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Discover the charm of America's oldest city with a full-day trip from Orlando, including options for sightseeing, cruises, interactive museums, and more.

The St. Augustine Day Trip with various tour options from Orlando offers a comprehensive dive into Florida’s oldest city. Priced at $99 per person and lasting 12 hours, this tour provides a convenient way to explore the historic streets, landmarks, and attractions of St. Augustine. Known as the Ancient City, it features colonial Spanish neighborhoods, magnificent architecture, and old-world charm that have captivated visitors for centuries.
This tour is ideal for those who want a well-rounded experience, with roundtrip transportation, a live guide, and multiple activity options to tailor your day. While it offers ample free time to explore, it is important to note that food and drinks are not included, so bringing snacks or dining in local cafes is recommended. The tour’s small group size (limited to 10 participants) ensures a more personal and engaging experience, but this also means early booking is advisable.
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While in Orlando, here are other experiences we've covered

The tour departs from Orlando, with pick-up points at various convenient locations such as hotels, ICON Park, and Golden Corral. Participants are advised to wait outside the designated pickup spot, and the Gray Line of Orlando guide, identifiable by a gray uniform, helps coordinate the journey. The transportation is comfortable, and the overall trip duration is approximately 12 hours, including travel time and sightseeing.
The drive to St. Augustine typically takes just over 3 hours, with some reviews mentioning a scenic detour along the way. This means travelers spend more time exploring the city itself rather than sitting in transit. The return trip usually lasts around 2.5 to 3 hours, providing a smooth and relaxed experience. The small group setting, with up to 10 participants, adds to the cozy and engaging atmosphere.

Once in St. Augustine, the tour gives you plenty of free time to wander the cobbled streets, browse boutique shops, and enjoy local cafes and bars. Highlights include Castillo de San Marcos, the oldest masonry fort in the continental U.S., and Flagler College, famed for its stunning architecture. The Lightner Museum and the Fountain of Youth are also popular stops, rich in history and stories.
The town’s charming atmosphere and beautiful climate make strolling around a pleasure, especially in good weather. The historic district is compact enough to explore on foot, but some may find the 20-minute walk back to the trolley station in the heat a minor inconvenience. Still, the variety of landmarks offers a well-rounded glimpse into the area’s past and present.

For an immersive history experience, the Colonial Quarter Museum stands out. This living history museum features interactive demonstrations like musket firings, blacksmithing, and colonial dress-up. Guided by a person in period attire, visitors get a hands-on look at what life was like during Florida’s colonial days.
This stop is particularly engaging for families or anyone interested in history brought to life. The live demonstrations make the past feel immediate and real, adding a layer of fun and education to the tour. It’s a great way to see history as more than just static exhibits and to understand the living culture of early settlers.
More Great Tours NearbyOne of the extra tour options is the Scenic Cruise around Matanzas Bay. This narrated boat tour offers a unique view of the city’s horizon, including many historic landmarks accessible from the water. The cruise emphasizes the natural beauty of the area alongside the historic sights.
Guests appreciate the relaxing atmosphere, which provides a break from walking and a fresh perspective on the city’s layout. The narration enhances understanding, making it an excellent choice for those seeking a more leisurely way to see the city.

The Road Train Tour offers a hop-on, hop-off experience via a vintage trolley that loops around 7 miles of St. Augustine. With 22 stops, this trolley allows visitors to explore attractions at their own pace, making it a flexible option for those who want to see multiple sights without rushing.
Travellers enjoy the informative commentary provided along the route, which covers interesting facts about each site. The frequent stops and easy boarding make this a practical way to cover more ground, especially in a city where attractions are spread out.

For families or fans of adventure, the Pirate & Treasure Museum is an exciting destination. It features one of the largest collections of authentic pirate artifacts and shipwreck treasures. The interactive exhibits include displays where visitors can handle treasures, participate in puzzles, and learn about the Golden Age of Piracy.
The museum’s hands-on approach and award-winning displays make it an engaging visit for all ages. It’s a lively way to experience the pirate lore that is deeply woven into the history of St. Augustine.

This tour’s biggest advantage is the ability to choose from several activity options. Whether you prefer a full guided tour, a scenic boat ride, an interactive museum, or a trolley adventure, there’s a way to customize your day. The full-day schedule ensures you have enough time to enjoy each chosen activity and explore at your leisure.
All options include roundtrip transportation, a digital Eat & Play Card for discounts at local restaurants and attractions, and guide assistance. This flexibility makes the tour appealing to a variety of interests, from history lovers to casual travelers seeking a laid-back day.

Participants are encouraged to wear comfortable shoes and bring sunscreen, since much of the day involves walking outdoors. The tour does not include food or drinks, so packing snacks or planning to dine at local eateries is advisable. The pickup points are outside hotel lobbies or designated spots like ICON Park and Golden Corral.
The small group size (limited to 10 people) enhances interaction and personalized attention. Booking in advance is recommended, as all tours must be purchased at least 2 days ahead. The cancel policy allows full refunds with 24 hours’ notice, offering peace of mind for flexible planning.
This tour suits history buffs, families, and small groups looking for a convenient, guided day to explore Florida’s oldest city. It’s perfect for those who want variety—from walking tours to boat rides—within a manageable schedule. The small group format ensures a more intimate experience, while the multiple activity options mean you can tailor the day to your interests.
However, travelers should be prepared for early mornings and some walking, especially during free exploration time. For those seeking a relaxed pace without feeling rushed, this tour offers a balanced day filled with sights, stories, and history.
The Gray Line of Orlando – Gator Tours provides dependable transport, knowledgeable guides, and well-organized activities. The 4.6-star rating from 65 reviews reflects consistent satisfaction with guide expertise, scenic views, and fascinating attractions.
While some reviews mention minor delays or walk-back distances in hot weather, overall, the experience maintains high standards. The tour’s affordable price point combined with its comprehensive itinerary makes it a strong choice for travelers eager to see Florida’s oldest city in a single day.
What is included in the tour price?
The $99 per person includes roundtrip transportation from Orlando, driver/guide assistance, and tickets or passes for museum entry, cruises, or trolley rides if options are selected.
Are food and drinks included?
No, food and drinks are not included, so it’s recommended to bring snacks or plan to dine during free time in St. Augustine.
How long is the drive from Orlando to St. Augustine?
The trip takes approximately just over 3 hours, with some scenic detours noted in reviews.
Can I customize my experience?
Yes, travelers can choose from several options, including full sightseeing tours, scenic cruises, interactive museums, and trolley tours.
What should I bring on the tour?
Comfortable shoes and sunscreen are recommended, as well as any personal items needed for a day of outdoor exploration.
Is the tour suitable for children?
Yes, the Pirate & Treasure Museum and interactive stops make it family-friendly, especially with the small group size.