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

Enjoy a day in America's oldest town, St Augustine. On this day trip from Orlando, head northeast to the picturesque town, where you can wander the cobbled streets and enjoy a...

Ensure to purchase the option including the trolley to see the most of the city
  • Orlando, Florida
  • 10 hours
  • Day Trips
  • Free cancellation

4.5 (256 reviews)Rated 4.5 out of 5

About this experience

Enjoy a day in America's oldest town, St Augustine. On this day trip from Orlando, head northeast to the picturesque town, where you can wander the cobbled streets and enjoy a meal in one of the many promenade cafes. St Augustine is a unique city filled with colonial Spanish neighborhoods, magnificent buildings and a wonderful, old-time charm.

As the oldest continuously occupied European-established settlement in the USA it has lots of history. From the Castillo de San Marco, to the Fountain of Youth there is something for everyone. Upgrade to add a scenic cruise, trolley tour or the Medieval Torture Museum to your visit.

If you select the option including the Hop-On Hop-Off Trolley than you can have a guided tour throughout the historic old town, and jump on an off as you wish. The scenic boat tour option is a 1-hour boat ride with views from the waterways of the Bay of Matanzas! At the Medieval Torture Museum you see first hand the. grueling history of mad men and tyrants!

What is included

  • Trolley tour (if option selected at time of booking)
  • 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)
  • Medieval Torture Museum (If option selected at time of booking)

Not included

  • Gratuities
  • Food and drinks

Our take

An easy, well-reviewed day trip to St. Augustine, the oldest continuously occupied European-established city in the U.S., with hotel pickup from Orlando and free time to explore.

Best for

  • History lovers
  • Couples
  • Travelers without a car

Skip it if

You prefer to set your own pace; driving gives more flexibility.

Tips before you book

  1. Wear comfortable shoes for brick and cobblestone streets.
  2. Visit the Castillo de San Marcos early.
  3. Plan lunch on or near St. George Street.

How it compares

ExperienceRatingFromLength
Day Trip to Historic St. Augustine from Orlando with Hotel Pickup (this tour)4.5 (256)$10010 hours
Clearwater Beach Bus Express4.9 (23)$10012 hours
Daytona Beach Day Trip with Hard Rock Resort Pass & Hotel Pickup4.6 (37)$1199 hours

Similar experiences in Orlando, compared by traveler rating, starting price and length. Prices update with our latest data.

Meeting point

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.

Additional information

  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels

Cancellation policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Frequently Asked Questions

How much does Day Trip to Historic St. Augustine from Orlando with Hotel Pickup cost?

Day Trip to Historic St. Augustine from Orlando with Hotel Pickup starts from $100 per person. The final price depends on your date, group size and any options you choose, and is shown before you pay on Viator.

How long is Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?

This experience takes about 10 hours. Allow extra time for check-in and travel to the meeting point.

Is Day Trip to Historic St. Augustine from Orlando with Hotel Pickup worth it?

Travelers rate it 4.5 out of 5 based on 256 reviews on Viator. Read recent reviews on the booking page to see what past guests enjoyed most.

Can I cancel Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?

For a full refund, cancel at least 24 hours before the scheduled departure time.

Where does Day Trip to Historic St. Augustine from Orlando with Hotel Pickup start?

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.

How do I book a tour on ThingsToDoOrlando.com?

Choose an experience, then select Check availability. You will be taken to Viator, a Tripadvisor company, where you pick a date, see the final price and pay securely. Your confirmation and tickets come from Viator by email.

Similar tours you may like

Live availability and traveler ratings from Viator.

Related experiences our readers book alongside this one.

All day trips

Back to all experiences

From$100
Availability for your date is confirmed on the booking page.
Check availability