35 days. 4 countries. 28 riding days from Nairobi to Victoria Falls, through Kenya, Tanzania, Malawi and Zambia, ending in Zimbabwe.

This isn't a holiday. It's the trip Sigge has wanted to organise his whole life, and one he's riding himself again this edition.

You'll ride carefully chosen routes, selected on 20 years of experience in the region. Every day brings a new landscape, a new border, a new reason to keep pedalling.

Semi-supported, not easy. Your luggage is transported so you can focus on the road, but the climbing is yours to do. A medical team travels with the group, and fixed lunch stops are provided on every riding day by the team we've now worked with for 15 years.

28 riding days require serious preparation, physical and mental. This trip is for experienced cyclists who know what a long day in the saddle means, and who are ready for something beyond a cycling holiday.

At the end, Victoria Falls is waiting: the Zambezi crashing into the gorge below with a roar you'll hear before you see it. The moment 35 days come together.

We travel with a minimum of 20 and a maximum of 35 participants, a group large enough to make friends along the way, small enough to stay personal.

Route: Nairobi 🇰🇪 → Tanzania 🇹🇿 → Malawi 🇲🇼 → Zambia 🇿🇲 → Victoria Falls

Some things are too good to keep to yourself, but too special to shout about.

What is included

Meals

Full board during the trail - breakfast, lunch on the road and dinner.

Accommodation

All nights in lodges and camps along the route.

Support

Guides, support vehicle, mechanic and first aid on the road.

Extras

Safaris, park entrance and local experiences as per the programme.

Departure 27 September 2027 - 31 October 2027

Registrations

Open now

Reserve this adventure →

Frequently asked questions

Physical preparation

What's the challenge level of this trip?

This is our toughest and most demanding trip: 28 riding days covering a total of 3,275 km, spread across 35 travel days with 7 rest days. Challenge level 5/5.

What preparation is recommended for 28 consecutive riding days?

We recommend training for time in the saddle, not just distance. Being able to comfortably cover the daily riding distance, with room to spare, is a good starting point, but just as important is being able to do this several days in a row. Build your training around consecutive long rides, so your body gets used to the fatigue that builds up day after day, not just a single tough ride on its own.

How should I build up my training for a trip of this length?

To be ready for 2027, start training regularly now, and increase the intensity as the departure date gets closer. Riding often gets your body used to long distances. It should become second nature to cycle at least 3 times a week, with at least one of those being a long ride.

What if I can't keep up the pace during a ride?

There's no fixed pace during the rides, everyone rides at their own speed, and groups naturally form based on similar pace. There's always someone from our team riding at the back, so you can join them at any time. And if it really isn't working out, our support vehicle is always there for you to hop in.

Can I take a rest day if I really can't manage, or is the schedule completely fixed?

A number of rest days are built into the trip. If a particular day really isn't working out for you, you can ride along in the support vehicle to recover, and get back on the bike fresh the next day.

Bike & gear

What type of bike do I need for this trip?

This trip needs to be ridden on a mountain bike. There will be sections where a mountain bike isn't strictly necessary, but there will also be sections where you'll be very glad you're not on a gravel bike.

Is maintenance provided along the way?

Yes, a mechanic is present for the entire trip, but as support for exceptional cases, not as a replacement for your own basic skills. We expect you to be able to handle basic repairs yourself, such as fixing a flat tire. If something comes up that you can't solve on your own, our mechanic is there to help.

How do I get my bike there?

You bring your own bike on the plane. The exact way to transport it depends on the airline, so check this in advance. Important: your bike needs to travel in a cardboard bike box, not a hard bike case, because that box needs to travel with us for the entire trip.

Health & safety

What vaccinations or malaria prevention do I need for this route?

Contact your doctor for this. We do cycle through malaria areas on this trip, so be sure to ask about this specifically.

Is travel insurance mandatory?

Yes, this is mandatory, including repatriation cover.

What happens in case of a medical incident or injury on the road?

A medical team travels with the group, so support is never far away. Minor issues (blisters, sore muscles, mild fatigue, a graze) are handled on-site by that team. For more serious incidents, we contact local hospitals, and if necessary, we arrange repatriation, which is exactly why travel insurance with repatriation cover is mandatory.

Is this trip suitable if I have a medical condition?

Check with your doctor, who can assess this best. Do always let us know about any medical condition you have, so we can prepare as well as possible. We'll also be upfront: this is a physically very demanding trip, and even the support vehicle isn't always comfortable, think this through carefully before signing up.

How is participants' health monitored over such a long period?

Someone with at least basic first-aid knowledge travels with the group at all times. We take into account any medical information you've shared with us in advance. Participants' health is checked daily, but we also expect participants to use common sense and report any serious issues to the team promptly.

Practical & logistics

How do I get to the starting point in Nairobi?

We pick you up from the airport and take you to the start.

What's the arrival and departure protocol?

You let us know your flight details, and we pass them on to our drivers. They make sure to be on time both for pick-up on arrival and for your departure, so you never miss your flight. We welcome you at the starting lodge for a briefing and to assemble your bike.

How does the accommodation work exactly?

We alternate between lodges, guesthouses, and camping along the route.

How does the payment structure work for a trip of this scale?

Once we're certain the trip will run, we send a payment request for the deposit. Your booking is confirmed once this deposit is paid. At the same time, we send the payment request for the remaining balance, which is due at the latest 2 months before departure.

What are the cancellation terms?

The full cancellation terms are explained in our Terms and Conditions. In short: the closer you cancel to the departure date, the higher the percentage of the trip cost that isn't refunded, this is structured in tiers. Given the scale of investment and preparation for this trip, we'd recommend reviewing these terms carefully in advance.

Can I transfer my booking to someone else?

Yes, that's possible. We do need to know this at least 14 days in advance, and the new participant must meet all of our participation requirements.

What happens if there aren't enough registrations?

Just like on all our other trips, the trip would be cancelled well in advance in that case, though this has never happened so far.

Who guides the trip?

An experienced team guides you throughout the trip: a mix of regular staff and volunteers.

Can I join without a partner or friend?

Absolutely. Our group is always a great mix of solo travellers and couples or groups of friends. Everyone's welcome, and in the evenings there's always a chance to get to know everyone during group activities, or simply relax in your room. Our trip is an individual group trip: you're welcome to join group activities and ride together, but you don't have to. The choice is entirely yours.

How does communication/preparation work in the lead-up to such a long and demanding trip?

We keep you updated in the lead-up to departure, but just like on our other trips, all the practical information is included in the registration guide. The GPX routes are sent to you well ahead of departure, and you'll receive additional information shortly before the start.

About the destination

What's the weather/climate like during September–October?

We travel outside the rainy season. It will be warm, though never unbearably so, and the occasional tropical shower usually isn't a big deal. Above all, this period offers plenty of sunshine to enjoy along the way.

The Legendary Trail