The Perfect Tampa Boating Itinerary

It's no wonder Tampa Bay is a boater’s paradise with warm Gulf waters, beautiful islands, a vibrant downtown area, and miles of shoreline to explore. Whether you’re a local looking for a weekend adventure or a Freedom Boat Club member visiting the area, this 3-day boating itinerary is your ultimate guide to soaking up the best of Hillsborough and Pinellas counties—on the water. Each day focuses on a different area, with morning and afternoon suggestions that balance relaxation, exploration, and waterfront dining. Let’s dive in!

Day 1: Explore Downtown Tampa from Harbour Island

Morning

Depart from the Harbour Island Freedom Boat Club location and ease your way into the heart of the city. Cruise up the Hillsborough River, taking in downtown skyline views and the iconic Tampa Riverwalk. This stretch is packed with cultural gems like the Tampa Museum of Art and the historic University of Tampa—perfect for a leisurely float and some great photo ops. We also recommend that you grab breakfast on the dock at Ulele or Armature Works, both accessible via boat with nearby dock space.

Afternoon

After lunch, drop anchor near Davis Islands Beach for a swim or sun session. If you're up for a little walking, dock the vessel at the Tampa Convention Center marina and stroll through Downtown Tampa. Wrap up your day with a cocktail and sunset view at Jackson’s Bistro, just steps from where you started.

Day 2: Island-Hopping Adventure from John's Pass

Morning

Kick off your day at the John’s Pass Freedom Boat Club location in Pinellas County and cruise south toward the Skyway Bridge. Beneath this iconic span, head toward Egmont Key, a secluded island rich with wildlife such as manatees. Tour the historic lighthouse, snorkel along the ruins, or hike shaded trails. We recommend packing a cooler for a beachside picnic—it doesn’t get much more Florida than this!

Afternoon

Return north and explore the sandy shores near St. Pete Beach. If you’re craving a sit-down meal, dock at The Hut in John’s Pass Village, where you can find live music and fresh seafood. Spend your afternoon browsing local shops or relaxing with an ice cream cone along the boardwalk before heading back to the boat.

Day 3: Coastal Cruising from Clearwater City Harbor Marina

Morning

Start your final day from the Clearwater City Harbor Marina. Set out early for some dolphin watching in Clearwater Bay—these playful creatures are often spotted near Caladesi Island and Honeymoon Island. Then head to a nearby sandbar to swim. The bustling sandbars in this area present the perfect opportunity to socialize with fellow boaters.

Afternoon

Dock near Clearwater Beach to enjoy one of the Gulf Coast’s most beautiful stretches of sand. Grab lunch at Frenchy’s Rockaway Grill, a local institution just steps from the beach. End your adventure at Pier 60’s Sunset Celebration, where street performers, crafters, and stunning views give your trip a perfect send-off.

Start Your Tampa Bay Boating Adventure!

Tampa Bay offers the best of both urban excitement and coastal escape. From Downtown Tampa and St. Petersburg to Egmont Key and Clearwater, this 3-day itinerary highlights why boating in the waterways of Hillsborough and Pinellas counties is second to none. With dozens of Freedom Boat Club locations in Tampa, like the ones located in Harbor Island, John’s Pass, and Clearwater, every adventure is just a reservation away. Ready to launch into your Tampa, FL boating experience? Skip the one-off boat rentals and learn more about how to join Freedom Boat Club.