Corporate Team Events
Chicago Corporate Team Outings on the Water
For HR leaders, office managers, department heads, and chiefs of staff who want a standout team event without managing 15 vendors. One call to Playpen and the entire experience is handled -- vessel, food, drinks, entertainment, and activities.
Team Outing Scenarios
Whether it is a casual summer Friday or a seated milestone dinner, we build the outing around your team size, culture, and budget.
Summer Friday Outing for 40 Employees
40 guestsDual-deck catamaran, BBQ buffet, DJ with portable setup, water toys deployed at the Playpen. 4 hours.
Engineering Team Celebration for 15
15 guestsSport yacht, paddleboards and float mats, coolers with craft beer, afternoon swim stop. 4 hours.
New Hire Welcome for 25 Interns
25 guestsSkyline cruise with group photo, pizza and soft drinks, scavenger hunt activity, branded welcome kits. 3 hours.
Quarterly Milestone Celebration for 30
30 guestsPremium yacht, seated dinner with awards presentation, custom cake, sunset route. 4 hours.
Recommended Formats and Group Sizes
We scale the experience to your headcount. Small teams get an intimate yacht day; large companies get a coordinated fleet.
Department-size
10-30 guests
Single vessel, casual or semi-formal. Ideal for team lunches, department celebrations, and intimate offsites. Flexible vessel selection from sport yachts to classic cruisers based on your vibe and budget.
Company-wide
30-100 guests
Larger vessel or multi-vessel coordination. Suitable for summer company outings, all-hands celebrations, and cross-departmental events. Full catering, entertainment, and activity programming included.
Multi-vessel Flotilla
100+ guests
Coordinated fleet with unified programming, food and beverage, and entertainment across multiple vessels. Dedicated event coordinator ensures timing and service consistency for the entire group.
Make It Your Own
Add on activities, entertainment, and decor to create the perfect team experience. Every add-on is coordinated by Playpen so you do not have to manage extra vendors.
Water Toys
Paddleboards, float mats, inflatables, swim platforms
Learn moreMusic & Entertainment
DJs, live bands, curated playlists, karaoke
Learn morePhotography & Content
Group photos, event coverage, drone footage
Learn moreCelebrations & Decor
Custom cakes, balloons, banners, themed decorations
Learn moreRepresentative Events
Anonymized examples of real team outing charters we have produced. Names and identifying details are omitted.
SaaS Company Summer Outing
A SaaS company brought 45 employees to the lake for a summer afternoon with BBQ, music, and a swimming stop at the Playpen. The dual-deck catamaran featured a DJ on the upper deck, a taco bar on the main level, and paddleboards and float mats deployed during a 90-minute swim stop. Employees called it the best company event of the year.
Consulting Firm Partner Retreat
A consulting firm organized a partner retreat for 12 with a private chef dinner, team-building activity, and sunset views. The intimate yacht departed from the Chicago River, cruised the lakefront at golden hour, and returned after a four-course dinner paired with wines selected by the group in advance.
Frequently Asked Questions
Common questions from HR leaders and office managers planning corporate team outings.
Request a Team Outing Proposal
Tell us about your team, your preferred dates, and your budget. Most proposals are delivered within two business days.