Rides and tours

Rides & tours

At BB, we do a weekly beginner's ride and all kinds of tours around all parts of Winchester but, like the name says, our trips are mainly organised around you. So we do coaching for those who might feel a bit wobbly about getting on a bike. We do cycle know-how: how to get about the city, how to negotiate traffic and how to stay safe. But most of all we do friendly and fun rides. You’ll see how as you wheel through the site.

Come and explore our bike-friendly city routes. We operate in small groups and show you the hidden gems of this beautiful city. Through picturesque streets, lined with history, we go where the buses can’t take you. See more of the city than on foot. We have a range of one off reasonably priced tours. Below are some of the tours we can take you on; contact us for more details.

Forthcoming organised rides

No Events

Custom guided tours

We can arrange guided rides to order - below are some examples.

Discover Winchester

A 90 minute ride around Winchester, Our guide will lead you around the key sights of Winchester and introduce you to the layout to help you familiarize yourself with the sights. Ride by the Cathedral, City Mill, Wolvesey Castle, Jane Austen’s last home, St Cross Hospital and the Hockley Viaduct. Mostly flat, and all on quiet roads.

Enjoy scenic streets, countryside and city, historic features and quirky tales. Experience some of the history of this fascinating ancient city from Roman times to today.

Price: £30 per rider including bike hire; £15 per rider if you bring your own bike. Discounts available for groups.

Discount bike hire available after the tour if you want to carry on exploring (deposit required).

Children must be accompanied by a responsible adult.

The Bespoke Winchester Sights tour

The Cathedral, The Great Hall, St Cross Hospital, The Westgate and Hyde Abbey.
This tour can be tailored to your needs. Mostly flat and all on quite roads. Enjoy scenic streets, countryside and city, historic features and quirky tales. Experience some of the history of this fascinating ancient city. From Roman times to today.

Bespoke Three Teas

Welcome to the bike friendly city with the most glorious tea rooms. Cake to savour! Tea to taste! From economy to gourmet. This tour meets at a tea shop, rides out to a tea shop and returns to your third tea shop! Taking in the sights along the way. Country side and city.

Email for availability and to book.

Bespoke Eglise

This tour captures the ecclesiastical history of Winchester, travels in the path of pilgrims and journeys on ancient pathways. Visiting, St Cross Hospital, Winchester Cathedral, learn about the importance of St Swithun, the role of St Lawrence, and the ancient journey of King Alfred’s body. For keener riders this tour can be extended to take in some of the outer lying villages, and their ancient churches.

Good Life

Journey out to Kings Worthy, enjoy the Hampshire countryside and the village church of St Swithun, enjoy a refreshment stop and fresh, local produce at the rural farm shop and café at The Good Life.


Begin to explore the gateway to the South Down’s National Park. A beautiful peaceful ride out to a Saxon church and beautiful views. A bit of a climb out of the city but a great ride back down again.

Suggest a ride!

Fancy riding somewhere else? Let us know, we can probably arrange something!