Ultimate 5-Day Clearwater, Florida Experience Itinerary

Start your day with a hearty breakfast at Pearly's Beach Eats. After breakfast, take a short drive to Caladesi Island, one of the few completely natural islands along Florida's Gulf Coast. Spend the morning exploring the pristine beaches and nature trails.

For lunch, head to Island Way Grill for a waterfront dining experience. Afterward, enjoy a guided kayaking tour with Tarpon Springs Guided Anclote River Kayaking Tour and immerse yourself in the natural beauty of the area.

Dine at Salt Cracker Fish Camp, known for its fresh seafood and Southern hospitality. After dinner, take a private sunset cruise with Private Boat Tour, Sunset Cruise, Island Hopping and more! and experience the beauty of the Gulf Coast at dusk.

Enjoy a leisurely breakfast at Clear Sky Cafe, a local favorite. After breakfast, visit the Sim Center and experience the thrill of flight simulation. Spend the morning flying virtual missions and testing your piloting skills.

For lunch, head to Jimmy Hula's Clearwater Beach for a laid-back atmosphere and delicious tacos. Afterward, embark on a sightseeing tour in an electric cart with St. Petersburg, Fl Sightseeing Tour in Electric Cart. Explore the historic neighborhoods and vibrant downtown area.

Dine at Frenchy's Rockaway Grill, a beachfront restaurant known for its seafood and live music. After dinner, take the St. Petersburg Sunset Cruise with Sunshine Skyway Bridge and admire the stunning Sunshine Skyway Bridge illuminated against the night sky.

Start your day with a delicious breakfast at Crabby Bill's Clearwater Beach. After breakfast, embark on a thrilling speedboat adventure with St. Pete Beach Dolphin Racer Cruise by Speedboat. Hold on tight as you zip across the water and keep an eye out for dolphins.

For lunch, head to Bobby's Bistro & Wine Bar for a sophisticated dining experience. Afterward, visit the St. Petersburg, FL Imagine Museum Admission Ticket and explore the world of contemporary studio glass art.

Dine at Caretta on the Gulf, a fine dining restaurant with stunning ocean views. After dinner, take the Twilight Sip and Dine St. Petersburg and enjoy a guided walking tour of the city's vibrant murals, accompanied by craft beer and wine tastings.

Enjoy a leisurely breakfast at Gondolier Pizza Italian Restaurant, known for its authentic Italian cuisine. After breakfast, spend the morning relaxing at Clearwater Beach, soaking up the sun and enjoying the warm Gulf waters.

For lunch, head to Rumba Island Bar & Grill - Clearwater Beach for Caribbean-inspired dishes and tropical cocktails. Afterward, take a private pontoon tour with Clearwater Beach Private Pontoon Tours and explore the hidden gems of the area.

Dine at Columbia Restaurant, a historic restaurant serving Spanish and Cuban cuisine. After dinner, enjoy a private transfer to/from Tampa Airport with Tampa Private Transfer to/from Tampa Airport (TPA) as you bid farewell to Clearwater.