Looking for a two-day adventure that includes exploring the area by bicycle, splashing in turquoise water, and a beachside picnic?

Day one of your excursion begins on Pine Avenue on Anna Maria Island, self-proclaimed as one of “The Greenest little Main Streets in America”. This half-mile, walkable avenue stretches from the sugar-white sand of the Gulf of Mexico to the tranquil waters of Tampa Bay, and includes everything an authentic Florida adventure needs in between.

Your first stop is Beach Bums, which rents all sorts of island gear, including bicycles, stand-up paddle boards, and other beach necessities. Their meticulously maintained fleet of rentals are why they’re considered one of the top shops on the island. (Their super-friendly staff also contribute to that title).

After renting your bike and receiving safety pointers, don your helmet and set out toward the Gulf of Mexico.

Taking in the sights of Pine Avenue is a must, and you’ll soon understand why. As you pedal toward the gulf you will pass by pastel-colored houses and buildings with covered porches, reminiscent of the original 1920s island architecture. Palm trees provide ample shade as you explore the many unique sights, including the locally-owned shops & boutiques, galleries, and restaurants. Keep a lookout to find that perfect keepsake, and tasty treats for tomorrow’s picnic, too!

After exploring the shops and galleries, a pleasant ten-minute pedal toward Bean Point will reward you with a spectacular view off the northern tip of the island. Many locals don’t even know about this amazing place!

Bike toward the City Pier (which is currently under reconstruction) and turn north onto North Bay Boulevard and travel until you reach the secluded beach access point. Park your bikes on the bike rack and walk through the tunnel of greenery until you reach the beach outlook—trust us, you’ll know it when you see it. You will definitely want to spend time here, walking the shoreline and soaking in the unforgettable seascape of Passage Key National Wildlife Refuge and Egmont Key State Park.

Day two starts with a quick stop to stock your picnic basket with delicious, house-made sandwiches from Scott’s Deli. You’ll likely see Chef Scott as you choose your made-to-order sandwich.

With a picnic in tow, your next destination is Bayfront Park, which overlooks the tranquil waters of Tampa Bay. See that bridge with brilliant yellow accents in the far distance? That’s the Sunshine Skyway Bridge spanning the mouth of Tampa Bay. At nearly 430 feet tall and over four miles long, it’s one of the world’s longest cable-stayed bridges. Cool!

After a quick phone call to AMI Paddle Board Adventures, their helpful staff will meet you at the park to deliver your stand-up paddleboard, complete with necessary safety equipment and pointers. They are known for being paddleboard and eco-tour experts, so lots of questions are encouraged.

Once ready, take a deep breath, step onto your board, and paddle away from the shoreline and into the brilliant blue water of the bay. Looking back at the beach provides a perfect Instagram-worthy picture opportunity—and so will spotting friendly sea life, like a green sea turtle or bottlenose dolphin!

After your water-going adventure, paddle back to shore to find that perfect, picturesque picnic spot on the beach. Relax in the balmy breeze, soak in the ample sunshine and munch on your delicious picnic lunch: those tasty Scott’s Deli sandwiches, unique cheeses from Olive Oil Outpost, and unique mini-donuts that you created at The Donut Experiment.

No trip to the area is complete without spending some time discovering the authentic charm of Anna Maria Island by pedal, paddle, and picnic.