A Day Trip To St Augustine

Expert View Column
A Day Trip To St Augustine
By ATD’s Florida Experts, Susan and Simon Veness
St Augustine is the oldest city in Florida, founded by Spanish explorers in 1565 and occupied continuously since then. In European terms it’s an infant. In US terms it’s a grandfather. In tourist terms it’s a day trip from Orlando, and we’ve prepared an itinerary just for you.

St Augustine has the hum of excitement found in Orlando, with a heaping helping of history to boot, and we’ve made it the first Itinerary in our new once-a-month series of Day Trip and Overnight visits beyond the theme parks.  Just print and go!

How To Get There:

St Augustine is just over 2 hours’ drive from Walt Disney World. Take I-4 east to I-95 North, then take Exit 311 east to FL-207 north to Ponce de Leon Blvd, and continue to Water Street and the heart of the city’s tourist area.

What To Do:

Whether you’re visiting with small children or you’re adults-only, you’ll get the most out of a day here by purchasing tickets for a hop-on, hop-off tour. There are two options (Old Town Trolley and Red Train) and each has stops at the area’s highlights. The city is compact and you can use your hire car to hit the hotspots, but parking (usually free) can be an issue, making the hop-on tours more efficient.

Our recommended itinerary proceeds in the order you’ll find each location on the Old Town Trolley tour.


St Augustine Trolley Tour


1) The Old Jail is located in the same plaza as a ticket kiosk for the trolley, so it’s a good starting point for your visit. And while the jail’s history is dark at times, your tour guide (dressed in prisoner stripes!) keeps the descriptions relatively humorous and entirely kid-friendly. (Apx 1 hour)

The Oldest Store Museum is in the same plaza, and it’s worth a look for a quirky overview of early 1900s life in the US. Consider saving this for a Day Two visit if you decide to stay overnight. (45 min)

2) Take a tasting tour at Whetstone Chocolates and learn how chocolate is made! Enjoy a scrummy sample at the end. (45-55 min)

3) Castillo De San Marcos is the biggest draw in St Augustine, and its tours are extremely interesting, especially as they relate to French, Spanish and British sieges and occupations. We do recommend taking a tour, but if you’re visiting with younger children, who may not get as much out of it, stop here even if you don’t plan to take the tour. You can walk around the fort’s outer grounds, enjoy its gorgeous waterside views, and watch the daily cannon firings. Plug your ears; they’re LOUD! (1-2 hours)


Castillo de San Marcos


4) While you’re in the Castillo area, take a walk along the historic district’s pedestrian-only St George Street for its cute shops and restaurants. (30-60 min)

5) Just across from the Castillo is the St Augustine Pirate and Treasure Museum, where audio-animatronics meet actual artefacts in a hands-on environment kids really enjoy. There is plenty to keep teens and adults amused too, and a gift shop for all your pirating needs. (1 hour)


St Augustine Pirate and Treasure Museum


6) Ponce de Leon’s famous search for health-enhancing waters is remembered at Fountain of Youth archeological park, and you can take a sip of these “magical waters” in the Spring House and make your own decision about their energising properties. The park also boasts a blacksmith, a native Timucuan village and burial grounds, plus historical exhibits, cannon firings and ongoing excavations. (variable; 1-3 hours)

Especially for youngsters: Exit the trolley at stop 16 (or park near the Bridge of Lions) and make the short walk to the river, where you’ll find the Black Raven Pirate Ship. Daytime tours are geared toward young swashbucklers, while evening tours are definitely not! (90 minutes)


Black Raven St Augustine


Especially for Adults:  Families can tour the San Sebastian Winery and the St Augustine Distillery, but the alcoholic samples at the end are for ages 21 and up only, with valid photo ID. Each offers a walk-through of the facility, and the distillery especially is a fascinating look at the spirit-making process. Flagler College is another location adults will enjoy, for a fantastic look at its history, architecture and décor, including the dining room’s gorgeous Louis Comfort Tiffany windows. Boring? Not at all! (Apx 45 min for each)

Where To Eat:

For a casual lunch or dinner along St George Street, try the British pub style of Bull & Crown Publick House for a burger and a pint. Ask to sit outside if the weather is nice. For something a bit more sophisticated, especially at dinner, go for The Floridian on Spanish Street, where Southern cooking takes on a gourmet twist, or our favourite, Harry’s Seafood Bar and Grille. Their courtyard dining is superb after dark. For excellent fine-dining, try Collage on Hypolita Street.


The Floridian St Augustine


Good Nightlife:

There’s nothing like a Ghosts and Gravestones or Secrets of St Augustine haunted history tour to help the kiddies sleep at night! In all honesty, they’re good fun, not overly creepy, and while you’re unlikely to meet up with a spirit, you’ll certainly hear some amusing and authentic tales. (75 minutes)

Adults (ages 21 and up with photo ID) who definitely want to meet up with a spirit (of the alcoholic kind) should book the Paranormal Pub Crawl or The Original Haunted Pub Tour. For something a bit less strenuous, kick back with a craft beer at Ancient City Brewing, or enjoy live music at Scarlett O’Hara’s or Stogie’s Jazz Club and Listening Room (but only if you don’t mind lots of cigar smoke; it’s called Stogie’s for a reason).

Where To Stay:

While a day trip will give you a terrific taste of what’s on offer, there is more than enough in St Augustine to fill two days, so if you decide you’d like an overnight, our hotel recommendation goes to TRYP by Wyndham on Sebastian Street, with large rooms, mini-fridge, wet bar, and balconies overlooking the San Sebastian River.

If you extend your one-day visit, consider a dolphin-spotting boat tour, a kayak adventure, an eco-tour, or the chance to hire a water craft with Bay Ray Boat Rentals or Bluewater Adventure. Or, soak up a little sun along St Augustine Beach before heading back to Orlando and more theme park fun!

Are you planning a trip to St Augustine? Come and ask your questions – or tell us your experiences – on the ATD forums!

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