Bespoke Tours offer you the opportunity to create your very own trip, all you need is at least six people.
Creating a Private Trip helps tailor it to your group’s needs. You can convert any of our scheduled offerings into your own, suggest your own destination or multiple destinations. You can even mix road and gravel! We will then help you craft the details – difficulty level, distance, budget level. Everything!
Whether you want to ride for 50km or 200km, if you want 5 star luxury accommodation or simply the best routes for less. All we ask is that you are a group of at least 6 people.
Bespoke Tours
Whether on a mountain bike, road bike, or e-bike, our routes are carefully designed, tested, and tweaked personally by the Red Cherry team. This way, we ensure you experience the very best the Western Cape has to offer.
MTB Guided Tours
Explore some epic trails on a Mountain Bike.
Road Cycling Tours
Explore scenic routes on a bike while cycling the open road.
Guided Gravel Tours
Take on beautiful cycling trails through gravel roads.
Custom Private Tours
Mix road, gravel and road! Suggest your own destination or multiple destinations. We will then craft the finer details.
Our Bespoke Tour Rates
3 – Day Tour
from R12,000pp
5-Day Tour
from R18,000pp
7-Day Tour
from R22,000pp
What We Handle
Accommodation
Back Up Vehicles
Routes & Permits
Guides for Trails
All Meals and Drinks
Photographer on Trip
Shuttle Transfer
Bike Hire & Equipment Rental
Where We Go
Our tours take you on two of the most beautiful routes in the country, the Cape Winelands and Overberg.
The Cape Winelands is a breathtaking destination celebrated for its extraordinary wines, captivating history, scenic landscapes, and delectable cuisine. Expansive vineyards and historic Cape Dutch homes grace the area, framed by majestic mountains, with exceptional wine always within reach.
While guests typically relish tasting the globally acclaimed wines and savouring the top-notch local fare, an array of additional activities awaits. Leisurely drives through the picturesque countryside, exploring quaint towns, and enjoying family-friendly activities, like strawberry picking and visiting local farms, are all popular choices for travellers.
The Overberg is a region that stretches along coasts with beautiful beaches, and over mountain ranges with interesting geological formations, abundant birdlife and fynbos. The roads will take you on a journey through valleys with picturesque vineyards, orchards and beautiful landscapes of green, gold and brown.
Memories from the past – as illustrated by the Overberg’s rich collection of mission stations, ship wrecks and old architectural treasures – exist harmoniously with new developments in our towns, ensuring visitors find all they need.
What We Have Done
We create events from the ground up, utilising our practical skills and experience to ensure client satisfaction. From concept development to event design, we make use of our own infrastructure, making us a leading competitor in an ever-evolving market.
With 14 different events nationwide (M&G Investments PE PLETT, Inner City Enduro, Weekend Warrior, etc.) and 5000+ participants per year, we are sure that you will find the adventure you are looking for!
Brands We’ve Worked With
Create Your Own Bespoke Tour Now!
If you already have an idea, get in touch today! Our team is waiting to help you put together your dream Private Tour.
Frequently Asked Questions
How fit do you have to be? How demanding are the bike rides?
All you need to enjoy our cycling trips is the ability to ride a bicycle and a passion for seeing a destination on two wheels. That’s about it.
While there are occasionally longer days on some itineraries, the vast majority of our cycling days are between 30-70kms and are done at a leisurely pace with plenty of opportunities to stop and enjoy the scenery and just take a break.
I am very fit, will this tour be challenging enough for me?
Our standard tour routes are designed for the average recreational cyclist. That said, almost every tour allows for added mileage for those with extra energy. We’ll suggest optional longer rides on most days.
What should you wear for the cycling itself, casual clothing or actual cycle gear?
Our cycling trips are not races so feel free to wear whatever you feel comfortable in – casual cycling gear or lycra. Having said that, we definitely recommend bringing a pair (or 3!) of padded cycling shorts. Sure they look a bit funny, and feel pretty weird the first time you wear them, but it’ll make a world of difference to the comfort of your ride.
Can we hire a bike or do we have to bring our own?
You can freely use your own bike on our tours. Should you wish to hire a bike, we can offer you a quality bike of our own. It comes equipped a basic repair kit, bottle holder and lock. Weekly hire depends on the tour chosen. You can also hire a cycling helmet, we suggest you bring a scarf / bandana to wear under the helmet.
What are the road conditions and traffic like? and the type of terrain?
We design routes that are not only scenic or that take you to the not to be missed spots. We also pay attention to safety and look for the best cycling options, avoiding roads with any type of significant vehicle traffic, opting instead for quiet backroads. On some itineraries, there may be sections of the route where you will have to cross a busy intersection or maybe share the road with traffic for a short stretch – when that is the case, we always look for bike lanes or the safest passage across.
Can my non-riding spouse/partner/friend join a tour?
Yes of course they can, many non-riding (or wanting to do a little less) partners have a wonderful time seeing the winelands slightly differently from the vehicle, and you of course meet up at various spots along the way and at lunch. There are also many interesting walking sections as part of the tour.
I want to cycle more than what your tour is doing. Is that possible?
Yes, of course! If we are not off to our next destination there is time to do an early morning or late afternoon/early evening cycle. We have some great spots for you to venture to.
What should I pack?
We recommend you start you packing list with the following items:
- A few pairs of bicycling shorts and jerseys
- A few non-bicycling outfits to wear for your time off the bike
- Helmet (we recommend attaching it to the outside of your carry on if it does not fit in your luggage)
- Sunglasses
- Sunscreen
- Toiletries
- Spare glasses, contact lenses
- Dress pants/ skirts and shirts (layering is always encouraged)
- Two pairs of shoes (a pair for cycling and a pair to wear around town after cycling)
- Any prescription medication you might need and prescriptions in case you need to refill.
What are accommodations on tour like?
Getting a good night’s sleep is essential, so we choose comfortable, well-managed and ideally centrally-located accommodations. All rooms have a private bathroom. We also look for charm and personality, as well as hotel staff and hosts that go out of their way to make your stay a delight!
The type of accommodations vary slightly by tour and destination – please check your specific itinerary (or email us), for more details on the lodging.
What type of bike should I choose?
We suggest choosing the type of bike you are most familiar with at home – if you are up for it, you may want to try a new type of bike! On most tours, you will have the option of renting a road bike with drop-down handlebars, or a hybrid bike with flat handlebars. We also offer pedal-assist e-bikes. If you have any questions about our bike options please check the specific itinerary page or ask us.
Who do I contact in the event of any changes made to my stay?
We’ll provide all the necessary contact numbers for you to communicate changes or last-minute requests.
The type of accommodations vary slightly by tour and destination – please check your specific itinerary (or email us), for more details on the lodging.
Do you provide helmets?
We require everyone to wear a helmet on tour. We recommend you bring your own for best fit and comfort (as well as hygiene reasons). If you prefer to not travel with your own helmet, we can provide a lightly used helmet upon request. Please be sure to provide your helmet size.
Who is responsible for the bikes if they are damaged or stolen?
You are responsible for bike damage or theft, and you’ll agree to this when you sign our contract at delivery. so please be careful! That said, we offer plenty of advice and tips on how to properly store and secure your bikes every night or when you stop along the way every day. We will store the bikes for you every night.
Are E-bikes available?
We’ve included the option to hire an e-bike on trips. While it won’t do all the work for you (you still need to pedal!) it can help you hold a higher average speed and make the hills a lot easier. Many groups where one person is not as strong as the other find our e-bike option a great way to enjoy the trip together.
What if I have not ridden an e-bike before?
We have a training session at the beginning of each tour.
For those that are experienced e-bike riders, we show you how our bikes work. And for those novices, we give you a lesson and some tips and time to practice.
But our bikes are easy to handle and fun to ride. They make cycling much easier overall.
How fit do you have to be? How demanding are the bike rides?
All you need to enjoy our cycling trips is the ability to ride a bicycle and a passion for seeing a destination on two wheels. That’s about it.
While there are occasionally longer days on some itineraries, the vast majority of our cycling days are between 30-70kms and are done at a leisurely pace with plenty of opportunities to stop and enjoy the scenery and just take a break.
I am very fit, will this tour be challenging enough for me?
Our standard tour routes are designed for the average recreational cyclist. That said, almost every tour allows for added mileage for those with extra energy. We’ll suggest optional longer rides on most days.
What should you wear for the cycling itself, casual clothing or actual cycle gear?
Our cycling trips are not races so feel free to wear whatever you feel comfortable in – casual cycling gear or lycra. Having said that, we definitely recommend bringing a pair (or 3!) of padded cycling shorts. Sure they look a bit funny, and feel pretty weird the first time you wear them, but it’ll make a world of difference to the comfort of your ride.
Can we hire a bike or do we have to bring our own?
You can freely use your own bike on our tours. Should you wish to hire a bike, we can offer you a quality bike of our own. It comes equipped a basic repair kit, bottle holder and lock. Weekly hire depends on the tour chosen. You can also hire a cycling helmet, we suggest you bring a scarf / bandana to wear under the helmet.
What are the road conditions and traffic like? and the type of terrain?
We design routes that are not only scenic or that take you to the not to be missed spots. We also pay attention to safety and look for the best cycling options, avoiding roads with any type of significant vehicle traffic, opting instead for quiet backroads. On some itineraries, there may be sections of the route where you will have to cross a busy intersection or maybe share the road with traffic for a short stretch – when that is the case, we always look for bike lanes or the safest passage across.
Can my non-riding spouse/partner/friend join a tour?
Yes of course they can, many non-riding (or wanting to do a little less) partners have a wonderful time seeing the winelands slightly differently from the vehicle, and you of course meet up at various spots along the way and at lunch. There are also many interesting walking sections as part of the tour.
I want to cycle more than what your tour is doing. Is that possible?
Yes, of course! If we are not off to our next destination there is time to do an early morning or late afternoon/early evening cycle. We have some great spots for you to venture to.
What should I pack?
We recommend you start you packing list with the following items:
- A few pairs of bicycling shorts and jerseys
- A few non-bicycling outfits to wear for your time off the bike
- Helmet (we recommend attaching it to the outside of your carry on if it does not fit in your luggage)
- Sunglasses
- Sunscreen
- Toiletries
- Spare glasses, contact lenses
- Dress pants/ skirts and shirts (layering is always encouraged)
- Two pairs of shoes (a pair for cycling and a pair to wear around town after cycling)
- Any prescription medication you might need and prescriptions in case you need to refill.
What are accommodations on tour like?
Getting a good night’s sleep is essential, so we choose comfortable, well-managed and ideally centrally-located accommodations. All rooms have a private bathroom. We also look for charm and personality, as well as hotel staff and hosts that go out of their way to make your stay a delight!
The type of accommodations vary slightly by tour and destination – please check your specific itinerary (or email us), for more details on the lodging.
What type of bike should I choose?
We suggest choosing the type of bike you are most familiar with at home – if you are up for it, you may want to try a new type of bike! On most tours, you will have the option of renting a road bike with drop-down handlebars, or a hybrid bike with flat handlebars. We also offer pedal-assist e-bikes. If you have any questions about our bike options please check the specific itinerary page or ask us.
Who do I contact in the event of any changes made to my stay?
We’ll provide all the necessary contact numbers for you to communicate changes or last-minute requests.
The type of accommodations vary slightly by tour and destination – please check your specific itinerary (or email us), for more details on the lodging.
Do you provide helmets?
We require everyone to wear a helmet on tour. We recommend you bring your own for best fit and comfort (as well as hygiene reasons). If you prefer to not travel with your own helmet, we can provide a lightly used helmet upon request. Please be sure to provide your helmet size.
Who is responsible for the bikes if they are damaged or stolen?
You are responsible for bike damage or theft, and you’ll agree to this when you sign our contract at delivery. so please be careful! That said, we offer plenty of advice and tips on how to properly store and secure your bikes every night or when you stop along the way every day. We will store the bikes for you every night.
Are E-bikes available?
We’ve included the option to hire an e-bike on trips. While it won’t do all the work for you (you still need to pedal!) it can help you hold a higher average speed and make the hills a lot easier. Many groups where one person is not as strong as the other find our e-bike option a great way to enjoy the trip together.
What if I have not ridden an e-bike before?
We have a training session at the beginning of each tour.
For those that are experienced e-bike riders, we show you how our bikes work. And for those novices, we give you a lesson and some tips and time to practice.
But our bikes are easy to handle and fun to ride. They make cycling much easier overall.
Testimonials
With over 5000 competitors taking on our events year-on-year.
Whether you are a hardcore motorbiker or a social weekend cyclist, we have something that will speak to you, click here to view our upcoming events.
Red Cherry Events Technical Partners
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