Team-Building Activities in Italy: Choosing the Right Experiences for Your Group

For many of my clients, a pleasant experience together is enough. They want colleagues to relax, talk and enjoy the destination without every activity becoming a competition or a structured exercise.

A cooking class gives people something to do together. A guided walk creates opportunities for conversations beyond the meeting room. A creative workshop introduces something unfamiliar, with no expectation that anyone should already be good at it.

If your brief involves a specific organisational challenge, such as conflict resolution or leadership development, that calls for a different approach and potentially a specialist facilitator. The experiences described here focus on shared enjoyment, local discovery and time together.

The balance also changes with the purpose of the trip. A retreat with substantial meeting time needs activities that fit around the working day. An incentive programme can give more space to exploring and celebrating.

I like the experiences to have a connection with the place where the group is staying. The food, landscape and local expertise should help shape the retreat.

Here are some examples of programmes I have organised.

The Langhe: wine, chocolate and quieter moments

For a group of 22 guests travelling from London, I organised a five-day programme in the Langhe.

The experiences included Barolo tastings, a hazelnut and chocolate workshop, a cacao ceremony, Tibetan singing bowls and meditation in the hills.

The programme brought together regional food and wine with quieter activities, giving the group different ways to spend time together during the stay.

Rome: culture, creativity and shared evenings

For a group of 45 guests travelling from the United States, I organised a four-day programme in Rome, with hotel accommodation and a coworking space.

Alongside the working sessions, the programme included a guided Colosseum visit, an escape room, a street-food tour, a painting class with wine, dinner at a Michelin-starred restaurant and an aperitif cruise on the Tiber.

In a city programme, timing and distances deserve particular attention. The experience needs to fit comfortably around meetings, meals and the journey back to the hotel.

Sicily: Etna, local flavours and time on the water

For 25 guests visiting from the United States, I organised a three-day programme in Sicily.

Activities included trekking on Etna, an Etna wine tasting, a boat trip, a Sicilian cannoli class and a workshop focused on Modica chocolate.

Modica chocolate has a distinctive granular texture associated with its low-temperature production process. A workshop offers a way to explore that local tradition through participation.

When combining experiences in different parts of Sicily, the location of the accommodation and the travel time between activities are essential to the planning.

Lake Como: an incentive programme with time to work

For a Canadian group of 14 guests, I organised a three-day incentive programme around Lake Como.

The programme combined boat trips, visits to lakeside villages, wine and cheese tastings and a visit to Varese, alongside coworking facilities and meeting rooms.

An incentive trip can still include time for work. The programme needs to give both parts enough space.

An activity that works beautifully for 12 people may need a different format for 50.

For street-food tours involving more than 50 guests, I recommend dividing the group into smaller groups. Otherwise, queues become longer, people struggle to hear the guide and the experience can feel scattered.

For cooking classes, I generally recommend smaller groups once attendance exceeds around 20 people. This is my planning preference rather than a fixed venue limit: I want guests to have space to prepare, ask questions and participate.

Depending on the venue and programme, we can arrange parallel sessions or offer different activities before bringing everyone back together for a meal.

Keeping the whole team together is valuable at selected moments. It does not mean everyone needs to do the same thing throughout the retreat.

My recommendation is to plan no more than one main organised activity per day, alongside meals and working sessions.

For a four-day retreat, the programme might include two half-day experiences and one full day out, with the remaining time available for meetings, arrivals, departures and rest. When work takes priority, shorter morning or evening sessions can replace the half-day activities.

A full-day excursion should be given the day it needs. There is little value in returning everyone to the hotel tired and immediately sending them out for another scheduled experience.

Allow time to change, answer messages, use the hotel facilities or simply sit with colleagues. Those unscheduled conversations are part of the stay, too.

An activity is one part of a larger event. Its timing needs to work with meetings, transfers, meals and the rest of the group’s plans.

With The Italian Chapter, I remain your main point of contact throughout the planning and the event. I coordinate the selected providers, communicate the group’s requirements and make sure each experience fits into the overall schedule.

That includes checking practical details, arranging transport, organising smaller groups where appropriate and planning alternatives for weather-dependent activities.

If something changes, you have one person to contact who understands the programme. I remain available in real time during the event and can also be present on site when requested, with on-site attendance quoted separately.

The intention is to give the person organising the retreat the opportunity to take part and spend time with their colleagues.