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Roam Around

5 Days in Clearwater Florida Itinerary

Last updated: 2024 Jun 14

Welcome to Clearwater

Morning

Start your day with a visit to the beautiful Clearwater Beach. Enjoy the pristine white sands and clear waters that make this beach famous. Relax under the sun or take a refreshing swim in the Gulf of Mexico.

Afternoon

After a relaxing morning at the beach, head over to Clearwater Marine Aquarium where you can learn about marine life and meet Winter the dolphin. This aquarium is dedicated to the rescue and rehabilitation of marine animals.

Evening

In the evening, enjoy a delightful dinner at Frenchy's Rockaway Grill, known for its fresh seafood and vibrant atmosphere. After dinner, embark on a serene Clearwater Sunset Celebration Cruise to witness a breathtaking sunset over the Gulf.

Bedtime

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4.64
Clearwater Beach
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4.67
Clearwater Marine Aquarium
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Island Adventures and Marine Life

Morning

Begin your day with an exciting trip to Caladesi Island. Accessible only by boat or ferry, this island offers untouched beaches and nature trails perfect for hiking and bird watching.

Afternoon

For lunch, visit Palm Pavilion Beachside Grill & Bar which offers great food with stunning views of the beach. Post-lunch, explore Sand Key Park, another beautiful beach park known for its peaceful ambiance and picnic areas.

Evening

Dine at Columbia Restaurant Sand Key, an iconic restaurant serving delicious Spanish cuisine. End your day with a fun-filled Clearwater Beach Island Sandbar & Swim Tiki Cruise.

Bedtime

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Caladesi Island
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4.21
Sand Key Park
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Water Sports and Wildlife

Morning

Kick off your morning with some adventure by going on a thrilling Kayaking clear through Clearwater. Paddle through calm waters while enjoying scenic views of Clearwater's coastline.

Afternoon

Have lunch at Marina Cantina, offering Mexican cuisine with rooftop views of Clearwater Bay. Afterward, join an educational experience at the Clearwater Eco-Certified Marine Aquarium General Admission.

Evening

Enjoy dinner at Island Way Grill, known for its seafood dishes. Conclude your evening with an enchanting experience on the Clearwater Beach Sunset Tiki Cruise.

Bedtime

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4.67
Kayaking clear through Clearwater
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4.40
Clearwater Eco-Certified Marine Aquarium General Admission
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Exploring History and Local Flavors

Morning

Start your day by exploring local history on the intriguing Safety Harbor Haunted History Guided Walking Tour. Discover eerie tales as you walk through historic sites.

Afternoon

For lunch, try out some local favorites at The Bait House Tackle & Tavern, known for its fresh seafood dishes. Spend your afternoon visiting nearby attractions or relaxing by the beach.

Evening

Dine at Sea-Guini, offering Italian-inspired dishes made from fresh ingredients. In the evening, embark on a unique adventure with the spooky yet fascinating Clearwater Haunted History Tour on a Vintage Trolleybus.

Bedtime

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Safety Harbor Haunted History Guided Walking Tour
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3.33
Clearwater Haunted History Tour on a Vintage Trolleybus
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Final Day Fun in Clearwater

Morning

Begin your last day in Clearwater with an exhilarating experience on a private boat tour such as the Private Boat Tour Sunset Cruise Island Hopping and more!. Enjoy island hopping and possibly spotting dolphins along the way.

Afternoon

Have lunch at Shor American Seafood Grill which offers delicious seafood dishes in an elegant setting. Afterward, spend some time shopping or exploring any missed attractions from previous days.

Evening

For your final dinner in Clearwater, visit Bob Heilman's Beachcomber Restaurant, renowned for its classic American cuisine. End your trip on a high note with an unforgettable sunset view during the relaxing cruise of Clearwater Private Boat Sunset Cruise + Dolphin Watch.

Bedtime

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