Sailing Reservations

Book your unforgettable sailing charter experience on Lake Michigan and explore the beauty of Racine.

A white sailboat docked at a marina with the registration number 810. The boat features a tall mast with banners, surrounded by calm water. In the background, several historical buildings line the waterfront, under a clear blue sky.
A white sailboat docked at a marina with the registration number 810. The boat features a tall mast with banners, surrounded by calm water. In the background, several historical buildings line the waterfront, under a clear blue sky.

Gallery

Explore stunning views of Lake Michigan and nearby cities.

A row of small white sailboats is lined up on a textured surface with green grass nearby. Each boat has a sail, with the nearest one featuring a cheerful yellow star carrying a basketball and branding for Southern Cross Travel Insurance. The sailboat is labeled 'ATLAS CONCRETE' in red letters on its side.
A row of small white sailboats is lined up on a textured surface with green grass nearby. Each boat has a sail, with the nearest one featuring a cheerful yellow star carrying a basketball and branding for Southern Cross Travel Insurance. The sailboat is labeled 'ATLAS CONCRETE' in red letters on its side.
A wooden sailboat with a large white sail is on the ocean, seen through rigging in the foreground. The boat has several people on board and a banner that reads 'Jolly Pirates.' The water is a deep turquoise, and there is a coastline with palm trees in the background under a blue sky with some clouds.
A wooden sailboat with a large white sail is on the ocean, seen through rigging in the foreground. The boat has several people on board and a banner that reads 'Jolly Pirates.' The water is a deep turquoise, and there is a coastline with palm trees in the background under a blue sky with some clouds.
A large sailboat with three masts and white sails, sailing near a shoreline with residential buildings in the background. The boat is carrying several passengers, and the water appears calm. The sky is clear, suggesting a pleasant day.
A large sailboat with three masts and white sails, sailing near a shoreline with residential buildings in the background. The boat is carrying several passengers, and the water appears calm. The sky is clear, suggesting a pleasant day.

An unforgettable experience on Lake Michigan! The views of Racine and nearby cities were breathtaking. Highly recommend Heartbreaker Sailing for an amazing day on the water!

John D.

A large luxury yacht is sailing on a calm body of water, viewed from a terrace with awnings and part of a building with white walls and terracotta roofs. The backdrop features distant mountains and a clear blue sky.
A large luxury yacht is sailing on a calm body of water, viewed from a terrace with awnings and part of a building with white walls and terracotta roofs. The backdrop features distant mountains and a clear blue sky.

★★★★★