48 hours in Cheltenham and Cotswolds suggested itinerary

Inspire Me

  1. Suggested Cheltenham itineraries
    Looking for some inspiration planning your stay in Cheltenham? These suggested itineraries will help you to discover the unmissable highlights of the most Regency town in Britain and hidden gems, loved by locals.
  2. What's On in Cheltenham
    The most comprehensive Cheltenham 2025 what's on guide ft. the best things to do and events in Cheltenham, Cotswolds and Gloucestershire. Use our interactive event finder to help.
  3. Things To Do in Cheltenham
    Looking for things to do in Cheltenham? Get the latest information on attractions, activities, tours & sightseeing, shopping in Cheltenham and more.
  4. Restaurants and bars in Cheltenham
    Choose one of our many places to eat and drink in Cheltenham, whether it's coffee and cake, a bite to eat at lunch or dinner and cocktails...
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Highlights

Cirencester

Cirencester

Cirencester is a thriving market town with a bustling market place presenting a colourful and…

The Promenade and Long Gardens

The Promenade and Long Gardens

Cheltenham's famous Promenade dates back to 1818 at the height of the Regency period, when the…

Cleeve Hill overlooking Cheltenham

Cleeve Hill

Cleeve Hill is located on Cheltenham’s North-Eastern edge, on the way to Winchcombe, affording…

Stow on the Wold

Stow on the Wold

Famous as a centre for antiques, Stow-on-the-Wold, situated on the Roman Fosse Way, has a long…

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Number of results: 149

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  1. Escape Hunt exterior

    Add Escape Hunt to your Itinerary

    Escape Hunt

    Type

    Type:

    Escape Room

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Escape Hunting involves teammates losing themselves in incredible new worlds, taking on pulse-racing missions and challenges created by the Escape Hunt Studios team. Groups have to work together to follow a series of fiendishly clever clues and…

  2. Popworld Cheltenham

    Add Popworld Cheltenham to your Itinerary

    Popworld Cheltenham

    Type

    Type:

    Bars

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Popworld is a late-night bar with a difference – they are cheese with style!

  3. Under the Prom

    Add Under the Prom to your Itinerary

    Under the Prom

    Type

    Type:

    Nightclub

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Under The Prom is located in the heart of Cheltenham and composes of three different bars with an extensive range of premium spirits, champagne, bottled beer and cider and cocktails...

  4. The Roman Baths

    Add The Roman Baths to your Itinerary

    Tripadvisor Traveller Rating

    Tripadvisor Traveller Rating - from 24532 review(s)from 24532 review(s)

    The Roman Baths

    Type

    Type:

    Museum

    Bath

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Walk around the steaming Great Bath where people bathed nearly 2,000 years ago, see the ruins of the temple of Minerva where Roman worshippers gathered, and explore the fascinating museum.

  5. Stonehenge seen from above, © ENGLISH HERITAGE

    Add Stonehenge to your Itinerary

    Tripadvisor Traveller Rating

    Tripadvisor Traveller Rating - from 14912 review(s)from 14912 review(s)

    Stonehenge

    Type

    Type:

    Historic Site

    Nr Amesbury

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Stonehenge stands impressively as a prehistoric monument of unique importance, a World Heritage Site, surrounded by remains of ceremonial and domestic structures - some older than the monument itself.

    Facilities

    Bookable Product

    • TXGB Bookable Product
  6. Late Night Coco

    Add Late Night Coco to your Itinerary

    Late Night Coco

    Type

    Type:

    Bars

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    The Funky House BASS:ment bar that gets you in the mood for dancin'...

  7. Beautifully presented patisseries from Pastry Academy UK

    Add Pastry Academy UK to your Itinerary

    Pastry Academy UK

    Type

    Type:

    Cookery School

    Cheltenham

    Formerly Edible Art Patisserie, Pastry Academy UK was incorporated in 2024 with one main aim - to inspire pastry chef’s from across the UK and further afield to push the boundaries and strive for excellence.

  8. Couple relaxing on hire boat in Gloucester Docks

    Add Gloucester Boat Hire to your Itinerary

    Gloucester Boat Hire

    Type

    Type:

    Boat Trip

    Gloucester

    Self-drive electric motorboats that can be hired from the Barge Arm of the docks.
    Prices from £30. Boats seat up to 8 people.

    Open year-round and accept online bookings.

  9. Viewpoint along the Cotswold Way

    Add Compass Holidays (Trade) to your Itinerary

    Compass Holidays (Trade)

    Type

    Type:

    Outdoor Activity/Pursuit Centre

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Open 09:00 - 17:00

    A unique and active holiday with Compass Holidays allows you to get under the skin of the history, culture and natural beauty of some of the world’s most iconic and stunning locations...

  10. Lindy Hop Dance Classes

    Add Lindy Hop Dance Classes to your Itinerary

    Lindy Hop Dance Classes

    Type

    Type:

    Dancing

    Cheltenham

    Dates

    Learn to Lindy Hop, a Swing Dance from the 1930's, to the music of Big Bands and Jazz.

  11. Fallow Deer

    Wildlife Safaris with Ed Drewitt

    Type

    Type:

    Guided Tour

    Forest of Dean

    Dates

    Exploring the stunning landscapes and amazing wildlife of the Forest of Dean and Wye Valley can come no better than a trip out with local naturalist Ed Drewitt.

  12. Painswick Rococo Garden

    Add Painswick Rococo Garden to your Itinerary

    Painswick Rococo Garden

    Type

    Type:

    Garden

    Painswick, Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Painswick Rococo Garden is a unique and fascinating insight into early to mid 18th century English garden design. The only complete Rococo garden in England, it dates from a brief period (1720 – 1760) when English gardens were changing from the…

  13. Cheltenham Walks

    Add Cheltenham Walks to your Itinerary

    Cheltenham Walks

    Type

    Type:

    Walking Route

    Cheltenham

    Cheltenham is the cultural centre for the Cotswolds, offering a different festival for everyone, from cutting edge jazz, classical and folk music, to horse racing, cricket and literature - find out about walks in Cheltenham.

  14. People sat on a bench with a dog on Leckhampton Hill and Charlton Kings Common in Cheltenham.

    Add Leckhampton Hill and Charlton Kings Common to your Itinerary

    Leckhampton Hill and Charlton Kings Common

    Type

    Type:

    Viewpoint

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Leckhampton Hill and Charlton Kings Common lie within the Cotswolds Area of Outstanding Natural Beauty. The main aspect of the hill is visible from many parts of Cheltenham. It is a cherished landscape feature for residents and visitors.

  15. Children climbing boulders wall

    Add Boulders Cheltenham to your Itinerary

    Boulders Cheltenham

    Type

    Type:

    Sport/Leisure Centre

    Tewkesbury Road, Cheltenham

    As the only dedicated bouldering centre in Cheltenham, Boulders offers opportunities for 'Give it a Go' sessions for adults and children as well as monthly memberships for regular climbing enthusiasts.

  16. The stage at Gloucester Guildhall

    Add Gloucester Guildhall to your Itinerary

    Gloucester Guildhall

    Type

    Type:

    Event Venue

    Gloucester

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Located right in the heart of the city, Gloucester’s historic Guildhall is the cultural hub of the city and a vibrant venue home to an exciting programme of music, comedy, film, workshops and theatre with spaces available for meetings, conferences…

  17. Explore, Discover and Enjoy Cheltenham with Curious About Cheltenham

    Add Curious About Cheltenham to your Itinerary

    Curious About Cheltenham

    Cheltenham

    Dates

    Discover Cheltenham's "hidden treasures" with Curious About Cheltenham – quirky heritage walks for the curious.

  18. Football

    Add Brizen Farm Playing Field to your Itinerary

    Brizen Farm Playing Field

    Type

    Type:

    Outdoors

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Brizen Young People's Centre is situated on Up Hatherley Way. It is within walking distance of Morrisons, incase you need to buy drinks, snacks or use the toilet.

  19. Cotswold Driving Experiences

    Add Cotswold Driving Experiences to your Itinerary

    Tripadvisor Traveller Rating

    Tripadvisor Traveller Rating - from 501 review(s)from 501 review(s)

    Cotswold Driving Experiences

    Type

    Type:

    Motor Sports and Karting

    Cirencester

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Experience the range of rally driving thrills at the Gwynne Speed rally school based in the varying terrains of the neighbouring Cotswold Water Park.

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