6 History Tours in Orlando Worth Booking

1.2 Hour Historical Wildlife Tour of the Chain of Lakes

★★★★★★★★★★5.0 · 293 reviews · 2 hours (approx.) · from $41Our pick

Join Living Water Boat Cruises for a two-hour pontoon trip through Winter Haven’s connected lakes and canals. Captains such as Rue, Randy, Bryce, Saige, and Darrell point out birds, alligators, historic sites, celebrity ski spots, Cypress Gardens, and the famous Florida-shaped pool.

“Great afternoon spent on the water and so relaxing. We would highly recommend this to anyone!! Bryce was kind and very educational!”

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

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

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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3.1 Hour Historical Wildlife Tour of The Famous Chain of Lakes

★★★★★★★★★★5.0 · 141 reviews · 1 hour (approx.) · from $26

Board a private pontoon at Harborside in Winter Haven for a one-hour cruise through connected lakes. Guides such as Rue, Randy, Saige, and Darrell share local history while you watch for alligators, turtles, ospreys, herons, eagles, and other birds.

“Oh! We had a great captain, Randy who was exciting, fun and a great educator. We had a absolute ball with him. I just moved here to the Chain of lakes area and had family in visiting. Captain Randy educated me on the birds and the Lakes my family was very impressed. Thank you Captain Randy.”

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4.Skip the Line: Museum of Military History Ticket

★★★★★★★★★★4.5 · 37 reviews · 2 hours (approx.)

Spend about two hours exploring Orlando’s Museum of Military History, arranged in chronological order from the Revolutionary War onward. Your mobile ticket includes skip-the-line entry, and you can visit independently rather than follow a group. Guided tours may also be available, including tours led by Al.

“The museum is informative regarding the United States involvement in military wars around the world.”

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5.Sanford’s Craft Beer and History Tour

★★★★★★★★★★4.0 · 5 reviews · 1 hour 45 minutes (approx.) · from $33

Spend about 1 hour 45 minutes with guide Gary, a BJCP Certified Beer Judge, exploring Sanford’s historic center, the Sanford Homebrew Shop, Sanford Brewing Company, and Wop’s Hops Brewing Company. Expect a small group, local beer, brewery questions, and a short walk between stops.

“We had such a great time . Everything flowed so smooth and our guide had an answer for every question ! Highly recommend”

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6.Downtown Sanford Historical Tour

★★★★★★★★★★5.0 · 3 reviews · 1 hour 30 minutes (approx.) · from $25Best value

Walk historic downtown Sanford with a local guide, often including Nancy, for 90 minutes of stories, old photographs, and architecture dating to 1883. See the old fire station, jail, PICO Building, theater, and more. The group is capped at 15 people.

“More standing than walking, but explanations were great as was the use of the guide's tablet to show photos of the buildings " before"”

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