Saint Augustine Day Trip from Orlando

Overview

Enjoy a day in America's oldest town, St Augustine.

On this day trip from Orlando, head northeast to the picturesque town, where you can wander the cobbled streets and enjoy a meal in one of the many promenade cafes.

St Augustine is a unique city filled with colonial Spanish neighborhoods, magnificent buildings and a wonderful, old-time charm. As the oldest continuously occupied European-established settlement in the USA it has lots of history. From the Castillo de San Marco, to the Fountain of Youth there is something for everyone.

Upgrade to add a scenic cruise, trolley tour or the Medieval Torture Museum to your visit.

If you select the option including the Hop-On Hop-Off Trolley than you can have a guided tour throughout the historic old town, and jump on an off as you wish.

The scenic boat tour option is a 1-hour boat ride with views from the waterways of the Bay of Matanzas!

At the Medieval Torture Museum you see first hand the. grueling history of mad men and tyrants!

City: Orlando

Thu 12 Jun

Other dates

You can choose the date already on the booking website

Starting at $99.00

Make a reservation

Thu 12 Jun

Starting at $99.00

Make a reservation

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What's Included

Trolley tour (if option selected at time of booking)

Pick up and drop off at a meeting point (Orlando, Kissimmee, Disney Lake Buena Vista & Universal)

Boat cruise (if option selected at time of booking)

Medieval Torture Museum (If option selected at time of booking)

Additional Info

Infants and small children can ride in a pram or stroller
Infants are required to sit on an adult’s lap
Suitable for all physical fitness levels

What To Expect

Old St. Augustine Village

The Historic District in St. Augustine is the heart of the city. This is where guests will find a majority of the city's restaurants, shopping, hotels, and attractions. The Historic District is the oldest part of the city with many buildings dating back to the 1700s. Even the streets are laid out as they would have been centuries ago, and are more walkable than a lot of cities visitors are used to seeing in America. Along with being a beautiful area for finding things to do like shopping, visiting museums, and dining, the Historic District is also home to the beautiful bayfront with lovely panoramic views of the Matanzasa Bay. The top rated attractions in the area are centered around the Historic District and reflect the importance of history in shaping St. Augustine into what it is today. For example, the Colonial Quarter is a living history museum with costumed reenactors and interactive experienes. The Castillo and the Fountain of Youth both have weapons demonstrations so guests can expect to hear the sound of canon and musket fire around the Historic District. Another defining feature of the Historic District is the architecture. The design on building facades represents the height of Spanish Colonial and Spanish Renaissance Revival architecture. The area of town showcases everything from early European design, Florida bungalow style houses, and Gilded Age extravegance. Being the nation's oldest city, the Historic District of St. Augustine represents all that history has built here since 1565.

Oldest Wooden School House

The Oldest Wooden School House is located at the entrance to St. George Street. During your free time be sure to stroll past it and down this cobble stoned street where there is great souvenir shopping and some great restaurents .

Fort Matanzas National Monument

Upgrade your tour and enjoy a one-hour-and-15-minute cruise aboard the Victory III through Matanzas Bay. Narrated by your captain, this boat tour provides an incomparable way to view St Augustine’s historical landmarks and natural sites of interest.

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (185)

Nicky_G

Mar 2025

An enjoyable small group trip to the oldest city in North America. Greyline provide transportation and you are then free to spend the agreed time as you wish. I took a tout on the Old Town Trolley and strolled around the pedestrian area. I also visited the 17th century Spanish star fort and the old town jail both of which were very interesting.

Rachael M

Feb 2025

Efficient transport and really interesting and educational day at St Augustine. Our guide was great and told us lots of Floridian history on the way

Explorer30572476969

Feb 2025

Another great day in St Augustine. Brad was a great host and driver. Never enough time, we always need more so this was our second trip.