person sailing on ocean

Experience Lake Michigan Like Never Before

Join us for unforgettable sailing adventures on Lake Michigan's beautiful waters.

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Sailing Charters

Explore Racine and nearby cities on the water.

Enjoy a relaxing day on the lake.

Create lasting memories with family and friends.

Boat Rentals
Unwind and enjoy the scenic views.

Experience the Best of Lake Michigan

At Heartbreaker Sailing, we offer unforgettable sailing charters on Lake Michigan, showcasing the beauty of Racine and nearby cities. Join us for a memorable day on the water.

A sandy beach area featuring two sailboats with red, white, and blue sails near a small rental shack. The shack has a sign reading 'THE SANDBOX BIKE RENTAL.' A billboard advertises 'Hurricane Boat Rentals' beside it. The scene is set against a calm body of water, with trees and amusement park rides visible in the distance.
A sandy beach area featuring two sailboats with red, white, and blue sails near a small rental shack. The shack has a sign reading 'THE SANDBOX BIKE RENTAL.' A billboard advertises 'Hurricane Boat Rentals' beside it. The scene is set against a calm body of water, with trees and amusement park rides visible in the distance.
An unforgettable sailing adventure awaits!

Emily

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Book

Memorable Sailing Adventures

Experience Lake Michigan with us and explore the beauty of Racine and nearby waterways.

Sailing Charter Experience

Join us for an unforgettable sailing charter exploring the scenic views of Lake Michigan.

A small wooden boat with an orange canopy sails across a calm blue ocean. The boat has lettering on its side and a person steering at the rear. The sky is partly cloudy with a light blue hue.
A small wooden boat with an orange canopy sails across a calm blue ocean. The boat has lettering on its side and a person steering at the rear. The sky is partly cloudy with a light blue hue.
Boat Rental Services

Rent a boat and enjoy a day on the water, soaking in the stunning cityscape.

A sailboat with white sails is calmly floating on clear, turquoise waters. Two people are visible on the boat, appearing relaxed. In the background, rugged, tree-covered cliffs rise, providing a serene and natural backdrop. A smaller dinghy is tethered nearby.
A sailboat with white sails is calmly floating on clear, turquoise waters. Two people are visible on the boat, appearing relaxed. In the background, rugged, tree-covered cliffs rise, providing a serene and natural backdrop. A smaller dinghy is tethered nearby.

Sailing Adventures

Experience Lake Michigan, exploring Racine and nearby beautiful cities.

A sailboat named 'Carpe Diem' is docked in a harbor, filled with people enjoying a sunny day. The boat has white sails and wooden accents. In the background, other boats and a clear blue sky with some clouds are visible.
A sailboat named 'Carpe Diem' is docked in a harbor, filled with people enjoying a sunny day. The boat has white sails and wooden accents. In the background, other boats and a clear blue sky with some clouds are visible.
A large red sailboat glides through the water with several people on board, wearing life vests. The boat features a prominent red sail with markings. A picturesque landscape with a grand house, neatly trimmed hedges, and trees serves as the backdrop.
A large red sailboat glides through the water with several people on board, wearing life vests. The boat features a prominent red sail with markings. A picturesque landscape with a grand house, neatly trimmed hedges, and trees serves as the backdrop.
A group of people is sailing on a wooden boat with a vibrant red-orange sail. The boat features blue and black accents, and several men are standing or seated, engaging in conversation as it moves across a body of water.
A group of people is sailing on a wooden boat with a vibrant red-orange sail. The boat features blue and black accents, and several men are standing or seated, engaging in conversation as it moves across a body of water.
An aerial view of a catamaran sailing on clear turquoise water. The boat is positioned towards the right of the image, with its white surfaces contrasting against the deep colors of the ocean. Shadows from the sail and frame create patterns on the deck.
An aerial view of a catamaran sailing on clear turquoise water. The boat is positioned towards the right of the image, with its white surfaces contrasting against the deep colors of the ocean. Shadows from the sail and frame create patterns on the deck.
Three brightly colored catamarans are situated on a sandy beach. The sails feature vivid stripes in colors such as yellow, red, orange, purple, and green. The turquoise sea and clear blue sky create a serene backdrop. A jetty of rocks stretches into the sea, and another small sailing vessel is visible in the distance along with a trailer on the beach.
Three brightly colored catamarans are situated on a sandy beach. The sails feature vivid stripes in colors such as yellow, red, orange, purple, and green. The turquoise sea and clear blue sky create a serene backdrop. A jetty of rocks stretches into the sea, and another small sailing vessel is visible in the distance along with a trailer on the beach.
A sailboat docked at a marina, featuring a spacious deck and dual steering wheels. The sky is clear with bright blue hues, and several other boats are visible in the background. A small red flag can be seen on the boat's mast, and the marina is bustling with nautical activity.
A sailboat docked at a marina, featuring a spacious deck and dual steering wheels. The sky is clear with bright blue hues, and several other boats are visible in the background. A small red flag can be seen on the boat's mast, and the marina is bustling with nautical activity.

Customer Reviews

See what our guests say about their unforgettable sailing experiences.

The best sailing experience! Stunning views of Racine and a fantastic crew.

Emily Johnson
A blue boat with seating and a green canopy, equipped with life jackets and ropes. The boat is docked on a calm waterway with a view of palm trees and a coastal landscape in the background.
A blue boat with seating and a green canopy, equipped with life jackets and ropes. The boat is docked on a calm waterway with a view of palm trees and a coastal landscape in the background.

Racine, WI

Heartbreaker Sailing provided an amazing day on Lake Michigan. The views were breathtaking, and the crew was incredibly friendly and knowledgeable. Highly recommend for anyone looking to relax!

Several sailboats navigate close to each other on the water, each displaying prominent sails with unique numbers and logos. The scene involves individuals actively participating in a sailing activity, with one person in a red shirt and blue cap clearly visible.
Several sailboats navigate close to each other on the water, each displaying prominent sails with unique numbers and logos. The scene involves individuals actively participating in a sailing activity, with one person in a red shirt and blue cap clearly visible.
Michael Smith

Racine, WI

★★★★★
★★★★★
Sailing

Experience the beauty of Lake Michigan today.

contact us

Relaxation

info@heartbreakersailing.com

(262) 210-0702

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77 DR. MARCUS WHEATLAND BOULEVARD, NEWPORT, RI 02840