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5-Day Clearwater Beach Getaway Itinerary

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day 1

Arrival and Beach Fun

Clearwater Itinerary - March 4

Morning. Start your day by enjoying a delicious breakfast at Clear Sky Beachside Cafe. Afterward, head to Clearwater Beach and spend the morning soaking up the sun, swimming in the crystal-clear waters, and relaxing on the sandy shores.
Afternoon. For lunch, head to Frenchy's Rockaway Grill and indulge in their famous seafood dishes. Afterward, visit the Clearwater Marine Aquarium to get up close and personal with dolphins, sea turtles, and other marine life.
Evening. Enjoy a beautiful sunset dinner at Caretta on the Gulf, a beachfront restaurant known for its fresh seafood and stunning views. After dinner, take a leisurely stroll along the beach and experience the Clearwater Sunset Celebration Cruise, where you can enjoy live music and breathtaking views of the sunset.
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day 2

Island Adventures

Clearwater Itinerary - March 5

Morning. Start your day with a hearty breakfast at Clear Sky Draught Haus. Then, embark on a day trip to Caladesi Island and Honeymoon Island, two pristine barrier islands known for their white sandy beaches and nature trails.
Afternoon. For lunch, head to Island Way Grill, a waterfront restaurant offering a variety of fresh seafood dishes. Afterward, visit the Clearwater Eco-Certified Marine Aquarium General Admission to learn more about the local marine ecosystem.
Evening. Enjoy dinner at Crabby's Dockside, a popular waterfront restaurant known for its seafood specialties. Afterward, take a relaxing Clearwater Dolphin Exploration Tour and admire the playful dolphins in their natural habitat.
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day 3

Water Adventures

Clearwater Itinerary - March 6

Morning. Start your day with a delicious breakfast at Sandpiper Grill and Tiki Bar. Then, embark on a thrilling St. Petersburg, FL 4-Hour Catamaran Cruise to Egmont Key and explore the beautiful Egmont Key State Park, known for its historic lighthouse and pristine beaches.
Afternoon. For lunch, head to The Island Grill and Raw Bar and enjoy their fresh seafood and tropical drinks. Afterward, experience the Madeira Beach Pirate Adventure Cruise with Beer and Wine and embark on a swashbuckling adventure aboard a pirate ship.
Evening. Enjoy a relaxing dinner at Jimmy's Fish House & Iguana Bar, a waterfront restaurant with stunning sunset views. Afterward, take a St. Petersburg Sunset Cruise with Sunshine Skyway Bridge and admire the illuminated Sunshine Skyway Bridge.
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day 4

Cultural Exploration

Clearwater Itinerary - March 7

Morning. Start your day with a delicious breakfast at Columbo's Pizzeria & Italian Restaurant. Then, visit the Sim Center and experience a realistic flight simulation.
Afternoon. For lunch, head to Carmel Kitchen & Wine Bar and enjoy their Mediterranean-inspired dishes. Afterward, visit the St. Petersburg, FL Imagine Museum Admission Ticket and explore the world of contemporary glass art.
Evening. Enjoy dinner at Bob Heilman's Beachcomber, a historic restaurant known for its classic American cuisine. Afterward, experience the vibrant nightlife of downtown St. Petersburg and visit Madeira Beach Sightseeing Cruise to John's Pass with Guide for a guided tour of the famous John's Pass Village and Boardwalk.
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day 5

Relaxation and Farewell

Clearwater Itinerary - March 8

Morning. Start your day with a leisurely breakfast at Clearwater Social Club. Then, spend the morning relaxing on the sandy shores of Sand Key Park and enjoying the peaceful atmosphere.
Afternoon. For lunch, head to Salt Cracker Fish Camp, a local favorite known for its fresh seafood dishes. Afterward, visit Sim Center for another thrilling flight simulation experience.
Evening. Enjoy a farewell dinner at K. Orozco's Mexican Restaurant, a cozy restaurant serving authentic Mexican cuisine. Afterward, visit Madeira Beach Guided Dolphin Watching Eco-Friendly Cruise and witness the beauty of dolphins in their natural habitat. End the night with a visit to The Lucky Anchor, a lively bar known for its craft cocktails and live music performances.
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