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Roam Around

Clearwater Florida Adventure - 4 Days Itinerary

Last updated: 2024 Jun 14

Beachside Bliss and Local Flavors

Morning

Start your day with a visit to Clearwater Beach, one of the most beautiful beaches in the United States. Enjoy the pristine white sands and clear blue waters. Take a relaxing walk along the shore or indulge in some beach sports.

Afternoon

Head over to Frenchy's Rockaway Grill for a delightful lunch with a view of the beach. After lunch, visit Clearwater Marine Aquarium where you can meet Winter the dolphin and learn about marine life conservation.

Evening

End your day with a sunset cruise on Clearwater Sunset Celebration Cruise. Witness the breathtaking sunset over the Gulf of Mexico while enjoying live music and refreshments.

Bedtime

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Island Adventures and Waterfront Dining

Morning

Take a morning trip to Caladesi Island. Accessible only by boat or ferry, this island offers beautiful hiking trails and secluded beaches. Spend your morning exploring this natural paradise.

Afternoon

For lunch, head back to Clearwater and dine at Island Way Grill. Post-lunch, embark on an exciting adventure with Clearwater Beach Dolphin and Island Sandbar Boat Tour. Spot playful dolphins and relax on sandbars.

Evening

Enjoy dinner at Marina Cantina, known for its vibrant atmosphere and delicious Mexican cuisine. After dinner, take a leisurely stroll along Clearwater Beach's Pier 60.

Bedtime

Find amazing hotels in Clearwater, Florida, USA.

Cultural Experiences and Scenic Cruises

Morning

Begin your day with breakfast at Clear Sky Cafe, offering an extensive menu in a charming setting. Then visit Sand Key Park, where you can enjoy bird watching or simply relax by the water.

Afternoon

Have lunch at Bob Heilman's Beachcomber, renowned for its classic American dishes. In the afternoon, explore local history with the Safety Harbor Haunted History Guided Walking Tour. Discover intriguing stories from Clearwater's past.

Evening

Dine at Palm Pavilion Beachside Grill & Bar while enjoying live music and ocean views. Later in the evening, experience another stunning sunset on the water with Clearwater Sunset Cruise and Dolphin Watching.

Bedtime

Find amazing hotels in Clearwater, Florida, USA.

Marine Wonders and Culinary Delights

Morning

Start your final day with a tour of Aspirations Winery by joining their popular activity: Clearwater; Aspirations Winery Tour and Tasting Experience. Sample some local wines as you learn about their production process.

Afternoon

For lunch head to Salt Cracker Fish Camp for fresh seafood dishes right by the marina before heading out for an afternoon of fun on Private Boat Tour Sunset Cruise Island Hopping and more! . Enjoy swimming island hopping dolphin watching or just relaxing aboard your private vessel.

Evening

Conclude your trip dining at Sea-Guini known for its exquisite Italian cuisine paired perfectly with Gulf views.

Bedtime

Find amazing hotels in Clearwater, Florida, USA.