also the St. Augustine Distillery, which offers tours and tastings.
No city can be fully enjoyed in only two days. The following list provides a bunch of alternates to what we did, which we wish we had done had we more time in the city:
Alligator Farm Zoological Park
Fountain of Youth
Ice Plant
St. Augustine Distillery
St. Augustine Lighthouse
St. Augustine National Cemetery
The Hyppo
St. Augustine Pirate & Treasure Museum
Oldest Wooden School House
Old Town Trolley Tours
Sheriffs Ghost Walk Tours