Miss Deane dressed in a pale blue regency dress with a surprise or astonished expression, a wide-brimmed straw hat, and standing against a peach-colored background.
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Experience WINCHESTER like never before

with fun and informative guided tours lead by characters from history.

Join Miss Charlotte Deane for a jolly walk around Winchester. She has all the Georgian gossip and all the tall tales from Winchester’s history.

Just don’t call her a blue stocking else she’ll never catch a husband!

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Tour Highlights include…

  • A woman in a blue and white dress and hat standing in an ancient stone archway with ruins in the background.

    Wolvesley Castle

  • A woman dressed in historical clothing standing outside a beige brick house with a black door, a white doorframe, and windows with green curtains. There is a black plaque above the door stating it was Jane Austen's residence when she lived her last days, dying on July 18, 1817.

    Jane Austen's House

  • Woman in historical dress smiling in front of a large Gothic cathedral with pointed arches and tall spires.

    Winchester Cathedral

  • A woman in a long, blue striped dress and hat standing in front of a large war monument depicting a warrior holding a sword and shield, in an urban area on a cloudy, rainy day.

    King Alfreds's Statue

  • Unstuffy tour of Winchester with joyful 19th century lady

    ‘‘I have lived in Winchester for 50 years but learned so much history that was new to me.
    Our delightful host shared titbits of hot historical gossip over an hour and 40 minutes as we wandered round the beautiful city.
    It was also lovely to witness the smiles of passers-by when they saw our guide’s costume. She truly adds colour and value to the city centre.’’

  • A delightful and enlightening tour.

    ‘‘This was a delightful tour of Winchester. The city has a fascinating history and Miss Dean brought major events from Saxon times to life. Told with humour and a delightful and informative tone it is an experience not to be missed.’’

  • So much fun!

    ‘‘This was SUCH a fun tour! Miss Dean walked us through the streets of Winchester and shared all the gossip, history and stories with us. She was wonderful! What a brilliant way to discover the beautiful legends and tales tucked into the backstreets of this lovely city. Highly recommend!’’

  • Winchester history tour goes regency

    ‘‘What a wonderful 90minute walk with Regency attired ‘Miss Deene’! We strolled to all the best historic spots in the city as she performed her history lesson in a light hearted and fun way. It was most informative and also a highly original performance by a great actor.
    I can thoroughly recommend this for history officionados of all ages.’’

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Frequently asked questions

  • While the tour has not specifically been designed for children it will be a great trip for any history obsessed child.

    Unlike regular historical guided tours, these tours are lead by characters from history creating a fun and light hearted atmosphere.

  • While we have designed the route to be as accessible as possible, Winchester has historic streets, uneven surfaces, narrow areas and some changes in level. Paving conditions include cobbles and gravel which may cause issues.

  • The tour lasts approximately 1 hour 30 minutes. This may vary slightly depending on group pace, weather and questions.

    Please allow for additional time should the tour overrun for any of the above reasons.

  • The tour starts at Abbey Gardens, 65 The Broadway, Winchester SO23 9BE on the grass looking at King Alfred’s statue. Full meeting details will be included in your booking confirmation email.

  • The tour finishes on Winchester highstreet.

  • Not quite. This is a character-led historical walking tour. Your guide is dressed and acting as a historical character, while taking you through real Winchester history, places, people and stories.

  • No. The tour is designed for visitors, locals, families and curious beginners. You do not need any prior knowledge.

  • You can cancel up to 48hrs before the start of your tour for a full refund minus the booking and processing fees charged by the ticket platform.

    48hrs before the tickets are non refundable unless the tour is sold out and your tickets can be resold.

    For a refund please get in touch at walkwinchesterwith@gmail.com or call 07449332841.

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