The 4 Best St Augustine Day Trips from Orlando

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

★★★★★★★★★★4.5 · 230 reviews · 10 hours (approx.) · from $100Our pick

Travel from Orlando to St. Augustine in a small group of up to 14 people, with hotel pickup, free time around St. George Street, and optional trolley or Matanzas Bay cruise upgrades. Drivers such as Kevin and Ishmael add local stories to the long but worthwhile day.

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

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2.Day Trip to St. Augustine with Hotel Pickup

★★★★★★★★★★4.4 · 81 reviews · 12 hours · from $100

Ride from Orlando to St. Augustine with an English-speaking Gray Line guide, then explore America’s oldest continuously settled town. Choose a trolley, cruise, Colonial Quarter, or Pirate Museum option. Guides such as Kevin, Ishmael, Gino, and Donald have helped make the long day informative and easy to manage.

“This was by far the best trip I have ever taken. Our Grey Line driver was unbelievably knowledgeable and friendly. The trolley tour was the best way to see the whole city and be able to explore multiple points without the stress of time. Next time I go to Florida I will be booking this tour again.”

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3.St Augustine Tour and Pirate & Treasure Museum

★★★★★★★★★★4.7 · 3 reviews · from $119

Ride from Orlando in a small group of up to 14, then explore St. Augustine on your own. Your day includes Pirate and Treasure Museum admission, a real cannon-firing experience, free time for cobblestone streets, shops, and meals, plus Gray Line driver assistance.

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4.St. Augustine Nights of Lights Celebration from Orlando

★★★★★★★★★★4.5 · 3 reviews · from $119

Travel from Orlando to St. Augustine for the Nights of Lights celebration. You’ll see the old city glowing with millions of white lights, ride the Holly Jolly Holiday Trolley with special light-enhancing glasses, and enjoy hot apple cider and cookies. Ismael may be your driver.

“Beautiful lights! So many great restaurants to choose from like Harry’s, Colombia, Casa Reina. Gorgeous old city. Trolley ride & singing Christmas songs, so fun. Ismael, our driver, was WONDERFUL! Thanks for a great experience.”

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