Known as the lesbian capital of Central Florida, Dunedin is the perfect mix of big city and small town life. You can buy fresh fruit at the farmer’s market, go boating off Honeymoon Island and dance the night away downtown all in one place, making it the perfect place for a lesbian couple to enjoy a date or even an entire weekend!
Take her to the Farmers’ Market
A great way to start your date in Dunedin is by visiting the open-air farmer’s market in downtown Dunedin, where you can sample local, organic and often vegan food for breakfast and/or buy items for a picnic later on during the day (see Honeymoon and Caledisi Islands below). Stroll through stalls of home-made dishes, fresh produce right from the farm (or someone’s yard) while listening to live music and checking out local artists. Vendors set up every Friday and Saturday in John L. Lawrence Pioneer Park from 9am to 2pm.
Take her to Hammock Park
One of our favorite things to do in Dunedin is to visit Hammock Park, which offers a variety of fun activities. Go on a leisurely walk with her through the forest and over swamp land, engage her in an amusing game of frisbee golf, or visit the butterfly garden. All of these activities offer a great way to get to know each other in a serene setting.
Hammock Park’s main entrance is off San Mateo drive.
Take her to Dinner… and Brunch
Dunedin is full of restaurant options but we frequent two: the Dunedin Brewery and Serendipity Cafe. The first claims to be Florida’s oldest craft brewery and has recently expanded their menu to include more vegan options. The latter serves health-conscious food that has vegan and gluten free options, including vegan waffles, french toast and other tasty brunch options.

Breakfast Burrito and Sweet Potato Hash at Serendipity Cafe – Photo Credit
Take her to a Nightclub
Blur Nightclub and Showbar, located at 325 Main Street, offer daily happy hour, live music nights (Wednesdays), karaoke nights (Thursdays), drag shows (Fridays) and so much more. The giant Jenga game and the drag queen bingo are additional reasons to go. If your date is into football, they also offer all day NFL tickets.
Take her to a Special Event
You can also impress your date by coordinating your weekend with one of Dunedin’s many special events. These events include a wonderful celebration of Black History (February), Highland Games (Spring), wine/art walk every second Friday and a sunset music series in Weaver Park. It seems like there is always something going on in Dunedin!
Take her to a Baseball Game
Dunedin is also home to the Florida Auto Exchange Stadium, where you can watch the Blue Jays play during Spring Training and the minor league play during baseball season (April-September/October). Unlike the large stadiums in big cities like Toronto, Dunedin’s stadium is small, making it easier to feel a part of the game. (We recommend not parking directly in the stadium parking lot as it is not uncommon for windshields to get broken during the games.) Be sure to bring your glove as there is a very good chance you could impress your date by catching a ball for her.
Take her to Honeymoon Island
Dunedin is home to one of Florida’s most treasured beaches; Honeymoon Island is exactly as lovely as it sounds. So avoid the traffic and crowds of neighboring Clearwater and charm your lady at Honeymoon Island State Park, which offers hiking, swimming, boating, and beautiful beaches one of which is dog-friendly. There are often free birdwatching guided walks as well.
If you arrive by car, the entrance fee is $8 for two people. Or you are feeling more active, you can rent bicycles in downtown Dunedin and bicycle across the bridge into the park, which will also decrease your entrance fee by $6.

There are lots of benches in Honeymoon Island State Park to sit and watch the waves or enjoy the sunset
Taker her to Caladesi Island
If you really want to charm the pants off her (figuratively or hey, maybe even literally), take your date to Caladesi Island, only a 15 minute ferry ride from Honeymoon Island ($14 each round trip – starts at 10am and returns on the half hour every hour from Sept to mid-Feb and on every half hour from mid-Feb to Sept).
You can rent kayaks on the island and explore the ocean or the mangroves (we call them “womangroves”). The island offers several hiking trails (go left off the ferry), one of which leads to a gorgeous beach that is often secluded. If you go to the right, you will get to the beach more quickly and can walk all the way to the end of the island. In the winter, you can see many migrating birds on this section of the beach, but no matter what time of year you go, you will always see many types of local birds. If you are not inclined to do much walking, no worries – just go straight and you will hit the beach where you can simply relax and talk to the backdrop of gentle waves and vibrant blues.
We think Caladesi Island is a perfect place for a romantic picnic but if you are not prepared, don’t fret. There is a cafe on Caladesi Island that includes a veggie burger made with veggies versus soy-based. They confirmed that the burger is fried in vegetable oil, just like the fries. They also sell souvenirs, towels, sunscreen and anything else you might need for the beach.
Take her to a B&B
No doubt after your day of woo-ing at Honeymoon and Caledisi Islands, she might want to see more of you (aka you might get lucky). If you simply don’t want your date to end, we suggest checking into Meronava Guest Inn, which is located right downtown and is gay-owned and lesbian-friendly. Frank and David are both the owners and operators of this B&B. Frank is proudly the chef and he can happily make a delicious breakfast for you and your date to fit any dietary requests, including vegan.
Dunedin is a great place to spend a day, a weekend or even an entire week. There is plenty to do in this small coastal town with something for everyone!