TEDDY'S ITALY

Journey alongside Teddy McDonald and experience Italy beyond the expected. This is not a traditional tour, but a carefully curated travel experience shaped by aesthetic sensibility, cultural insight and quiet expertise. Teddy is less a guide and more a discerning companion — relaxed, thoughtful and well-informed — introducing you to boutique accommodation, authentic dining, and the subtle details that define Italian elegance.

Created for solo travellers, couples and small families, each experience weaves together iconic landmarks, hidden cultural treasures and refined culinary moments. For those drawn to seamless movement and variety, Teddy’s knowledge of Italy’s high-speed Frecciarossa allows for beautifully fluid travel between cities — breakfast in Milan, lunch in Florence, an evening in Rome.

Teddy accepts only a small number of clients each year, ensuring a discreet and highly personal experience. Alternatively, he may be commissioned to curate bespoke recommendations — from exceptional places to stay and dine to thoughtfully selected cultural experiences in Florence, Milan, Rome and their surrounding regions.

Whether joining a carefully planned itinerary at short notice or designing a future journey from the ground up, each experience is shaped with care and intention. For those willing to embrace the season, the winter months offer a particularly elegant perspective on Italy — fewer visitors, luminous blue skies and a quieter cultural rhythm, especially in Florence and Rome.

Teddy’s primary language is English, with a basic and constantly improving knowledge of Italian.

To discuss a refined Italian journey tailored exclusively to you, please tap below.