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Best Sailing Destinations on Lake Michigan 

When people think of the word “yachting,” they typically think of sun-drenched sandy beaches, crystal clear blue water teeming with brightly colored fish, and mega-yachts anchored right offshore. People are smiling, sipping fruity cocktails, and smelling like coconut sunscreen.

Here at Anita Dee Yacht Charters, we know that yachting can be all that – and so much more. Chicago is nestled on the shore of Lake Michigan, and for anyone native to the area, you know the Great Lakes are a treasure trove of breathtaking sights and a wealth of sailing lore and legend.

There is a rich history in these waters and a beauty that is just as captivating as what you’d find in any of the more tropical waters. For centuries, sailors have navigated the Great Lakes in search of trade routes and goods that could help them make their living. What they left us is even more valuable – rich stories and legends intermingled with sights you’ll remember forever. These are some of the best sailing destinations in Lake Michigan.

Navy Pier

Let’s begin in our own backyard, Navy Pier, which dates back more than 100 years. There is no shortage of fun for all ages at this destination, one of Chicago’s most celebrated entertainment hubs. There are rides and games, cruises, and public art exhibitions that celebrate the rich naval history of the area, plus more contemporary artistic endeavors.

In case you work up an appetite exploring all the sites at the pier, there is an abundance of restaurants to cater to any taste and, of course, plenty of shopping. Let’s not forget one of the most popular attractions at Navy Pier, the biweekly Summer Fireworks show. This amazing display is synchronized to music on Lake Michigan and is a must-see event if you are in the area from Memorial Day to Labor Day.

Chicago Harbor Lighthouse

Just east of the busy and bustling Navy Pier is the Chicago Harbor Lighthouse. This lighthouse was built in 1893 for the World’s Columbian Exposition before it was moved in 1919 to its present site. In 1925, the steam fog signal was replaced by an air diaphone one to increase its range on the water. Today it is an automated active lighthouse with modern technology that hasn’t lost its sense of history.

Bowers Harbor

Amidst the calm waters along the west coast of Lake Michigan sits Bowers Harbor. These relatively peaceful waters offer wonderful views and a perfect place to relax and take in the sights. Bowers Harbor boasts an amazing onshore history, as well, like the Bowers Harbor Inn. Built as a private residence back in 1928, it has since been renovated into a restaurant, but still holds the charm of the past. Bowers Harbor also has its own vineyard, in addition to the beautiful Bowers Harbor Park and Lighthouse Park.

Beaver Island

Towards the north end of Lake Michigan, you’ll find Beaver Island. This area is an outdoors man’s paradise. Also known as America’s Emerald Isle, Beaver Island is the largest island in Lake Michigan. Not only are there the expected fantastic spots for fishing, but there are also great areas for scuba diving and snorkeling. The island itself has abundant hiking trails, and its own unique version of Stonehenge called the Stone Circle. It is also one of the best places in the U.S. for stargazing because of its isolated location and dark skies.

Indiana Dunes National Park

Looking to enjoy the water and the sand? You don’t need a ticket to Florida, look no further than Indiana Dunes National Park, situated on the southwest coast of Lake Michigan just 50 nautical miles from Chicago. There are picture-perfect images of blue water lapping against soft sand along the park’s 15 miles of shoreline. There are plenty of outdoor activities, hiking trails, geocaching, and a host of other special interests.

There are also a number of secluded spots on the water that offer nothing but peace and solitude for those looking to get away from it all. This park has something for everyone. It is a diverse natural landscape that is well-deserving of a spot on our list.

Great Travers Bay

We admit it, the Great Lakes have a reputation for being unforgiving in times of inclement weather. They can be some of the roughest waters to cross, and there are numerous shipwreck stories to prove it. Nestled in a well-protected area is Grand Traverse Bay, where the water is calm pretty much year-round.

The bay is filled with ports worth exploring like Traverse City, which claims to be the Cherry Capital of the World due to their abundant cherry orchards lining the bay. Not to be outdone, there are also grapes that produce a healthy wine scene in the area, as well. There are smaller historic ports worth exploring. You’ll even find the town of Charlevoix, the old stomping grounds of a young Ernest Hemingway.

Explore with Anita Dee Yacht Charters

There is so much to explore on the Great Lakes, especially Lake Michigan. Food, culture, history, natural beauty, it is all here on the water ready to be discovered.

Yachting is the perfect avenue for exploring what the water has to offer. At Anita Dee Yacht Charters, we are passionate about sharing the beauty of Lake Michigan with others and proving that yachts don’t just belong in the Caribbean.

Are you ready to set sail and see what the waters around Chicago have to offer? Give us a call and let us help you take to the water in style. We are Chicago’s premier private yacht charter group. We cater to you to make your wedding, social gathering, corporate event, or any other special occasion something memorable. We have two vessels to choose from that can accommodate small intimate gatherings or large parties. We even offer catering and onboard event planning, so you don’t have to lift a finger.

Let us show you why we think yachting on the Great Lakes is something special. Call us today at (312) 379-3191 for more information.

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Anita Dee Yacht Charters 200 N Breakwater Access Chicago, IL 60601 (312) 379-3191
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