The best investment leaders can make? Time away from the everyday.

Leadership is a funny job. You spend most of your time making decisions, solving problems, answering questions and trying to make sure everyone else has what they need. Your calendar fills up quickly, your inbox never really goes away, and somehow there is always another meeting.

But when do you actually get time to think? Not react. Not firefight. Not jump from one call to another. Just think.

In my experience organising team trips and offsites at Laika, this is exactly what makes a good leadership retreat different from simply taking a team somewhere nice.

The location matters. But what happens because of the location matters much more.

When people step away from their usual desks, routines and job titles, conversations change. People have more time to challenge ideas, listen to each other and talk about the things that are difficult to fit into a normal working week. That is the real value of a leadership offsite.

And after organising team travel and experiencing some of these places with our own team and clients, these are five destinations I would genuinely put on the list.

1. The Dolomites, Italy: big mountains, better conversations

The Dolomites have a very useful effect on a group: they make everyone look up.

Instead of another conference room, you have mountains, hiking trails, alpine huts and long dinners where nobody is checking the time every five minutes.

We experienced this ourselves this spring, when we brought the Noxtua team to the Dolomites. One of the things I noticed was how quickly the atmosphere changed once people were outside. Conversations that might have felt formal in a meeting room became much more natural over dinner.

It was a great example of how much more can happen when an offsite has a proper experience around it rather than simply a meeting agenda. And yes, the Italian home food and wine definitely helped.

2. Costa Rica: when nature becomes part of the agenda

Costa Rica is probably not the first place that comes to mind when you think of a leadership meeting — and that is exactly what makes it interesting.

You can start the day in a cloud forest, explore volcanic landscapes, relax in natural hot springs or simply spend time surrounded by nature. And somewhere along the way, you often realise that the team is having just as many meaningful conversations while walking together as they would around a meeting table.

For me, that is one of the strongest arguments for taking a team somewhere completely different. You don’t need to turn every moment into a team-building exercise. Give people a great environment, enough time and something memorable to experience together, and the conversations tend to happen naturally.

I’m heading to Costa Rica in October to explore the country and find the best routes and experiences we can offer our Team Travel clients, stay tuned!

3. Madeira, Portugal: strategy with an ocean view

Madeira is one of those places where it is almost impossible to have a boring offsite.

There are levada walks through the mountains, volcanic landscapes, dramatic viewpoints and the Atlantic all around you. You can combine focused working sessions with hiking, boat trips or simply a long lunch somewhere with a view.

I particularly like destinations like Madeira for teams because you can build a programme around different energy levels. Not everyone wants to climb a mountain at 7am and they don’t have to.

A good offsite should give people space to participate, but also space to breathe.

4. Georgia: mountains, hospitality and the best food on the planet
Georgia is one of those destinations I keep coming back to, and I’ve now travelled there with teams five times. Every trip has reminded me why it works so well for group travel: it is easy to combine nature, culture, adventure and genuinely memorable food without making the programme feel overly organised.

You can spend a day exploring Tbilisi, head into the mountains, visit wineries in Kakheti or simply sit around a long Georgian table and let the evening unfold. And honestly, I would put Georgian food among the best in the world, the kind of cuisine that turns a team dinner into an experience people actually remember.

For me, that is one of Georgia’s biggest strengths. There is plenty to do, but you don’t have to fill every minute with activities. The hospitality, food and atmosphere naturally bring people together, which is exactly what you want from a team trip.

5. Pula, Croatia: strategy, sunshine and then jump in

For this one, I don’t have to imagine the experience, we did it with the Laika team.

Pula was one of those trips where the destination itself became part of the team experience. We had the Adriatic, historic streets, good food, boats and plenty of opportunities to get away from the laptop.

And Croatia works particularly well for team trips because you can mix very different things without spending hours travelling between them.

One day can include a workshop, exploring Pula and dinner together; the next can be spent on the water, swimming and discovering the coastline.

For me, that’s the sweet spot: enough structure to make the trip useful, but enough freedom for people to actually enjoy being together.

Why leadership teams should leave the office sometimes

After organising team trips for Laika and our clients, I’ve learned that the destination is only part of the story. What really changes the dynamic is taking people out of their usual environment and giving them time to connect without rushing from one meeting to the next.

I’ve seen some of the best conversations happen while walking through a new city, travelling together or sitting around a dinner table, often when nobody planned them. That’s what makes a team trip worthwhile: creating the space to reconnect, exchange ideas and come back with a fresh perspective.

Planning your next team trip? Let’s talk. I can take care of the logistics and create an experience your team will actually remember.