DIONYSIOS CHAIKALIS
Athens,Greece
Summary
Freelance Tour Leader and Mountain Leader, specializing in hiking and biking tours. Passionate about providing authentic, safe, and unforgettable experiences across Greece and beyond. Dedicated to offering high-quality guiding services tailored to individual and group needs.
Overview
8
8
years of professional experience
Work History
Tour Guide
DuVine
04.2025 - Current
- Guided premium bike tours, blending luxury hospitality with active exploration of landscapes and cultures.
- Ensured seamless daily operations, including coordinating van support and maintaining high-end bike equipment.
- Delivered personalized guest service, adapting itineraries and activities to group interests and fitness levels.
- Shared in-depth knowledge of Greek cuisine, wine, and history to create rich, memorable guest experiences.
Tour Guide
Boat Bike Tours
04.2024 - Current
- Led multi-day tours combining boat and bike experiences across Greek islands and mainland.
- Managed daily logistics, collaborating with boat crews and local partners to ensure smooth guest experiences.
- Provided mechanical support and bike repairs during rides, ensuring guest safety and satisfaction.
- Delivered cultural insights and local storytelling to enrich guest connection with each region.
Mountain Leader
TrailPath & Self-Organised
09.2023 - Current
- Guided groups on various hiking trails, focusing on safety, education, and client engagement.
- Organized and executed custom outdoor adventures tailored to clients' skill levels and interests.
- Ensured adherence to safety protocols while promoting environmental conservation practices.
- Delivered informative and engaging narratives about local history, flora, and fauna.
Tour Guide & Product Manager |
Inselhuepfen & Cycle Expeditions Greece
04.2022 - 03.2024
- Designed and led multi-day biking and hiking tours across Greece, ensuring a memorable experience for international visitors.
- Managed logistics, including route planning, equipment coordination, and group dynamics.
- Trained and supervised new guides to maintain high service standards.
- Developed new tour products, incorporating customer feedback and market trends to drive business growth.
Sales Director and Customer Service
Pavlidis Iordanis O.E.
02.2019 - 03.2021
- Directed sales strategies and managed a team to achieve revenue targets.
- Built and maintained strong customer relationships, resolving complaints and ensuring satisfaction.
- Analyzed market trends to identify growth opportunities and adjusted business plans accordingly.
Sales Representative
We Marketing
02.2017 - 03.2018
- Promoted and sold products through direct marketing campaigns, consistently meeting sales targets.
- Developed persuasive pitches and maintained a customer-focused approach.
- Collaborated with the team to plan and execute marketing strategies.
Sales Representative
Factory Outlet
04.2017 - 01.2018
- Assisted customers in selecting products, offering tailored recommendations to enhance their shopping experience.
- Managed inventory and maintained visual merchandising standards.
- Contributed to achieving monthly sales goals by employing effective upselling techniques.
Education
Professional Certification - International Mountain Leading (IML)
UIMLA
03-2026
Certificate - Professional Skills Development For Tour Guides
National And Kapodistrian University of Athens
09-2025
Certificate - Children's Rights
National And Kapodistrian University of Athens
07-2025
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
Certifiacte of Participation - Explore Around Myanmar
AIESEC
09-2019
High School Diploma -
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
Professional Trainings & Workshops
Islandhopping, DuVine, Cycle Expeditions (2022–2025)
- Advanced bike mechanics, on-tour troubleshooting, guest safety & group management
- Conflict management, team leadership, communication & storytelling techniques
- Use of guiding apps (RWGPS, guest reports), logistics planning & operations
- Archaeological site interpretation, mini-presentations & cultural briefings
- Regular First Aid certification & emergency response workshops
- Role-playing in real-case scenarios, slideshow creation, public speaking and mentoring
Additional Information
I enjoy spending my free time in nature, engaging in physical activities such as calisthenics, biking, running, hiking, mountain climbing, and football.
I strongly believe in the importance of volunteering and have participated in activities including tree planting initiatives, blood donations, summer fire patrols, and streetwork outreach through Emfasis Foundation and other organizations.
Languages
English
Bilingual or Proficient (C2)
Greek
Bilingual or Proficient (C2)
Timeline
Tour Guide
DuVine
04.2025 - Current
Tour Guide
Boat Bike Tours
04.2024 - Current
Mountain Leader
TrailPath & Self-Organised
09.2023 - Current
Tour Guide & Product Manager |
Inselhuepfen & Cycle Expeditions Greece
04.2022 - 03.2024
Sales Director and Customer Service
Pavlidis Iordanis O.E.
02.2019 - 03.2021
Sales Representative
Factory Outlet
04.2017 - 01.2018
Sales Representative
We Marketing
02.2017 - 03.2018
Professional Certification - International Mountain Leading (IML)
UIMLA
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+
Certifiacte of Participation - Explore Around Myanmar
AIESEC
High School Diploma -
Arsakeio Tositseio Ekalis Lyceum
International Diploma - IT Skills
Cambridge University