How to Plan a 50-Person International Company Offsite Without Owning Every Detail
Outbuild brought 50 team members to Costa Rica for a company offsite at ONDA Playa Grande. The CEO had the vision, but the planning challenge was real: flights, rooms, meals, excursions, updates, and onsite changes for a distributed team.
If you are the Chief of Staff, People lead, Executive Assistant, marketing lead, or “get it done” person tasked with planning a company offsite, the venue is only one part of the job. The harder part is making the trip feel organized, intentional, and low-stress for everyone else.
Outbuild’s offsite worked because the internal planner did not have to become a one-person travel agency, hotel manager, meal planner, activity scout, shuttle dispatcher, and crisis desk. ONDA carried the local operating layer so the internal team could keep the retreat aligned with leadership’s goals.
Read the full Outbuild case study.
Pain point 1: “Where do I even start?”
“Getting all 50-plus team members to one location on a specific date, coordinating flights and everything–there were so many logistics.”
– Laura, Outbuild
Large group travel gets complicated quickly. The planning list usually includes flights, passports, room assignments, meals, dietary needs, excursions, internal updates, budgets, and leadership expectations. If those pieces are not organized early, the planner becomes the bottleneck for everyone.
For Outbuild, the planning process became manageable because the work was broken into clear steps: flights, rooms, excursions, meals, and team communication. That structure gave the internal team confidence that nothing major was floating loose.
Pain point 2: “What happens when plans change onsite?”
“They’ve been on top of any last-minute hurdles, any room changes, any flight situations, all shuttle coordination from the airports for team members that might have missed a flight or had flights canceled.”
– Laura, Outbuild
Offsites do not need everything to go perfectly. They need a team ready to respond when something changes. Flights get delayed, rooms change, people need help, and schedules move.
The difference is whether every issue lands on the internal planner, or whether there is an onsite team already close enough to solve it. For Outbuild, ONDA acted as the local support layer during the retreat, not just the venue booked months earlier.
Pain point 3: “How do I balance the CEO’s vision with what the team needs?”
“I was basically the face behind the retreat, speaking on behalf of Franco. I think it’s important to stay organized, to stay focused on the end goal, and to make sure you know what you’re looking to achieve.”
– Laura, Outbuild
Most internal planners sit between leadership’s goals and the team’s lived experience. The CEO may want alignment, momentum, and a culture-defining event. The team needs the trip to feel smooth, useful, comfortable, and worth the travel.
That is why planning a company offsite is not just logistics. It is translation. The planner has to turn a leadership vision into meals, rooms, activities, meeting time, downtime, and communication that actually works for the people attending.
Pain point 4: “I have planned the Airbnb version before. I do not want to do that again.”
“I helped plan our sales kickoff in January, and that was a little bit more intense because I was booking our Airbnbs, coordinating all the meals, and being more hands-on with the logistics.”
– Laura, Outbuild
A DIY retreat can look cheaper at first because the lodging line item is easier to understand. But the real cost shows up in the planner’s time and stress: sourcing houses, coordinating meals, handling local vendors, managing arrivals, fixing problems, and staying available for every small question.
The ONDA model gives companies a more complete operating lane. The internal team still shapes the goals and preferences, but it is not left to build the whole event from scratch in a destination it may not know.
Pain point 5: “How do I create something local and memorable if I do not know the destination?”
“We wanted to go on a waterfall hike. What’s the best waterfall hike that we could go on when we have 50 people on a retreat?”
– Laura, Outbuild
Great retreats are not built from generic top-ten lists. A group of 50 people needs activities that are memorable, realistic, safe, and logistically sound. The best option for two travelers may be the wrong option for a company group with a schedule, transportation needs, and different comfort levels.
Local knowledge matters because it turns a generic destination into a retreat that feels specific. For Outbuild, that meant local activities, meals, vendor support, and group experiences that fit the size and purpose of the trip.
A practical planning checklist
For a 50-person international offsite, the planning owner should clarify these early:
- Business goal: alignment, celebration, onboarding, strategy, relationship-building, or all-hands reset
- Group profile: headcount, team geography, languages, travel comfort, dietary needs, and accessibility needs
- Dates: preferred dates, backup dates, travel windows, and blackout periods
- Work needs: meeting space, breakout space, AV, Wi-Fi, privacy, and agenda rhythm
- Lodging: rooming preferences, leadership rooms, shared/private room mix, and arrival patterns
- Meals: number of shared meals, dietary requirements, snacks, drinks, and special dinners
- Activities: adventure level, optionality, local experiences, downtime, and weather backup
- Transportation: airport arrivals, group shuttles, late arrivals, missed flights, and offsite movements
- Communication: internal updates, attendee instructions, leadership updates, onsite point person, and emergency channel
- Budget: lodging, food and beverage, activities, transportation, taxes, tips, contingency, and payment timing
What ONDA changes for the planner
ONDA is useful when the internal planner needs one coordinated lane for the retreat instead of a set of disconnected vendors. The team still gets a custom-feeling event, but the internal owner is not left coordinating every local detail alone.
For Outbuild, that meant the planner could stay focused on internal communication, leadership alignment, and attendee readiness while ONDA helped with the destination, property, local logistics, meals, activities, and onsite support.
FAQ
Who usually owns company offsite planning?
It depends on the company, but the role often lands with a Chief of Staff, People lead, Executive Assistant, operations lead, marketing lead, or founder’s right hand. The person may not be a full-time event planner, which makes the right operating partner more important.
What is the hardest part of planning an international company offsite?
The hardest part is usually coordination across many small details: travel, rooms, meals, activities, local vendors, internal updates, and onsite changes. The challenge is not any one task. It is keeping all of them moving at once.
Why not just book a large Airbnb?
A large Airbnb may solve lodging, but it usually does not solve meals, local activities, transportation, onsite support, room changes, or vendor coordination. For a 50-person group, those missing pieces become the planner’s workload.
How early should a team start planning?
For a large international offsite, start as early as possible once dates and rough headcount are known. Early planning gives the team better control over rooms, flights, activities, meal planning, and budget.
Planning a company offsite?
ONDA hosts corporate offsites at ONDA-operated boutique hotels in Costa Rica and Panama. For beach-based Costa Rica offsites, teams use ONDA Playa Grande for private lodging, coworking, shared meals, group activities, and local support from inquiry through arrival.
Use the offsite cost calculator, read the CEO-objection version of Outbuild’s story, explore ONDA corporate offsites, or read the Outbuild case study.