Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

Privately explore the captivating allure of Lake Michigan aboard the DRUID, showcasing the magnificent Chicago skyline on a personalized 2-hour sailing charter.

Discover the captivating allure of Lake Michigan with a private sailing charter that showcases the magnificent Chicago skyline. Aboard the DRUID, you’ll embark on a personalized 2-hour cruise guided by a seasoned US Coast Guard licensed captain. As you bask in the stunning panoramas, you can enjoy your favorite tunes through the vessel’s Bluetooth speakers, creating an unforgettable experience. This intimate adventure promises a stress-free outing, leaving you eager to uncover more about the exclusive details and policies that govern this enchanting excursion.

This experience made our article of 3 Top-Rated Chicago Sailing Experiences.

Overview and Details

Offering a private Lake Michigan sailing charter and sightseeing cruise of the Chicago skyline, this activity provides an opportunity for guests to enjoy the city’s iconic waterfront views from the comfort of a sailboat.

Departing from the Come Sailing dock, the 2-hour experience takes place aboard the DRUID, a vessel captained by a US Coast Guard licensed professional.

With a 5.0 rating from 2 reviews, the charter includes use of Bluetooth speakers, all taxes, and a lowest price guarantee.

Parking and gratuities are also provided, making this a comprehensive sightseeing package.

Inclusions and Prohibited Items

The private Lake Michigan sailing charter and sightseeing cruise comes with several inclusions to enhance the experience.

Passengers can enjoy the use of Bluetooth speakers to play their own music. The charter also includes a professional US Coast Guard licensed captain, as well as all applicable taxes.

Food, drinks, and parking are provided, and gratuities are included.

However, certain items are prohibited, such as animals, glass containers, weapons, and smoking.

Passengers must also be mindful of their behavior and consumption of alcohol, as inappropriate conduct may result in early termination of the charter without refund.

COVID-19 Policies

As the ongoing COVID-19 pandemic remains a concern, the private Lake Michigan sailing charter and sightseeing cruise adheres to several health and safety protocols. Guests are asked to self-diagnose their health status before boarding and stay home if feeling unwell. Masks are optional for both passengers and crew, and social distancing is at the discretion of guests. The charter allows guests to bring their own beverages, but cleaning fees may apply for excessive spills. Restroom access is minimized, with only one person allowed in the cabin at a time.

| Health Guidelines | Food and Beverage | Restroom Access |

| — | — | — |

| Self-diagnose health status before boarding | Bring own beverages; limited cooler space | Minimize time below deck |

| Stay home if feeling unwell | Clean up spills; cleaning fees may apply | One person at a time in the cabin |

| Masks optional for passengers and crew | | Use public restrooms on shore if possible |

| Social distancing at passenger discretion | | |

| | | |

Customer Conduct and Behavior

What can guests expect in terms of customer conduct and behavior during the private Lake Michigan sailing charter and sightseeing cruise?

Appropriate behavior is required at all times. Inappropriate conduct may result in the early termination of the charter without refund.

Reasonable amounts of alcohol are permitted within Illinois state law. If seasick, guests should remain on deck, as cleaning fees may apply for vomiting below deck.

The captain reserves the right to cancel the charter for weather, mechanical failure, or safety concerns.

Boarding implies consent to be filmed or photographed for promotional purposes without financial compensation.

Booking and Cancellation Policies

Reservations may be canceled due to incorrect pricing or availability.

To avoid disappointment, double-check all details when booking. Late arrivals may result in a shortened charter without refund, so plan accordingly.

The captain reserves the right to cancel for weather, mechanical failure, or safety concerns, but rescheduling options are available.

By boarding, guests consent to being filmed or photographed for promotional purposes without financial compensation.

  • Booking Errors

  • Late Arrivals

  • Termination of Charter

  • Consent to Filming

Charter Experience

A private charter aboard the DRUID on Lake Michigan promises an unforgettable experience. Guests can sit back and relax as the professional US Coast Guard licensed captain navigates the serene waters, offering stunning views of the Chicago skyline. The charter includes the use of Bluetooth speakers, allowing passengers to create their own ambiance. To ensure a comfortable journey, the boat features a small restroom and limited cooler space for bringing beverages. Whether seeking a leisurely sightseeing cruise or a chance to experience the joy of sailing, this private charter delivers an exceptional adventure.

| Highlights | Details |

| — | — |

| Intimate Experience | Private charter for your group |

| Stunning Skyline Views | Panoramic vistas of the Chicago skyline |

| Music Onboard | Bluetooth speakers for personal playlists |

| Onboard Facilities | Small restroom and limited cooler space |

| Professional Captain | US Coast Guard licensed skipper |

Scenic Sightseeing

As the DRUID glides across the tranquil waters of Lake Michigan, passengers are treated to a mesmerizing panorama of the iconic Chicago skyline.

The sweeping vistas showcase:

  • The soaring skyscrapers of the Loop, including the renowned Willis Tower and Aon Center

  • Navy Pier’s vibrant ferris wheel and lively entertainment

  • The sleek, modern architecture of Millennium Park and the Cloud Gate sculpture

  • The historic grandeur of the Adler Planetarium and Field Museum along the shoreline

This serene sailing experience offers an unparalleled opportunity to soak in the breathtaking sights of the Windy City from a unique vantage point on the lake.

Preparation and Attire

To fully enjoy the sailing charter and Chicago skyline cruise, guests are encouraged to dress comfortably and prepare accordingly.

Wear lightweight, breathable fabrics that can withstand potential wind and sun exposure. Bring a light jacket or sweater in case of cooler temperatures on the water. Comfortable, non-slip shoes are recommended for stability on the boat.

Sun protection, such as sunglasses and sunscreen, is highly advised. Plus, stay hydrated by bringing a reusable water bottle.

The Sum Up

The Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise offers a unique and memorable way to experience the city’s stunning waterfront. With a professional captain, Bluetooth speakers, and stunning panoramas, this intimate 2-hour adventure is the perfect escape from the bustling streets. Guests can relax, soak in the views, and create lasting memories on the serene waters of Lake Michigan.

📍 This experience made our list of the 3 best Sailing Experiences in Chicago