9 Hours in St. Augustine Itinerary

A good day trip does wonders for refueling your life, whether it's heading to one of the many beach towns nearby or traveling to the small shops and restaurants of nearby cities like Winter Park and Deland. Traveling to St. Augustine from Orlando will take you about 90 minutes in the car, and it's worth it!

Exploring The Nation's Oldest City like a local while learning about its rich history is well worth the trip. We've outlined how to spend a day in St. Augustine right down to the minute to help you make the most of your day trip.

You can also explore more romantic day trips from Orlando. And no day trip to St. A would be complete without dining at one or two waterfront restaurant in St. Augustine.

Day Trip to St. Augustine from Orlando

Our itinerary is based on spending the afternoon and evening in St. Augustine after the 90 minutes drive from Orlando. You can easily switch up the itinerary to be earlier in the morning and into the late afternoon.

While you're enjoying your day trip to St. Augustine, remember to spend some time enjoying a stroll along the many romantic streets too.

a couple sitting at The Ice Plant bar in st. augustine
Ice Plant Bar -image by Maria DiCicco

Ice Plant Bar is a must do for unique bars in St. Augustine.

1-1:45 pm: The Peña-Peck house and Cathedral Basilica

Why not make your first two stops in St. Augustine some beautiful historic buildings? The Cathedral Basilica is typically open Monday – Friday from 8am – 5pm. So if you visit on a weekend this first stop is more about strolling the outside of the building and getting your bearings.

The Peña-Peck house is nearly 300 years old! This historic coquina stone house was built for Spanish Royal Treasurer Juan Estevan de Peña and his wife Maria Antonia Adrisola. Now it is maintained by The Women's Exchange.

The Woman's Exchange is a 129-year old non-profit organization whose volunteers serve as custodians of the historic Pena-Peck house. The members showcase the landmark home through educational tours and share the story of the residents of the [ante-bellum] home and the impact they had on the city of St. Augustine, the state of Florida, and the founding of America.

Important note: The Peña-Peck House is open to shoppers Wednesday through Saturday from 12pm – 4:30pm. Museum tours are from 12pm until 4pm.

2-2:15 pm: The Kookaburra Coffee Shop

24 Cathedral Place, St. Augustine, FL
HOURS Everyday: 6:30a – 9:00p

The Kookaburra is where you’d find me every day if I lived in St. Augustine or attended Flagler College. While the inside is small, the service was great and my iced vanilla latte was perfect for strolling the city streets. The modern interior of the shop is a cool contrast to the exterior, which is consistent with the architecture of historic downtown St. Augustine.

The Kookaburra St. Augustine
The Kookaburra Coffee Bar – image Arlene Laboy

By the way, if you find yourself at St. Augustine in the morning hours, then treat yourself to the most important meal of the day at these best restaurants for breakfast in St. Augustine.

2:25-3 pm: Stroll St. George Street and Oldest Wooden Schoolhouse

St. George Street is located steps from the city gates and is home to a variety of boutiques, coffee and ice cream shops, and gift shops. This is also where you’ll find the Oldest Wooden Schoolhouse.

Built in 1716, the schoolhouse is now a museum that can be visited daily.

Oldest Wooden Schoolhouse St. Augustine
Tour the Oldest Wooden Schoolhouse daily beginning at 9am. – image by Arlene Laboy

3-4pm: Castillo de San Marcos

1 South Castillo Drive, Saint Augustine

The Castillo de San Marcos was built as a way to defend against attack from enemies. The fort was made of coquina and took 23 years to build, was impenetrable to enemy attack, and is fire resistant. Visitors can walk through the fort and enter various rooms that housed cannons, a guard room, and a prison. There is a large courtyard in the center of the fort, and the upper deck provides a beautiful view of the city as well as a closer look at the gun deck and bastions.

On Fridays, Saturdays, and Sundays, you can view a cannon being fired several times throughout the day with the last demonstration taking place at 3:30pm.

School group visitation is quite high October-November and February-May.

Castillo de San Marcos
The Castillo de San Marcos is open daily from 8:45am-5pm. Admission is $15/adult.

4:30-5:30 pm: Tini Martini Bar

24 Avenida Menendez, St. Augustine, Florida

This little bar packs a punch! Found while exploring Avenida Mendez, the Tini Martini Bar is actually the Casablanca Inn's hotel bar and is located just a short walk from Castillo de San Marcos.

You have 23 martini options to pick from, as well as a selection of wines and cocktails. We chose the Mango Martini and the Sailor’s Punch cocktail, which were so good one could easily drink 2 or 3 without noticing.

There is an outdoor patio where you can enjoy your drink while partaking in some prime people watching, however, it was extremely hot so we opted for the air-conditioned seating indoors.

Mango martini from Tini Martini Bar in St. Augustine
Mango Martini from Tini Martini Bar – image by Arlene Laboy

6-7 pm: Uptown Scratch Kitchen

We stumbled upon this gem after hungrily scanning Yelp last minute, and didn’t realize it was a food truck until we arrived at the address. You'll find Uptown Scratch Kitchen parked next to Dos Coffee and Wine daily from noon to 7pm.

Their menu specializes in contemporary American cuisine and changes often as they incorporate fresh seafood, seasonal and local ingredients.

Their Famous Fried Chicken with hand-cut fries and house BBQ sauce was an unexpected highlight of the trip.

Uptown Scratch Kitchen St Augustine food truck
Uptown Scratch Kitchen – image by Arlene Laboy

7-8 pm: DOS Coffee and Wine

DOS Coffee & Wine

300 San Marco Ave, Saint Augustine, FL
Monday – Saturday 7:00AM – 7:00PM
Sunday 7:00AM –5:00PM

What better way to finish off dinner than by walking a few steps and being inside a coffee and wine bar? In addition to coffee, DOS Coffee and Wine offers a variety of red and white wines, several toasts, muffins, desserts, salads, and small bites.

Dos Coffee and Wine – image by Arlene Laboy

8:30-10pm: Hornski's Vinyl Lounge/Love Is The Answer Mural


Hornki’s Vinyl Lounge combines two of my favorite things: a record shop and a bar. You can also play some pool while you enjoy your brew or wine in a cool, laid-back atmosphere. Hornski’s feels like you're going to your friend’s basement to hang out, drink, and listen to music.

Next door at Rochelle’s Boutique you'll find a vibrant, colorful mural titled “Love Is The Answer” by artist Christie Chandler on its side wall – a great example of public art in this historic city.

Hornski's Vinyl Lounge St. Augustine
Hornski's Vinyl Lounge – image by Arlene Laboy

You can also end your day at one of the locally-owned St. Augustine breweries.

Downtown St. Augustine Parking

The City of St Augustine maintains a parking lot in front of the Castillo de San Marcos. The cost is $2.50 per hour which is paid at automated stations.

You may want to consider using the city's parking garage which is only a block away from the Castillo. It is conveniently located and will provide shade for your vehicle.

More ideas:

Feature image credit: Stephanie Patterson.