Chat with us, powered by LiveChat Escorted UK Breaks for Solo Travellers | Winchester | Solos Holidays

What to expect

Winchester Cathedral

Winchester Cathedral

Visit Jane Austen's resting place

Guided Walking Tour

Guided Walking Tour

Discover Winchester's historic charm

Free Time

Free Time

Freedom to discover more of the city

Highclere Castle

Highclere Castle

Explore the castle & its grounds

About this trip...

Join Solos for a captivating weekend in England’s first capital, Winchester. Begin your three-night escorted break with a warm welcome dinner in Winchester, where you’ll meet your fellow travellers. Discover the rich history of Winchester on a guided walking tour, stepping back in time to tales of Alfred the Great and taking in the breathtaking Winchester Cathedral. Visit Highclere Castle, famous for being the filming location of Jeeves and Wooster and Downton Abbey. Conclude your weekend with a final group breakfast before departing, filled with unforgettable memories!

Activity Level: Activity Level Rating
What's this?

What's Included

  • Twin room for sole use with private facilities
  • Half-board with breakfast & dinner daily
  • Welcome drink
  • Walking tour of Winchester including Winchester Cathedral
  • Entry to Highclere Castle & grounds
  • Accompanying tour leader
  • Fully financially protected

Itinerary

  • Arrive in Winchester
  • Walking tour and Winchester Cathedral
  • Highclere Castle
  • Depart Winchester

What you'll be doing

Day One: Arrive in Winchester

Day One: Arrive in Winchester

Arriving at our hotel in Winchester at your leisure, we’ll enjoy a welcome drink before having dinner together at the hotel as a group.

Day Two: Winchester

Day Two: Winchester

After breakfast, we meet our guide for a walking tour of historic Winchester. Our walk takes us along the beautiful River Itchen, the ancient city walks, the ruins of a medieval bishop’s palace Wolvesey Castle, College Street with Winchester College and No 8 College Street - where Jane Austen spent the final six weeks of her life, the ancient Kingsgate arch and the Cathedral Close, before visiting the famous Winchester Cathedral. We can then opt to re-join our guide for a tour taking in the Peninsula Barracks and the Westgate,  enjoy continuing to explore this historic city at our leisure, or we have the option to head back to relax at the hotel before joining our fellow travellers for dinner.

Day Three: Highclere Castle

Day Three: Highclere Castle

After a leisurely breakfast, we'll make the short journey to Highclere Castle - famous for being the filming location for Downton Abbey and Jeeves and Wooster. With access to wander the castle and its grounds, you can explore how the castle has been transformed from its roots in Anglo Saxon Times to a medieval palace, a Tudor place house, a Georgian house and to this iconic Victorian Castle. Highclere sits within an arcadian parkland designed by Capability Brown in 1771 where we can explore the many areas including the original Monk’s Garden, the Secret Garden and the Healing Herb Garden.

Day Four: Depart Winchester

Day Four: Depart Winchester

After a final breakfast as a group, we depart Winchester at our leisure.

Trip Reviews

Very informative

The Winchester day was very informative and enjoyable. The guide we had in the morning was excellent.
The situation of the hotel so close to the cathedral was great. 

Gill

Central location of hotel

Lovely guided tours of Winchester and Cathedral. Central location of hotel made it easy to walk around.

Andrea

Close to Cathedral

Being close to the Cathedral meant we could and did join in Cathedral activities.

Keith

Excellent tour leader

Excellent tour leader and day trips

David

Accommodation

Four-Star Winchester Wessex Hotel by Sunday

The Winchester Wessex Hotel by Sunday is a comfortable property with an amazing location overlooking the cathedral and cathedral grounds in the heart of historic Winchester.  It’s prime location means that you are just steps from everything this wonderful city has to offer including traditional pubs and dining overlooking the catherdral and everything the High Street has to offer.

Facilities include

The Winchester Wessex Hotel by Sunday offers Brasserie-style meals in the Wessex Restaurant, which offers unbeatable views of Winchester Cathedral and those looking to relax can take a drink from the selection offered in the King’s Lounge bar. Guests can enjoy free Wi-Fi throughout the hotel. Please note that although there is a lift to most rooms, there are some steps around the property which you will need to be able to manage independently.

Room includes

The Winchester Wessex Hotel by Sunday features comfortable and recently renovated rooms featuring double bed and traditional décor to match the historic setting of the city. Each room offers a flat screen TV, complimentary WiFi, tea & coffee making facilities, hairdryer, iron and board. Bathroom with shower over bathtub.

Dates & Prices

Departure Return Nights Price from Other Info Regional flights
17 Jul 2026 20 Jul 2026 3
£699
 

Essential Information

Gratuities
There is often confusion on the question of gratuities, since it frequently depends on the type of holiday, location and, of course, your attitude towards tipping, as to what is normally expected. To give you a rough idea, we have given appropriate guidance below. The Tour Leader will be on hand to offer advice or suggestions if required but gratuities are offered entirely at the sole discretion of the individual. We suggest a group collection at the beginning of your holiday to cover drivers, guides, porters and hotel staff of approximately £20. Your Tour Leader will collect this on your behalf and distribute it accordingly, thus relieving you of the burden of who, when and how much to tip.
Location & Transport
The Winchester Wessex Hotel by Sunday, Paternoster Row, Winchester, SO23 9LQ by car or a 15 minute walk or a 5 minute taxi ride from Winchester railway station which is directly connected by rail to cities such as London, Reading, Oxford, Birmingham and Manchester.
 
Porterage is availble at the hotel for £3 per bag in and out.
Parking
Parking is available at the hotel on a first come first served basis and carries a charge of £15 per night payable directly to the hotel. Alternative parking can be found opposite the hotel on Colebrook Street or nearby Tower Street with a charge of £18 per 24 hours.
Dress Code
The dress code for during the day is casual. In the evenings the dress code is smart casual. Comfortable shoes for walking and sightseeing are recommended.

Rated as Excellent (4.8/5) by our customers

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First Class

I’d highly recommend Solos to people looking to travel on their own with a group of like minded people.
-David F

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Fabulous experience

Solos are extremely organised and provide fantastic holidays for people on their own. The tour leaders are of a very high standard and are extremely caring with the guests.
-Carole

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Don't Delay any Longer!

This was my first Solos holiday and it hugely exceeded my expectations. Lovely, lovely people made the holiday so special.....it will stay with me for always
-L Heaton

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Well worth going

I’ve recently returned from my first Solos holiday and had a fantastic time. I can honestly say that I enjoyed every minute, and the memories will last a lifetime.
-Patricia B

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