5 Days in Clearwater Florida Itinerary

Begin your day with an exciting trip to Caladesi Island. This pristine island offers beautiful beaches and nature trails perfect for exploring.

For lunch, enjoy a meal at Palm Pavilion Beachside Grill & Bar, offering delicious food with stunning ocean views. Afterward, take part in the Clearwater Beach Private Pontoon Tours for an exclusive experience on the water.

In the evening, embark on the Clearwater Sunset Celebration Cruise to witness a breathtaking sunset over the Gulf of Mexico. Dinner can be enjoyed on board or afterward at one of Clearwater's many fine dining options.

Kick off your morning with a visit to Sand Key Park, which offers beautiful beach areas as well as picnic spots and nature trails.

Have lunch at Marina Cantina, which offers Mexican cuisine with waterfront views. Post-lunch, enjoy a unique experience with the Clearwater Dolphin Exploration Tour, where you can see dolphins in their natural habitat.

Wrap up your day with dinner at Island Way Grill, known for its seafood dishes and elegant setting. After dinner, take part in the fun-filled Clearwater Scavenger Hunt.

Start your day by kayaking through clear waters with Kayaking clear through Clearwater. It's an exhilarating way to explore Clearwater's waterways.

Enjoy lunch at The Bait House Tackle & Tavern, offering fresh seafood right by the marina. Following lunch, join the adventurous Private Fishing Charter in Clearwater Beach, Florida for some thrilling fishing action.

In the evening, dine at Bob Heilman's Beachcomber Restaurant before heading out on a spooky adventure with the Safety Harbor Haunted History Guided Walking Tour.

Spend your last morning enjoying more of Clearwater's beautiful beaches or perhaps some shopping in downtown Clearwater.

For lunch try out some local flavors at Clear Sky Cafe. Afterward take part in one last water adventure with the exciting  Private Boat Tour Sunset Cruise Island Hopping and more!. It's a perfect way to end your trip.