Orlando · HISTORICAL TOURS

10 Historical Tours near Orlando Worth the Drive

10 tours  ·  from $25 per person

The good historical tours book out first in winter and on summer weekends. Below are the 10 to reserve early, what each includes and how they differ.

2 Hour Historical Wildlife Tour of the Chain of Lakes - Cypress Gardens, seen from the water
2-Hour Experiences, Historical Tours, Orlando Wildlife Tours, Tour Reviews, Tours, Tours in Orlando

2 Hour Historical Wildlife Tour of the Chain of Lakes

1.2 Hour Historical Wildlife Tour of the Chain of Lakes

★★★★★★★★★★5.0 · 293 reviews · 2 hours (approx.) · from $41Top choice

This two-hour pontoon cruise from Harborside takes you through Winter Haven’s connected lakes, past Chain of Lakes Park and the remains of Cypress Gardens. Captains such as Rue, Randy, Bryce, Saige, and Darrell share local stories and help you spot birds, alligators, and other wildlife. The boat holds no more than 11 people, and you can bring snacks or drinks.

“Very fun way to get out on the water! Our guide, Bryce, was full of knowledge and very nice! Thank you!”

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Day Trip to Historic St. Augustine from Orlando with Hotel Pickup - Six hours in the historic district
1-Day Tours, Day Trips from Orlando, Historical Tours, Tour Reviews, Tours in Orlando

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

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

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

Ride from select Orlando-area hotels to St. Augustine for about six hours in the walkable historic district. Browse St. George Street, see the Oldest Wooden School House and Castillo de San Marcos, and add a Matanzas Bay cruise or 90-minute trolley tour. Gray Line Orlando provides round-trip transport for groups of up to 14.

“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!”

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1 Hour Historical Wildlife Tour of The Famous Chain of Lakes - Wildlife watching is a matter of looking up and down
1-Hour Experiences, Historical Tours, Orlando Wildlife Tours, Tour Reviews, Tours, Tours in Orlando

1 Hour Historical Wildlife Tour of The Famous Chain of Lakes

3.1 Hour Historical Wildlife Tour of The Famous Chain of Lakes

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

Set out from Harborside in Winter Haven for a one-hour pontoon cruise through the famous Chain of Lakes. A local captain such as Rue, Randy, Saige or Darrell shares stories about the lakes, Cypress Gardens and the area’s past while you watch for alligators, turtles and birds. The boat holds no more than 10 people, and bottled water is included.

“It was delightful! Saw wildlife and floated in three different lakes! Enjoyed our skipper, she did a great job!”

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Village Food Tours Lunch & History Tour - The Porcher House and the stories in its walls
Food & Drink, Historical Tours, Lunch Experiences, Orlando Food Tours, Tour Reviews, Tours, Tours in Cocoa Beach

Village Food Tours Lunch & History Tour

4.Village Food Tours Lunch & History Tour

★★★★★★★★★★5.0 · 80 reviews · 2 hours (approx.) · from $100

Walk historic Cocoa Village with a guide such as Halim, stopping at four restaurants for a generous lunch and at local landmarks including the Porcher House and riverfront parks. Expect local history, dishes such as brisket and key lime pie, and a group capped at 10. The tour starts and ends in Cocoa, Florida.

“Great lunch and history tour experience. Our tour guide took us to some great places. We ate some really good food. Worth doing with some close friends or family.”

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Skip the Line: Museum of Military History Ticket - When a guide is worth asking about
Historical Tours, Museums, Orlando Attraction Tickets, Skip the Line, Tour Reviews, Tours in Orlando

Skip the Line: Museum of Military History Ticket

5.Skip the Line: Museum of Military History Ticket

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

Visit Orlando’s Museum of Military History with a mobile ticket and explore its exhibits at your own pace. The displays follow American military history from the Revolutionary War onward, with artifacts and accounts from former service members. A docent-led walkthrough may add context; Al is one guide named in accounts, but a guided tour is not guaranteed with this ticket.

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

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Orlando’s Historical Highlights: A Self-Guided Audio Tour - Rosalind Club and the Lake Eola stretch
Audio Tours, Guided, Historical Tours, Self-Guided Tours, Tour Reviews, Tours, Tours in Orlando

Orlando’s Historical Highlights: A Self-Guided Audio Tour

6.Orlando’s Historical Highlights: A Self-Guided Audio Tour

★★★★★★★★★★5.0 · 14 reviews · 1 hour to 1 hour 30 minutes (approx.) · from $8Lowest price on this list

This self-guided VoiceMap tour follows downtown Orlando from the Public Library past Lake Eola, the Cathedral of St. Luke, Church Street Station, and historic buildings to the Orange County Regional History Center. Plan for about 1 to 1.5 hours. The creator introduces the route, and audio, map, and location data work offline after download.

“Easy course to travel. Narrated perfectly and super informative. Love that it took us by some resteraunts and started at a place that had a bathroom.”

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Ocala: Gypsy Gold Horse Farm Horses & History Tour - A horse photo, then a walk around the farm
Farms, Historical Tours, Horses, Tour Reviews, Tours

Ocala: Gypsy Gold Horse Farm Horses & History Tour

7.Ocala: Gypsy Gold Horse Farm Horses & History Tour

★★★★★★★★★★4.5 · 11 reviews · 2 hours · from $50

At Gypsy Gold, Dennis Thompson gives a one-hour talk about the Gypsy Vanner Horse and the British Gypsy culture behind it. Then you’ll pose for a horse photo and take a guided walk around the 40-acre farm, home to the breed’s first 16 registered horses, plus mules, donkeys, and parrots.

“it was not at all what we thought it was going to be , definitely not for children, they were bored”

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Orlando Manatee and Olde Florida History Adventure Tour - A Private Outing, Not a Mixed Group
Crystal River Manatee Tours, Historical Tours, Tour Reviews, Tours, Tours in Orlando

Orlando Manatee and Olde Florida History Adventure Tour

8.Orlando Manatee and Olde Florida History Adventure Tour

★★★★★★★★★★5.0 · 6 reviews · 2 hours (approx.) · from $65

Spend about two hours on the St. Johns River near Sanford with Three Brothers Boards. Paddle a stand-up board or kayak with guide Seth, who shares local history and explains the area’s wildlife, including manatees and alligators. Equipment is included, and the private tour returns to its starting point.

“Had a blast with Seth on this Orlando freshwater tour! The weather was perfect and the water was calm. Couldn’t have asked for a better end to my vacation. Thanks for taking us out Seth!”

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Sanford's Craft Beer and History Tour - A short route with more than beer on the agenda
Craft Beer, Drinking Tours, Food & Drink, Historical Tours, Tour Reviews, Tours, Tours in Orlando

Sanford’s Craft Beer and History Tour

9.Sanford’s Craft Beer and History Tour

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

Start at Sanford Homebrew Shop, then visit Sanford Brewing Company and Wop’s Hops Brewing Company on a 1-hour-45-minute walk through downtown Sanford. A BJCP Certified Beer Judge leads the small group, with time for questions about brewing and local history. The tour starts at 5:00 pm and ends at Wop’s Hops.

“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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Downtown Sanford Historical Tour - Small Group, Local Stories, and Possible Detours
Historical Tours, Tour Reviews, Tours, Tours in Orlando

Downtown Sanford Historical Tour

10.Downtown Sanford Historical Tour

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

In a small group of up to 15, you’ll spend about 90 minutes walking Historic Downtown Sanford with a local guide. See the Old Firestation, Old Jail House, Wayne Densch Performing Art Center, PICO Building, and more, while hearing stories of the city since the 1800s. Guide Nancy has led tours that included a surprise theater visit, though access can vary.

“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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