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Discover historic St Augustine on a full-day tour from Orlando, including optional trolley or boat cruises, for just $99 per person in approximately 10 hours.

The Saint Augustine Day Trip from Orlando offers an accessible way to explore the oldest city in the United States. Priced at $99 per person, this 10-hour tour combines transportation, sightseeing, and optional activities, making it a convenient and educational escape from Orlando’s theme parks. The tour departs early in the morning, with pickup points at Orlando, Kissimmee, Disney Lake Buena Vista, and Universal, ensuring easy access for visitors staying in key locations.
While the day is packed with exploration, the tour’s relaxed pace allows plenty of free time to wander, shop, and enjoy the city’s historic ambiance. A highlight is the guided visit to Castillo de San Marcos, the oldest stone fort in the country, which many find especially impressive. The tour is especially suitable for those interested in history, architecture, and local stories, with positive reviews highlighting friendly guides and engaging narration.
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This tour begins at 7:30 am, with convenient pick-up points at Orlando, Kissimmee, Disney Lake Buena Vista, and Universal hotels. The transportation is operated by Gray Line of Orlando, with comfortable vans featuring individual seats. Many reviews praise the knowledgeable and friendly drivers, especially highlighting Kevin for his engaging personality and local expertise.
The journey to St Augustine takes about an hour, providing travelers with a smooth and relaxed ride. The small group size, capped at 14 travelers, helps maintain an intimate atmosphere and allows for more personalized commentary.

The Old St. Augustine Village is the first stop, offering a pedestrian-friendly district filled with shops, cafes, and historic buildings. The area dates back to the 1700s and is the heart of the city’s historic core. Visitors enjoy wandering along St. George Street, where many buildings, including the Oldest Wooden School House, are over 300 years old.
In the village, there’s free time to explore shops, sample local treats, or relax at waterside cafes. The Oldest Wooden School House, located at the entrance to the street, is a notable stop. Many find the walk along cobblestone streets to be charming and full of character.

A key highlight is the visit to Castillo de San Marcos, the oldest masonry fort in the US. Many visitors appreciate the chance to walk around the historic ramparts and learn about military history and colonial defenses. It’s a must-see landmark that offers stunning views of Matanzas Bay.
The tour includes free time at this site, allowing visitors to explore at their own pace and take photos of the imposing stone structures. It’s a favorite among history enthusiasts for its well-preserved architecture and stories of early American defense.

For those who upgrade, the tour offers a one-hour and 15-minute boat cruise aboard the Victory III. This narrated scenic cruise provides a relaxing way to see St Augustine’s waterfront, with the captain sharing insights about the city’s maritime history. Dolphins and other wildlife sightings are common, adding to the experience.
The cruise departs from Matanzas Bay, offering beautiful views of the city’s skyline and historic landmarks from the water. Many reviews highlight the fun and informative nature of the cruise, though it is an optional extra with additional costs not included in the base price.

Another upgrade option is the 90-minute hop-on-hop-off trolley tour. This flexible way to see St Augustine’s major sights allows visitors to get on and off at their leisure. The trolley stops at key attractions, including museums, distilleries, and historic sites.
Many passengers find the trolley very convenient to explore the city without excessive walking, especially in the summer heat. The guide on the trolley is praised for being caring, knowledgeable, and personable, making the tour both informative and enjoyable.

During the day, visitors have the chance to enjoy a relaxing lunch in the historic district. Many choose waterside restaurants serving delicious seafood or other local specialties. Although food and drinks are not included in the tour price, the free time allows ample opportunity to sample local flavors and shop for souvenirs.
The city’s vibrant eateries and charming cafes make lunch a highlight, with options to fit all tastes and budgets. Many reviews mention the pleasure of sampling sweet treats or enjoying casual dining along St. George Street.
Feedback from past participants highlights friendly and knowledgeable guides, especially praising Kevin and Ismael for their caring attitude and storytelling skills. Travelers appreciate the comfortable transportation, well-organized schedule, and flexibility offered by optional activities.
Many reviews mention the value for the price, noting that the full-day experience enhances understanding of St Augustine’s history and culture. The small group size fosters a personalized experience, while the optional extras add to the adventure.
While the tour generally receives high marks, some mention the hot weather in July as a challenge, making shade and hydration important. The tour operates in good weather conditions, and cancellations due to weather are fully refundable if needed.
Travelers should plan for comfortable walking shoes and sun protection, especially if they choose to explore on their own after the guided segments. The maximum of 14 travelers keeps the group manageable, but it’s wise to arrive promptly and be ready for a full day of sightseeing.
The Saint Augustine Day Trip from Orlando offers a cost-effective way to explore the historic charm of the city with round-trip transportation and free time to explore. The inclusion of optional activities like boat cruises and trolley tours allows customization to match interests and budget.
This tour is especially suited for history buffs, architecture enthusiasts, and those seeking a relaxed day outside Orlando’s theme parks. The positive reviews about guides and the overall experience reflect good value and genuine hospitality. However, travelers should be prepared for the heat in summer months and plan accordingly.
“Van was comfortable. Individual seats. Kevin our driver was extremely knowledgeable and friendly. Boat cruise was fun too”
Does this tour include food and drinks?
No, food and drinks are not included. The tour provides free time for lunch in the historic district.
What optional activities can I add?
You can upgrade to include a scenic cruise through Matanzas Bay or a 90-minute hop-on hop-off trolley tour.
How long is the boat cruise?
The cruise lasts approximately 1 hour and 15 minutes and offers narrated views of St Augustine’s waterfront.
Is this tour suitable for all ages?
Yes, most travelers can participate, but comfortable walking shoes are recommended. The tour emphasizes history and scenery.
What is the maximum group size?
The tour is limited to 14 travelers, ensuring a more personal experience.
How do I cancel if my plans change?
Cancellation is free up to 24 hours in advance, with a full refund issued if canceled before then.