The Cotswolds- Paige MacLeod and Friends

Monday 19th May – Saturday 24th May 2025

Duration: 6 Days / 5 Nights

Overview

On a bespoke, thoughtfully curated trip, enjoy exploring the beauty of the Cotswolds. A region cherished for its pastoral charm, the landscape is a tapestry of lush river valleys, rolling green fields and villages of honey-coloured stone. Designated an Area of Outstanding Natural Beauty, the region is also rich in history – peppered with ancient ruins, tumbling castles and intriguing archaeological sites. With a fantastic network of quiet rural lanes, leafy bridleways, and winding riverside trails, it’s the perfect place to explore by foot and by bicycle. Joined by a knowledgable Wilderness guide, visit the stunning cities of Bath and Oxford, Snowhill’s famous Lavender Fields. As the soft evening light slips below the hedgerows, relax in hand-picked, bespoke accommodation and enjoy delicious meals full of fresh, seasonal produce.

 

 

Highlights

  • Enjoy cycling along leafy bridleways and quiet country lanes with your knowledgable Wilderness guide.
  • Explore pretty limestone villages full of classic Cotswold architecture and quintessential English charm.
  • Stay in traditional local inns, enjoying excellent cuisine and welcoming hospitality.

Day by Day

Day 1 - Monday 19th May - Arrival and Blenheim Palace

Arrive at Oxford train station this morning to meet your Wilderness guide and start your tour of the Cotswolds. A short drive north will take you out of the city and into the easterly folds of the Cotswolds. Visit the incredible Blenheim Palace, a UNESCO World Heritage Site and the birthplace and ancestral home of Sir Winston Churchill. After lunch, explore the peaceful grounds before visiting Churchill’s grave in the nearby village of Bladon. Travel to Bibury and visit Arlington Row – a stunning string of cottages built in 1380. This evening, settle into your lovely accommodation.

Meals Included: Lunch and Dinner

Day 2 - Tuesday 20th May - Windrush Valley and Chedworth Villa

Following a leisurely breakfast, enjoy a circular walk through the Windrush Valley. Begin by meandering through the pretty market town of Burford, looking out over sweeping arable fields and passing through the now deserted hamlet of Widford. Not much remains of the settlement now, apart from the tiny 13th-century St Oswald’s Church that sits quietly in a grassy meadow. Enjoy a packed lunch, listening to the skylarks and blackbirds, before heading to explore the  remains of Chedworth Villa – one of the grandest Roman villas in Britain. Tucked beneath old trees, the peaceful tranquillity of the place is matched only by its exceptional insight into life during the Roman period in Britain. This evening, enjoy a delicious, locally sourced dinner.

Meals Included: Breakfast, Lunch and Dinner

Day 3 - Wednesday 21st May - E-biking Malmesbury and Cirencester

As the morning light spills through the windows, join your guide for an engaging circular ride that passes in and out of honey-coloured villages. Cycle past Highgrove, a private residence of His Majesty King Charles III, before continuing to Malmesbury to visit the Abbey. With a rich history, Malmesbury Abbey is thought to have been home to the first king of England (King Athelstan the Glorious). Continue towards Cirencester to enjoy lunch. This afternoon, make your way along the leafy lanes back to your hotel, where a hot shower followed by a cool drink will carry you into another relaxing evening.

Meals Included: Breakfast, Lunch and Dinner

Day 4 - Thursday 22nd May - Bourton and the Slaughters

This morning, enjoy visiting Bourton-on-the-Water, which is regularly voted one of the prettiest villages in England. Known for its five stone bridges that arch across the River Windrush, it’s an idyllic place to enjoy a morning meander. Transfer over to Lower Slaughter and enjoy a circular walk that ribbons its way through the countryside. Along with wonderful views, the trail passes a 16th-century Dovecote and through Upper Slaughter, another quintessential Cotswold village home to a beautiful parish church. After the walk, transfer to your award-winning hotel nestled in the charming town of Chipping Camden.

Meals Included: Breakfast, Lunch and Dinner

Day 5 - Friday 23rd May - The Cotswolds Way and Stratford-Upon-Avon

After breakfast, spend the morning hiking a beautiful section of the Cotswold Way – a 164km trail that stretches from the old wool merchants’ town of Chipping Camden to the Roman city of Bath. Along the way, pause to ascend the famous gothic folly Broadway Tower, which offers panoramic views of the surrounding countryside. After lunch, visit Stratford-upon-Avon, the birthplace and burial ground of William Shakespeare. Enjoy a guided tour of the Royal Shakespeare Company, learning about those who have played a pivotal role in its unique and fascinating history. Enjoy dinner at a historic country inn this evening which brims with traditional charm.

Meals Included: Breakfast, Lunch and Dinner

Day 6 - Saturday 24th May - Snowshill and Depart

As sunshine pools in through the open window, enjoy your last breakfast before heading out with your guide for another cracker of a walk. From Snowshill Manor, stroll through the village and enjoy the sweeping views of the valley towards Stanton. Joining the Cotswolds Way, wander through a quiet woodland, an old orchard and across a babbling brook before returning to the Manor.

Time permitting there are a number of options before we head back to Oxford. Perhaps a visit to the wonderful Daylesford  organic farm shop or a visit the ancient site of the Rollright Stones and learn about the history and folklore of the King’s Men and the Whispering Knights.

Your guide will bid you a fond farewell at Oxford Station where you can continue your return journey to the city.

Meals Included: Breakfast and Lunch

Trip Details

Inclusions Read More
  • All accommodation from Day 1 to Day 6
  • Meals as indicated above
  • Services of an experienced and knowledgeable qualified guide from Day 1 to Day 6
  • Ground transportation from Day 1 to Day 6, including all parking fees
  • E-Bike hire and equipment for day 3 (Road bikes can be available if preferred)
  • All guided hikes and activities mentioned in the itinerary, including:
    • Entry to Blenhiem Palace and Gardens
    • Entry to Chedworth Roman Villa
    • Entry to Snowshill Manor
    • Entry to Shakespeares Birth Place
    • Entry to the Royal Shakespeare Company
    • Entry to Broadway Tour
  • Personalised trip design and delivery
  • Snacks throughout the trip
  • 24 hour in-country support from the Wilderness Team
Exclusions Read More
  • Flights
  • Travel insurance
  • Train travel from Oxford to London
  • Meals not mentioned in the inclusions
  • Activities and entrance fees not mentioned in the inclusions
  • Gratuities
Pricing Read More

The price of this trip is as follows  and is based on availability at the time of booking.

6 people £3035.00 per person

7 people £2905.00 per person

8 people £2810.00 per person

10 people £3215.00 per person

Pay a 25% deposit

Terms & Conditions Read More

Please see our booking terms here.

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