Step 3 of 3 · Planning Mode
Let's figure out what you're actually trying to accomplish before we start booking things.
No itinerary yet. First we agree on the shape of the thing.
What I Understand
You are planning a three-day company retreat for approximately 42 employees. The team is distributed across New York, Washington DC, Austin, Chicago, and San Francisco. Your goal is to rebuild connection after a year of rapid growth while giving leadership protected time to align around 2027 priorities.
Approve, edit, or reject each one
Assumptions I'm Making
If an assumption is wrong, everything built on top of it is wrong. Fix them here first.
Individual hotel rooms
No shared rooms; drives lodging cost to ~$27K.
Domestic travel only
No international attendees or visa lead time.
No partners or spouses
Headcount stays at 42 for food and transport.
Moderate activity level
Nothing requiring physical screening or waivers.
Roughly 60% structured / 40% social
Balanced agenda, not a conference.
Flights included in the $75K budget
This is the assumption I am least sure about.
Two nights, arrive Wednesday afternoon
Departures Friday late afternoon.
Missing information the plan depends on
Questions We Should Answer
You don't have to answer all of these today. You do have to know they exist.
- Does leadership need private working time before the full group arrives?
- Should employees have meaningful unstructured time, or is this a working retreat?
- Are there accessibility considerations you already know about?
- How much alcohol should be incorporated into social events?
- Does everyone need to attend every session?
- Is the $75,000 budget inclusive of airfare?
- How far are you willing to make people travel — is a connecting flight acceptable?
Before you spend a dollar
Risks I Already See
Employees are traveling from four time zones, so a 9:00 AM Day 1 session may not be realistic for West Coast attendees.
Your current budget works out to approximately $1,785 per attendee before contingency, which is workable but tight once airfare is included.
You're trying to accomplish both strategic planning and team bonding. The agenda will need to explicitly protect time for both or one will quietly eat the other.
Charlottesville has limited direct flight access from Austin and San Francisco; some attendees will connect through Charlotte or drive from Richmond.
Recommended Approach
Treat this as two events sharing one venue. Protect a half day of leadership working time before the full group arrives, then design the remaining two days around shared experience rather than presentations. Anchor the agenda on three decisions you need made, cap structured programming at five hours per day, and hold roughly $7,500 back as contingency until the venue and airfare are both committed.