Explore Historic St. Augustine from Orlando on a Guided Day Trip
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Discover the charm of America’s oldest city on a full-day trip from Orlando to historic St. Augustine. Travel northeast and wander through cobbled streets lined with centuries-old buildings, charming cafes, and vibrant shops. This trip offers a perfect blend of history, architecture, and local flavor.
Explore iconic sites like the Castillo de San Marcos, the Fountain of Youth, and the Oldest Wooden School House. You can also upgrade your experience with a scenic boat cruise, a hop-on hop-off trolley tour, or a visit to the Medieval Torture Museum for a fascinating glimpse into the city’s darker past.
Whether you’re a history buff or just looking for a relaxing day in a picturesque setting, this day trip to St. Augustine from Orlando is packed with memorable sights and activities designed to give you a true taste of this historic city.
Frequently asked questions
How long does the trip to St. Augustine last?
The full-day tour from Orlando to St. Augustine lasts approximately 10 hours.
What options can I add to enhance my visit?
You can upgrade to include a scenic boat cruise, a hop-on hop-off trolley tour, or a visit to the Medieval Torture Museum.
Is hotel pickup included?
Yes, hotel pickup is included from select hotels and resorts in Orlando, Kissimmee, Disney Lake Buena Vista, and Universal.
Are there any age restrictions or accessibility options?
The tour is suitable for all ages, including infants (0-2), children (3-11), and adults (12-99). Infants and small children can ride in a pram or stroller, and the tour is accessible for all physical fitness levels.
What’s included and what isn’t?
Included are the trolley tour (if selected), hotel pickup and drop-off, boat cruise (if selected), and Medieval Torture Museum (if selected). Exclusions are gratuities, food, and drinks.
Can I cancel my booking?
Yes, you can cancel for a full refund if you do so at least 24 hours before the scheduled departure. Cancellations within 24 hours or due to weather or low enrollment may be subject to cancellation.
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund. Cancellations within 24 hours, bad weather, or insufficient bookings may result in cancellation.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 10 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Trolley tour (if option selected at time of booking)
- Pick-up and drop-off at designated meeting points in 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)
Not included
- Gratuities
- Food and drinks
Itinerary
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Stop 1
The Historic District in St. Augustine is the city's core, filled with restaurants, shops, hotels, and attractions. Many buildings date back to the 1700s, and the streets are laid out as they were centuries ago. Highlights include the Colonial Quarter, Castillo de San Marcos, and the Fountain of Youth. The area offers stunning views of Matanzas Bay and showcases architecture from Spanish Colonial to Gilded Age styles.
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Stop 2
Visit the Oldest Wooden School House at the entrance to St. George Street. Enjoy strolling along this historic cobblestone street, known for great shopping and dining options.
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Stop 3
Upgrade your experience with a 1-hour 15-minute boat cruise aboard the Victory III through Matanzas Bay. Enjoy narrated views of St. Augustine’s landmarks and natural scenery.
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Stop 4
Opt for a 90-minute hop-on hop-off trolley tour to explore the city at your own pace. Get on and off as you wish, with entertaining guides sharing local history and humor.
Meeting point & pickup
Hotel pickup included for all travelers
Gray Line Orlando offers hotel and resort pickups from select locations. Pickup times are confirmed the day before your tour. Please wait outside the main lobby of your hotel or resort for your driver-guide, who will arrive in a Gray Line Orlando vehicle and uniform. If you do not see the vehicle within 5 minutes of your scheduled pickup, contact us immediately.
Open in Google MapsHow to get there
Pickup is available from 303 listed hotels. Exact times are confirmed after booking.
Cancellation & confirmation
Free cancellation
Cancel at least 24 hours before your scheduled departure for a full refund. Cancellations within 24 hours, bad weather, or insufficient bookings may result in cancellation.
- 100% refund if canceled at least 1 day in advance
- No refund if canceled within 24 hours
- May be canceled due to bad weather or low enrollment
Booking confirmation
Confirmation details are provided at checkout with our booking partner.
From $100.00 per person
- Free cancellation
- Secure checkout with our booking partner
