Every time an HR director or COO first considers a corporate sailing offsite, they run into the same problem of choosing a format. A regatta sounds vivid, team building sounds safe, a strategy session sounds serious. All three do take place on the water, but they solve fundamentally different problems and call for a different level of team maturity, a different budget and a different level of operational readiness from the host.
Over seven years working with 247 teams we have arrived at a simple rule: the format of an offsite should follow the business goal, not the wish to do "something unusual". In this article we break down the three most-requested formats across four axes — goal, team composition, operational complexity and budget — and show how not to get the choice wrong.
Regatta: competitive energy and a visible result
A corporate regatta is a series of friendly races between 5 to 15 yachts, each crewed by a team of 6 to 8 employees. The format is ideal when you need to create the energy of a shared achievement: a financial-year kickoff, a company anniversary, entry into a new market, or merging two subsidiaries after an M&A.
The main strength of a regatta is that each day's result is visible: a scoreboard hangs at disembarkation, a short debrief runs in the evening, and every team has its own yacht and its own skipper. An employee who has never held a helm can, by day three, clearly explain the tactics of beating upwind — and that sense of competence carries back to the office.
“A regatta creates healthy competitiveness, not a toxic one: you compete with the elements, not with a colleague.”
When to choose a regatta
- A group of 30 to 80 people, which can be split into yachts of 6 to 8.
- You need to bring together several teams, departments or offices that have little live interaction.
- The company is ready for 3 to 4 days of programme — two race days, plus arrival and departure.
- There is a budget from €1,800 per person — the minimum acceptable bar for a quality format.
When a regatta does not fit
If your team is smaller than 15 people, a regatta loses its competitive edge — too few yachts for a meaningful scoreboard. If people have a strong fear of water or seasickness, a format that means a full day in the open sea becomes stressful. And finally, if the goal is deep work on culture or strategy, a regatta is too dynamic for it: you get the emotion but not the structured dialogue.
Team building: horizontal bonds and trust
Sailing team building is an intimate format on 1 to 3 yachts (12 to 24 participants), where the main goal is horizontal bonds within a single team. There is no competition: the yachts sail together, stop in the same bays and dine at a shared table. The programme is built around rotating roles — helm, trimmer, navigator — and a short reflection after each exercise.
This format works especially well for teams after a reorganisation, the arrival of a new leader, or fast growth — when a department has grown from 8 to 24 people in six months and people do not yet know one another. Sailing puts everyone on an equal footing: a company co-owner and an intern pull the same sheet, and that disrupts the office hierarchy in a single day.
When to choose team building
- A team of 10 to 24 people — one or two yachts, everyone dining together.
- The goal is to bring people closer, ease tension after a restructuring, or integrate new joiners.
- The team includes introverts for whom a regatta's dynamic would be too much.
- A budget from €1,400 per person.
Strategy session: depth and C-suite decisions
A strategy session on the water is the most specific of the three formats. It involves 8 to 14 participants — usually a leadership team or a board of directors — and focuses not on physical activity but on facilitated dialogue in an unfamiliar setting. The yacht here is not the object of an adventure but a backdrop that helps people step out of their usual context and think differently.
The daily rhythm of such a session is 6 hours of sailing plus one anchorage with a 4-hour strategy block run by a certified facilitator. The themes are setting annual goals, reviewing the failures of the past quarter, redistributing roles. Sailing adds an important layer: solving operational tasks together — setting sails, moving to anchor — creates a neutral context in which a CEO and a CFO can talk to one another without the usual office triggers.
“The most memorable offsite of recent years. Three days at sea changed the way the leadership team works.”
When to choose a strategy session
- A group of 6 to 14 people at C-suite or VP level.
- There is a clear strategic agenda — an annual plan, a repositioning, a conversation about values.
- The team is ready for long, difficult conversations.
- A budget from €3,200 per person — the format includes a facilitator and premium locations.
Decision matrix: which format for which goal
When we run a discovery call with a new client, we ask four questions in a strict order. These questions rule out unsuitable formats faster than any brochure.
- What result do you want to see in six months? If it is "people talk to each other differently" — team building. If it is "teams have got to know one another" — a regatta. If it is "we have a plan and we are executing it" — a strategy session.
- How many people are travelling? Fewer than 15 — a strategy session or team building. 15 to 40 — team building or a regatta. More than 40 — almost always a regatta.
- What is the team's level of readiness? A new team after a merger — team building. A mature leadership team — a strategy session. A large department that is fragmenting — a regatta.
- What is the per-person budget? Up to €1,600 — team building. €1,600 to €2,800 — a regatta. From €2,800 — a strategy session with a facilitator.
After those four questions the format is usually obvious. All that remains is to pick a location, a date and a participant list — but those are the technical details we help with.
What to keep in mind
An offsite format is not a question of fashion. A regatta, team building and a strategy session are three different tools, and the attempt to make a hybrid — "so everyone has fun and we discuss strategy at the same time" — almost always ends in a blurred result. It is better to run one focused format than to squeeze three goals into three days. If you are in doubt, start with team building for a group of 15 to 24 people: it is the most universal format and the fastest way to test how a team interacts on the water.
