TOP 30 Chartered sailing trips in Clearwater, Florida

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Vitamin Sea Sailing Charters is a premier travel agency located in Destin, Florida, United States. Specializing in sailing charters, they offer unforgettable experiences on the crystal-clear waters of the Gulf of Mexico. Whether you're looking for a relaxing sunset cruise, a thrilling adventure on the open sea, or a romantic getaway for two, Vitamin Sea Sailing Charters has something for everyone. Their experienced crew and top-of-the-line sailboats ensure a safe and enjoyable experience for all passengers. Book your next nautical adventure with Vitamin Sea Sailing Charters and make memories that will last a lifetime.

Clearwater SunCoast Charters, LLC is a travel agency located at 2691 Woodette Drive in Dunedin, Florida. From their moorings in Ozona, they offer private charters with access to stunning water vistas of Caladesi Island, Honeymoon Island, Three Rooker Island, and the Gulf of Mexico. All charters are captained by Captain D and can accommodate up to 4 persons. Boat pick-ups can be arranged at their Mandalay Bay/Clearwater Beach location for an additional fee, or guests can drive to their Palm Harbor location. Charters range from 2 to 4 hours, with longer trips allowing for exploration and enjoyment of Three Rooker Island. Additionally, Jennifer Patterson, Captain D's wife, is a local Realtor specializing in relocation services for those moving to Pinellas County and Clearwater Beach.

Schooner Clearwater is a premier travel agency located at 25 Causeway Boulevard in Clearwater, Florida. Specializing in unique and unforgettable travel experiences, Schooner Clearwater offers a wide range of services to help you plan the perfect getaway. Whether you're looking for a relaxing beach vacation, an adventurous cruise, or a cultural tour, our knowledgeable staff is dedicated to providing top-notch customer service and personalized travel recommendations. Let Schooner Clearwater be your guide to the world's most exciting destinations.

Kai Lani Catamaran is a premier travel agency located at 25 Causeway Boulevard in Clearwater, Florida. Known for its luxurious catamaran cruises, Kai Lani offers a unique and unforgettable experience for those looking to explore the beautiful waters of the Gulf Coast. Whether you're seeking a relaxing sunset cruise or a thrilling adventure on the open sea, Kai Lani Catamaran has something for everyone. With experienced crew members and top-of-the-line amenities, this institution is the perfect choice for your next nautical excursion.

Flying Pelican Tours is a travel agency located at 3900 West Bay Drive in Belleair Bluffs, Florida, United States. Specializing in Clearwater Beach Private Boat Charters, they offer luxurious and personalized experiences on the stunning waters surrounding Clearwater Beach. With options for 3-hour and 4-hour private charters, guests can enjoy time at local sandbars, dolphin watching, sightseeing celebrity homes, and even island-hopping. Safety is a top priority, with a thorough safety briefing before setting sail and all required safety equipment on board. The professional and knowledgeable crew, led by Captain Sharon, ensures a fun and engaging experience for guests. The 25ft sundeck boat provides unparalleled privacy and comfort, while being meticulously maintained for a clean and beautiful ride. With a variety of charter options available, including sunset tours and half-day trips, Flying Pelican Tours aims to provide the best possible experience for their guests. Captain Sharon, a US Coast Guard licensed captain with years of experience, is dedicated to providing safe navigation and unforgettable adventures on the water.

A Boat Day is a travel agency located at 198 Seminole Street in Clearwater, Florida, offering unique and unforgettable boating experiences. With friendly and experienced boat captains to guide you, you can enjoy cruising the waterways, island hopping, or anchoring up at sand bars in Clearwater Beach, Dunedin, Indian Rocks Beach, and St. Pete Beach. Choose from a variety of boats, including the luxurious Tahoe Funship, the spacious Hurricane deck boat, the Platinum Funship with a water slide, the Avalon Funship with a Bluetooth sound system, the Buccaneer Funship for a pirate adventure, the Four Winns yacht class deck boat, and more. Sailing charters on the 41-Foot Morgan Out Island Ketch are also available for a relaxing day on the water.