OG & The MATCH International Women’s Fund present…


Kilimanjaro 360

Arrows MASTER sm

Apply before September 1 to secure your spot!

Program Description

Sponsored by The MATCH International Women’s Fund, Operation Groundswell’s Eastern Tanzania on 2 Wheels Challenge takes participants to East Africa for a 12-day adventure bridging two of Tanzania’s most iconic landscapes. After arrivals and a brief stop in Nairobi to connect with Match partners in the region, we’ll head south into Tanzania and the shadow of Mt. Kilimanjaro. Then after a little orientation, participants will mount their two-wheeled chariots and challenge themselves to a 350km bike ride east to shores of the Indian Ocean. Our routes passes through traditional Masai and Chagga territory as well as a variety Tanzania’s most abundant biospheres and captivating landscapes from the plains beneath Mt. Kilimanjaro to the mountains of Usambara and, finally, the white sands of Zanzibar island. Along the way we’ll also visit some of East Africa’s most vibrant cities from the enterprising outposts of Moshi and Arusha, to the metropolis of Dar es Salaam and ancient Stone Town.

What better way is there to challenge ourselves, support The MATCH Fund and inspire each other to carry on fighting for a more equitable and just world.

Program Basics

Program Sponsor

Program Dates

March 2020

Program Fees + Environmental Contribution

[currency_amount cad=”$TBD CAD + $TBD CAD” usd=”$TBD USD + $TBD USD”]

[currency_change default=”CAD”]

Approximate Airfare

Approx. $1200-$1800 CAD

Program Highlights

  • Cycle in the shadow of Africa’s giant, Mt. Kilimanjaro, and stay with the Jane Goodall Foundation in local Maasai and Chagga communities.
  • Visit a monkey filled forest and follow a Tanzanian coffee bean from seed to shelf with the change making women at Femme and Rau in Moshi.
  • Explore the back alleys and famous bazaars of one of the world’s oldest trading posts in Stone Town. Then, dip your toes in the Indian Ocean and sail on a dhow around the amazing island of Zanzibar.

Sample Itinerary

*This itinerary is based on our previous experiences with the region. Programs change every year based on the needs of our partners. This should give you a sense of what our program may look like.


We’ll begin our East African adventure in Nairobi, Kenya. Upon arrivals, you’ll be met right outside Jomo Kenyatta International Airport by your intrepid team of Program Leaders who will accompany you into the city, help you get settled and show you around this bustling metropolis.

Orientation & The MATCH Fund Partners

After a big breakfast, we’ll do a little orientation and acclimatize ourselves to the sights, sounds, smells and tastes of the region before travelling to nearby Machakos where we’ll spend the day with one of the MATCH Fund’s incredible local partners . The Resource Center for Women and Girls (RCWG) works with young rural and rural-urban girls and women from all parts of Kenya. The RCWG uses their prestigious empowerment and mentoring camps as a tool to promote personal transformation and empowerment among these girls.

Karibu Tanzania

Next, we’ll hop aboard a bus and travel south across the boarder and into Tanzania. By mid-afternoon, we should arrive in Moshi, a small but vibrant city that sits in the shadow of Mt. Kilimanjaro. Recently, it’s become a popular base for would-be climbers of Africa’s tallest peak but it’s also bubbling with entrepreneurialism and social innovation. So, we’ll wander the streets and get to know each other better. We’ll get a little intro to Tanzanian culture, eat chapatti, and maybe even take a quick Swahili lesson in preparation for the journey ahead.

Moshi to Tinga Tinga

Our ride today takes us from the greener southern side of Mt. Kilimanjaro towards the more arid western side of the mountain. Your ride today will initially take you through coffee and banana plantations as you cycle through the more fertile areas of southern Kilimanjaro but as you head west you will cycle through the more arid open plains and acacia woodlands. These plains support a remarkable variety of wildlife and spectacular views of Mt. Kilimanjaro. While Moshi is home the Chagga people west Kilimanjaro plains are home to the nomadic Maasai people who co-exist with the surrounding wildlife and it is why this area is known as the Maasai Lands. Your ride today will be on both dirt and tarmac roads and you will finish the ride at the Ngabobo village where you will be spending the night.

Tinga to W. Kili Farm

Our ride today takes us through the Enduimet Wildlife Management Area which is one of Tanzania’s best kept secrets. Enduimet borders Amboseli National Park and serves as an important migratory route for wildlife including the African elephants. This area is inhabited primarily by the Maasai people but there are large populations of other tribes such as the Chagga, Meru and Pare people. Your ride starts off on the wide-open plains dotted with acacia trees but it gets greener as you approach the lower slopes of Kilimanjaro where a lot of cultivation takes place. Your cycling tour today ends at Simba Farm which is situated on top of the vast wheat and barley fields overlooking the west Kilimanjaro plains.

W. Kili Farm to Nalemoru

Today you will be cycling towards the north east side of Mt. Kilimanjaro to Nalemoru village near the Kenyan border. Nalemoru village is where the Rongai route up Kilimanjaro starts off. Your ride today takes you through beautiful open farmlands with breathtaking views of the west Kilimanjaro plains behind you. You will cycle through several vibrant towns as you head up the foothills of the mountain towards the Rongai forest. Your ride today ends at the Snowcap Cottages which are nestled right on the edge of the Rongai forest. On a clear day you can enjoy amazing views of Kilimanjaro’s Kibo and Mawenzi peaks.

Nalemoru to Lake Chala

Today you will enjoy a downward hill ride towards the beautiful Lake Chala, a crater lake lying right on the border between Kenya and Tanzania. Lake Chala is one of Tanzania’s hidden gems. Fed entirely by underground springs from Mt Kilimanjaro, the turquoise blue and green waters are surrounded by diverse plants, trees and wildlife. The camp where you will be spending the night is situated on the edge of this mystical caldera lake, against a dramatic volcanic backdrop providing the perfect place to unwind and absorb the serenity and tranquility of the area.

Lake Chala to Marangu

Today’s ride will be short but challenging as you ride up to Marangu village in the foothills of Kilimanjaro. As you cycle through Marangu village you will pass banana and coffee plantations along the way as well as the friendly Chagga people who will be waving and shouting “Jambo!” as you cycle by. Before getting to your camp you will take a detour to the iconic Kinukamori waterfalls where you can stretch your legs and walk down to the base of the waterfalls. While here, a local Chagga guide will give you a brief history of the area, the people, their traditions, and customs as well as the mystical legend about the waterfalls. After spending some time refreshing by the waterfalls you will finish the last downhill stretch of your ride towards the camp where you will be spending the night.

Marangu to Moshi

You will be wrapping up your last day of cycling by traversing the villages and plantations on the slopes of Mt. Kilimanjaro. The first half of the ride will be comprised of several steep ascents and descents followed by a second half which is a gradual downhill ride towards the bustling and vibrant Moshi Town. You will cycle through the suburbs and outskirts of Moshi Town on the back roads as you head towards the Keys Hotel which marks the end of your incredible 6-day journey around Mt. Kilimanjaro, on two wheels. You will seal of the evening with a nice celebratory dinner and sparkling wine to toast to your achievement.

Fly to Zanzibar for Disorientation 

A staple of every OG program, disorientation is an opportunity to debrief as a group. So, we’ll find a sandy shore on the island of Zanzibar, kickback, relax and reflect on our incredible journey. We’ll listen to the waves of the ocean and think about our impact and how we can do to bring it back home.

From here, we’ll say a fond farewell.






Approx. 400km


Scroll below for more program details

How Groundswell Challenges Work

Register with OG

Submitting an application is the first step on the way to an unforgettable experience. We will review your submission and then reach out with next steps. Don’t worry, you won’t be asked to commit to anything until you’re ready.

Fundraise for The MATCH Fund

Once you’re a part of the team, you’ll pay a deposit and then get fundraising on a personal fundraising page. Your fundraising goal for The MATCH Fund is $10,000. When you hit that target, the rest of your program fee is covered.

Get Ready for Adventure!

With our support, you’ll gear up and get ready for the trip of a lifetime. Start training on that bicycle and daydreaming of an East African sunset over the Usambara mountains. Tanzania awaits!

Learn More ↓


Every participant is required to pay a non-refundable deposit of $500, to secure their place on the program. These funds are used to begin making commitments on your behalf.


Then, we’ll set you up with a personal fundraising page that you can share with friends and family to help you reach your goal.


Every participant is then required to contribute a minimum of $10,000  to the charity sponsor. These funds are collected using Operation Groundswell’s fundraising platform.

The goal is to have completed:

  • 50% of your fundraising goal 90 days before program
  • 75% of your fundraising goal 60 days before program
  • 100% of your fundraising goal 30 days before program

When you have hit the minimum fundraising goal, the charity sponsor will pay any remaining program fees on your behalf.  100% of every dollar that your fundraise above the minimum fundraising goal goes to the Charity sponsor.

What’s Included?

A comprehensive program itinerary that will help you explore the region

Experienced and caring program leaders with you 24 hours a day

All lodging and accommodations throughout the program

Three local meals a day

All group tours, entrance fees, and excursions

All group transportation on the ground

Regular discussions and workshops to help you internalize and reflect on your experience

Support from OGHQ whenever you need it


We immerse ourselves locally.

This is not a budget backpacker’s trip nor is it a five-star jet-setter’s cruise. We will be sleeping in clean, comfortable locally-run hotels and guesthouses that reflect our sustainable travel ethos. There is a mix of private and shared rooms and bathrooms but Operation Groundswell can accommodate special requests for a nominal fee. In addition the hotels and guesthouses, we may have the opportunity to stay with local families along the way. Here you’ll find amenities are basic and Western comforts should not be assumed but there is simply no better way to build relationships and share cultures. Wherever we are, our hosts will help us feel right at home.

Meet Some of Our Program Leaders

Claire grew up travelling. From riding horses in the Egyptian desert at age 9 to sailing between Indonesian islands at 12, being on the road was the only way to roll! She’s lived in a mountain village in Costa Rica, camped her way across Europe, went scuba diving in Thailand, and has spent a lifetime of moments getting lost in the chaos of India. She believes in the power of travel to expand us, to humble us, to change us forever – and wants to spread that passion with a worldwide community of ethical backpackers!

Ana was born in San Jose, Costa Rica and has since travelled whenever possible in pursuit of her passion for education, development, and nature! She has worked as an English teacher in public and private schools in Costa Rica, and volunteered in Quijingue, Bahia (Brazil) on community development projects. After completing her Masters in Translation, she worked with Peace Corps, Costa Rica until returning to the world of NGOs as a Program Coordinator in Riobamba, Ecuador. Now, she’s super excited to be part of the OG family and looking forward to establishing new partnerships, working with and training awesome program leaders, and designing more amazing programs in South America!

If Not Now, Then When?

The world is changing. Help change it for the better.
Join the growing community of ethical travellers.