Most Florida tourists and snowbirds head straight to Orlando or the beaches, missing out on some of the prettiest areas in our state. Although Ocala doesn’t rank as a top destination for a gay Florida vacation, if chaps and saddles are your thing, then you’ll enjoy Florida’s laidback and lush farm country.
Ocala is sandwiched between the prettiest natural springs in the state. If you’re looking for relaxation or nature-packed fun, then a gay-friendly Ocala road trip is just what you need!
History of Ocala
Located in Marion County, Ocala is north-centrally located in Florida. Originally called Ocale, meaning “Big Hammock”, Ocala is theorized to have originated as a major Native American village for the Timucua tribe, although the full history of Ocala is unclear.
In 1821, after back and forth foreign rule between Britain and Spain, America acquired Florida and in 1827, its army built Fort King here as a buffer between Seminole Indians who had inhabited the region and white settlers. Ocala was planned around Fort King. Plantations with slave laborers were also prevalent in this region.
With added rail service in 1881, Ocala had the potential to grow rapidly. Sadly, in 1883, most of downtown Ocala was destroyed in a fire on Thanksgiving day. Using brick, granite and steel rather than lumber, the city was rebuilt and in 1888, Ocala became known statewide as “The Brick City”.
The 1940’s brought horses to Ocala and in 1978, Affirmed, who was bred and trained in Marion County, won all three races of the Triple Crown. This boosted further interest in the region. Ocala is now one of five “Horse Capitals of the World”.
Although its history is bumpy and divisive, today, Ocala is home to over 60,000 people and 44,000 jobs sustained by the equine industry, generating $2.2 Billion for the region. It’s also one of the prettiest places to add to a future Florida road trip.
My Ocala Road Trip
This was one of the few road trips on which my wife joined me. Road tripping and traveling are not her thing. She can’t stand crowds, avoids kids, and doesn’t appreciate the “facade” of what a tourist experience creates (like a Disney boat ride through a fake canal…no Jungle Cruise for her). She’s as real as it gets and she prefers real life experiences. She’s also my little redneck and LOVES animals and nature. So, when I said I was headed away from the crowds to horse country, she was all in.
We spent two nights in Ocala and regretted not adding an additional day after leaving. Our experience was a blend of non-stop fun and free time. But most importantly, we had plenty of time for romance and together time outside of our COVID isolation house.
We even ran into Food Network’s Guy Fieri, Country’s Kip Moore, and NSYNC’s Joey Fatone, but more on that later!
How Gay is Ocala?
On a “How gay?” scale, when compared to Fort Lauderdale, Ocala is a 3. It’s definitely not a “gay” destination, but that doesn’t mean you won’t feel welcome. In fact, we sat at the bar a couple of times with fellow LGBTQ couples. Although Ocala isn’t swarming with rainbows and drag queens, there are a still a few places, organizations and events to check out on a gay Ocala Road Trip.
Ocala Pride, Inc.
Believe it or not, Ocala Pride, Inc. has been around for over a decade. According to their website, “Ocala Pride Inc. is a non-profit organization dedicated to the advancement and well-being of the Ocala LGBT community.” The organization organizes fundraisers and community events to help those in need and bring people together.
Although cancelled this year, the annual Ocala Pride takes place in October in Tuscallow Park while the Mr. and Miss. Pride Pageant is hosted at The Copa in April.
They also host a Big Gay Day BBQ. Due to the cancellation of the 2020 Big Gay Day BBQ caused by the COVID-19 pandemic, the Big Gay Day Annual LGBTQ Family Cookout and the 3rd annual Cornhole Tournament will be held together on Saturday, February 20th 2021 at Tuscawilla Park.
To learn more about Ocala Pride and the above mentioned events, click here.
Where to Stay in Ocala?
There are several places to stay in Ocala and many chain hotels along I-75. I would also suggest looking into FabStayz, AirBnB and Vacation rental options. I’ve also included a Booking.com link below to make your life easier.
Hampton Inn & Suites by Hilton Ocala
We were invited to stay at the Hampton Inn & Suites by Hilton, along I-75 and not far from Rainbow State Park. It’s about a 15 minute drive into downtown Ocala and in the vicinity of the new Ocala Equestrian Complex. The hotel is also close to the College of Central Florida, Paddock Mall, Sholom Park and the Appleton Museum of Art. And if you’re hungry, there are several restaurants nearby.
A complimentary hot buffet breakfast is served each morning and goodies are available at the snack bar. The staff went above and beyond to welcome us and to assure us that all guests are welcome, including LGBTQ travelers. They even left an adorable basket of “Horse Country” goodies in our room with a gift certificate to their recommended local restaurant, Ivy on the Square, along with plenty of hand sanitizer.
The Hampton Inn & Suites Ocala was the perfect place for us to stay to get around town with ease.
Pro Tip: If you want to stay in the downtown area, check out Hilton’s newest Ocala property, the Hilton Garden Inn Ocala Downtown.
Other Places to Stay in Ocala
As mentioned, there are several places to stay in Ocala on an Ocala road trip. Feel free to browse the map below for options.
Where to Eat & Drink in Ocala
Are you hungry? That’s a good thing, because there are several food options in the Downtown Ocala area as well as its outskirts. From Diners to Drive-Ins to high end fare, you have nothing to worry about – you won’t starve in Ocala.
Ivy on the Square
Speaking of Diners and Drive-Ins, Ivy on the Square is neither. This trendy restaurant with a relaxed vibe is all about pleasing the palate with finer dining comfort food. The friendly staff and fifties decor also add to the experience. I’d road trip to Ocala just to dine at Ivy on the Square.
Do not leave without ordering the Dijon Seared Scallop Stack. This might be my favorite dish in all of Florida. Also try the Salmon Citrus Salad or Skirt Steak. In reality, anything on the menu is delicious so have fun and sample it all!
Ivy on the Square is a hot spot for well-known celebrities, like John Travolta, Guy Fieri, Joey Fatone and more! In fact, I had the pleasure of exchanging hair talk with Guy, smiles with Joey and sports banter with Kip Moore. Ok… I didn’t really exchange hair talk with Guy. I may have screamed, “Love the Hair, Guy!” to him as he headed to the bathroom. He said, “thanks” and gave me a thumbs up on the way out the door. My wife about fell out of her chair when she saw Guy. My fishmonger, seafood-loving wife has admired Guy for years. It made her night. That, and the drinks she was being served by the bartender/barista.
Although we didn’t see John Travolta, I hope to stalk him soon.
To book your table at Ivy on the Square, click here. And keep reading, because we’re sharing the skinny on their new Speakeasy below.
Harry’s Seafood Bar and Grille
A popular Florida restaurant, Harry’s Seafood Bar and Grille has locations throughout the sunshine state, including Ocala, Lakeland, Tallahassee, St. Augustine, and Gainesville. The food is consistently tasty.
Just a note from the Florida fishmonger – the Redfish served at Harry’s is not caught in Florida, as you can’t commercially catch and serve redfish in Florida. While the redfish dishes are delicious, especially the Crab Crusted Redfish Royale, the redfish most likely comes from overseas. I always recommend asking the server where fish comes from.
My wife recommends the Jambalaya and I enjoyed the Redfish with Collard Greens and Rice. The collard greens reminded me of Thanksgiving. So good!
To see the limited menu, click here.
Swampy’s Bar and Grille
Swampy’s Bar and Grille, in nearby Dunnellon, sits along the Rainbow River and is the perfect spot for a bite to eat. It is here where you can truly take in the beauty that Marion County has to offer.
If you arrive early enough, you may observe the family of otters that swim, eat, and live right here at Swampy’s river bank. As early afternoon arrives, you’ll find local residents and tourists lazily floating down the river in tubes, kayaks, canoes, and a few boats. As the day ends, and the sun sets, you may again observe the family of otters venture out to enjoy their river dinner, as you enjoy yours.
Live like a Floridian and try the gator bites! I loved the gator wrap comprised of blackened gator, lettuce, tomatoes and Swampy’s remoulade sauce in a wheat wrap. It was fabulous.
The fishmonger says to sample the seafood gumbo but skip the mahi. If you’re looking for the best seafood in Florida, this is not it, but if it’s the ambiance, good food, and relaxed vibe that you’re after, you’ve come to the right place.
To view the menu, click here.
For authentic Mexican food and happy hour specials, head to Las Margaritas. With locations in Ocala and Gainesville, this local favorite serves up margaritas at 2 for $6 during happy hour. Just make sure to have Uber or Lyft on speed dial. You can sit comfortably at their long bar or cozy up in a booth. And the decor perfectly fits the theme of the restaurant from colorful wood carved booths to Mexican murals.
It is common for authentic Mexican food to have simple but delicious flavors and ingredients and that’s what you should expect at Las Margaritas. With a 12-page menu, your choices are limitless. I ordered from the lunch menu and had the Chicken Acapulco with 1/2 chicken breast marinated in orange, pineapple, garlic, and tropical spices. It was served with Mexican rice and refried beans. The lunch portion was more than enough for a main meal. Plus they serve every meal with an endless supply of chips and salsa. And they are addictive!
Also called a blind pig or blind tiger, a Speakeasy is an illicit establishment that sells alcoholic beverages. These establishments became popular in the United States during the Prohibition era.
Today, speakeasies are back and have become the latest libation trend. In downtown Ocala, you have two from which to choose.
This downtown speakeasy is Ocala’s first authentic Speakeasy and connected to and technically part of Ivy on the Square. But Thirsty Cobbler has its own separate entrance at 11 East Ft King and doesn’t open until evening hours (usually after 8:00 PM). Once inside, you are transported into the roaring 20s.
Seating is limited and space is cozy, so I recommend getting there as soon as the lights go on. The prices are also a bit steep, but the worth it.
But do not go yet – you need a password to enter and it changes daily! You can find it here.
Anti Monopoly Drug Store
The newest speakeasy in Ocala, Anti-Monopoly Drug Store is located above The Lodge Brick City Craft Pub & Eatery. This speakeasy is a bit more laid back than the higher-end Thirsty Cobbler, but it’s always a fun time at the Drug Store.
When you enter The Lodge, go to the back hallway and you will find a bookcase. Knock 3 times on the wall next to the bookcase. You will be asked for a password. You can find it here.
Bonus Info: Make sure to follow both Speakeasy Facebook pages for insider info about speakeasies and Ocala.
Brick City Southern Kitchen and Whiskey Bar
This BBQ and libation station is one of 8 Central and Northern Florida locations under the MOJO brand. The local chain prides itself as a premier barbecue, southern food, and craft cocktail destination. Barbecue, blues, and bourbon — three distinctly American products — come together at MOJO to offer a good-natured atmosphere.
Although we did not dine here ourselves, we hear nothing but good things! Click here to learn more.
What to Do in Ocala
As mentioned, there are an endless number of outdoor activities to do. And since that was our focus during this trip, given COVID times, we have highlighted those below.
Zip Lining at The Canyons
If you are scared of heights, then you need to “Zip the Canyons”! Trust me. My wife, who has been scared of heights since she can remember, looked at me as if I had three heads when I said, “YAY! We’re going zip lining across the canyons!” Her face read, “yeah, no – not on your life.” But alas, I won that debate and she has no regrets.
It was a breathtaking experience to fly among the tops of the palm trees and over the water-filled canyons below. And the tour guide was a hoot and a half. He kept us relaxed and safe. Zip the Canyons also offers horseback rides, chocolate and wine tours, kayaking and gem mining.
To learn more or to book your next adventure, click here.
Horseback Riding with Cactus Jack
This adventure is designed for the beginner horseback rider in mind, but enjoyable for someone more seasoned. I thoroughly enjoyed the relaxing pace through the wooded areas and trails of Ocala. My wife was waiting to kick the horse in the rear to put him into high gear. Still, she was happy as a thoroughbred and enjoyed connecting with the sights and smells of nature – and horse potty breaks (ick)!
Our tour guide was pleasant and conversational and answered all of the questions we had about the surrounding area.
Pro Tip: If you’re looking for a bit of sizzle in Ocala, there is something super hot about a partner riding a horse and wearing cowboy boots.
Kayaking Rainbow River at KP Hole Park
You know that I love rainbows, so it comes as no surprise that Rainbow River was high on my list. Ok, you won’t actually see rainbows here on a normal basis, but the Rainbow River kayak experience is filled with color and fun.
Kayaking on the Rainbow River and finishing our experience with a dip at KP Hole Park was probably the most romantic activity that we enjoyed while in town. She and I paddled upstream like salmon, which made paddling back to where we started that much easier.
Once we made it to the state park, we docked our kayaks and roamed around for a bit. It’s a hilly part of the state, so make sure you have comfy shoes for walking. And stop by the waterfall for an Instagramable moment. You can also set sail from Rainbow River State Park, but starting downstream at KP Hole Park was a much better idea.
When we returned to KP Hole Park, we took a dip in the chilly, clear waters before heading out.
Click here to learn about rental info.
Glass Bottom Boat Ride in Silver Springs State Park
Imagine the prettiest boat ride you’ve ever enjoyed and then make it even prettier. That’s how you’ll feel on this Glass Bottom Boat ride in Silver Springs State Park. Not only do you have the opportunity to enjoy the views around you, but you also get a chance to take in the views below the boat. The crystal clear waters of the Silver Springs provide a wide angle view of the creatures below the surface. This is a must-do activity while in town.
And while you’re in the park, stroll around the walking path to enjoy the wildlife. And make sure to look up! Although not native to Florida, we hear that there’s a monkey or two in the parks as well.
Explore Downtown Ocala
I’ve pointed out several restaurants in the downtown Ocala area to visit during your Ocala road trip, but there are a smattering of adorable shops, too! Take a stroll during evening hours and you may also enjoy live music in the downtown square. Several events are hosted here annually, although many have been rescheduled or cancelled due to COVID.
Downtown Ocala also has an old time movie theatre, the Marion Theatre. Grab some popcorn and watch your favorite classics with your partner or on your own.
Movie at the Ocala Drive-In
Speaking of romance, Ocala has a Drive-In movie theater! And it’s open seven nights a week. Tickets are sold at the gate only. Cash and credit are accepted. You can also enjoy a beverage or refreshment from the concession stand. Food orders can be placed online as soon as you are parked and ready for the movie.
The Drive-In is pet friendly, too! “If you consider it a dog than leave it home. If you consider it a 4-legged family member in a fur coat then bring them along because we are a family theatre and they are part of the family.”
I think a Drive-In movie fits in perfectly with an Ocala road trip. Just make sure to clean out the car before you leave. Otherwise romance might be off the table.
Click here to see the full movie schedule.
Dreamed of petting a llama? Fantasized about feeding an ostrich? No? Well, whether you’ve always wanted to or not, now’s your chance! A stroll through the Ocala Petting Zoo farm gives visitors a chance to meet camels, llamas, goats, a cow, monkeys, and so many more animals.
The zoo also offers pony rides, train rides, and camel rides. A covered picnic area is available for parties, events and relaxation.
To learn more about visiting the zoo, click here.
Marion County is providing regular updates on the latest regarding COVID-19 in the community, including re-openings, local cases and more. To access this most up-to-date information, visit Marion County’s Facebook page: Facebook.com/MarionCountyFlorida
Ocala/Marion County, our hotels, restaurants and attractions are taking your safety seriously. To find out how the destination is a safe place to explore for visitors and residents, click HERE.
Plan Your Ocala Road Trip
Out of all of my Florida road trip journeys, this was the best experience to share with my wife. We also lucked out with perfect weather. If you are ready to plan your Ocala Road Trip today, then pack your bags and book your hotel room now! But don’t forget these important items to make sure that your Ocala road trip experience is perfect.
And a reminder – if you are from another country and planning a drive then you need to get an IDP on International Driver’s Association.
**Disclaimer: There is a good chance that this post contains affiliate or sponsor links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).
Also, while we do our best to highlight LGBTQ-friendly destinations and businesses, info provided is based solely on personal experience and recommendations by community partners. We hope that nobody experiences discrimination or homophobia while visiting Florida, but we make no guarantees. Please inform us if you experience discrimination or homophobia while visiting any destination so we can make updates to our recommendations.