Your Guides & Hosts

Whether it is in Chile, Argentina, Japan, or Canada, we look forward to hosting you on your DreamSki Adventure and sharing with you our passions of skiing, teaching, and travel.

We are grateful to have the opportunity to live and share our passions in the intimate format DreamSki Adventures provides. We pride ourselves on our professionalism and organisation, our love of working with people, and supporting you in having an adventure of a lifetime. We truly love what we do and have a lot of fun doing it!

We are all professional Canadian certified ski instructors (CSIA) with a minimum Level 3 certification or Canadian certified snowboard instructors (CASI). This means we have achieved a high level of mastery in skiing/snowboarding and in ski/snowboard instruction such that we are qualified to train and certify other ski & snowboard instructors. This requires extensive training and experience and takes years to attain.

Therefore we have the proven personalities and skills, and the experience to manage groups very effectively and o ffer you the help or challenge you desire, all within a fun and exciting environment.

Your guides play a big part in the quality of a tour and we are fortunate to have some of the best.

GERRY WINCHESTER , Founder & Lead Guide
Santiago - Chile
Skier (CSIA 3, CSCF 2, CSIA 1 Course Conductor, CSIA 4 Course 2002, 2003, 2004)
Languages: English, Spanish
Gerry Winchester

Gerry is originally from Alberta, home of the Canadian Rockies. He has been involved in the ski industry for over 15 years as an instructor and guide and full time for 10 of those, since leaving his career as a professional engineer. He taught for the renowned Club Ski in Banff, where he was selected “Rookie of the Year” and went on to become their senior instructor and instructor trainer, and conducted CSIA instructor certification courses. He also taught several seasons for the prestigious Fairmont Banff Springs Snow School.

During this time Gerry began travelling to South America, starting in 2001, in search of endless winter. He has since traveled and skied extensively throughout Chile and Argentina, founding DreamSki Adventures in 2004, and now calls Santiago, Chile home. He currently spends his time conducting tours all year round in Chile, Argentina, Japan and Canada. He is passionate about providing people the opportunity to experience unique skiing and culture throughout the world in a fun and intimate manner.

“I could not recommend the trip highly enough. As soon as we met Gerry in the reception area we knew it would be good. He has a very warm and very professional manner that made me and everybody else feel safe all trip.”
- Monica Bigg, Australia

San Martín de Los Andes – Argentina
Skier  (CSIA 3, CSCF 2, CSIA 4 Course 2006)
Languages: Spanish, English
Jesse Randall
Ski or esquiar, he does them both; referring to the fact growing up in Argentina Jesse had the best of two worlds with his mother being Argentine and his father Canadian. He loves the freedom of the mountains and the sport induced adrenalin skiing provides. To pursue this passion he spent seven years traveling back and forth from the Canadian Rockies to the Argentine Andes to be on the snow year round and surrounded by the mountains.

Jesse began his instructing career in Banff, Canada earning his Canadian Instructor and Instructor Trainer qualifications while teaching 6 seasons for Banff’s renowned Club Ski. He has also trained the Canadian military in both alpine and backcountry skiing, coached racing in Argentina, and trained teenagers in freestyle skiing. He now bases himself in his home country of Argentina where during the summers he runs his own off-road motorcycle touring business in Patagonia.

Jesse leads our Argentina tours and having grown up at the ski areas he is your ideal host and guide.

“Jesse was fantastic and made the whole experience really special. He went out of his way to make sure that everything was looked after for us. We are really grateful for all his help. It was so nice to have such great tour guide-instructor who really just blended in as part of the group.”
- Jennie Mead, England

Banff, Alberta – Canada
Skier (CSIA 3, CSCF 1, CSIA 1 Course Conductor, CSIA 4 Course 2009)
Languages: English, Spanish
Charlie Valentine
Charlie is originally from London, England where he graduated University with majors in Economics and Spanish before spending a few years as a successful estate agent in the London market.  He then made the decision to pursue his passions of skiing, travelling and language. He lived in Spain for 2 years, travelled extensively throughout South America, Australia, Southeast Asia, the Himalayas and Nepal, then he headed for Argentina where he began his ski teaching career.  This has since taken him to New Zealand, Chile, Argentina and currently Sunshine Village in Banff for the past 6 seasons as a senior instructor and course conductor for Instructor Certification Courses .  His current life philosophy is “ski”.  So he does just that year round and loves sharing his experience and passion for skiing with others.

“Charlie absolutely made the holiday for everyone.  Perfect blend of professionalism and fun – fantastic instructor and lovely guy.  Wouldn’t have been the same without him!”
- Clare Coulter, England

Vancouver, British Columbia – Canada
Skier (CSIA 4, CSCF 2, CSIA 2 Course Conductor)
Languages: French, English, Spanish
Jonathan has been very passionate about skiing since a young age and found a way to ski often and inexpensively by becoming a ski instructor at the age of 16. Since then, he has taught for more than 10 seasons across North America from Quebec where he grew up, to Vancouver where he now lives. His summers have been all about skiing as well, having taught in New Zealand and Argentina, and coached a race team in Chile. He started his career, as a part time instructor while in school and has turned it into a full time profession. He conducts Instructor Certification course for the CSIA and currently works at Red Mountain, British Columbia training individuals to become ski instructors.
Jonathan has lived and traveled extensively throughout Argentina and Chile for two years before joining DreamSki Adventures and brings this knowledge along with his enthusiastic manner to every tour. He really loves to teach and see his guests exceed their expectations while enjoying skiing as much as he does.

“Jonathan is a very observant and happy individual. He helped me a lot with my skiing and is a great guy to have around. Very much enjoyed his company.”
- Gojko Trifunovic, England


Calgary, Alberta – Canada
Snowboarder & Skier (CASI 2, CSIA 1)
Languages: English, Spanish, Polish
Jared grew up next door to the Canadian Rockies and has been sharing his love for snowboarding as an instructor for over a decade. He began his teaching career at 16 as a junior instructor at Fortress Mountain in Kananaskis country, a little powder haven on the way to Banff. He went on to attend the University of Calgary and received his degree as a school teacher with a minor in Spanish. All the while he was teaching at Canada Olympic Park and continued to for 9 seasons. During his time there, he became a staff supervisor and was responsible for the training of other snowboard instructors, receiving the staff-voted award "Coordinator of the Year".
When not on snow, Jared practices his profession as international primary school teacher. He spent the last two years teaching in the Dominican Republic, immersing himself in the Spanish language and living Latin-American culture. He brings this experience, combined with his love of teaching and his easy going manner to provide you with a great time on and off snow.

Jared is currently residing in Wrocław, Poland teaching and tackling the Polish language for the next couple of years.

“ You found an excellent boarding instructor-guide in Jared. We both really enjoyed being on the mountain with him, as well as learning a lot from him. He helped us all improve and tackle slopes which would have been daunting before.”
- Paul Beard, England


SUE DUNFORD, Assistant Guide
Perth, Australia
Skier (British BASI 3, Australian APSI 1)
Languages: English, Italian, Spanish, Thai
Sue is originally from England but has made the world her home for the last 20+ years as an avid traveller and skier. She began skiing at 18 and started living around the world after University with her professional career as a Chartered Surveyor, working in the UK, Australia and Thailand on large construction projects. Then in 1996 she decided to pursue a career in tourism within the ski industry in order to combine her passion for skiing and helping people. She has since worked as a Resort Representative and Resort Manager in Canada, Spain and Italy, and taught skiing in Australia. Her last four years have been spent in the Italian Dolomites looking after her own guests, guiding and providing a holiday experience with a very personal touch.
Sue explored Chile and Argentina extensively in 2011 and discovered that the skiing, the people and the culture had a special warmness and magic for her. Therefore she decided to make South America her new summer destination and joined DreamSki Adventures in order to share the ski experience with others.

Her easy going manner, warmness and clever wit have made her a client favourite where ever she has been and we look forward to having her as our first female guide in South America to bring her perspective and keep the guys in line!

MAMIKO KAWONA, Assistant Guide
Banff, Alberta – Canada
Skier (CSIA 3, CSCF 1)
Languages: Japanese, English
Mamiko was born and raised in Japan. She immigrated to Canada in the mid 90’s so she could ski full time. She spent 5 years in Whistler-Blackcomb guiding Japanese tourists and began obtaining her ski instructor qualifications. She then moved to Banff in 1998 to pursue her ski instructing career with her husband, also an instructor. She joined Banff’s well known Club Ski ski school and taught there for many seasons before joining her current ski school, the prestigious Fairmont Banff Springs Snow School, all the while raising two daughters. IN th e summer she is a Tour Guide in Banff leading Japanese interpretive tours.
Mamiko is known for her enthusiasm and cheerfulness, always smiling. She will be your invaluable translator and cultural expert to take you inside the country and the culture on our Japan Tours.


Edmonton, Alberta – Canada
Skier (CSIA 3, CSCF 2, CSIA 1 Course Conductor, CSIA 4 Course 2007)
Languages: English
Craig has done everything in skiing from competing in national mogul competitions to ski patrolling as a result of growing up in Calgary, Alberta, an hour from Banff. He has been teaching skiing and training instructors for the past 10 years and has received “Rookie of the Year” and “Ski Pro of the Year” honors during that time. He is now the Director of Instructor Training for one of the largest ski schools in western Canada, Rabbit Hill Ski Resort.
When not skiing, Craig is an engineer and senior manager with an international chemical company. He is the most positive and enthusiastic person you will ever ski with!

“Craig made the trip as the ski host with the most, keeping everyone upbeat and handling everyone very well. Under his coaching my skiing really advanced.”
- Bridget Walker, England
JULIÁN PÉREZ de CAMINO, Assistant Guide
Canmore, Alberta – Canada
Skier & Snowboarder (CSIA 3, CASI 2, CSCF 1, Diploma from Escuela Española de Esquí)
Languages: Spanish, English
Julián is originally from Spain and has lived in Canada for the past 14 years. He has been teaching skiing since 1988 in Spain, Andorra, USA, Chile and Canada. He currently is a senior ski instructor at Sunshine Village in Banff and also runs his own guiding company touring Spaniards throughout the Canadian Rockies in both winter and summer. Julián has made a life career out of skiing and teaching and loves it more each day. He enjoys working with people and taking them places they may not get to on their own. He is a passionate guy who loves to ski all day and “socialize” all night and can do it day after day with the best of them!

“I could not recommend the trip highly enough. As soon as we met Gerry in the reception area we knew it would be good. He has a very warm and very professional manner that made me and everybody else feel safe all trip.”

- Monica Bigg, Australia