top of page

First time sailing in Chicago? Here’s what to bring on your charter!

Updated: Mar 12

Are you ready to take your first yacht charter in Chicago? Whether you’re embarking on a romantic getaway or an exciting adventure with family and friends, there are certain essentials you need to bring along. Before you set sail on your Chicago sailboat charter, make sure to check out this list of must-haves for your first yacht charter.


When choosing what to wear on your first yacht charter, you’ll want to dress for the season. In the summertime, lighter clothing such as shorts, T-shirts, and tank tops are great choices. To layer up, pack sweaters or jackets if the weather is cooler. For cooler weather, you’ll want to bring warmer items like sweaters, long pants, and waterproof coats. Hats and gloves can also be helpful in colder temperatures. You may want to bring a throw blanket for added warmth. If you plan to host an event onboard, dressier or formal clothing could be appropriate. No matter what type of clothing you choose, make sure it is comfortable for the duration of your charter.


Regarding shoes for a yacht charter, comfort and practicality should be your priority. This doesn’t mean you have to forgo style – make sure that whatever you choose suits the activities you plan on doing.

For daytime activities, sandals or water shoes are best. They should have a good grip and be comfortable to wear. Ensure that your sandals have straps or other fastenings to stay secure when walking on the boat.

Boat shoes, dress sandals, or loafers are great at night. You can wear these if you’re attending formal events or just going out for dinner. They’ll keep you safe while also looking fashionable.

No matter what type of footwear you choose, bring several pairs so you have plenty of options. You can switch them up depending on the activity and weather conditions.


When packing accessories for your first yacht charter in Chicago, there are a few items you will want to remember. Sunscreen and hats are essential, especially if you plan to spend time out on the deck of your yacht. Also, don’t forget sunglasses, bandanas, and a lightweight waterproof jacket. Additionally, you’ll want to bring binoculars to appreciate the beauty of the Windy City from the deck of your yacht. These essential accessories will help make your first yacht charter in Chicago an unforgettable experience.

Other useful accessories include lip balm, bug spray, aloe vera, wet wipes, medications, and insect repellent. Bringing a few biodegradable wet wipes or paper towels to clean up without leaving any waste behind is also helpful. With all these accessories packed, you’ll be ready to embark on your adventure!


When it comes to electronics, there are a few important items you’ll want to bring with you on your charter. Cell phones and chargers are essential for staying in touch and taking pictures of beautiful views. It’s also a good idea to bring a camera and charger, memory cards, and extra batteries so you won’t miss out on any memories. A power bank is also great for charging multiple devices at once.

Our sailing charter boat has Bluetooth speakers for music, so sit back and relax while sailing around the city. Lastly, don’t forget to pack any other electronic accessories you may need, like an e-reader or headphones.

Final Thoughts

At Windy City Sailing, we strive to provide a one-of-a-kind experience when sailing in Chicago. Whether you’re looking for a romantic evening on the water or an adventurous day exploring Lake Michigan, our team is here to ensure your time on the water is safe, enjoyable, and unforgettable.

When you book your charter with us, bring all the items mentioned in this blog post. We guarantee that with the proper preparation, your yacht charter will be an amazing experience you’ll never forget!

2 views0 comments
bottom of page