Here are some of the coolest walking trails near Havana Square.
Bayshore Boulevard Trail
Let’s start with the classic. The Bayshore Boulevard Trail is one of Tampa’s most famous walking paths—and for good reason. It’s the longest continuous sidewalk in the country, stretching for 4.5 miles along the water.
This is where the city meets the sea. On one side, you’ve got views of Tampa Bay. On the other, you’ll see charming homes, palm trees, and the downtown skyline in the distance. The breeze is constant, the vibe is upbeat, and there’s always something to look at—boats, runners, bikers, and sunsets that hit just right.
Tampa Riverwalk
If you want energy, art, and endless views, head to the Tampa Riverwalk. This 2.6-mile trail winds along the Hillsborough River, right through the heart of the city. It connects parks, museums, restaurants, and more.
You’ll walk past murals, sculptures, and maybe even catch some live music. There are places to stop and grab a snack or just sit and take it all in. It’s perfect for an evening stroll with lights twinkling on the water, or a daytime adventure full of life and color.
Al Lopez Park Trail
Looking for something a little more laid-back but still exciting? Al Lopez Park is the hidden gem you’ve been waiting for. Located just north of Raymond James Stadium, it’s got a paved walking loop that’s about 1.2 miles long—just right for an easy, relaxing walk.
The trail goes around a pond, through shaded areas, and past open green fields. It’s full of ducks, turtles, and quiet corners that make you feel miles away from the city, even though you’re still close to home.
Upper Tampa Bay Trail
Ready for a bigger walk with lots of room to explore? The Upper Tampa Bay Trail is where you want to go. This paved trail stretches for more than 7 miles and offers a smooth path through forests, fields, and wetlands.
You’ll spot birds, maybe even deer, and enjoy long, peaceful stretches where you can just walk and unwind. It’s great for a weekend trip or when you want a more adventurous route with plenty of space to breathe.