Orlando isn’t just about theme parks and roller coasters. The city also offers a surprising variety of historical tours that let you explore Florida’s past in authentic, engaging ways. Whether you’re interested in exploring the natural beauty of Winter Haven’s lakes, uncovering military relics, or strolling through historic downtowns, Orlando has something for every history lover. Some of our favorite experiences include the 2 Hour Historical Wildlife Tour of the Chain of Lakes — a relaxing boat trip filled with wildlife, and the Museum of Military History — an educational peek into America’s military past. We’ll walk you through each option to help you find the perfect fit for your interests and schedule.
Quick Overview
This list features a variety of historical tours in Orlando, including lake cruises, walking tours of historic districts, bike rentals, and museum visits. From serene wildlife cruises on the Chain of Lakes to the cultural richness of Downtown Sanford, and even a kayak adventure to see manatees, there’s no shortage of ways to experience Florida’s history firsthand. Check out each tour below to find the one that matches your travel style.
1. 2 Hour Historical Wildlife Tour of the Chain of Lakes
At number 1, this 2-hour wildlife tour takes you on a relaxing pontoon boat cruise through Winter Haven’s famous Chain of Lakes. Led by a guide with over 40 years of experience, you’ll glide past six to eight lakes, many of which are connected and rich in wildlife and tropical scenery. The tour emphasizes nature, with chances to spot alligators, otters, turtles, and a variety of bird species.
What makes this tour special is its blend of history and habitat. You’ll pass landmarks like the Cypress Gardens and the Florida-shaped pool from the classic Esther Williams movie “Easy to Love,” along with the lakes where Elvis Presley and Johnny Carson once skied. The guide shares stories about the area’s role in Hollywood and its importance as the Water Ski capital of the world. Guests praise the informative narration, wildlife sightings, and the relaxing pace.
Practical details include the option to bring your own snacks and drinks, and reservations for lakeside dining are available if you want to extend your visit. This tour is perfect for families, wildlife enthusiasts, and anyone seeking a peaceful, scenic experience.
Bottom line: For a laid-back, educational glimpse into Florida’s natural and cultural landscape, this tour offers exceptional value at $41.50 per person.
2. 1 Hour Historical Wildlife Tour of The Famous Chain of Lakes
At number 2, this 1-hour wildlife tour offers a shorter, more affordable way to explore Winter Haven’s famous lakes. It’s an ideal choice if you’re short on time but still want to see wildlife and historical sites. Led by a friendly guide, you’ll cruise past five or six lakes, including the Spring Training grounds of the Boston Red Sox and Cleveland Indians, and get a brief history of the area.
Guests rave about the knowledgeable guides like Rue and Sage, who share stories about the lakes’ Hollywood connections, such as the famous Florida-shaped pool, and point out wildlife like gators, otters, and birds. The tour provides bottled water onboard, making it an easy, comfortable experience for all ages.
While shorter, this tour doesn’t skimp on the informative content or wildlife sightings. It’s particularly suited for families or travelers with limited time who still want a taste of Florida’s lake lifestyle.
Bottom line: At just $26.50 per person, this tour offers a compact, engaging introduction to Winter Haven’s lakes and history.
3. Skip the Line: Museum of Military History Ticket
Number 3 on the list is the Museum of Military History, a 2-hour visit that’s perfect for military enthusiasts or anyone interested in American wartime artifacts. This skip-the-line ticket allows you to bypass long queues and get straight into exploring a comprehensive collection of uniforms, photographs, and relics from various conflicts.
The museum emphasizes educational value, with exhibits arranged chronologically to show the evolution of military gear and strategy. Visitors often comment on the moving stories and rare artifacts, providing context for the sacrifices made by service members. With the freedom to wander at your own pace, you can focus on the displays that pique your interest most.
The ticket price is just over $12, making it an accessible option for a few hours of immersive history. It’s well-suited for history buffs, families, and school groups, offering a chance to learn about America’s military past without the rush of guided tours.
Bottom line: For an in-depth, self-paced history lesson, the Military Museum delivers powerful artifacts and stories at a very reasonable price.
4. Orlando Manatee and Olde Florida History Adventure Tour
Number 4 is the Manatee and Old Florida History Adventure, a 2-hour kayak or paddleboard trip near Disney and Universal Studios. This tour is a rare chance to see more than 90% of the tours encounter manatees in their natural habitat. The guide begins with a brief safety lesson before paddling down the scenic Florida cypress waterways.
What sets this experience apart is its focus on wildlife viewing and environmental education. You’ll learn about the manatees, their habitat, and the history of the surrounding Old Florida. The tour is ideal for active travelers who want a close-up encounter with Florida’s gentle giants while enjoying a peaceful paddle through lush waters.
Guests say the water safety instructions are clear, and the manatees are often close enough for photos. With the guide sharing interesting facts about the river’s flora and fauna, this tour is both educational and fun. It’s perfect for families, nature lovers, or anyone eager to combine outdoor activity with wildlife watching.
Bottom line: For $65, this tour offers a unique, intimate encounter with Florida’s wildlife and landscape, especially appreciated by those seeking a more adventurous experience.
5. Downtown Sanford Historical Tour
Number 5 takes you on a Downtown Sanford Historical Tour, a 1.5-hour walk through one of Florida’s most charming historic districts. Starting at the Sanford Information Center, you’ll explore 19th-century architecture, including landmarks like the Old Jail House and Old Firestation.
Led by a knowledgeable local guide, this tour shares stories from the 1800s, revealing how Sanford grew from a quaint river port to a vibrant city. You’ll pass by popular spots like the Wayne Densch Performing Arts Center and learn about Sanford’s evolving culture. The tour’s small-group format (limited to 15 travelers) ensures an intimate and personalized experience.
Guests appreciate the well-rounded narration that combines architecture, local anecdotes, and modern culture. It’s suited for those interested in urban history and lovers of small-town charm, especially during the morning or early afternoon.
Bottom line: For a relaxed walk that combines history and local flavor at a reasonable price, this Sanford tour is an excellent choice.
6. 2-Hour Bike Rental in Historic Downtown Sanford
Number 6, the Bike Rental in Sanford, offers a flexible way to explore the historic district and scenic Lake Monroe. Rent a hybrid bike and set your own pace as you cruise the Sanford Riverwalk or explore the neighborhood’s vintage homes.
This is a straightforward, practical option for travelers who prefer to explore independently. The bikes are adventure hybrids, suitable for paved trails and residential streets. It’s especially good for those who want a hands-on experience or to combine sightseeing with some gentle exercise.
Guests comment on the ease of rental, friendly staff, and the ability to craft your own route. Whether you want to soak in the historic architecture or enjoy lake views, this option lets you customize your day.
Bottom line: For $25, this bike rental suits independent travelers or those wanting a more active, self-guided experience.
$25.00 per person
7. Sanford’s Craft Beer and History Tour
Number 7 features the Craft Beer and History Tour, a 1 hour 45-minute stroll through historic Sanford’s brewery scene. Led by a BJCP Certified Beer Judge, you’ll visit three local breweries, each with its own unique story and flavor.
Starting at the Sanford Homebrew Shop, the tour explores Sanford’s Prohibition-era history and how it shaped today’s craft beer scene. Each brewery offers tastings of locally brewed beers, making it a fun way to combine history and beer. Guests highlight the guide’s wealth of knowledge and the relaxed, small-group atmosphere.
While not as long or comprehensive as other tours, this experience fits well for beer lovers interested in local culture. It’s also suitable for those who enjoy casual walking and discovering hidden local gems.
Bottom line: For $33.99, this tour provides a flavorful look at Sanford’s brewing heritage intertwined with its historic roots.
$33.99 per person
8. E-Bike Rental – 2 Hour Rental in Historic Downtown Sanford
Number 8 offers the E-Bike Rental, a sporty, pedal-assist option that makes exploring Sanford’s historic streets easier. The Specialized Turbo Como SL 4.0 bikes are designed for comfort and ease of use, perfect for those who want to cover more ground without breaking a sweat.
Ideal for active travelers or those with limited mobility, this rental allows you to explore the residential district, riverfront, and Sanford Riverwalk at your own pace. Helmets and locks are provided, making it a convenient way to see the sights.
Guests note the quality of the bikes and the flexibility they offer. You can enjoy Lake Monroe views, visit local historic homes, or simply enjoy cruising through a quaint Floridian town with ease.
Bottom line: At $45, this e-bike rental is a fun, effortless way to see Sanford’s historic districts and scenic waterways.
$45.00 per person
9. Urban Canvas: A Downtown Orlando Cultural Tour
Finally, number 9 is the Urban Canvas Cultural Tour, a 2.5-hour walk that focuses on Orlando’s modern art and cultural scene. This guided tour takes you through art galleries, cultural venues, and iconic landmarks like Lake Eola and the Sculptures on the Lawn.
Perfect for art lovers and history enthusiasts, this tour combines visual art with city history. Along the way, you’ll sample tastings from trendy, locally owned eateries, making it a well-rounded experience of Orlando’s cultural evolution.
Guests appreciate the insightful commentary about public art, architecture, and the city’s transformation from a citrus town to a vibrant metropolis. It’s ideal for those wanting a blend of artistic and urban history.
Bottom line: For $60, this tour offers a comprehensive look at Downtown Orlando’s creative spirit, perfect for those interested in urban culture.
$60 per person
How to Choose the Best Historical Tour in Orlando
Choosing between these options depends on your personal interests, time, and budget. If you love nature and wildlife, the Wildlife Tours of the Chain of Lakes are hard to beat, especially for families. For a deep dive into military history, the Museum of Military History provides a well-curated collection.
If you prefer outdoor adventure, the Manatee and Old Florida History Tour offers a rare chance to see manatees up close. For those interested in urban history and local flavor, Sanford’s walking, bike, or beer tours give authentic insights into small-town Florida. Lastly, art lovers should consider the Urban Canvas Tour for a taste of the city’s modern cultural scene.
Practical tip: Book early, especially for popular outdoor tours during peak season, and consider combining a wildlife experience with a cultural walk to diversify your visit.
Final Thoughts
From tranquil wildlife cruises to immersive museums and lively urban explorations, Orlando’s historical tours offer something for every curiosity. The 2 Hour Wildlife Tour and the Museum of Military History stand out as excellent options for different interests—nature and military history, respectively. Meanwhile, the Sanford area provides charming historic districts and brewery scenes worth exploring.
No matter your choice, these experiences are best booked in advance, especially during busy travel seasons. Dive into Orlando’s past and enjoy an enriching, authentic slice of Florida’s history.