Adventurous 5-Day Clearwater Beach Escape Itinerary

Embark on the Madeira Beach Pirate Adventure Cruise with Beer and Wine for a swashbuckling morning on the high seas.

Enjoy a unique dining experience at The Lucky Lobster Co. and then visit the famous Clearwater Marine Aquarium to meet Winter the Dolphin.

Have a fun-filled evening at the Clearwater Sunset Celebration Cruise with live music and dancing on board.

Get your adrenaline pumping with a session of Jet Skiing or Parasailing at Clearwater Beach.

For lunch, savor the flavors of the sea at Pearly's Beach Eats and then take a Clearwater Beach Dolphin and Sandbar Boat Cruise for a relaxing afternoon on the water.

Dine at the iconic Frenchy's Rockaway Grill and enjoy the vibrant beachfront atmosphere.

Embark on a Private Boat Tour, Sunset Cruise, Island Hopping and more! for a personalized island-hopping adventure.

Have a leisurely lunch at Crabby Bill's Clearwater Beach and then explore the natural beauty of Caladesi Island with a Kayaking clear through Clearwater tour.

Experience the magic of a Twilight Sip and Dine St. Petersburg with a guided kayak tour as the sun sets over the water.

Conclude your Clearwater adventure with a thrilling Clearwater Beach Dolphins and Donuts Morning Cruise for a memorable final morning.

Enjoy a farewell lunch at Bobby's Bistro & Wine Bar and spend your last afternoon relaxing on the beach or indulging in some shopping at the local boutiques.

For your final evening, savor a gourmet dinner at Caretta on the Gulf and take a romantic Clearwater Sunset Cruise and Dolphin Watching to bid goodbye to the sun, the sea, and the dolphins.