Luxury Boat Charters Near Glencoe, Illinois — Private Yachts & Cruises

Bella is presented as one of the fleet’s sexiest Italian yachts, configured to host up to 13 guests for 3–6 hour charters. The listing emphasizes social use—bachelorette and bachelor parties, birthdays, corporate outings—and highlights waterfront swimming and skyline cruising as common itineraries. Onboard amenities include two refrigerators, an ice chest, a full kitchen, two bathrooms, and a state-of-the-art Sonos sound system for music while underway or at anchor.

Operational details stress safety and compliance: the vessel meets U.S. Coast Guard safety requirements and carries required permits and insurance. Captains are arranged separately: per operator notes, you may provide your own certified captain or choose from a vetted list. Practical guest guidance includes towel and sunscreen recommendations and confirmation that alcohol is allowed aboard, while captain fees and gratuity are not included in the base charter.

The 62' Azimut Checkmate shares a similar brief with other Italian yachts in this collection: roomy sunbathing areas up front, a swim platform, and conveniences intended to keep food and drink cold during multi-hour charters. Operators list two refrigerators, a full kitchen, and a Sonos-equipped sound system among the on-board amenities—features that make long afternoon or evening cruises comfortable for groups up to 13.

Like comparable private charters, captains and gratuities are handled separately from the vessel hire. The Azimut’s configuration lends itself to celebrations and photo-ready skyline passages; operators note evening cruises that time the skyline glow and occasional fireworks over Navy Pier as highlights for guests who book night runs.

The 51' Sea Ray Sundancer is described as a versatile choice for groups that want creature comforts on the water: two bedrooms, two bathrooms, a large foredeck capable of seating the whole group, and an interior dining and lounge area. Its equipment list includes a sizeable refrigerator and freezer and a four-person inflatable raft kept for swim stops, a practical inclusion for families and mixed-age groups planning to anchor and play.

Included in the charter are a captain, life jackets, and a cooler; the operator also offers advice on what to bring—towels, sunscreen, a change of clothes—and cautions against red wine or other dark mixers that could stain upholstery. The Sea Ray’s combination of shaded cockpit seating and below-deck accommodations makes longer 6–8 hour excursions more comfortable for guests who may want to freshen up or nap between swim breaks.

This four-hour Sail & Swim Playpen Charter departs from Navy Pier Marina and centers on a relaxed sailing experience with a certified USCG captain. The operator supplies complimentary snacks and beverages, a fridge with ice, and basic flotation gear—life jackets, noodles, a Lillypad, and pool floaties—so guests can anchor at the Playpen and swim with minimal fuss.

Groups choose this offering for its straightforward, all-inclusive feel: a trained captain, basic refreshments, and a maintained 37' yacht that emphasizes ease over party theatrics. The operator notes accessibility considerations and participant waivers; weather-related cancellations are handled with full refunds when necessary, and children under 18 must be accompanied by a guardian.

The Chicago River Cruise frames the city as the destination: guests glide past architectural landmarks and the lively Riverwalk, enjoying patios and waterfront life from a unique vantage. The 44-foot platform described in operator notes includes a spacious cockpit, wet bar, air-conditioned salon, galley, private head with shower, premium sound system, and an expansive swim platform for water access.

This cruise suits travelers focused on cityscape photography and waterfront atmosphere rather than open-lake swimming. Meeting point details list Diversey Harbor as a harbor access; groups that prioritize architectural context and close-in river cruising will find this format best aligned with their objectives.

The Day Cruise on the 32' Larson Cabrio markets itself as a comfortable, amenity-rich dayboat: a cozy bedroom, full kitchen, bathroom, and two refrigerators. A captain is provided to handle navigation while guests relax in the salon or on deck. The operator notes the availability of floaties and a social layout suited to family groups or small gatherings.

Because the vessel includes cabin facilities, it’s a good option for trips that may extend into the evening or for guests who want the ability to change clothing or rest below deck. The listing stresses that space fills quickly due to demand and points to a central meeting point at North Cannon Drive for boarding.