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 the 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?

Simply put, getting around Orlando is best done with a car. Especially if you want to reach Orlando’s hidden gem attractions. While there are some public transportation options, 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. Thus, it’s much easier to get around Orlando by either borrowing or renting a car.

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.

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!

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

1) Kayaking in the Crystalline Waters of Wekiva State Park

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.

2) 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.

3) 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:

  • Eating at Blu on the Avenue
  • Having a cocktail at Hillstone Restaurant’s outdoor patio overlooking Lake Killarney
  • Ethos Vegan Kitchen for vegetarian/vegan travelers
  • Winter Park Food Tour


4) 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, there are several markets in the Orlando region to visit. 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)

5) 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 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 Pizza 14 or Yellow Dog Eats Cafe. And take a stroll through one of the quiet unpaved streets that lead to one of the many local parks like Lake Street Park.

6) 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:

7) Day Trip to a Crystal-Clear Swimming Hole

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!

8) Explore Ocala National Forest

Spanning across 600+ square miles of natural beauty, Ocala National Forest offers outdoor lovers endless things to explore. In this natural protected area, visitors can:

  • Access several springs to swim in (such as Juniper Springs and Alexander Springs)
  • Kayak along lush river trails
  • Explore hiking trails
  • Go biking or horseback riding
  • Rent a boat and so much more!

Silver Glen Springs is located within and along the eastern edge of Ocala National Forest. This recreation area is home to springs that produce over 65 million gallons of water daily! This water empties into Lake George (the second largest lake in Florida after Lake Okeechobee).

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.

9) 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.

10) 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.

11) Garden Brunch +Tea Workshop & Permaculture Tour

The Gather Garden, located 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.

12) 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” which have a contemporary Latin influence. He shows up with every equipment and ingredient 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.

Visiting Orlando: Safe Travel Practices

It would suck to get sick while you’re on vacation! So while traveling through Orlando, remember to follow healthy travel practices like washing your hands regularly, wearing a mask, and keeping a safe distance from others. 

Please keep your safety and the safety of others in mind at all times. When you are comfortable traveling, please do so mindfully and respect the local regulations. And finally, consider booking a hotel with free cancellation options in the case that you may need to change your travel plans at the last minute.

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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