Following much of the 170 mile Chiltern Cycleway, this tour covers the entire Chiltern Hills area: from the Thames at Henley in the south west, to Hitchin in Hertfordshire in the north east. The chalk hills are a designated area of outstanding natural beauty, known for their red kites, beech woods, soaring views, idyllic brick and flint villages and innumerable hidden dry valleys. The cycling is challenging but rewarding, and we have found a characterful selection of wonderful village inns for your overnight stays.

Holiday details



from £1,290 per person

Based on two people sharing a room

What’s included?

There are no extras, however you’ll love what’s included as standard


4 nights

Start & Finish

Starts daily from Tring and is circular. By train, Tring is 45 minutes from London Euston



Hand picked accommodation in outstanding village inns

Holiday type


This tour is priced without a guide and you are free to explore on your own.  If you would like a guide for part or all of your trip, we are happy to provide a knowledgeable, local guide

Activity level

Not so gentle cycling. More info...

Electric bikes



4 days of 36 to 52 miles (58 -83km) per day


Several tough hills, generally short but steep, each day


Almost totally on roads but most with low traffic


  • Stay 2 nights at any of the stops and enjoy our circular rides or a day's rest
  • Enjoy a guide for your first day of cycling

Itinerary day-by-day


  1. 1. Day one

    Arrive Tring

    Arrive in Tring and make your way to your overnight stay in a charming village nearby. Your cosy inn for the night, looking over the village green and at the foot of the Chilterns is just one mile from Tring station if you are arriving by train. Parking is available if you are arrrivng by car. Settle in, smell the fresh air and enjoy the delicious food.

  2. 2. Day two

    Tring to Near Welwyn

    Today your host will meet you after breakfast and run through your itinerary. The ride runs northwards through the Ashridge estate, skirting Dunstable Downs with many undulating lanes and an essentially farmland landscape dotted with woods, appealing inns and characterful villages. You briefly shortcut the cycleway at its northern tip to avoid a muddy bridleway before arriving at your 14th Century village inn, not far from Welwyn. Your luggage will be awaiting you!

    38 miles (61 km)

  3. 3. Day three

    Near Welwyn to Great Missenden

    There's more variety today with great cycling along a disused railway and a short section of paved Grand Union Canal towpath. Cross the beautiful Chess valley, ride some serious slopes, visit a Tudor manor house and gardens and enjoy the rural scene as you head for Berkhamsted and on to Amersham. Beyond lies the village of Great Missenden, once home to Roald Dahl and your stay for the night in an ivy clad inn, proud of its excellent food.

    36 miles (58 km)

  4. 4. Day four

    Great Missenden to the hills above Henley

    Start the day with a long steady climb - you are used to these by now, and head for West Wycombe where the Hell Fire Caves may be what you need. They also sell cream teas and sandwiches. Once over the M40 there are breathtaking views as you freewheel down the Hambleden valley past a winery to Henley, and dip your toe in the River Thames. Your overnight stay lies a little further on, back in the wooded hills through narrow sunken lanes to a typical Chiltern village housing an atmospheric inn.

    36 miles (58 km)

  5. 5. Day five

    The hills above Henley to Tring

    Open countryside with views over the Thames floodplain greet you first as you ride to the ancient village of Ewelme. Beyond, you follow the top of the Chiltern escarpment with a stop on Watlington Hill, a good place to see red kites. With challenging slopes come fantastic scenery, amazing viewpoints and picturesque villages. The ride leads close to Chequers and through the charming market town of Wendover and the rolling countryside to your final destination of Tring. Yes, it's a challenge, but boy what a reward!

    42 miles (67 km)