From venue selection to activity scheduling, everything you need to plan a successful retreat for 100+ employees.
Planning a corporate retreat for 100+ employees is complex, but Toronto offers exceptional infrastructure and experiences for large groups. After managing dozens of major retreats, here's our comprehensive guide to success.
12-Month Planning Timeline
12 Months Before
Define objectives: What should participants gain from this retreat? Team connection? Skills training? Strategic alignment? Clear goals drive all subsequent decisions.
Set budget: Large retreats typically cost $200-500 per person per day, depending on accommodation, activities, and meals.
Choose dates: Consider fiscal calendars, busy seasons, other corporate events, and Toronto weather. May-June and September-October offer the best weather with moderate hotel rates.
Form planning committee: Include representatives from different departments and levels. Large retreats require diverse perspectives.
9 Months Before
Select venue: For 100+ people, consider:
- Hotels: Marriott Eaton Centre, Fairmont Royal York, Sheraton Centre hold large groups with meeting space
- Conference centres: Metro Toronto Convention Centre for major events
- University venues: U of T and Ryerson offer summer availability
- Unique spaces: Evergreen Brick Works, Steam Whistle Brewing
Book accommodation: Block rates require early booking. Negotiate free rooms (typically 1 per 25), complimentary meeting space, and AV equipment.
Hire team building provider: Quality providers get booked 6-9 months ahead for large groups and preferred dates.
6 Months Before
Plan transportation: If attendees are traveling to Toronto, negotiate hotel shuttle services from Pearson Airport. For local transportation, consider charter buses between venues.
Schedule activities: Balance types: some high-energy, some reflective, some skill-building. Don't overschedule - downtime matters.
Arrange meals: Large groups need confirmed reservations or private dining. Plan for dietary restrictions (assume 20% of your group).
Send save-the-date: Give employees time to arrange personal schedules, especially if travel is required.
3 Months Before
Finalize schedule: Hour-by-hour agenda including buffer time for transitions.
Send invitations: Include schedule overview, what to bring, dress code, accommodation details, and transportation arrangements.
Confirm all vendors: Venues, activities, catering, AV, transportation.
Plan contingencies: Weather backups, virtual participation options for last-minute absences.
1 Month Before
Finalize headcount: Lock numbers with all vendors.
Prepare materials: Name tags, schedules, welcome packets, team building supplies.
Brief leadership: Ensure executives know their roles, speaking times, and transitions.
Create communication plan: How will you make announcements, handle changes, and address issues during the event?
1 Week Before
Confirm all details: Call every vendor to verify timing, setup, and special requests.
Prepare contingency plans: Have backup activities and contact information for key vendors.
Brief staff: Ensure your team knows the full schedule and their responsibilities.
Activity Selection for Large Groups
Large group activities require different considerations than small team events:
Scalable Activities
City Hunt: Teams of 5-8 explore different Toronto neighbourhoods simultaneously. Scales to 200+ easily.
Olympic-style competitions: Rotating stations keep everyone active. Works for 50-300 people.
Large group workshops: With proper facilitation and breakout groups, workshops work for 100+.
Activities to Avoid for Large Groups
Cooking classes: Maximum 40 people in most kitchen venues
Escape rooms: Require many simultaneous bookings and complex logistics
Activities requiring close attention: Anything where people can't hear or see facilitators well
Budget Planning
Sample budget for 150 people, 2-day retreat:
Accommodation: $175/night x 150 = $26,250
Meeting space: Often complimentary with room block
Team building activities: $75/person x 150 = $11,250
Meals:
- 2 breakfasts: $25 x 150 x 2 = $7,500
- 2 lunches: $35 x 150 x 2 = $10,500
- 1 dinner: $75 x 150 = $11,250
Transportation: $3,000 for charter buses
AV and technology: $2,500
Miscellaneous: $2,000 (signage, materials, gifts)
Total: $74,250 ($248 per person)
This is moderate-tier. Luxury retreats can reach $500+/person, while budget-conscious events can hit $150/person with strategic choices.
Common Challenges and Solutions
Challenge: Diverse interests and abilities
Different employees want different experiences. The marathon runner and the retiree approaching team building differently.
Solution: Offer options. During activity time, provide 2-3 choices ranging from high-energy to low-key. Everyone finds something appealing.
Challenge: Remote participants
Some employees can't attend in person due to location, health, or personal circumstances.
Solution: Decide whether to include remote participation or make it in-person only. Hybrid events are challenging but possible with proper planning. If including remote workers, use platforms like Zoom and design activities that work for both audiences. Assign "virtual ambassadors" to ensure remote voices are heard.
Challenge: Weather in Toronto
Toronto weather is unpredictable, especially in spring and fall.
Solution: Always have indoor backup plans for outdoor activities. Book flexible venues that allow last-minute changes. Communicate backup plans in advance so participants aren't surprised.
Challenge: Alcohol expectations
Some teams expect alcohol at retreats, others prefer alcohol-free events. You'll struggle to satisfy everyone.
Solution: Make alcohol available but not central. Offer it at one dinner but not all meals. Ensure equally appealing non-alcoholic options. Never pressure anyone to drink.
Challenge: Introverts and extroverts
Large group events can overwhelm introverts while failing to energize extroverts enough.
Solution: Balance group activities with downtime. Schedule free time where attendance is optional. Vary activity types so introverts get quiet reflection time and extroverts get high-energy engagement.
Measuring Success
How do you know if your retreat worked? Track these metrics:
Participation rates: What percentage of invitees attended? High rates suggest good planning and buy-in.
Survey responses: Send post-event surveys asking about specific elements. Use a mix of rating scales and open feedback.
Observed engagement: Did people participate actively? Stay for optional activities? Continue conversations during free time?
Follow-up behavior: Do you see improved collaboration between departments in the months after? Do people reference retreat experiences in meetings?
Executive feedback: What did leadership observe about energy, engagement, and conversations?
Toronto-Specific Advantages
Toronto offers unique benefits for large retreats:
Hotel capacity: Major downtown hotels can accommodate 100-300 people with meeting space.
Transportation: UP Express provides fast airport access. Downtown is walkable. TTC handles large groups.
Diverse activities: From urban adventures to waterfront experiences to cultural attractions.
Food scene: Can accommodate any dietary restriction and budget level.
Professional services: Toronto has experienced event coordinators, AV companies, and team building providers accustomed to large corporate groups.
Sample 2-Day Schedule (150 people)
Day 1
8:00 AM - Registration and breakfast (hotel)
9:00 AM - Welcome and objectives (general session)
10:00 AM - Department breakout sessions
12:00 PM - Lunch
1:30 PM - City Hunt team building (various Toronto locations)
4:00 PM - Return to hotel, free time
6:30 PM - Group dinner at Steam Whistle Brewery
8:30 PM - Optional: Drinks and networking (hotel bar)
Day 2
8:00 AM - Breakfast
9:00 AM - Strategic planning session (general session)
10:30 AM - Break
11:00 AM - Innovation workshops (breakout groups)
12:30 PM - Lunch
2:00 PM - Final session: Key takeaways and next steps
3:30 PM - Closing remarks
4:00 PM - Depart
Final Tips
Communicate constantly: Over-communicate before, during, and after the event.
Build in buffer time: Everything takes longer with large groups.
Have on-site support: Assign staff members to handle real-time issues so you can focus on big picture.
Celebrate small wins: Acknowledge great participation, creative ideas, and positive energy throughout.
Collect content: Photos, videos, and quotes for internal communications afterward.
Plan follow-up: How will you maintain momentum from the retreat? Schedule follow-up meetings or activities.
Ready to Plan?
Large corporate retreats require significant planning but deliver tremendous value. Toronto provides the perfect backdrop with infrastructure to support groups of any size.
