Travel Designer & Bookings Assistant; Apprendistato

Position: Travel Designer & Bookings Assistant (Apprendistato contract)
About the Company

We’re a small, experienced team designing thoughtful, high-quality travel experiences for private clients. We work in a high-trust, collaborative way, giving people space to take ownership while always being available for guidance when needed. If you enjoy responsibility, asking good questions, acting with urgency, and learning through real experience — and you’re looking to build a long-term career in travel — you’ll feel at home here.

About the Role

We’re looking for a smart, self-motivated, and exceptionally detail-oriented Travel Design & Bookings Assistant  (Apprendistato contract)   to join our fully remote team. You’ll primarily work on bespoke Italy itineraries for private clients, while also supporting projects in the UK & Ireland, Spain & Portugal, France, and Greece at various stages. This role spans Travel Design and Bookings & Operations (you’ll focus on one at a time depending on seasonality).

A strong sense of urgency and responsiveness is essential in both parts of the role, particularly when communicating with clients and suppliers.

Responsibilities

Travel Design (Italy-Focused)
Design accurate, thoughtful, and highly curated Italy-based itineraries
Communicate directly with clients via email and phone, responding promptly and proactively
Show a natural flair for understanding clients, with innate curiosity to ask the right questions and uncover what truly matters to them
Tailor experiences to client interests, pace, and travel style
Treat clients with genuine care — as you would friends or family — while maintaining professionalism
Participate actively in the sales process and work towards targets

Bookings & Operations
Manage client relationships from booking confirmation to departure
Maintain a strong sense of urgency when responding to clients, suppliers, and time-sensitive situations
Book and reconfirm hotels, transfers, guides, tickets, and activities
Liaise with suppliers and manage relationships
Handle emergencies and last-minute changes calmly and efficiently
Perform meticulous itinerary checks (timings, meeting points, contacts)
Follow up on supplier invoices and liaise with accounts

Qualifications

C1 English (written & spoken)
C1/C2 Italian (written & spoken)

Required Skills

Smart, quick-thinking, and adaptable
Highly self-motivated — you take ownership naturally
Exceptionally detail-oriented, with zero tolerance for errors
Solution-oriented: you take initiative to assess situations, explore options, and implement solutions independently, escalating to your manager only when necessary
A strong communicator, able to express ideas clearly and confidently in both writing and conversation
Responsive and reliable, with a natural sense of urgency when dealing with clients
Comfortable picking up the phone and speaking with clients and suppliers
Naturally curious, with a strong instinct for understanding people
Client-focused, with a genuine desire to look after people properly
Calm under pressure and able to prioritise effectively
A team player who also works just as well independently
Tourism studies completed

Preferred Skills

Comfortable learning new systems:
Google Workspace, Zendesk, Airtable, and itinerary development software

Pay range and compensation package

Fully remote position
Company laptop, mobile phone, and SIM
Buoni pasto
Supportive, high-trust working environment
Annual team retreats
International clients and suppliers

Contract:

Apprendistato professionalizzante CCNL Turismo (3 years)
Under 30, or 30+ and receiving NASPI

Equal Opportunity Statement

We are committed to diversity and inclusivity.

How to Apply

Please send:
Your CV
A cover letter explaining why you’d be a great fit for this role and our company

Applications in English only.