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Selected Trips

    Simon Harry

    Enthusiastic | Spirited | Engaging

    Mini Bio

    I make a yearly pilgrimage to France to catch at least a few stages of le tour, and have actually managed to get my wife interested. I’m a qualified British cycling coach, mountain bike guide and currently help wee ones get into the racing scene through skills tuition and coaching.

    With my other hat on I work in the environmental education field helping deliver outdoor learning for organisations such as the forestry commission. Having taken a 2 year ‘Lets go to the other side of the world’ sabbatical with my wife to be, I headed to New Zealand to live out of a van to get to know the country – the results of which was that on my return I needed to live in a place that had mountains, open roads and a slower pace of life – The Highlands it was.

    Ten years later I have children with Highland accents, enjoy that slower pace of life and can actually do a passable ‘gay gordon’ at any ceilidh.

    Place to Play

    West coast cycling: it’s beautiful, lacks cars and has some fantastic cake & coffee shops.

    Not a lot of people know this

    I was in 2 episodes of Dr Who and 1 bond film, I have also fought the boxer Joe Bugner (it’s on film!).

    Adventurer's Stories about Simon

    Simon and Ben were excellent!

    Garmin were OK most of the time...screen a little hard to read with glare. My garmin shot down unexpectedly a few times while I was cycling.

    Joanne St-Coeur
    Road Cycling - The Five Countries Tour
    Reviewed on 10/06/2024

    SIMON & BEN WERE MORE THAN EXCELLENT…. THEY MADE OUR TRIP
    ( and I was not paid to say this)
    They said they had never worked together before and they made sure not to show it. They worked their A$&### off for us. Some of us were very demanding and they just pushed forward. Their support on the ride was always welcomed , be it van support for our breaks or encouragement on the ride. Their operation was clockwork, from the morning debrief , the ride support and hotel transfers. These two superb gentlemen provided us with as much info that they could for the day’s ride but also facts about the countries we were visiting. I would definitely hope that I would have them as my partners on my next tour with you. They were able in such a short period of time, to make us feel special as if we were part of their family.

    Andre Michaud
    Road Cycling - The Five Countries Tour
    Reviewed on 10/06/2024

    As I have already posted Simon and Ben went above and beyond. Also their individual knowledge of plants, animal, geology, geography and historical background was so much fun for me to learn about.

    Judith Pyle
    Road Cycling - The Five Countries Tour
    Reviewed on 07/06/2024

    As mentioned earlier, Scott and Simon were excellent!!! They were very knowledgeable about the local areas as well as the history. They were amazing bike riders and it helped them go back and forth to constantly be checking in on the other tour members. They were also helpful in making bike adjustments and repairs in a timely manner.

    Rahul Ravel
    Road Cycling - The Grand Tour
    Reviewed on 17/10/2023

    Scott and Simon were very friendly and personable. Their riding prowess and route knowledge was evident. Loved hearing about the routes and the corresponding history and facts.

    Lori Avis
    Road Cycling - The Grand Tour
    Reviewed on 06/10/2023

    Simon and Scott were outstanding guides. Very knowledgeable, attentive, and also very amusing.

    Jill Bobek
    Road Cycling - The Grand Tour
    Reviewed on 04/10/2023

    Simon and Scott were friendly, approachable, knowledgeable and warm. They kept the stories flowing every evening and are great fun. I felt safe with them as guides and they genuinely came across as people who are passionate about their jobs

    Yvonne Neubauer
    Road Cycling - The Grand Tour
    Reviewed on 03/10/2023

    Simon and q did an outstanding job looking after our needs/wants

    Stephen Chappell
    Road Cycling - Outer Hebrides
    Reviewed on 05/09/2023

    We were constantly looked after by our guides,..Simon stood out because he was always checking in, regardless of the time of day. The care was so appreciated by both Simon and Q.

    Pamela Millar
    Road Cycling - Outer Hebrides
    Reviewed on 04/09/2023

    Simon and Dan were the best guides I have ever had and I have ridden in guided tours to Croatia, Bosnia, Montenegro and Spain.

    Gregory Reeks
    Road Cycling - Outer Hebrides
    Reviewed on 08/08/2023

    Simon & Dan are rock stars!! Kind, generous, easy going, interesting, fun good people. Thank you so much to both of them for making this experience as memorable as it was.

    Jeff Faber
    Road Cycling - Outer Hebrides
    Reviewed on 03/08/2023

    Guides were prefect in every way. Simon and Dan went out of their way to be amazing perfect wonderful kind thoughtful helpful marvellous all week

    Samantha Barker
    Road Cycling - Outer Hebrides
    Reviewed on 24/07/2023

    Detailed previously. Very pleased with both caring, professional and often funny guides. Couldn't have dine better.

    Patricia Mulcahy
    Road Cycling - Outer Hebrides
    Reviewed on 24/07/2023

    I cannot say enough about our guides. Simon was kind, supportive, and thorough in setting expectations. He made sure we were always safe. Gave us realistic expectations for what was in store, and cheered me on when I thought I could go no further/higher. He even gave me one final push to help me crest the top of a particularly challenging ascent.
    Simon and Dan were knowledgeable about the areas we cycled through. History, customs, flora and fauna were shared. Really added to the experience.
    And Dan's cheese jokes cracked me up!

    Eve Barringer
    Road Cycling - The Grand Tour
    Reviewed on 31/05/2023

    Both Dan and Simon were great guides. I think they are super assets to the company and make the experience more safe and more fun. I appreciated their kindness, understanding, and lastly their encouragement during the ride. They were patient, empathetic, and genuine people to keep us company during the ride.

    James Faklis
    Road Cycling - The Grand Tour
    Reviewed on 26/05/2023

    Our guide Simon was great, he looked after our every need, he provided sustenance advice and encouragement . He was good company and knowledgeable.

    Peter Morrison
    Self Guided+ Cycling - The Outer Hebrides
    Reviewed on 02/05/2023

    Only feedback (and I let the guides know too) was on the last day riding, when we left the Kelpies after lunch, for the guide to INSIST we follow them leaving. They suggested it, but said if "we just follow our Garmins, we should be fine." I made the mistake of following another guest the wrong way before our guide left, which I figured out quickly. However, all my Garmin could tell me at that point was that I was off course and couldn't tell me how to get back on course. When my guide came back to get me, my Garmin was still confused and the route through the city was complicated... even had my Garmin not been confused, I likely would have made multiple wrong turns. I think it is critical this day for riders to follow the guide (after the kelpies) to ensure they do not end up lost.

    Melissa Reger
    Road Cycling - The Grand Tour
    Reviewed on 22/09/2022

    Simon and Craig were amazing!!! Excellent communication, organization of all the moving parts, as well as fun and informative!

    Julie Brundle
    Road Cycling - The Grand Tour
    Reviewed on 12/09/2022

    Guides were FABULOUS!!!!!

    Carolyn Hock
    Road Cycling - The Grand Tour
    Reviewed on 12/09/2022

    I could not recommend a single change in how our guides handled all the details from bike fitting to TLC to great cultural insights and concern for our trip being fun!!

    Lucia Howorth
    Road Cycling - The Grand Tour
    Reviewed on 06/09/2022

    They’re fantastic

    Tom Howorth
    Road Cycling - The Grand Tour
    Reviewed on 05/09/2022

    Simon and Cube were fantastic, didn't get lost once and they kept a close watch so we didn't miss stopping spots.

    Sande (Sandra) Mawhinney
    Road Cycling - The Grand Tour
    Reviewed on 25/07/2022

    Simon and Alistair were superb, especially as not all tour participants were inclined to group riding, making their jobs more difficult. They did an excellent job responding to the group needs and abilities and provided great detail on our context each day!

    Dan Hemme
    Road Cycling - The Grand Tour
    Reviewed on 18/07/2022

    Top notch. Great communication.

    Barbara Gasper
    Road Cycling - Arran, Islay & Jura
    Reviewed on 01/07/2022

    Paul and Simon were excellent. Felt very safe in their hands. Paul very knowledgeable and obviously had a love of the history of the OH. We couldn’t have been better cared for!!

    Marilyn (Becky) Ellis
    21WSTM Tailor Made trips
    Reviewed on 26/09/2021

    routes great, guides wonderful - incredibly knowledgeable and wonderful to work with.

    Susan Rees
    21WSTM Tailor Made trips
    Reviewed on 21/09/2021

    A great team. Simon and Paul were a good balance of information, support and personality.

    Sarah Rogers
    21WSTM Tailor Made trips
    Reviewed on 20/09/2021

    Both Simon and Paul were excellent. They were very knowledgeable about the islands - stopping to show us points of historical interest and also very informative about the fauna and flora. They guaged our biking speeds and were very aware of the groups different abilities and so adapted the days schedule. We very much enjoyed their company at dinner. Overall they did an excellent job in looking after us.

    Anne Treadwell
    21WSTM Tailor Made trips
    Reviewed on 18/09/2021

    Friendly and helpful and also seemed to enjoy working with new clients.

    David Pike
    Road Cycling - Outer Hebrides
    Reviewed on 06/09/2021

    Simon and Graham really made the trip for me. They were always positive and relaxed and dealt with everything efficiently but in a laid back manner. They were really superb :-)

    Nicky Richards
    Road Cycling - Outer Hebrides
    Reviewed on 06/09/2021

    Always fantastic as all other trips I've taken :)

    Amy McPherson
    Road Cycling - Outer Hebrides
    Reviewed on 06/09/2021

    Simon was excellent, providing on-route advice and mechanical assistance when needed. He was very knowledgeable about the areas we visited.

    Neil Symons
    Self Guided+ Cycling - North Coast 500
    Reviewed on 19/06/2021

    Simon was fab!

    Steve Brown
    20WSPD_Private Departure
    Reviewed on 05/10/2020

    Just superb. Knowledgeable, friendly, super attentive, enough without being too much. Just understood the group and what we needed.

    Nick Habgood
    20WSPD_Private Departure
    Reviewed on 30/09/2020

    Simon and Jono are excellent.

    Frank Bouley
    Mountain Biking - The Hebridean Trail
    Reviewed on 02/09/2019

    Is there something better than excellent? I have run out of words for telling Simon and Will how good they are as guides. I hope they know how much our group truly appreciates them and all their hard work. They are the benchmark that all professional guides should aspire to. It was their first time on this itinerary and we honestly couldn't even tell. Not even 60mph, falling trees and a bonafide hurricaine threw them - they just quietly made a plan B and it was amazing. They are delightful, thoughtful, intelligent gentlemen and we would be so lucky to travel with them again.

    Karen Dean
    Road Cycling - The Five Countries Tour
    Reviewed on 08/10/2018

    Simon and Will are simply the best guides we have ever experienced and we have cycled all over the world.

    Guy Dean
    Road Cycling - The Five Countries Tour
    Reviewed on 07/10/2018

    Will and Simon are very special to our group. They are part of it, not just our guides but also our friends. Only warm thoughts, big smiles and huge thanks from me.

    Donna Mosford
    Road Cycling - The Five Countries Tour
    Reviewed on 05/10/2018

    Simon and Will could not have done more for us- they thought of everything. When they found out about our Dublin room days later, they were horrified that we hadn't said anything.

    They not only looked after us, they gave us confidence that we could achieve the demands of the trip, and were good company throughout.

    Kerry Davey
    Road Cycling - The Five Countries Tour
    Reviewed on 03/10/2018

    I have never been on a tour with two better guides than Will and Simon. Their thoughtfulness, tirelessness and attention to detail is extraordinary.

    Joan Dean
    Road Cycling - The Five Countries Tour
    Reviewed on 24/09/2018

    Both guides were great. Not only guided us through the trip but added a lot regarding the history of the things we saw....and if they didn't know the found out and let us know. Junior guide did get us lost once, but he was very professional and really did a wonderful job.

    Joel Smith
    18WSPD_Private Departure
    Reviewed on 09/07/2018

    Simon was fantastic. Very good at assessing the needs of the group and adapting the plans. John was wonderful as well. A great team; they worked hard to make our experience an enjoyable one.

    Amy Madden
    18WSPD_Private Departure
    Reviewed on 02/07/2018

    Will and Simon were attentive, thoughtful, kind and informative throughout. They did a great job and were keen to share their insights and knowledge about the islands (especially the machair!)

    Penny Jose
    Road Cycling - Outer Hebrides
    Reviewed on 13/09/2017

    Great at responding to changes caused by cancelled ferries etc

    Karen Parry
    Road Cycling - Outer Hebrides
    Reviewed on 11/09/2017

    Responsive, flexible, friendly and knowledgeable. Both Will and Simon were a credit to Wilderness Scotland.

    Chris Jose
    Road Cycling - Outer Hebrides
    Reviewed on 11/09/2017

    Both Simon & Will were excellent. They provided enthusiasm, clarity & humour where needed whilst managing adversity in a truly professional manner

    James Harris
    Road Cycling - Outer Hebrides
    Reviewed on 11/09/2017

    Simon Harry and Will Snow were absolutely brilliant, they managed the different abilities and interests within the group and made everyone feel very well looked after. They adapted the sequence of rides to take account of poor weather and the cancellation of ferry services but discussed these proposed changes with the group. They were always there with a hot cup of coffee, a jelly baby and encouragement.

    Miles Murison
    Road Cycling - Outer Hebrides
    Reviewed on 11/09/2017

    My guides were Simon Harry and David O'Brian. Both of them worked extremely hard, but made it look effortless. There were many different personalities and they were kind and gracious to everyone. They were very well organized. In mid-morning or sometimes mid-afternoon, we stopped for a snack break, the coffee was good and the snack choices were abundant.

    Regina Daly
    Road Cycling - Outer Hebrides
    Reviewed on 22/08/2017

    Great

    Philip Ciniglio
    Road Cycling - Outer Hebrides
    Reviewed on 21/08/2017

    excellent

    Jane Sinclair
    Road Cycling - Outer Hebrides
    Reviewed on 18/08/2017

    Simon and David couldn't do enough for us.

    Caitriona Conway
    Road Cycling - Outer Hebrides
    Reviewed on 18/08/2017

    Simon and Dave were both so enthusiastic and accommodating and encouraging. They were an absolute pleasure and we couldn't have asked for better guides.

    Caroline Campbell
    Road Cycling - Outer Hebrides
    Reviewed on 17/08/2017

    Enthusiastic, engaging and eager to please ... Simon was born to do this job. David was a great support to Simon and to the team, always there with a smile and whatever you needed to keep you focused on the completion of the ride.

    Jennifer Gibson
    Road Cycling - Outer Hebrides
    Reviewed on 17/08/2017

    Will definitely tell friends to ask for Simon?

    Felicity Kerr
    17WSTM Tailor Made trips
    Reviewed on 01/07/2017

    Simon was a fabulous guide. The quick lesson he gave us on how to mountain bike safely, I used for the entire trip - made my downhills go much better, avoiding the "ballistic" method as much as possible. Appreciated his passion for the environment and his sharing of his stories and interests throughout the trip. It made for a much richer experience.

    Siri Bliesner
    17WSTM Tailor Made trips
    Reviewed on 01/07/2017

    Simon Harry was the BEST!! He was very flexible when we had changes in our plan. Total professional but fun. Knowledgeable and willing to share his thoughts and insights. Offered great options. Love him!!

    Kathy MacNeil
    17WSTM Tailor Made trips
    Reviewed on 02/06/2017

    Our guides were amazing. Thanks Will and Simon for taking such good care of us all. You guys were fountains of local knowledge, anticipated our every need and kept us well fuelled and motivated as we took on those undulating landscapes and occasional cross winds. You were also fun and funny. You were the icing on the (birthday) cake.

    Donna Mosford
    Road Cycling - Outer Hebrides
    Reviewed on 22/09/2016

    The guides went to great lengths to make sure every thing was perfect. The were fun, friendly, knowledgeable and well organized. In short, they were amazing.

    Joan Dean
    Road Cycling - Outer Hebrides
    Reviewed on 20/09/2016

    They were the best guides one could wish for. the attention to detail and their professionalism was beyond reproach.A quality tour company needs quality guides and you had two on this trip.

    Janet Bowers
    Road Cycling - Outer Hebrides
    Reviewed on 20/09/2016

    I have been on 9 bike tours with 5 different companies, and think that Will and Simon are easily the best guides I’ve ever had. They were kind, friendly, sincere, professional, and so on top of every detail throughout the trip – always anticipating every need or question. They were right there at every big hill or tricky turning offering support and my favourite quirky snacks (milk and green banana? OK!). Actually, I'm even going to give them props for helping me up hills on the next trip because their jelly babies saved me on the last bit of the Cairn O'Mount. Will and Simon went out of their way to be thoughtful and help everyone get the most out of their vacation – making snack fairy deliveries after a tough day of riding, helping me hunt down yarn, running us back up to the standing stones just because the light had changed (thanks Will!), and teaching us all sorts of things about Scotland and its people. You could tell that they are both natural teachers/coaches with a real love of people, which is truly admirable. I also need to give Simon a nod for the mad bike mechanic skills (way to whip out the putty and the tool roll on day one!). Both men were unsurpassed guides, but what’s more, they were also just really cool people on a human level – interesting, fun individuals with a passion for the outdoors, love of world travel, and care for the children of the world. It’s always a little sad when after a great week of travel everyone says their goodbyes and goes back to their respective lives, but this time I was more gutted than usual, and I think that speaks to the quality of our guides and our group. Well done fellas, and I hope we meet again!

    Karen Dean
    Road Cycling - Outer Hebrides
    Reviewed on 20/09/2016

    Fantastic and very knowledgeable.

    Yolandi Roos
    16WSTM Tailor Made trips
    Reviewed on 20/09/2016

    The best support, friendly approach, and attention to detail I've ever experienced on a guided tour, and I've done a few. Thanks Simon for sorting me out with a more suitable bike when I was going to persevere. These two men are surely the jewels in wilderness Scotland's crown? Honestly- cant fault them!!

    Kerry Davey
    Road Cycling - Outer Hebrides
    Reviewed on 15/09/2016

    Both were very informative and helpful. Simon in particular was outstanding (as noted in my previous comment)

    Lisa Dunn
    16WSPD_Private Departure
    Reviewed on 10/09/2016

    Simon was truly wonderful

    Jill Moretto
    16WSPD_Private Departure
    Reviewed on 10/09/2016

    If you would direct these comments to Will and Simon, it would be appreciated. Everyone thought they were wonderful. So helpful, both very knowledgeable and together they worked well as a team. The local information re history and geology was so interesting that either you might think of info sheets or a microphone system for the back seat of the van. The main comment is that both Will and Simon are people's people with an engaging personality. They have the most essential quality for a guide of managing all people on the trip equally and with respect.

    Peter Bath
    Road Cycling - Outer Hebrides
    Reviewed on 21/05/2016

    Both guides were absolutely fantastic. adaptable and able to keep multi level group in one piece.

    Merrill Varn
    Road Cycling - Outer Hebrides
    Reviewed on 17/05/2016

    Very impressed with Will and Simon. Great knowledge of all the places on the route and very attentive to all the details. They gave good advice and looked after everyone appropriately. Great fun as well.

    Jane Tapp
    Road Cycling - Outer Hebrides
    Reviewed on 12/05/2016

    See previous comments. Different personalities made for a fun and interesting trip. Good fun in the van. The guides highlighted life on the island from culture to the geography.

    David Bain
    Road Cycling - Outer Hebrides
    Reviewed on 10/05/2016

    Will and Simon were both fantastic- both came across as professional, experienced, and relaxed- and they worked really well together. They took everything in their stride and dealt extremely well with the challenging weather forcing changes in the planned itinerary. They went above and beyond to make things run smoothly & the trip enjoyable, and did so in a very unassuming way. They brought their own personalities to the trip and were fun people to spend a week with!

    Emma Louise McCarroll
    Road Cycling - Outer Hebrides
    Reviewed on 09/05/2016

    Book a trip with Simon

    Trip / DepartureAvailabilityStatusPriceBook
    Road Cycling – Outer Hebrides
    27th Jul - 2nd Aug 2024
    3 place(s) leftGuaranteed £2,795Book Now

    Make Trip Private

    Sometimes it's nice to get family and friends together and travel privately for some quality time. This means you benefit from all the features of the group departure, including hand-picked accommodation and expert local guides and we'll take care of it all. Then you can make your choice of departures dates and we'll get back to you to finalise the details.

    We work together with our team of guides to decide which departures they lead each year. As part of that, guides provide available dates that they are free to be booked. This means that any of the dates you see in the first field of the form below, could be perfect for your private departure or customised tour.

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    © Simon Harry / Wilderness Scotland

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