When the fall weather hits and that first hint of crisp air kicks in, being in Tampa Bay means making time for outdoor adventures. From horseback riding to nature preserves, zip lining, and water sports, here are our go-to outdoor activities in Tampa Bay for an adventurous date.
Updated March 2023 by Brie Gorecki
1. Pinellas Trail
Stretching from Tarpon Springs to St. Petersburg, the 38-mile Pinellas Trail is a former railway that was repurposed as a multi-use trail. Hit the trail on two wheels making pitstops to check out the Tarpon Springs sponge docks, park for a refreshing brew, and stroll through hip downtown Dunedin.
If you feel like making a side trip to the beach, you can follow another pedestrian trail across the Dunedin Causeway for a visit to Honeymoon Island State Park. If you don’t have wheels of your own, rentals are available through companies like Kafe Racer, which is conveniently located close to the trail in downtown Dunedin.
2. Tampa Riverwalk
The Tampa Riverwalk is one of downtown’s best features. Waterfront views, a wide multi-use trail and plenty of activities along the way make it a one-stop shop for a fun and cheap date night by the water. Notable stops and activities include Armature Works, Curtis Hixon Waterfront Park, the Pirate Water Taxi (such a fun way to get around) Ulele, and Tampa Bay SUP, just to name a few.
Get your adrenaline pumping on a multi-hour adventure zipping above water and the treetops at Empower Adventures in Oldsmar. This zip line adventure park boasts five zip lines, a 200-foot suspension bridge over water, plus fun challenges like rope bridges and log swings along the way. Options include the Zip Line Adventure, Moonlight Canopy Tour (select weekends), and the romantic Sunset Zip Line Adventure (Saturdays and Sundays).
Reservations in advance are required.
4. Myakka River State Park
Florida’s State Parks are all beautiful in their own way, but Myakka River State Park is a crown jewel with its diverse landscape comprised of wetlands, prairies, hammocks and pinelands. Plan a visit to traverse the canopy walk above the trees, embark on a boat ride to spot alligators, or take a hike and see how much wildlife you can spot.
Kayaking is pleasurable year-round in Florida, but especially during the breezy, cooler months of spring and fall. Paddle among dolphins and other wildlife in a clear kayak at Shell Key Preserve, weave your way through mangroves in Lido Key and Weedon Island Preserve, or visit a sandbar and paddle out into the gulf from Longboat Key.
6. Paddle boarding
For fans of water sports like kayaking, stand-up paddle boarding (referred to as SUP) is an equally fun activity that’s surprisingly easy to pick up, even as a first timer. Tampa Bay SUP offers rentals, lessons and eco-tours from their location along the Tampa Riverwalk downtown. Urban Kai also offers rentals plus fun tours through Downtown Tampa or in dense mangroves.
7. Horseback riding
Immerse yourself in a slice of Old Florida on a peaceful horseback trail ride right outside of downtown Tampa. Local companies In the Breeze Ranch and Cypress Breeze Farm both offer guided trail rides for couples to enjoy.
You can also ride horses along the beach on a bucket list ride with Florida Beach Horses.
8. U-Pick Farms
Spring is the height of the u-pick season throughout Tampa Bay. Visit a surrounding farm for a day outdoors picking your own bounty. Our guide to u-pick farms has options for strawberries, blueberries, citrus, fresh greens and more.
9. Honeymoon Island + Caladesi Island
Situated off the coast just minutes from Dunedin, Honeymoon Island State Park offers natural beaches, crystal clear waters, spectacular sunsets and unspoiled coastline dotted with unique shells. Besides lazing on the beach, there are kayak rentals and nature trails to explore. For an added fee, you can hop on the ferry to secluded Caladesi Island for more fun in the sun. Admission to the park is $8 and the ferry to Caladesi Island is $18/person (or $6 per boat).
10. Sunken Gardens
Get lost in a botanical oasis together while walking hand in hand through St. Pete’s lush Sunken Gardens. Besides the gorgeous plants lining the paths of the 100+ year old park, the resident flamingoes are a main draw. Admission is affordable and parking is free.
11. Swim with manatees
Did you know that Crystal River and Homosassa are the only areas in North America where you can legally swim with and passively observe manatees in their natural habitat? While you can swim with manatees year-round, the cooler winter months are the best time to go as this aligns with peak manatee season. Reputable companies like Adventure Center at Plantation on Crystal River offer manatee swim tours complete with all necessary gear plus photos of your experience.
12. Westgate River Ranch
Are you looking for the ultimate campfire experience? Look no further than S’mores ‘n Pours, the latest outdoor activity that combines the sweet satisfaction of s’mores with the smooth, delicious taste of bourbon!
Westgate River Ranch Resort & Rodeo’s newest exclusive World of Westgate (WOW) Member experience hand delivers two deluxe s’mores kits and one bottle of Buffalo Trace Bourbon to your campsite. The luxury glamping package also includes a $25 Resort Credit that can be applied to the resort’s amenities, including horseback riding, airboat rides, and Saturday Night Rodeo, dining options, and so much s’more.
If bourbon flights under starry nights sound like the perfect getaway, this unique date-night activity is available when you stay in a luxury glamping accommodation at Westgate River Ranch, including a Luxe Teepee, Conestoga Wagon, and Glamping Tent.
Whether planning a romantic getaway or a family vacation, S’mores ‘n Pours is the perfect way to add extra fun and flavor to your Florida adventures! Enroll in the World of Westgate Loyalty Program and book your S’mores ‘n Pours luxury glamping experience today!
13. Kraken CycleBoats
If a booze cruise is your idea of a good day, book a trip with Kraken CycleBoats, frequently spotted along the Hillsborough River. You will have to do a little work, pedaling the boat to earn your sips. You’ll need to supply your own alcohol while your captain supplies the cups and ice.
The tour also includes a bit of sightseeing as you paddle past the Tampa Riverwalk, Armature Works, Curtis Hixon Park and more.
14. Take a Hike
Florida’s cooler months are ideal for exploring Tampa Bay’s robust collection of parks and trails. And from November through March, you can participate in Hillsborough County’s annual hiking spree! Challenges include 26 trails across 22 unique parks, several of which are Florida State Parks. You’ll even receive a cool prize once you’ve registered (it’s free). The prizes are a patch, a medallion for a hiking stick, or a pet bandana.
15. Riverwalk Boating Company
Did you know you can rent a mini powerboat for two to cruise Tampa’s waterways? Riverwalk Boating Company rents these cute two-seaters which start at $79 for an hour or $149 for two hours. For some old-school fun, you can also rent one of their retro boats for $129. Pick up your rental along the Riverwalk and then head out on a self-guided adventure in any direction you choose. The boats go between 10-20mph, so plan for a relaxed trip on the water with your love.
16. Drive-In movies
For a nostalgic date, pack snacks and park the car for an old school date night at the local drive-in. Multiple drive-in movie theaters are accessible from Tampa including Ruskin Family Drive-In and the Silver Moon Drive-In in Lakeland, just 30 minutes away. Admission is affordable with one price for both movies being screened that evening.
17. Resort Day Passes
Have you heard of ResortPass? This website allows you to book day passes to visit local hotels and resorts without an overnight stay. You can lounge poolside with views of Tampa Bay at The Godfrey Hotel & Cabanas, switch between the pool and the beach at Hyatt Regency Clearwater Beach, hang out on the rooftop pool at Art Ovation Hotel and more. Private cabana rentals are also available at most properties.
18. Fort De Soto Park
From renting kayaks to playing on the beach with your four-legged friend, hiking the trails or hopping on the ferry to visit nearby Egmont Key, Fort De Soto Park is ideal for a full-day outdoors date. FYI: Admission is $5.
19. Sunset Cruise
If you really want to wow your date, book a sunset cruise. There are loads of options throughout Tampa, but our top picks for date night include the Yacht Starship–which includes dinner and open bar–and Island Ferry’s St. Pete Beach Sunset Cruise. The sunset cruise is a private experience limited to no more than 6 people. You’ll enjoy dolphin sightings along with a stunning Gulf sunset.
20. Aerial Adventure Parks
Aerial adventure courses like TreeHoppers and TreeUmph! Adventure Course combine zip lines and aerial obstacles for an exciting workout above the treetops. Think ropes, barrels, suspension bridges and nets. What a challenging and fun way to spend some time together!
21. Farmers’ Markets
The cooler months happen to offer some of the best bounties from our local farms. Enjoy a laid-back morning outside at one of our local farmers’ markets. A few of our favorites include the Ybor City Saturday Market and St. Pete’s Saturday Morning Market.
22. Outdoor + Rooftop Dining
Now is the perfect time to enjoy a romantic meal outside on a patio! Take your food, drinks and conversation outside with this guide to outdoor dining in Tampa Bay.
Want to dine with a special view? Grab drinks and light bites or a full meal at one of Tampa Bay’s best rooftop bars.
23. Pack a picnic
Whether you’re packing your own feast for two or grabbing takeout, picnics are a timeless activity for a memorable date. Lucky for Tampa locals, there are loads of scenic places for a picnic from the quintessential Curtis Hixon Waterfront Park to more romantic spots like Phillipe Park in Safety Harbor or Honeymoon Island StatePark.
24. Nature preserves
For a totally free date, visit a nearby nature preserve to climb a lookout tower, search for local wildlife, stroll on a boardwalk or hike quiet trails.
Weedon Island Preserve features multiple trails and observation towers, plus scenic boardwalks for walkers and paddling trails for kayakers. Also check out the Lower Hillsborough Wilderness Preserve, which includes 60 miles of hiking trails and loads of wildlife.
25. Pier 60 Sunset
A rite of passage for locals and visitors alike, the lively and iconic sunset celebration at Pier 60 in Clearwater is a fun way to end a perfect day at the beach. The daily festival kicks off a few hours before sunset and lasts several hours after the sun has dipped below the horizon.
After a romantic stroll on the beach towards the pier, sit and stay awhile to watch an outdoor movie or interact with street performers.
26. St. Pete Mural Tour
St. Pete’s colorful murals are a fixture of the vibrant city, adding pops of color and interest to local buildings. Map out a route for a self-guided tour of your favorites using this handy map or join an official St. Pete Mural Tour for $20/person. On the guided walking tour, you’ll visit 30+ murals while learning more about the artists who created each.
There’s also a bicycle tour option for $30/person, depending on whether you bring your own bike or opt for a bike share.
27. Hit the beach
We’d be remiss not to mention Tampa Bay’s array of top-notch beaches on this list. Honeymoon Island, St. Pete Beach, Clearwater Beach, Indian Rocks Beach, Madeira Beach and Anna Maria Island beaches are some notable favorites.
Floating down a river in a tube is a must-do for any Floridian, at least once. It’s also an incredibly popular summertime activity, so it’s smart to plan your visit during an off season for fewer crowds on the water. While quite a hike from Tampa (1 hour and 45 minutes to be exact), the drive to tube down the spring-fed Rainbow River is totally worth it. You can leave from KP Hole or Rainbow Springs State Park. The latter is a shorter tube run, but either way the journey lasts for hours so pack snacks, water and plenty of sunscreen.
29. Riverwalk Pub Crawl
Did you know you can take drinks to-go to enjoy as you walk along the Tampa Riverwalk? Secure a designated driver then head out on a pub crawl to sip beverages in a special Riverwalk to-go cup.
The Riverwalk cups are available at the following locations along the Riverwalk: Anchor & Brine at Tampa Marriott Water Street, Columbia Cafe at Tampa Bay History Center, Four Green Fields, Garrison Tavern at Tampa Marriott Water Street, Malio’s Steak House, Remedy, Riverwalk Cafe at Tampa Museum of Art, Sheraton Tampa Riverwalk, SIP at the Straz Center for the Performing Arts, The Sail at the Tampa Convention Center and Ulele.
30. Hot Air Balloon Ride
If a hot air balloon ride is on your bucket list, check it off right here in Tampa. Big Red Balloon offers hot air balloon tours at sunrise, allowing you to see the landscape from above, in the golden morning light. American Balloons also offers rides in the Wesley Chapel area.
Feature image credit: Empower Adventures Tampa Bay