Dionysios Chaikalis
Athens
Summary
Experienced Freelance Tour Leader and International Mountain Leader (UIMLA), specializing in hiking and cycling tours across Greece. I lead small-group active travel experiences with a strong focus on safety, cultural depth, and operational excellence. Bilingual in English and Greek, I combine strong communication skills with group leadership, guide mentoring, and tour development expertise to deliver consistently high guest satisfaction.
Overview
4
4
years of professional experience
Work History
Tour Guide
DuVine
04.2025 - Current
- Maintained exceptionally high guest satisfaction across all tours, reflecting strong communication, adaptability, and cultural insight.
- Coordinated daily logistics, van support, and high-end bike setup while adjusting itineraries to meet group needs.
- Delivered immersive experiences through storytelling, wine and cuisine education, and personalized guest engagement.
- Upheld DuVine’s premium service standards through attention to detail, discretion, and proactive problem-solving.
Mountain Leader
TrailPath & Self-Organised
09.2023 - Current
- Consistently achieved a 5/5 guest satisfaction rating by providing safe, engaging, and well-informed guided hiking experiences.
- Designed and delivered custom outdoor adventures tailored to clients' skill levels and interests, enhancing overall experience.
- Ensured adherence to safety protocols while promoting sustainable environmental conservation practices.
- Shared detailed and captivating narratives about local history, flora, and fauna, deepening client connection to the region.
Tour Guide
Boat Bike Tours / Inselhuepfen / Cycle Expeditions Greece
04.2022 - Current
- Led over 50 multi-day biking and hiking tours, delivering memorable and personalized experiences for international visitors of diverse ages and backgrounds.
- Achieved a 4.84/5 average guest rating for the 2025 season and recorded the highest proportion of guest feedback submissions across the company’s European operations.
- Trained and supported new guides during seasonal onboarding, contributing to improved consistency and service standards
- Managed operational adjustments including weather shifts, docking changes, and route modifications while maintaining guest confidence and tour flow.
- Coordinated embarkation, equipment setup, and daily briefings, ensuring clear communication between guests, crew, and operations teams.
Product Manager
Cycle Expeditions Greece
04.2022 - 03.2024
- Developed and refined multi-day biking and hiking itineraries, incorporating guest feedback, regional insights, and seasonal operational needs.
- Coordinated suppliers, accommodation partners, and transport providers to secure availability, quality, and cost-efficient tour components.
- Produced detailed route notes, operational manuals, and documentation used by guides to deliver consistent, high-quality experiences.
- Collaborated with cross-regional teams to align product standards, streamline workflows, and improve overall tour performance.
Education
International Mountain Leading (IML)
UIMLA
02-2026
Emergency First Aid & CPR/AED
American Red Cross
02-2026
Outdoor Ethics & Environmental Stewardship
Leave No Trace Center For Outdoor Ethics
01-2026
Wilderness First Aid (Advanced) & CPR/AED
Mountain Training Hellas (ECSI Authorized Training Center)
11-2025
Stop The Bleed
The U.S. Department of Defense (DoD)
11-2025
Certificate - Professional Skills Development For Tour Guides
National And Kapodistrian University of Athens
07-2025
Certificate - Children's Rights
National And Kapodistrian University of Athens
06-2025
Training Certification - Mountaineering
Hellenic Mountain Guides Association
11-2024
Certificate - Emergency First Aid & BLS – CPR/AED
Red Cross
03-2024
Certified By ANENA - Avalanche Search & Rescue Level 1
Hellenic Rescue Team
01-2024
Post-Secondary - Mountain Leading
Ekpaideutiki Enosi
09-2023
Bachelor of Science - Business Administration And Management
University of West Attica
Athens03-2023
Certificate of Attendance - Strategic Partnership In The Youth Field
Erasmus+
09-2022
Certificate of Participation - Explore Around Myanmar
AIESEC
09-2019
High School Diploma - undefined
Arsakeio Tositseio Ekalis Lyceum
08-2014
International Diploma - IT Skills
Cambridge University
09-2011
Skills
- Dependable team player
- Composed in high-pressure situations
- Effective communicator
- Versatile in fast-paced settings
- Local history
Languages
English: Bilingual or Proficient (C2)
Greek: Bilingual or Proficient (C2)
Timeline
Tour Guide
DuVine
04.2025 - Current
Mountain Leader
TrailPath & Self-Organised
09.2023 - Current
Tour Guide
Boat Bike Tours / Inselhuepfen / Cycle Expeditions Greece
04.2022 - Current
Product Manager
Cycle Expeditions Greece
04.2022 - 03.2024
Certificate - Professional Skills Development For Tour Guides
National And Kapodistrian University of Athens
Certificate - Children's Rights
National And Kapodistrian University of Athens
Training Certification - Mountaineering
Hellenic Mountain Guides Association
Certificate - Emergency First Aid & BLS – CPR/AED
Red Cross
Certified By ANENA - Avalanche Search & Rescue Level 1
Hellenic Rescue Team
Post-Secondary - Mountain Leading
Ekpaideutiki Enosi
Bachelor of Science - Business Administration And Management
University of West Attica
Certificate of Attendance - Strategic Partnership In The Youth Field
Erasmus+
Certificate of Participation - Explore Around Myanmar
AIESEC
High School Diploma - undefined
Arsakeio Tositseio Ekalis Lyceum
International Diploma - IT Skills
Cambridge University
International Mountain Leading (IML)
UIMLA
Emergency First Aid & CPR/AED
American Red Cross
Outdoor Ethics & Environmental Stewardship
Leave No Trace Center For Outdoor Ethics
Wilderness First Aid (Advanced) & CPR/AED
Mountain Training Hellas (ECSI Authorized Training Center)
Stop The Bleed
The U.S. Department of Defense (DoD)
Professional Trainings & Workshops
Islandhopping, DuVine, Cycle Expeditions (2022-2025)
• Advanced bike mechanics, on-tour troubleshooting, and safety leadership
• Conflict management and team communication techniques
• Guide applications (RWGPS, reporting systems) and logistics planning
• Archaeological interpretation and cultural presentation skills
• Ongoing First Aid renewals and emergency response workshops
• Scenario-based role playing, public speaking, and mentoring
Previous Professional Experience
Sales Director & Sales Representative Roles (2017-2021)
Pavlidis Iordanis O.E. | We Marketing | Factory Outlet
- Led sales operations and customer service management, achieving revenue targets and overseeing team performance.
- Built and maintained strong client relationships, handling negotiations and resolving complex customer issues.
- Developed persuasive communication strategies and consistently met performance goals in competitive environments.
Additional Information
Active outdoor lifestyle including hiking, mountain climbing, cycling, running, and calisthenics. Committed to community engagement through volunteer work including tree planting initiatives, blood donation drives, summer fire patrols, and street outreach with Emfasis Foundation.