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Take a Bareboat Charter on the Magnificent Chicago Lakefront


Are you looking for a unique way to explore the magnificent Chicago lakefront? Bareboat chartering is the perfect solution! Whether you’re an experienced sailor or just beginning, sailing Chicago’s lakefront is an unforgettable experience. With a bareboat charter, you’ll have the opportunity to explore the many beaches, marinas, and picturesque harbors of the city, all while enjoying the thrill of the open water.


What is a bareboat charter? Chartering a yacht on the Chicago Lakefront is a great way to experience the city from a different perspective. You can enjoy the beauty of the lake, sail along the shoreline, and take in the majestic skyline. If you’re looking for an incredible adventure, a bareboat charter in Chicago offers complete control over your itinerary, privacy, and the freedom to explore at your own pace. With up to ten (10) people on board, you can enjoy quality time with family and friends while exploring all the Chicago Lakefront offers.

Why sail the Chicago Lakefront? A bareboat charter is perfect for those looking to explore the sights of Chicago from the water. Bareboat charters offer travelers the unique opportunity to take control of their sailing experience, allowing them to plan their own course and make the most of the spectacular scenery around them.

The experienced staff at Windy City Sailing will provide you with everything you need for a safe and enjoyable journey on the lake. They’ll ensure that your charter is tailored to your preferences and needs, from safety equipment and navigation tools to procuring gourmet food and drinks.

If you’re an experienced sailor, a bareboat charter allows you to hone your sailing skills in the waters of Lake Michigan. If you’re new to sailing, the USCG-licensed captain you hire will provide helpful instruction, giving you the confidence to take charge of your adventure. Whichever path you choose, a bareboat charter in Chicago promises a unique experience that you won’t soon forget!

What to expect when bareboat chartering with Windy City Sailing A bareboat charter in Chicago offers you the unique opportunity to explore the magnificent lakefront and have up to 10 people on board, including a licensed United States Coast Guard Captain and one crew member.

With a bareboat charter, you dictate where your yacht sails and when to drop anchor and go swimming. All drinks, food, and even ice must be provided per USCG regulations, so make sure to bring your own towels and sunscreen.

When chartering in Chicago, Windy City Sailing’s rate is $300 per hour for the sailboat, with a three-hour minimum. This does not include captain/crew compensation, which must be arranged directly with the captain you choose.

Safety is always the most important factor, and we may need to reschedule your charter should there be heavy rain or lightning. Consider chartering in Chicago for an unforgettable experience exploring the beautiful lakefront with your friends and family.

Tips for a successful bareboat charter When chartering a boat in Chicago, it is important to know about the Windy City Sailing Bareboat Charter Agreement. This document outlines all of the details of the charter and should be read carefully before embarking on your adventure. It is also important to plan ahead when chartering a boat in Chicago. Allow plenty of time for travel and check-in so you can get familiar with the port and avoid stress.

When it comes to onboard provisions, consider everyone’s dietary needs and draw up a list of items that need to be brought on board. Having enough food and drinks for the entire trip is essential, especially if you plan on eating and drinking on shore. Also, bring a dry bag to protect your belongings from getting wet while swimming.

If you’re sailing with children, keep the sailing legs short and provide plenty of activities such as snorkeling and paddling. This will ensure everyone enjoys their experience while chartering in Chicago! View Frequent Asked Questions for more information about sailing with Windy City Sailing.

Conclusion – why you should try bareboat chartering in Chicago For those looking to explore Lake Michigan from the water, chartering a boat in Chicago is the perfect way to get out and enjoy the lake. Chartering offers a unique experience that allows visitors to relax and appreciate the natural beauty of the lake and its surroundings. Windy City Sailing offers bareboat charters.

Not only do you get the chance to experience sailing on Lake Michigan, but you also get the opportunity to take in some of the most amazing sights that Chicago offers. From downtown Chicago to the city’s countless beaches, there are plenty of interesting sites to see while sailing. And with the help of experienced captains and crew, you can feel safe and secure while out on the lake.

Whether you’re looking to explore Chicago’s coastline or just spend some time on the lake, chartering a boat in Chicago is the perfect way to experience the great city and its beautiful lakefront. So grab some friends, hop on board, and enjoy an unforgettable day sailing on Lake Michigan.


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