Sailing Clearwater Beach, Florida

Clearwater Beach is more than soft white sand and beautiful sunsets. The calm, warm ocean waters of the Gulf of Mexico makes Clearwater Beach a great place to set sail. Sailing Clearwater Beach is a great way to relax and enjoy the beautiful atmosphere of the area.

Schooner Clearwater

Enjoy “a true sailing experience on Clearwater Beach”. The Schooner Clearwater is a 52-foot long sailboat built in 2016. The beautiful boat can sail around Clearwater Beach with up to 50 people, but limits reservations to 22 passengers to keep the boat open and always promise a fun, relaxing experience.

The Schooner Clearwater offers a Clearwater Beach sailing cruise each day and a sunset sail in the evening. Each cruise is two hours long and leaves from the Clearwater Beach Marina. The direction and total distance of each sail are determined based on weather and wind speeds.

For larger events, the Schooner Clearwater is also open for private charters. Private charters can even include a small catering and beverage service as you are sailing Clearwater Beach.

Kai Lani Catamaran

Sail around Clearwater Beach and feel a light spray of the ocean through the open netting of the Kai Lani Catamaran. The Kai Lani Catamaran is a performance catamaran capable of reaching speeds of 20 knots. The Kai Lani Catamaran offers daily cruises and evening sunset cruises. These cruises can hold up to 41 passengers and serve beer and wine while sailing Clearwater Beach.

Clearwater Community Sailing Center

Instead of just enjoying a relaxing Clearwater Beach sailboat cruise, learn to sail yourself! Just across the bridge headed towards Sand Key, you’ll find the Clearwater Community Sailing Center. The Clearwater Community Sailing Center offers a one hour cruise with an instructor to teach you how to sail. The one-hour sailing lesson costs $100 for a group of 4 or smaller.

Private sailing lessons are also available. Private lessons cost $75/hour for a single person ($35/hour for any additional participants). The instructors at the Clearwater Community Sailing Center are fantastic and can quickly teach you to sail. The instructors feel most individuals feel comfortable sailing on their own within two to three hours.

Outside of learning to sail, you can learn how to windsurf, paddleboard, and more! You can also rent kayaks, stand up paddleboards, windsurfers and small sailboats and catamarans!

Sail Honeymoon Kayak & SUP Rentals

Sail the north side of Clearwater Beach by renting sailboats and trimarans from Sail Honeymoon Kayak & SUP Rentals. As the name says, they are more than just sailboats. Sail, kayak or paddle the water surrounding the north side of Clearwater Beach, Caladesi Island and Honeymoon Island. After enjoying the beautiful area on the water, stop and taste the great food and drinks found in Dunedin, the town you drive through right before reaching the causeway to Honeymoon Island where Sail, Honeymoon Kayak & SUP Rentals is located.