Clearwater Loop Florida Fly Drive

Itinerary

• 3*Holiday Inn & Suites, Clearwater Beach - 4 Nights

  Clearwater, a picturesque haven on Florida's Gulf Coast, boasts pristine beaches kissed by turquoise waters. With its powdery sands and breathtaking sunsets, it's a paradise for beach lovers. Dive into a myriad of water sports or simply unwind under the warm sun. Stroll along the bustling pier or explore the quaint shops and cafes nearby. Home to marine life and natural wonders, Clearwater offers an unforgettable blend of relaxation and excitement. Whether seeking serene moments or thrilling adventures, this coastal gem promises an escape to cherish.

• 3*Best Western Naples Plaza Hotel, Naples - 3 Nights

  Naples, Florida is a picturesque city on the Gulf of Mexico, known for its upscale lifestyle, white-sand beaches, and vibrant arts scene. Renowned for luxury shopping, fine dining, and world-class golf courses, it also offers access to nature through nearby Everglades and pristine parks. With a warm, tropical climate and stunning sunsets, Naples attracts retirees, vacationers, and families seeking coastal charm and a relaxed yet refined atmosphere. Its small-town feel combined with elegant amenities makes it one of Southwest Florida’s most desirable destinations.

• 4*Tropic Isle at Anna Maria Island Inn 3 nights

  Anna Maria Island, a hidden gem on Florida’s Gulf Coast, enchants visitors with its sugar-white beaches and crystal-clear waters. This charming island exudes old Florida charm, where laid-back vibes meet stunning natural beauty. Bask in the sun on unspoiled shores, kayak through mangrove tunnels, or bike along scenic coastal paths. Explore the island’s quaint boutiques, waterfront eateries, and iconic piers, where breathtaking sunsets paint the sky. With its welcoming atmosphere and endless coastal adventures, Anna Maria Island offers the perfect escape—whether you seek total relaxation or unforgettable experiences by the sea.

• 4* Island Grand at Tradewinds St. Pete-Clearwater 4 nights

  St. Pete-Clearwater is renowned for sunshine with an average of 361 days per year and currently holds the Guinness World Record for the longest run of sunshine days, a massive 768. Clearwater Beach was ranked as the number one beach in Florida and even ranked amongst the top 20 for TripAdvisor's Best of the Best Beaches in the world for 2026!