Our Work · Private celebration · Chianti · September 2026
A 60th birthday celebration in Chianti
Four days in Tuscany, 25 friends and family travelling from around the world, and a year of planning behind them.
For this 60th birthday celebration in September 2026, the host wanted a relaxed gathering where guests could spend time together and choose how to enjoy their days. Alessia Piperno worked directly with him over the course of a year, organising the accommodation, activities, meals and guest arrangements before joining everyone in Chianti for the celebration.
A year of planning together
The programme developed through regular conversations with the client: where everyone would stay, which experiences would suit the group and when to bring all the guests together.
Alessia researched and coordinated the suppliers, managed bookings and followed up on the details as plans took shape. She also handled changes to guest numbers, accommodation arrangements and activity bookings, including cancellations and the related payment adjustments.
By the time the weekend arrived, she knew the plans and the people behind them.
A private villa and a countryside hotel
Guests stayed between a private villa and a nearby hotel. Alessia coordinated room allocations and reservations across both properties, alongside practical arrangements such as breakfasts and villa housekeeping.
The villa was the setting for the birthday gathering and a place for guests to spend time together between outings. Staying across two properties meant that each day’s meeting points and departure times needed to work for both groups.
Different ways to enjoy Tuscany
There was no expectation that everyone would follow the same itinerary. Alessia arranged a choice of activities, allowing guests to join the experiences that interested them.
The programme included Vespa rides through the Chianti hills, winery visits and wine tastings, an olive oil tour, cooking experiences and rafting. Guests could also go truffle hunting or horseback riding.
Making that choice possible meant coordinating several programmes at once. While one group headed out on Vespas, another joined an olive oil tour. Each needed clear directions, its own timings and arrangements for reaching the next shared meal.
Restaurant lunches, winery dinners and private dining brought everyone back together throughout the four days.
A direct connection with every guest
Alessia managed a WhatsApp group with all participants, sharing daily plans, locations, departure times and practical reminders.
Guests could ask her questions directly, whether they needed directions, clarification about an activity or help with their arrangements. Before outings, she shared the details that mattered: what to wear for rafting, where to meet for a tour and how much time to allow for the journey.
That communication continued throughout the stay, giving guests a familiar person to turn to and keeping the host from becoming the contact for every practical question.
The details that made it personal
The preparations also included personalised gifts: leather bookmarks with guests’ initials and commemorative leather trays made for the birthday.
Alessia coordinated these with the maker ahead of the celebration, alongside wine selections and dining arrangements. These smaller decisions were part of the same year-long planning process as the villa, hotel and activities.
On site, including when plans changed
Alessia was present throughout the celebration, coordinating suppliers, assisting guests and keeping track of the different schedules.
When a chef cancelled shortly before a private dinner, she found a replacement and arranged for the dinner to go ahead. Changes to bookings and guest numbers also needed attention, with suppliers updated and arrangements revised accordingly.
The person who had spent a year planning the celebration was there to see it through, with the knowledge and relationships to act when something needed resolving.
Related
Planning a birthday celebration in Tuscany?
Whether you imagine a villa gathering or several days of meals and activities, The Italian Chapter can help you organise the celebration and look after your guests throughout their stay.
You’ll work directly with Alessia on the plans, with on-site coordination to support you when everyone arrives.
Tell us about the occasion, your guest numbers and your preferred dates.