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Roam Around

Ultimate Clearwater Beach and Beyond Experience Itinerary

Last updated: 2024 Jun 14

Sun, Sand, and Seafood Delights

Morning

Start your Clearwater experience with a delightful breakfast at Clear Sky Cafe, known for its delicious options. Afterward, head to the famous Clearwater Beach to soak up the sun and enjoy the pristine white sands.

Afternoon

For lunch, savor the fresh seafood at Frenchy's Rockaway Grill with a beachfront view. Post lunch, take a leisurely walk to Pier 60 and explore the local shops and maybe catch a street performance.

Evening

In the evening, indulge in a fine dining experience at Caretta on the Gulf where you can enjoy a beautiful sunset along with your meal.

Bedtime

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Marine Life and Sunset Cruises

Morning

Enjoy a delicious breakfast at Clear Sky Cafe before heading to the Clearwater Marine Aquarium to get up close with marine life, including Winter the Dolphin.

Afternoon

For lunch, try the unique dishes at Pearly's Beach Eats. Afterward, embark on the Clearwater Sunset Celebration Cruise for a magical experience on the water.

Evening

Conclude the day with a dinner at Bob Heilman's Beachcomber, a local favorite for its seafood and steaks.

Bedtime

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Island Adventures and Winery Tour

Morning

Start your day with a delicious breakfast at Clear Sky Cafe. Then, take a ferry to Caladesi Island for a serene beach day.

Afternoon

Have a late lunch at Cesare at The Beach - Hilton Clearwater Beach Resort & Spa before embarking on a Clearwater; Aspirations Winery Tour and Tasting Experience for a unique local experience.

Evening

Enjoy a relaxed dinner at Tate Island Grill with waterfront views.

Bedtime

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Art, Culture, and Electric Cart Tour

Morning

Begin your day with a delightful breakfast at The Lucky Lobster Co. before visiting the Imagine Museum in St. Petersburg to explore a stunning collection of contemporary glass art.

Afternoon

For lunch, enjoy the vibrant atmosphere at Rumba Island Bar & Grill - Clearwater Beach. Afterward, take a St. Petersburg, Fl Sightseeing Tour in Electric Cart to discover the city's charm.

Evening

Dine at Basimo Beach Cafe and savor the flavors of the Mediterranean.

Bedtime

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Greek Heritage and Kayaking Adventure

Morning

Enjoy a traditional Greek breakfast at Gondolier Pizza Italian Restaurant in Tarpon Springs, known for its Greek cuisine. Explore the Tarpon Springs Sponge Docks and learn about the town's rich Greek heritage.

Afternoon

For lunch, indulge in the seafood specialties at Crabby Bill's Clearwater Beach. Afterward, experience a Tarpon Springs Guided Anclote River Kayaking Tour for a unique perspective of the area.

Evening

Have dinner at Bobby's Bistro & Wine Bar, a cozy spot with a great wine selection.

Bedtime

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Relaxation and Departure

Morning

On your last day, enjoy a leisurely breakfast at Forlini's Ristorante & Bar before spending some final moments at the beach or exploring the Clearwater; Sand Key Park.

Afternoon

For a farewell lunch, head to Island Way Grill for its fresh seafood and waterfront ambiance. Afterward, take a relaxing Cruisin' Tikis Clearwater Sunset Cruise to unwind before your departure.

Evening

Conclude your trip with a memorable dinner at the iconic Columbia Restaurant, known for its Spanish cuisine and historic setting.

Bedtime

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