Day Trip to Historic St. Augustine from Orlando with Hotel Pickup
Orlando, USA
- 10 hours (approx.)
- Pickup offered
- Mobile ticket
- Offered in: English
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Overview
Step back in time with a visit to enchanting St Augustine — one of America’s oldest towns — on this full-day tour from Orlando. This 10-hour excursion arrives in St Augustine by mid-morning, giving you hours to spend on your favorite activities. Stroll along cobbled pathways, admire Spanish Colonial architecture, indulge in delicious seafood at a waterside restaurant, see historic landmarks, and add on an optional sightseeing cruise or trolley tour.
- 10-hour trip to St Augustine from Orlando
- Explore and enjoy a relaxing lunch in colonial St Augustine, self-proclaimed oldest city in the US!
- See historic landmarks like Castillo de San Marcos, the oldest fort in the US
- Upgrade to include a scenic cruise through Matanzas Bay or a 90-minute sightseeing trolley tour
- Tour includes round-trip coach travel from select Orlando hotels
What's Included
- 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)
- Trolley tour (if option selected at time of booking)
- Medieval Torture Museum (If option selected at time of booking)
- Gratuities
- Food and drinks
Meeting and Pickup
Pickup points
Select a pickup point
Pickup details
Gray Line Orlando provides hotel and resort pickups for this tour. Pickups are available from select hotels and resorts only—we are unable to collect from private residences, vacation homes, condos, or Airbnb/villa properties. Gray Line Orlando will contact you by 3:00 PM (EST) the day before your tour to confirm your exact pickup time and location. If you have not received your pickup details by that time, please contact us. On the day of travel, please wait outside the main lobby entrance of your selected hotel or resort. Your driver-guide will arrive in a Gray Line Orlando vehicle and uniform. If you do not see the vehicle within 5 minutes of your scheduled pickup time, please contact our office immediately for assistance.
Start time.7:30 am
Itinerary
A vacation in Central Florida not only puts you in the theme park capital of the world, but also gives you speedy access to the oldest colonial settlement in the United States of America: St. Augustine. Prepare for a full-day in a city that’s full of Spanish-Colonial architecture, delightful dining, and reportedly more than a few ghosts roaming around.
This 10-hour excursion begins with pick-up in Orlando, Kissimmee, or Lake Buena Vista. Your first stop is the Old St. Augustine Village where the pedestrian throughway St. George Street is lined with shops and restaurants.
Many of the buildings in this area date back to the 1700s, including the Oldest Wooden School House in the country, which you’ll pass by. You’ll have free time to wander around the historic district, popping into pubs or sampling sweet treats. Be sure to visit the Castillo de San Marcos before driving back to Orlando.
This 10-hour excursion begins with pick-up in Orlando, Kissimmee, or Lake Buena Vista. Your first stop is the Old St. Augustine Village where the pedestrian throughway St. George Street is lined with shops and restaurants.
Many of the buildings in this area date back to the 1700s, including the Oldest Wooden School House in the country, which you’ll pass by. You’ll have free time to wander around the historic district, popping into pubs or sampling sweet treats. Be sure to visit the Castillo de San Marcos before driving back to Orlando.
1
Old St. Augustine Village
6 hours • Admission Ticket Free
Oldest Wooden School House (Pass By)
2
Fort Matanzas National Monument
1 hour 15 minutes • Admission Ticket Not Included
3
Historic Tours Of Am..
1 hour 30 minutes • Admission Ticket Not Included
Additional Info
- Confirmation will be received at time of booking, unless booked within 4 days of travel. In this case confirmation will be received within 48 hours, subject to availability
- Not wheelchair accessible
- Stroller accessible
- Infants must sit on laps
- Most travelers can participate
- This tour/activity will have a maximum of 14 travelers
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.5
based on 255 reviews
Sort by: Most insightful
Andrea_S, Sep 2026
Terrible experience overall, poor information given on Viator's website led to embarrassing situation with my 69 year-old mother. The "guide" was rude, asked for tips when in fact she wasn't even a guide, she was just a driver. When you get to the town you have to fend for yourself. You have to buy the trolley tour, otherwise you can't actually tour the town. None of this is explained in the description of the tour. Everything is extremely expensive in the town, you have to pay for simply everything - want to see the old school? Gotta pay. Want to see the fort? Gotta pay. And some folks are very rude as well, they don't seem to like tourists. Very bad experience!
Polly_K, Jul 2026
It was a lovely experience. Our pick up was on-time our guide assistant/driver Kevin was very knowledgeable. The van was comfortable even during an excess heat warning. We loved exploring on our own based on Kevin’s excellent recommendations. The time just went by so fast.
Ronald_A, May 2026
The van ride to St Austine was comfortable; the driver was a very entertaining, informative and talkative driver. The trolley driver we had was funny and informative.
robertdoggett71, May 2026
We have a wonderful day, St Augustine is as lovely city with a great history, our guide Bonni was very helpful and knowledgeable about just about anything. She made our trip even better and had a lovely personality.
Tina_P, May 2026
St Augustine is a good trip, we went on this trip on the 17th april drivers name was Mike, what im not happy with is the cocky attitude of the driver he didn't give much info it was like he couldn't be bothered when we got to saint Augustine he made all those that hadn't payed for the trolley get a ticket said it was the only way to see it so when me and my partner said we didn't want one has we had done it the last time we came he was not happy, at the end of the trip as we were getting back on the bus he thrust a clipboard in our faces demanding we give him 5 stars and a tip he wasn't bothered about any comments people put about him he just wanted the 5 stars it was his bad attitude that wasn't happy with and thrusting the clipboard in everybody's face everybody was shocked when he did it, on the way home he nearly crashed on the express lane all the traffic in front had stopped but he was speeding towards it and not slowing down someone shouted can someone wake him up before we crash he then had to pull over to the side to avoid hitting the cars in front several people also kept pipping their horns at him, he also ran out of fuel even though he had all day to get some.
Response from Host, May 2026
We appreciate you taking the time to share your feedback. While we’re pleased to hear you enjoyed visiting St. Augustine itself, we are very sorry to read about your concerns regarding the transportation experience.
What you have described does not reflect the level of service and professionalism we aim to provide, particularly in relation to guest interactions and the concerns you raised about the return journey. Guest comfort and safety are extremely important to us, and feedback of this nature is taken very seriously. Your comments will be reviewed as part of our ongoing commitment to providing a safe and positive guest experience.
Linda_A, Apr 2026
Fantastic experience. Just not enough time to see everything!
Trolley ride very worthwhile. Tour drive Mike… great job.
Double check leaving times. Our AM pick up time not as advertised. Heads up. I messaged company and they were quick to advise time and clarify location.
Response from Host, Apr 2026
Thank you for the great feedback! We’re glad you had such a fantastic day and that Mike took good care of you along the way.
We appreciate the heads up on timing as well—when we have contact details, we always confirm pickup times in advance to avoid any confusion, so we’re happy our team could quickly clarify things for you. Hope to see you again for another adventure soon!
swann150, Mar 2026
St Augustine is a lovely place to visit. Kevin our tour guide and driver was very knowledgeable and friendly. Would definitely recommend this day trip.
Daniel_s, Mar 2026
Kevin was my driver and he was very knowledgeable about st Augustine and the state of Florida in general. Highly recommend
Nicole_w, Mar 2026
The driver Mike was wonderful, he ensures all the guests in the vehicle are comfortable during the drive out to St Augustine. He also knowledgeable about St Augustine and surrounding areas.
Paul_W, Mar 2026
Kevin was a very personable driver and very knowledgeable about St. Augustine and Florida in general. He made the trip very comfortable. I will travel with Gray Line tours again.
Stephen_E, Mar 2026
Great trip on my own, tour company pick up was brilliant, went to torture museum had lunch on the rooftop of great seafood bar.
I even lost my wallet on the van but tour company kept hold of it which was a great relief.
Will def recommend this trip
Thomas_D, Feb 2026
Beautiful, historical town. So many shops, restaurants bars. This town is ready to entertain you. We took the cruise also.
Just a great day
Nancy_S, Feb 2026
We really enjoyed the hop on and off trolley. It's best to review the stops prior getting on, so you can plan where you want to get off.
Mark_S, Feb 2026
Well, the trip started out great, hotel pickup on time, ride upto St Augustine fantastic. Pulled into Old Jail parking lot, that's when everything unraveled. Mike said we should get trolley tickets for the day and some people were wary of giving cc info over the phone. That's when it went from bad to worse. Mike aka Tuck, was trying to call the office and nobody was answering. We arrived at 10 am and this went on for an hour, finally getting through and two couples, one was us, bought tickets for the trolley. Everyone else bought tickets at the booth right there. Anyway, with all this going on, we ended up being late for our boat cruise, missing it. So, now we have to take the 1 o'clock tour which really messed up our day. Had just enough time for lunch and back to the dock. Cruise went good. Off the boat at 115pm and onto the next trolley back to the start point which the bus was scheduled to leave at 4pm. Our day was ruined. We expected to be able to explore and shop St. Augustine, when in reality all the confusion wasted our time. We paid for a trolley we only rode once. Of course a few people were late. Now we're back on the road to Orlando around 4:30-5:00PM, heavy traffic, once again to be expected. We finally arrive to Orlando,but way off course, multiple wrong turns, 2 hours of driving lost, and several close calls with other vehicles. People on the bus started asking where we are going. Two couples ask to be let out at a random hotel, they were ordering an Uber. The rest rode on. Finally, the drop offs started. We left St Augustine at 430 pm and we're dropped off at our place at 9pm. Totally unexceptable! All of this could've been avoided if Viator had encouraged people to buy trolley tickets before arriving-to avoid all the time wasted in the confusion. Will be standing by for a response. Not at all happy with yesterday. So disappointing! Mark
Terry_K, Jan 2026
Could take longer than expected with hotel pickups and traffic. Took almost 2 hours to get there and almost 3 hours coming back. The driver, Ishmael, was a good driver and very personable.
St Augustine is such a quaint town and we loved the Lightner Museum and walking through the shops on St George St and seeing the inside of St Augustine church.
Mike_B, Jan 2026
Long drive from Orlando, but great stop 1/2 way there. Lots too see when there and not enough time. Trolley ride was good, but looped around to much
Zaineb_A, Nov 2025
This is my first visit to St. Augustine with my nine-year-old son. It is a beautiful place that you must visit.
We had a wonderful experience.
(Brad), our driver, made the trip easy, smooth, and comfortable.
He is a good driver and friendly.
Thank you!
JorgeDaniel_C, Nov 2025
Wonderful experience. Freedom to explore the town. Trolley was a great way to visit the town without driving. Kevin was a great driver / host. Good and very knowledgeable storyteller. He made the trip more interesting and entertaining. We appreciated his patience and help with our special needs. Very accommodating throughout the whole trip. Would highly recommend to everyone traveling from Orlando
Hazel_T, Oct 2025
Whole trip from start to finish was excellent, a wonderful place ,lots to do and see ,our driver was great ,we was caught in a storm comming back and his driving was brilliant
Susan_N, Oct 2025
Trolley tour was a good way to see everything and the guides are very informative. However everything is in walking distance,
Soina_F, Oct 2025
St augustine is a lovely place wish we had more time to explore and the weather didn't help if visiting orlando book this trip
William_B, Jul 2025
Van was comfortable. Individual seats. Kevin our driver was extremely knowledgeable and friendly. Boat cruise was fun too
Didithbon_D, Jul 2025
We took the trolley tour! I liked it because you can see all the important history of the place! Plus you don’t to do a lot of walking! You just hop on and off the trolley all day!
Our guide Ismael was excellent! Caring and compassionate! I thank him for assisting my husband at all times! I appreciate him very much!
Gail_J, Jul 2025
Don't go in July. Way to hot to really enjoy. Trip was good otherwise. Really enjoyed the boat ride.
Lucinda_M, Jul 2025
Kevin (Tour Guide) and Trip was lovely.
Highly recommended.
Kevin was very knowledgeable and felt safe as a solo passenger :)
Sayareh_O, Jul 2025
Beautiful city! Loved the sites but soooo hot and draining in summer. Would rather go another season.
luputania, May 2025
We enjoyed the scenery and beautiful historic buildings. The streets made every walk feel special. Lots of stores and very good ice cream 🍦 😋 @
Dorothy_E, Apr 2025
Amazing day trip to St Augustine from Orlando. Our driver with GrayLine, Kevin was so very nice & packed with info & history of the Orlando/St Augustine area. I would absolutely recommend this trip. 25 stars for Kevin!!!
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.
Janelle_P, Feb 2025
We had the absolute best experience. I would highly recommend booking the Trolley Tour. One of the best part was definitely the bus driver Ishmel that took us to St Augustine and back, he is truly a beautiful soul. We also enjoyed all of the Trolley drivers energy.
St Augustine is a gorgeous town with so much things to see (lots of historical landmarks). The atmosphere is really nice as well, people are really friendly.
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