WE DO WHAT OTHERS DON’T!

When you travel with visitingjamestown, you will notice that we do things differently, from the 1st pedal stroke down to the very last drop of wine. We call it “the twist”, that special something that provides our guests with unforgettable lifetime experiences.


Our collection of Cycling Tours are true holidays where you can focus on being in the present for every moment. Our itineraries understand the importance of downtime and peace.

We understand that booking a once in a lifetime adventure can be overwhelming. So, we are here to ensure you are comfortable with all the information you require before booking a tour with us.

Our tours cater to cyclists looking for a balanced, scenic, and culturally enriching adventure.

Additionally, most of our tours cater equally for non-riding partners who have their own daily itinerary planned with their own tour guide.

OUR FULLY SUPPORTED CYCLING TOURS ARE IDEAL FOR CYCLISTS WHO:

  • 1. ENJOY MEMORABLE RIDES

    Those who appreciate breathtaking landscapes and picturesque regions on roads less travelled, allowing you to immerse yourself amongst the culture and beauty of the land and its people.

  • 2. PREFER LEISURELY PACE

    Riders who are comfortable cycling for 3-5 hours at a moderate pace, rather than racing or engaging in high-intensity riding.

  • 3. LIKE GROUP ACTIVITIES

    Cyclists who enjoy the camaraderie and support of riding in a group, sharing the experience, and celebrating achievements together.

  • 4. ENJOY UNIQUE LUXURY ACCOMMODATION

    Thoughtfully selected incredible locations for downtime, rest and recovery.

  • 5. APPRECIATE GOOD FOOD & WINE

    Immerse yourself in the flavours of the region. Local cuisine, wine tasting in the vineyards…the list goes on!

  • 6. APPRECIATE LOCAL CULTURE

    Guests interested in exploring new areas and learning about local culture and customs both on and off the bike.

  • 7. LOVE ADVENTURE

    Those who seek a true cycling adventure with opportunities for both group riding on rolling terrain and individual efforts on challenging climbs.

  • 8. VALUE SAFETY & SUPPORT

    Riders who appreciate the safety and encouragement that comes with a supportive team atmosphere, ensuring everyone finishes the ride happy and safe.

  • PREFER EXPERT LOCAL GUIDES

    Our guides make magic happen, because they are showing you the special places they call home, you would otherwise not get to experience.

  • BELIEVE BIGGER ISN’T BETTER

    Large groups can't go where we go. There’s only so much place in a Nomad cave or a winemaker's private cellar, so our groups never exceed 16 guests.

  • ENJOY ENGAGING AND AUTHENTIC EXPERIENCES

    Both on and off the bike, catering for riders and their non-riding partners.

  • SEEK THE EXPERIENCE OF A LIFETIME

    Reward your life's hard work by joining us on one of our trips and discover some of the world’s most beautiful cycling and culinary destinations.

Looking For Your Next Cycling Adventure?

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