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

244 Reviews 4.63 out of 5 stars Based on 244 traveler reviews collected by Cool Shore Excursions and TripAdvisor |
Recommended by 91% of reviewers
91% of reviewers gave this experience a rating of 4 or higher.
|
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. Orlando, USA
Book online or call us

from $100 per person

Lowest Price Guarantee
Ensure to purchase the option including the trolley to see the most of the city
Ride the scenic boat to see the city from the water
See what like was like in passed with the Colonial Quarter option.
An original Jolly Roger flag on display at the Pirate and Treasure museum.
Shoot a cannon at the Pirate and Treasure Museum
Don't miss out!
On average, this is booked 17 (7) days in advance.
10 hours (approx.)
Hotel pickup offered
Mobile ticket
Offered in: English

Overview

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's 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)
  • Gratuities
  • Food and drinks
See 1 moreSee 2 more

Meeting and Pickup

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.

What To Expect

Book Online

Our secure website provides real-time availability, and free, no-hassle cancellations up to 24 hours before your tour begins.
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Safe & secure Easy breezy Hassle‑free

Old St. Augustine Village

The Historic District in St. Augustine is the heart of the city. This is where guests will find a majority of the city's restaurants, shopping, hotels, and attractions. The Historic District is the oldest part of the city with many buildings dating back to the 1700s. Even the streets are laid out as they would have been centuries ago, and are more walkable than a lot of cities visitors are used to seeing in America. Along with being a beautiful area for finding things to do like shopping, visiting museums, and dining, the Historic District is also home to the beautiful bayfront with lovely panoramic views of the Matanzasa Bay.The top rated attractions in the area are centered around the Historic District and reflect the importance of history in shaping St. Augustine into what it is today. For example, the Colonial Quarter is a living history museum with costumed reenactors and interactive experienes. The Castillo and the Fountain of Youth both have weapons demonstrations so guests can expect to hear the sound of canon and musket fire around the Historic District.Another defining feature of the Historic District is the architecture. The design on building facades represents the height of Spanish Colonial and Spanish Renaissance Revival architecture. The area of town showcases everything from early European design, Florida bungalow style houses, and Gilded Age extravegance. Being the nation's oldest city, the Historic District of St. Augustine represents all that history has built here since 1565.
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6 hours Admission Ticket Free

Oldest Wooden School House (pass by)

The Oldest Wooden School House is located at the entrance to St. George Street. During your free time be sure to stroll past it and down this cobble stoned street where there is great souvenir shopping and some great restaurents .
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Fort Matanzas National Monument

Upgrade your tour and enjoy a one-hour-and-15-minute cruise aboard the Victory III through Matanzas Bay. Narrated by your captain, this boat tour provides an incomparable way to view St Augustine’s historical landmarks and natural sites of interest.
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1 hour 15 minutes Admission Ticket Free

Historic Tours Of Am..

Should you purchase the option to choose to take a 90-minute hop-on hop-off trolley tour for an easy way to get around the city and see the sights you want to see.You can get on and off as much as you’d like, or simply sit back and ride the entire loop. The local conductors make the tour even more entertaining by providing history and humor.
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1 hour 30 minutes Admission Ticket Free

Show 3 more stops

Additional Info

  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • This tour/activity will have a maximum of 14 travelers

Frequently Asked Questions (8)

Q: What is the cancellation policy for the Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (EST).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-317042

Traveler Photos

Reviews

4.63
244 reviews

Average 4.63 out of 5 stars based on 244 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor

5 stars
188
4 stars
35
3 stars
12
2 stars
4
1 star
5
Don't miss out!
On average, this is booked 17 (7) days in advance.
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Frequently Asked Questions (8)

Activity name

The answers provided below were previously given in response to questions from Cool Shore Excursions customers.

Filter by:

Q: What is the cancellation policy for the Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (EST).
  • This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Apr 2025
Q: What's included in the price?
A:
The following 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).
The following is NOT included:
  • Gratuities.
  • Food and drinks.
Apr 2025
Q: What is the weather cancellation policy?
A:

This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Day Trip to Historic St. Augustine from Orlando with Hotel Pickup is as follows:

  • Suitable for all physical fitness levels
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Day Trip to Historic St. Augustine from Orlando with Hotel Pickup will be included in your confirmation email from Cool Shore Excursions. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

Oct 2026

What's Included

Activity name

  • 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)
  • Gratuities
  • Food and drinks

Additional Info

Activity name

  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • This tour/activity will have a maximum of 14 travelers

Report Product Issue

Activity name