Corporate Entertainment
Chicago Client Entertainment Yacht Charters
For sales leaders, managing directors, client relationship managers, and investor relations teams who need an unforgettable setting for their most important relationships. A private yacht on Lake Michigan is the one venue your clients have never been invited to before.
Client Entertainment Scenarios
Every charter is built around your objectives, guest list, and relationship goals. Here are four common configurations our corporate clients request.
Private Dinner Cruise for 8 VIP Clients
8 guests56ft yacht, skyline sunset route, sommelier with 5-wine pairing, professional photographer. 4 hours, DuSable Harbor departure.
Investor Day Reception for 30
30 guestsCatamaran with dual-deck capacity, passed hors d'oeuvres and open bar, branded welcome signage, jazz trio. 3 hours.
Prospect Entertainment During Conference Week
15 guestsExclusive-use vessel for 15, curated cocktail experience, skyline views for networking, photographer for social content. 3 hours.
Board Dinner for 12
12 guestsClassic yacht, private chef with custom menu, acoustic guitarist, after-dinner cognac service. 4 hours.
Recommended Formats and Group Sizes
We match vessel type, service style, and crew size to your guest count and entertainment objectives.
Intimate VIP
6-13 guests
Private yacht, seated dinner, curated wine or cocktail service, dedicated captain and steward. Ideal for key client dinners, prospect cultivation, and board entertainment where every detail matters.
Mid-size Reception
14-49 guests
Catamaran or larger yacht, cocktail-style service with multiple food and beverage stations, background music, and space for mingling across decks. Perfect for investor events, partner receptions, and client appreciation evenings.
Large Client Event
50-100+ guests
Multi-vessel coordination with unified catering, branding, and entertainment across the fleet. Suitable for annual client events, conference hospitality, and large-scale relationship programs.
Enhance the Experience
Layer on curated services to create a fully produced client entertainment experience. Every add-on is coordinated by our concierge team.
Dining & Beverage
Private chefs, sommelier pairings, custom menus
Learn morePhotography & Content
Professional photographers, drone footage, social content
Learn moreBrand Activations
Branded signage, custom decor, vessel wrapping
Learn moreMusic & Entertainment
Jazz trios, acoustic guitarists, DJs, live performers
Learn moreRepresentative Events
Anonymized examples of real client entertainment charters we have produced. Names and identifying details are omitted for confidentiality.
Annual Partnership Review Dinner
A wealth management firm hosted 20 clients for a sunset dinner cruise to celebrate their annual partnership review. The evening featured a private chef preparing a four-course meal, a sommelier guiding wine pairings, and a professional photographer capturing the skyline backdrop. Guests departed DuSable Harbor at golden hour and returned to a private dock reception.
Referral Partner Cocktail Reception
A law firm organized a private cocktail reception for 35 referral partners with passed hors d'oeuvres, a craft cocktail bar, branded welcome signage, and a live photographer. The catamaran cruised the lakefront while attorneys and partners networked across both decks, with a jazz duo providing ambient music.
Frequently Asked Questions
Common questions from corporate clients planning entertainment charters on Lake Michigan.
Request a Client Entertainment Proposal
Proposals are custom-built based on vessel, guest count, route, date, and service level. Most proposals are delivered within two business days.