Charming Hidden Gems in Orlando for a Lovely Vacation

Over 65 million travelers visited Orlando in 2016, with a large chunk interested in theme parks and the resort scene. However, did you know that the Orlando region also offers off-the-beaten-path delights to explore as well? So if you are wondering what to do in Orlando instead of Disney and/or you need a break from the crowds, then this guide on hidden gems in Orlando is for you! Don’t miss out on Orlando’s quaint foodie spots, cultural activities, and refreshing outdoors!

Is There More to Orlando Than Disney?

Yes! Although Orlando is famous for its many amusement parks, chain stores, and franchise restaurants (Bahama Breeze is actually pretty good though), there are so many other things to do in Orlando. Tucked between and beyond conventional attractions, the Orlando region can also offer stunning natural wonders, charming small towns, boutique restaurants, art museums, and much more.

We often travel to Orlando to visit family and are always pleasantly surprised by the amount of unique Orlando activities to do that do not involve being shot into the air by a slingshot or melting under the hot sun waiting in a long line for some crowded experience.

Getting Around Orlando: Uber? Car? Train?

Ubers: If you don’t want (or know how) to drive, you can order Ubers all around the area to take you between different places. This may be an especially attractive option because the Uber prices are about $20 for 30 minutes of driving. Not bad! And even better if you’re traveling with others because then that rate is divided by 2 or 3.

Train: There is a train in Orlando! The SunRail has 16 stops from the Kissimmee area to Orlando and beyond. It stops at some pretty cute towns, tool. Like Winter Park which we loved. You can also take the train to one of the towns and then Uber it to your next destination.

Bus: There are some buses. But they are not as consistent. I suggest taking an Uber over a bus depending on the time and price difference.

Traffic: Simply put, getting around Orlando is best done with a car. Especially if you want to reach Orlando’s hidden gem attractions. The infrastructure of this area is made for driving. In fact, the Orlando-Kissimmee region has been ranked as number one for the least walkable in the USA. However, there is almost always traffic in Orlando. To drive just 8 miles can take 30 minutes, which is pretty annoying. And you have to be careful as things don’t have as many signs here, so lanes will randomly become a turn-only but now you’re enclosed by a ton of cars because of the traffic and have to think fast. But despite that, it’s much easier to get around Orlando by either borrowing or renting a car. Just remember to drive super early or outside of the work/school rush hour.

Off-the-Beaten-Path Orlando Hidden Gems Things to Do

1. Kayaking in the Crystalline Waters Rock Springs Run (Emerald Cut)

Wekiwa Springs State Park spans across 7,000-acres of natural wonders and is one of only two National Wild and Scenic Rivers in the state of Florida. Located in Apopka, it is just a 30-minute drive north of downtown Orlando. In this park, you can go camping, biking, hiking, horseback riding, and canoeing/kayaking. There are different entrances to this park and different companies that provide kayak rentals along different canals.

My personal favorite was Kings Landing which offers two unique kayaking routes. One is through their Emerald Cut. You kayak for about 1.5 hours against the current but through crystalline-blue waters. The way back takes 30 minutes since you’re going with the current. Plan to stay here for the full 4-hour kayak rental since there are several stops along the way for swimming, wildlife viewing, and other stunning photo ops.

If you want to go on a guided tour, I recommend this 2-hour glass-bottom tour.

2. Historic Eatonville & Zora Neale Hurston

Just 10 minutes north of downtown Orlando is the historic town of Eatonville. The first Black community incorporated in the United States! Free Black Americans founded this town in 1887. Let’s put that into perspective: The United States abolished slavery in 1865. And many of the enslaved spent years after not knowing they were legally free. So imagine the effort required to successfully incorporate one of the first self-governing, Black municipalities in the United States at a time like that! That is monumental.

Today, Eatonville remains one of the oldest Black communities still in existence and thus is a part of the National Register of Historic Places. Come here to support such underrated and meaningful history as well as for the cultural attractions; such as the Zora Neale Hurston National Museum of Fine Arts. Here, you can ask for a tour of the town for $20 per person. It is well worth the experience!

For more history on Black American history, you can also add the Wells’ Built Museum of African American History and Culture to your Orlando bucket list.

3. Alligator Kayaking Safari in Rocks Springs Run

Kings Landing (mentioned above) also provides a second kayaking route. However, this one is done as a guided tour and you’ll be paddling with the current the entire time. However, it is an 8-mile trajectory and thus is not for travelers who have never kayaked before. Along this route, the water becomes darker but you’ll be in a dense and more preserved natural setting where wildlife is more easily spotted.

We saw alligators, spiders, birds, and turtles. We also heard wild pigs! You can also look out for other wildlife like coyotes, rabbits, deer, foxes, raccoons, and black bears.

4. Winter Park: For Food, Shopping & Museum Hopping

Winter Park is a semi-upscale neighborhood perfect for lovers of arts and culture. There are several outdoor opportunities here, too, such as boat rides through its canal/river and the region’s 70+ parks. If you love shopping for artisan goods, downtown Winter Park offers several cute shops, most within walking distance. You can easily park your car and spend an entire day at Winter Park strolling through its cute streets, popping in and out of its museums, and eating at boutique restaurants. Here are a few spots you can’t miss here.

If you love nature:

For foodies:


5. Explore Ocala National Forest

Spanning 600+ square miles of natural beauty, Ocala National Forest offers outdoor lovers endless exploring opportunities. Established in 1908, the forest features diverse ecosystems, including pine forests, hardwood hammocks, and wetlands. Most importantly, the forest is home to several pristine springs and lakes.

Things to do in the Ocala National Forest:

  • The forest is home to over 600 lakes, rivers, and springs, making it a popular spot for fishing, boating, and swimming. Most notably: Juniper Springs, Alexander Springs, and Silver Glens Spring.
  • Visitors can also explore the forest’s numerous hiking and biking trails, which offer scenic views of the surrounding landscape.
  • For those interested in wildlife, the Ocala National Forest is home to various species, including the Florida black bear, the gopher tortoise, and the red-cockaded woodpecker.
  • Go kayaking
  • Go biking or horseback riding
  • Rent a boat and so much more!

Fun fact: The forest also played a vital role in developing the United States space program, with NASA conducting numerous tests of rocket engines in the area.

6. Silver Glens Spring Swimming Hole + Lake George

Silver Glen Springs is a beautiful natural spring, located within and along the eastern edge of in the Ocala National Forest. These springs produce over 65 million gallons of water daily! And this water empties into Lake George (the second largest lake in Florida after Lake Okeechobee). The crystal clear water of the spring is surrounded by lush vegetation and is a popular spot for swimming, snorkeling, and kayaking. You can also enjoy BBQ, hiking on nearby trails, birdwatching, and exploring the forest.

It’s important to note that Silver Glen Springs is also a sacred and important archaeological site for Native Americans. Please respect these areas, especially the parts that are fenced and marked.

Bonus tip: You could pair a trip to Silver Glens Springs with Silver Springs State Park, about 45 minutes away. Just note that these two places can have wildly varying climates. It can be rainy in one and sunny in the other. So check the weather ahead of time to plan accordingly.

7. Shop at a Local Farmer’s Market

What better way to connect with locals, support artists, and small businesses, try local foods, and shop for cute artisan craft goods than to visit a local farmer’s market? Throughout the week, you can visit several markets in the Orlando region. Here are a few to consider:

  • Orlando Farmer’s Market – Sundays starting at 10 AM
  • Audubon Park Community Market – Mondays starting at 5 PM
  • Winter Parks Farmers Markets – Saturdays starting at 8 AM
  • Maitland Farmer’s Market – Sundays starting at 9 AM
  • Windermere Farmer’s Market – Fridays starting at 9 AM
  • Lake Eola’s Farmer’s Market – (They offer a morning outdoor yoga class for $5)

8. Lake Fairview Sunset Sailing Tour

This Fairview Lake Sailing experience is a fun way to relax while enjoying the natural beauty of Lake Fairview in Orlando, Florida. On the private two-hour tour, visitors can enjoy the serene sunset views over the water while listening to the sounds of nature. It is also led by an experienced captain who provides information about the area and points out interesting sights.

Lake Fairview is a popular destination for Orlando water sports and outdoor activities. The lake covers an area of approximately 400 acres and has a maximum depth of 29 feet. It is home to various fish species, including largemouth bass, bluegill, and catfish. The lake also has parks and recreational facilities, making it a great spot for picnics, hiking, and biking.

9. Visit the Cute Small Town of Windermere

As soon as you approach Windermere, you’ll realize it’s uniquely distinct from much of the Orlando region. Windermere is surrounded by several lakes and parks, making it more secluded and harder to stumble upon. Founded in 1889, this affluent town is one of the oldest communities in Florida. Beautiful old homes and historic buildings add to the charm of this quaint town of about 3,500 residents.

Consider a morning day trip here on a Friday when you can stop by the Farmers Market in downtown Windermere. Allow room in your belly for lunch at Yellow Dog Eats or coffee at Paloma Coffee Co. Then, stroll down the quiet unpaved streets leading to the many local parks like Lake Street Park (pictured above).

10. Hire a Photographer + Private Tour Guide Driver

Hire a photographer to take your pictures on your next Orlando adventure. Photographer Pedro Salcedo picked me up and drove me around hidden gem places in Orlando + surrounding regions. He was super reliable, on time, respectful, and took great photos and videos for me. Contact him for his Orlando photo tour + photo packages here.

11. Lake Tohopekaliga (with Boggy Creek Airboat Adventures)

Lake Tohopekaliga is the largest lake in Osceola County, and yet it remains a hidden gem oasis just 15-minutes south of Kissimmee. Here, you’ll enter Boggy Creek Airboat Adventures, a complex of several attractions on the edge of the lake. Here, you have the Native American village (history tours), a gem-mining station, a butterfly garden, a restaurant with actually good food, and the airboats!

Do not miss the sunset airboat tour! We saw alligators and lush waterways while surrounded by gorgeous sunset views. The virginal and serene atmosphere reminded me of my adventures in Botswana, Africa.

12. Kayaking with Manatees in Silver Springs State Park

This guided kayaking tour takes you on a journey through the crystal-clear waters of Silver Springs State Park, where you can observe manatees swimming and playing in the water alongside you. As you paddle along, you’ll also have the opportunity to see other wildlife, such as alligators, turtles, and a variety of birds. The tour is led by knowledgeable guides who provide interesting insights into the ecology and history of the area.

Please note: The season to see the manatees is typically during winter, from November to March. But if it gets warmer sooner, then they start to leave. You can also see them in many other natural springs in Florida, such as Crystal River, Homosassa Springs, and Blue Spring State Park.

13. Yoga with Goats at Alaska Farms

Picture this: frolicking in the grass, holding cute baby goats. Need we say more? On the beautiful property of Alaska Farms, you can enjoy quality time with their pet goats, cows, donkeys, alpacas, and other cute animals. Take one of their guided yoga classes for a much-needed full-body stretch and mindfulness practice. The perfect break between your Orlando off-the-beaten-path adventures. Book your spots in advance here.

14. Seafood Boil House

The Seafood Boil House in Kissimmee, Florida, is a popular restaurant serving delicious seafood dishes in a fun and festive atmosphere. The menu features a range of seafood boil options, including shrimp, crab, lobster, and clams, all cooked in a flavorful blend of spices and served with corn on the cob and potatoes. The restaurant has a casual, laid-back vibe, with a friendly staff and lively atmosphere. By the way, don’t be startled when you see the robot host!

15. Keel and Curley Winery at Keel Farms

Keel Farms is a farm, winery, brewery, and restaurant all in one! They are committed to serving “ground to glass” drinks and beverages. 

For a behind-the-scenes experience, you can try their wines, ciders, and beers through their farm tour. 

Keel Farms also offers a handcrafted restaurant menu where you can sit to eat sustainably grown ingredients. Don’t forget to order the Gator Tacos!

Bonus: sometimes they offer farm yoga classes!

16. Taste of Orlando: Private Chef’s Multicourse Meal

Tired of eating out? Want a homemade meal with local flavors and delicate touch? Chef Jose comes to your place (in Orlando or Kissimmee) and cooks a multicourse meal for you and your family/friends. He teaches you the “secrets hidden within each dish” with a contemporary Latin influence. He shows up with all the equipment and ingredients you need. And you’re free to either sit back and relax or join in and learn how to cook dishes with him. Prices are very reasonable, starting at just $108 for a private chef! Perfect for an intimate dinner with your loved ones. Book the experience here.

17. Everoak Farm & Farm Dinners

Everoak Farm is a small, bio-intensive farm. The family who runs this is committed to sustainability and promoting regenerative agriculture practices. 

Aside from growing “certified naturally grown” produce, they also raise poultry for both eggs and meat. 

Their mindful practices extend from cultivating meat and produce to supporting community agriculture (CSA). They also hold farm stands and host farm dinners on weekends.

18. Kennedy Space Center Day Trip

Just an hour east of Orlando is The Kennedy Space Center. You can book this day trip tour, which will take you to NASA’s launch headquarters, the site of some of the most significant moments in space exploration history! Such as the first manned mission to land on the Moon, Apollo 11, in 1969. Whoa!

This guided tour includes round-trip transportation from Orlando, admission to the Kennedy Space Center Visitor Complex, and access to numerous exhibits, displays, and interactive attractions, including the Space Shuttle Atlantis exhibit, the Astronaut Hall of Fame, and the Rocket Garden. Visitors can also enjoy various other attractions here, such as meeting an astronaut, touring launch areas, and watching a 3D IMAX movie about space exploration.

19. Day Trip to Other Crystal-Clear Swimming Holes

The state of Florida is home to hundreds of natural freshwater springs, including natural swimming pools for travelers to enjoy. Many of these swimming areas are crystalline blue and at great temperatures for swimming. If you want to experience something new and refreshing in Orlando, consider some of these beautiful rivers, swimming holes, and springs for an unforgettable experience in nature.

There are so many, but these are closest to Orlando. Look up each one of the above-listed swimming areas on Google to decide which works best for you! Avoid the weekends if you hate crowds.

20. Go Horseback Riding

Leave the hustle and bustle of Orlando city living behind you as you enter one of the many horse ranches in the area. These ranches offer several horseback riding experiences and different routes for a fun half-day experience trotting through nature. If you’re a beginner, consider hiring an instructor for private lessons. Book your spots ahead of time during the weekends, as there are limited spots available. We recommend:

21. Garden Brunch +Tea Workshop & Permaculture Tour

The Gather Garden in Winter Park offers workshops and permaculture experiences in their urban garden. Here, you can meet their pet chickens, go on a tour, take a workshop, learn how to propagate different foods, and harvest/sip on some local tea. The meals change every day so it’s always a new treat. If you love herbs, peaceful spaces, and good food, check out this Orlando hidden gem.

2022 Update: They are temporarily closed but the owner has told me they will open up back up eventually. So please check with them ahead of time.

Where to Stay in Orlando (& Where Not to Stay)

The Orlando region is expansive and connects to several other little towns and smaller districts. So if you’re looking for a more off-the-beaten-path vacation, avoid the busy International Drive area, as it’s bustling with crowds from around the world. There, you’ll also see streets lined up with bustling entertainment attractions such as indoor skydiving, chain restaurants like White Castle, and modern office towers. If the thought of this stresses you out, worry not. There are quiet options!

So what’s the best neighborhood in Orlando? Here are our favorite areas for peace and charm:

  • Windermere – This is probably the biggest hidden gem town in the Orlando region. This walkable town is surrounded by several lakes, parks, and offers a historic downtown area with cobblestone streets. I love this charming rental but if you want something more luxurious check out this villa in Windermere.
  • Winter Park – Winter Park is bigger than Windermere but is still a cute walkable town with tree-lined streets, foodie restaurants, acclaimed museums, and boutique shops. It’s the perfect quiet neighborhood to base yourself out of while exploring the rest of Orlando. And it has a train station for both Amtrak and SunRail!

As you can see, off-the-beaten-path Orlando adventures are not hard to find. So if you’re a foodie or culture/outdoor lover, be sure to add these hidden gems to your bucket list and enjoy all that the Orlando area has to offer!

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2 thoughts on “Charming Hidden Gems in Orlando for a Lovely Vacation

  1. Heather B. says:

    From a Florida native, these are great suggestions (in fact, you educated me on at least one item, the Gather Garden). May I suggest a correction? In the section on where to stay, it seems the area you identify as downtown Orlando is actually the International Drive area, based on the references to White Castle and large tourist crowds. Otherwise, I will definitely be saving your article for future reference!

    • Isabelle says:

      Oh my gosh, you are too kind! I’m glad it was helpful. I’ll be adding more gems as I continue exploring. Thank you for that correction. I will update it. You’re totally right I mixed them up in my head. 🙂

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