Luxury Lake Michigan Water Activities Near Waukegan, Illinois

Bella is presented as one of the operator's highly sought-after Italian yachts, available for three- to six-hour charters during the week and slightly longer weekend windows. The vessel is staged for social outings—bachelorette and bachelor parties, birthdays, corporate events and private celebrations—and accommodates up to 13 guests. Onboard amenities called out by the operator include a spacious sundeck, swim platform, two refrigerators and an ice chest, a full kitchen and a state-of-the-art Sonos sound system that lets you run a playlist from your phone.

The listing is explicit about what the boat meets and what guests should expect: the yacht complies with USCG safety requirements and holds the necessary permits and insurance. Operators note that a captain's fee is separate and paid directly to the captain, and that gratuity is not included. Practical items to bring are towels, sunscreen, food and drinks (alcohol is allowed) and music devices for Bluetooth hookup.

The 62' Azimut 'Checkmate' is positioned for four- to six-hour charters and shares the same operator framing as other Italian motor yachts in this collection: roomy sundeck seating, swim platform access, multiple refrigeration options and a powerful Bluetooth-enabled sound system. The operator markets this yacht for celebratory gatherings and skyline cruises, and points to the ability to enjoy coastline or river cruising by day or night.

As with the other motor-yacht listings, the operator clarifies inclusions and exclusions: the yacht meets USCG safety standards and carries required permits and insurance, while a captain is not supplied by the operator under USCG regulations—customers may provide their own captain or choose from a vetted list. Guests should expect to arrange captain payment separately and bring towels, sunscreen and provisions.

This four-hour Sail & Swim Playpen Charter operates from Navy Pier Marina aboard a well-maintained 37' luxury sailing yacht. The operator emphasizes an all-inclusive feel: a USCG-certified captain trained in First Aid and CPR is in command, complimentary snacks and beverages are supplied, and the boat carries a fridge with ice. Guests can swim and float at the Playpen or other anchorage areas using life jackets, noodles, a Lillypad, pool floaties and towels provided by the operator.

The listing is pitched toward social groups—bachelor/bachelorette parties and birthday celebrations—with space for up to 7 or 12 guests depending on configuration. The operator notes weather-cancellation policies, a participant waiver requirement, and mobility considerations for boarding. Catering and additional alcohol can be arranged for an added fee by contacting the operator.

The Rose Marie is a 47' Carver characterized by a modern, sporty hardtop and a balance of fast cruising and onboard comfort. According to the operator, this model can cruise at 24 knots and reach speeds up to 30 knots—attributes that suit guests who want to cover more water quickly while retaining generous accommodation for the vessel's size.

Onboard amenities outlined by the operator mirror those on other motor-yacht listings: full kitchen, two bathrooms, a Sonos Bluetooth audio system and refrigeration with coolers. The operator reiterates USCG compliance and required permits, and notes that captains are provided via a vetted list or supplied by guests; captain fees and gratuities are handled separately from the listed charter fee.

Pier Pressure shares the Carver platform's comfortable accommodation and entertaining orientation: a full kitchen, two bathrooms, refrigeration and a Bluetooth-enabled sound system. The operator highlights the model's blend of comfortable cruising and onboard social space—useful for small parties that want to mix lounging, skyline viewing and stops to swim.

As with other private motor-yacht offerings, the operator confirms required USCG safety compliance and insurance, and notes that a captain's fee and gratuity are separate. Guests should plan to bring towels, sunscreen and their own food and drink if they prefer to BYOB, although operators often provide guidance for catering or larger supplies.

The Navy Pier Fireworks Cruise is a three-hour private outing aboard the S/V Dragonfly, a 37' luxury sailing yacht. The operator positions this as an all-inclusive sunset experience with a USCG-certified captain, complimentary ice, drinks and snacks or a BYO option. The cruise sets a course on Lake Michigan designed to frame the skyline at dusk and to deliver an up-close view of the Navy Pier fireworks display on scheduled nights.

The operator notes standard weather-cancellation terms and that small groups can enjoy onboard music and relaxed seating while taking photographs of the illuminated skyline. This cruise is designed for special evenings—birthdays, anniversaries and intimate celebrations—where the fireworks display becomes the centerpiece of the outing.