Context Travel

We were founded in 2003 in Rome by Paul Bennett and Lani Bevacqua. We connect travelers with scholars and specialists who lead private and small group walking tours, online learning, audio guides, and lectures. Our goal is to offer deep cultural and educational experiences, taking travelers beyond typical attractions to truly understand a city’s history and culture.

Over 80% of our guides hold MA or PhD-level degrees, and we work in more than 60 cities across six continents. We’ve led over 250,000 tours since we started. We’ve been a Certified B Corp since 2011 and are committed to sustainable tourism.

Our mission is to take travelers off the usual tourist path and into the genuine life, history, and culture of cities. We believe travel is an education, made richer through real interaction and conversation.

Curiosity and a passion for sharing knowledge are central to what we do. As a Certified B Corp, we understand that travel should benefit a place. We strive to connect people with different times, places, and cultures.

We have between 51-200 employees. Our work environment is remote-first and global, attracting lifelong learners passionate about travel and people.

We foster a supportive, mission-driven culture that values communication, empathy, and delivering excellent experiences. Our team includes scholars, specialists, and curious travelers. We encourage growth and cross-regional teamwork, with support from in-person team gatherings and an annual company retreat.

• Flexible PTO (minimum two weeks annually), including parental leave.
• Health, dental, vision, and life insurance with employer contributions.
• An annual stipend for learning and wellness to support personal and professional development.
• A one-time tech stipend.
• Free access to our digital lectures, audio guides, and small group tours, plus one free private tour each year.
• Discount code for friends and family.
• An annual company retreat for team connection.