Day Trip to Historic St. Augustine from Orlando with Hotel Pickup

Recommended by 90% of travelers

Badge of Excellence

Orlando, USA

Popular pick

Booked 5+ times last week!

10 hours (approx.)
Pickup offered
Mobile ticket
Offered in: English

Why travelers loved this

4.6

· 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

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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.

Operating hours
.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.

Old St. Augustine Village

6 hours • Admission Ticket Free

Oldest Wooden School House (Pass By)

Fort Matanzas National Monument

1 hour 15 minutes • Admission Ticket Not Included

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

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Reviews

4.6

based on 247 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

A must see

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!

Lovely Day Trip

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.

St Augustine 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

The driver Mike was wonderful!!!

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.

St. Augustine day trip from Orlando.

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.

Great day

Stephen_E, Mar 2026

A great town to visit

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

We really enjoyed the hop...

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.

Didn't go so well

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

Could take longer than...

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.

Great trip,

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

So nice Trip!!

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!

Day trip to St Augustine

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

St Augustines

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

St Augustine with trolley tour

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,

St augustine is a lovely...

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

St augustine day trip

William_B, Jul 2025

Van was comfortable. Individual seats. Kevin our driver was extremely knowledgeable and friendly. Boat cruise was fun too

St Augustine Trolley Tour

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!

St. Augustine

Gail_J, Jul 2025

Don't go in July. Way to hot to really enjoy. Trip was good otherwise. Really enjoyed the boat ride.

St Augustine Day trip.

Lucinda_M, Jul 2025

Kevin (Tour Guide) and Trip was lovely. Highly recommended. Kevin was very knowledgeable and felt safe as a solo passenger :)

St. Augustine day trip

Sayareh_O, Jul 2025

Beautiful city! Loved the sites but soooo hot and draining in summer. Would rather go another season.

Very nice!

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 🍦 😋 @

A wonderful day!!

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!!!

Good way to experience history from Orlando

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.

We had the absolute best...

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.

Amazing trip

Anna_V, Jan 2025

Interesting and amazing experience, visit this historical city of St.Augustine. Highly recommended for every one who going to visit Orlando

Do not miss this tour.

Julian_P, Jan 2025

The friendly nature of every one we met, start with Ishmael our driver. He was amazing and very helpful and knowledgeable. Lovely quaint, laid back town, buildings were amazing as is the history.

Great day

Louise_H, Nov 2024

Great Day Great History Recommend the trolly ride. Drink from the fountain of youth well worth a visit

Excellent day out

Louise_L, Jul 2024

Had a really lovely day. We did boat trip as part of our package which was great. Saw dolphins and got to know a lot more about the place. Lovely to walk around we also got trolly tickets and the lady was very knowledgeable. Would recommend. Something different.