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17 Fantastic Places You Can Meet Single Cougars In Florida In 2024

The type of cougars in Florida you can meet

If you want the company of cougars in Florida, you need to know where to look. With so many places for you to explore--from Jacksonville to Miami, Tampa to Daytona--you’ll find lots of single women everywhere. But even if you’ve been living here for a while, it can be hard to find where these feisty women are. But worry not, we’re here now. We’ll give you tips on how to maneuver your way in the Florida jungle and find cougars on the prowl.

For starters, what about changing the neighborhood scene? If you’re in Orlando, try Rose Isle. It has an excellent location between Downtown Orlando and Winter Park, which means it’s perfect for night and daylight hunting.

If you want to practice your charms on Florida cougars, you can also try shopping malls and organic stores like Trader Joe’s. They’re simple but bountiful resources of attractive older women in the state. Don’t forget that you can find love at the most unexpected of places. Trying to meet Florida cougars at gyms and yoga studios like Prana Yoga won’t hurt too.

You just have to be brave enough to take a risk. With so many places to choose from, it can be tough to know where to go. But try out some of our favorite spots below and get started on your journey.

The Hot Spots for Attractive Cougars in Florida

These are some of our favorite places for meeting cougars in the Sunshine State:

Enjoy cougar town at Hillstone Restaurant

The dining area of Hillstone Coral Gables


If you happen to be around the Coral Gables area, make sure to check out Hillstone Restaurant. This place is cougar central and a true meat market for all young cubs like you. It’s a great steak house with an even better happy hour! You can’t go wrong eating at this place even if you’re not in the mood for steak. Try their ahi tuna tartare with sliced avocado or their signature tres leches with fresh fruit for dessert. They’re guaranteed fresh and bursting with flavor. You’ll surely enjoy your meal here.

Word of warning: don’t forget to dress up when you go here. They consider hats, tank tops and flip flops “too casual” for their restaurant. So if you don’t want your visit to go to waste, make sure you dress to impress. It will also work in your favor as older ladies like a guy who has a sense of style.

Pro-tip: The after-work bar scene is cougar town, so go here during that time. Enjoy!

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Guys who are actually willing to take a little action and not sit on their butts all day are going to get solid results with AFF. We have seen way better results on this site than the competition and have seen especially good results for normal dudes and guys looking for women over 30. It’s perfect for busy guys who don’t have time to commit.

AFF beats out all the competition when it comes to sites that will get you laid. So give it a try today!

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Get lucky with Florida cougars at Truluck’s

A woman on a date at Truluck's


Truluck’s is such a classy seafood hub and steakhouse. The decor and ambiance are beautiful. There are flowers throughout the space and a grand piano for live performances. Aside from the luxurious atmosphere, Truluck’s is a great place to grab dinner or a drink. Their happy hour provides 1/2 off their cocktails and bar bites menu. For a hearty meal, try their Californian Stone Crabs. They’re top-notch. This spot serves up the best Californian Stone Crabs in Florida.

This place also attracts an upscale professional crowd, so sophisticated cougars in Florida make this their regular hangout spot. If you're still haven't figured out how to meet and date more upscale cougars this is a place you can practice. The high cougar count in this area makes this perfect for mingling and meeting an attractive older lady. However, they have a strict dress code, so make sure you don’t look like you just got out of a discount store. Otherwise, you might miss out on all the single older ladies looking for a fun night with you.

eHarmony is the best way to meet cougars that want relationships (try it now)

eharmony.com homepage

If you’re single and dating but you haven’t taken your search online, you’re missing opportunities to meet cougars all over Florida and the rest of the South-east as well! We’ve tried out a lot of dating sites and apps (over 100 in our cougar site review and rankings), and we’ve found eHarmony to be the best site out there if you’re looking for older women, especially if you’re a little more relationship-focused.

We’re talking about a site with over 33,000,000 members that’s responsible for 15 million matches every single day. If you’re a guy looking for women that are a bit older, we haven’t found a better option, especially if you’re thinking a little longer term.

No other site is as good at connecting men and women together. So good in fact that eHarmony is responsible for nearly 75% of all marriages that start online. That nuts!

eHarmony’s matching process is pretty unique compared with other sites. During the signup process, members answer an in-depth series of questions. This is something that we actually love about the site (and you will, too). Not only does it help you get to know your potential matches better before you finally meet, but it weeds out women who are just curious. These women are usually time-wasters who never respond. It also draws in an older crowd of busy professional women who want to know that their own time isn’t being wasted on men who aren’t serious.

Trust us, eHarmony is worth that little bit of extra time and effort it takes to fill out a thorough profile. Sign up for their proven trial and you’ll see exactly what we’re talking about. You WILL meet quality women, and there’s really no other site that can compare.

When you’re not getting results like you want, you have to try something new. This is an easy way to mix things up.

eHarmony trial

You can’t Beat Culture

A large crowd of people in front of Beat Culture


If you would like to meet Florida cougars over a bottle of craft beers and board games, try Beat Culture. This Miami hotspot has a hip and chill vibe that’s perfect for socializing. Order a pour of their Raspberry Beer and join a game of deconstructivist architecture with Jenga. This is a great spot for game night because you get to drink unique brews and meet new people in the process.

They always have a wide variety of different style beers on tap. Plus, they come up with really witty names too, like “Irregardless.” There are also bands that play music on certain nights. And while this spot may appeal to the young crowd, you’ll find a lot of older women unwinding here after work.

This hidden gem tucked away attached to a Days Inn will not disappoint you. If you’re within the Doral area, make sure you check this out.

Experience the South Beach Food & Wine Festival

Cougars in Florida getting drinks at the South Beach Wine and Food Festival


The South Beach Food & Wine Festival is an event held in Miami every spring. It attracts people from all over the state and beyond. With wine tastings, culinary demonstrations and food vendors, it’s the perfect event to let loose and have some fun. But more importantly, it’s the perfect place to bump into cougars in Florida. This allows you to have some liquid courage when talking to an older lady. Ask her if she likes the wine she’s sipping or invite her to check out a demo that you just found.

There are tens of thousands of people in attendance. This means that there’s a high probability of meeting a single older woman. It might be worth it to get the ticket that grants admission for the whole weekend in order to increase odds even further.

Cougar dating promo

Enjoy wine with a cougar in Florida at Lakeridge Winery

Beautiful mature woman posing in front a large wine barrel at Lakeridge Winery


Located in Clermont, the Lakeridge Winery offers free wine tastings. So there’s always a crowd of people at the tasting bar. With so many fun events throughout the year, Lakeridge attracts lots of Florida cougars who just want to have some fun.

Jazz, chocolate, and other themed events are on the calendar. When you have a free weekend, it might be worth it to check out what’s going on in this area that’s only minutes from Orlando.

Apps Dating Coaches Actually Recommend To Meet Cougars in Florida

Older women enjoy dating, especially when they're able to meet more younger men from the comforts of their homes. That's why they often use dating apps to find potential dates. If you're not using at least one of the dating apps below, you're missing out!

US states -

SiteOur ExperienceOur RatingFree Trial Link
Best Hookup Site Cougars
Experience Highlights
Experience Highlights
  • The best way to meet cougars for hookups by far
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
2nd Best For Hookups
Experience Highlights
Experience Highlights
  • 2nd best option to find hookups
  • Attracts an older crowd than most hookup apps
  • Pretty popular
  • Great free trial
Try Passion

Trader Joes offers more than just groceries

Trader Joe's in Miami


Gluten-free entrees, organic wines, fresh produce and much more--sounds like a recipe for a cougar meetup! Trader Joes is one of the more unexpected spots on this list. But time and again, we meet lots of older women here.

You can scan the aisles and chat up the cougars doing their weekly groceries. Mention your favorite organic snack or suggest some cool ingredients to use. These ladies often hate the monotony of running errands, so they’ll be glad to chit chat for a bit. If you play your cards right, she might be up for a quick coffee date nearby.

Sip cocktails with cougars in Florida at the Blue Martini

A gorgeous woman posing at the bar in Blue Martini


The Blue Martini is an upscale cocktail bar that you can find all over Florida. This includes locations in Fort Myers, Tampa, Orlando and Miami. Certain locations have a “ladies night,” which makes it ideal to find cougars in Florida.

Blue Martini gives you a chance to meet a woman who loves to let loose and have fun. One offer to buy her a martini and it might be the hook that’s needed. The bar has a full restaurant too, making it easy to grab a table and have somewhere else to go in order to finish the conversation.

Grab some drinks at Jackson’s

Friends on the dance floor of Jackson's


Jackson’s Bistro in Tampa is in the Channelside District on Tampa Bay. There’s a bar, a Sunday brunch, as well as an extensive menu of creative American cuisine. Classy older ladies head here throughout the week to enjoy some drinks and the ambience.

Perhaps the biggest perk to Jackson’s Bistro is that it’s connected to the Westin Harbour Island, The hotel rooms overlook the water, and when you stay the night during Gasparilla or on New Year’s, you can see the fireworks right from your room.

Course promo

Chat with a Florida cougar over some wine at the Blind Monk

Two women holding beer bottles brewed by The Blind Monk


When searching for cougars in Florida on the Southeast coast, there’s the Blind Monk in Palm Beach. It’s a dive bar with dim lights and an extensive wine list. Women often drop by here to enjoy themselves after a long work day.

It’s here where a large number of professional women choose to gravitate. The best time to come is between 6 and 9 p.m. any day during the week. This time is the best chance to find a cougar who is all alone and looking for some company.

Experience some puppy love at Barber Park

Barber Park on a sunny day


Barber Park in Orlando is known as one of the best dog parks in Central Florida. No woman can resist a man with a dog, especially when she has one of her own. It’s a great way to bond with an older woman in the Orlando area.

The best time to go is on a Saturday between noon and 2 p.m., though you are also likely to see a lot of activity when you go after work during the week. With your dog in tow, it’s a chance for your canine companion to find your potential mate when they run up and give a kiss or fetch a ball. As you go to get your dog back, you can make your introduction.

The park is free to get into, so all that’s required is your furry friend. It’s open for long hours, seven days a week and it’s a great place to visit. Even if there are no Florida cougars there at the moment, you’ll surely enjoy your stay there.

Lynch’s Irish Pub in Jacksonville attracts lots of older women

Exterior of Lynch's Irish Pub


Whether you’re Irish or not, it might be beneficial to spend some time at Lynch’s Irish Pub in Jacksonville when you’re in the market for cougars in Florida. With Guinness, Smithwicks and other Irish favorites on tap, it’s easy to get a good pint. The menu is also full of classic dishes from across the pond.

The best thing to do is head to the bar, particularly next to an older woman who is attractive and single. Get some conversation going whether you’re asking her about her bangers and mash or asking her if you can buy her a Black and Tan.

Have some fun in the sun with frisky Florida cougars

Miami Beach in the summer


There are beaches along the Atlantic Coast as well as the Gulf Coast. Watching cougars in Florida when they’re lounging on the sand or heading to the bar in a bikini is one of the greatest pleasures in life. And you can definitely indulge in that here.

Some of the best bars on the beaches to visit are:

  • Jimmy B’s Beach Bar in St Pete
  • The Lanai Kai in Fort Myers Beach
  • Mai tai Bar in Daytona Beach
  • Clevelander South Beach Hotel and Bar in South Beach

Wherever it is that you’re looking for love, it’s a good idea to head to the beach. She might be there by herself or with some of her friends. Either way, it’s a great way to bump into a cougar and make an introduction.

Single woman

Find cougars in Florida at Maxine’s

A pretty woman holding a bag of wine from Maxine's


When you’re in Central Florida, head to Maxine’s on Shine for some drinks. This is a dive bar in downtown Orlando on Orange Avenue. It has a reputation for being a place where older women hang out. This spot has a full bar and restaurant, and if you plan on eating dinner, it’s best to grab reservations.

They’re closed on Mondays but open until 10 p.m. Tuesdays through Saturdays. The best time to go is later in the evening as that’s when it really starts to get crowded. You can also enjoy the occasional live music when there’s a band around.

The bar also features a great happy hour deal, and that makes it easier to get some drinks. Buy drinks for Florida cougars that might happen to sit down near you and see where it leads. It all begins at 5 p.m. when they open their doors.

Margaritaville Beach Hotel in Pensacola guarantees a great time

Two lovely women at the pool in Margaritaville Beach Hotel


Within the panhandle of the state lies some of the most beautiful beaches. The Margaritaville Hotel is conveniently located in Pensacola Beach. While the hotel is truly exceptional, most people visit for the bar that’s inside, including cougars in Florida.

The entire vibe at the hotel is laid-back, making it easy to simply enjoy yourself. Women will come and go from the bar and possibly take a dip into the water as well. The gulf view is breathtaking, especially at night. Should you hit it off with someone, there are several restaurants on the premises, including Frank & Lola’s Kitchen. This makes it easy to invite an older woman to have dinner with you after having a few cocktails.

For more guides to meeting single cougars check these out:

Meet cougars in Delaware - Meet cougars in Georgia

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