Chat with us, powered by LiveChat Short City Tours for Solo Travelers | Winchester, England | 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 guided city tour with a warm welcome dinner in Winchester, where you’ll meet your fellow travelers. 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!

 

*Please note: airport transfers are not included for our UK breaks. Our team can assist with adding on additional hotel nights to extend your stay based on availability.

Activity Level: Activity Level Rating
What's this?

What's Included

  • Private Room
  • Breakfast & dinner daily
  • Welcome drink
  • Walking tour of Winchester including Winchester Cathedral
  • Entry to Highclere Castle & grounds
  • Accompanying tour leader

What's Extra

  • International flights not included. Let us help you book them! Learn more.
  • Travel insurance
  • Tips & drinks
  • Meals when not included in the itinerary
  • Activities when not included in the itinerary
  • Airport Transfers not included for UK Breaks

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.

Accommodations

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.  Its prime location means that you are just steps from everything this wonderful city has to offer including traditional pubs and dining overlooking the cathedral.

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 a double bed and traditional décor to match the historic setting of the city. Each room offers a flat-screen TV, complimentary Wi-Fi, tea & coffee-making facilities, hairdryer, iron and board. The bathrooms have a shower over the bath.

Dates & Prices

Departure Return Nights Price from Other Info
Jul 17 2026 Jul 20 2026 3
$875
 

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.
Flights & Airport Transfers
Whether you'd like us to arrange your flights or prefer to book your own, we're here to make the process easy. Our team can secure flights from the location that suits you best, or provide all the arrival and departure details you'll need if booking independently.

Arrival & departure airport transfers are included for the majority of trips EXCEPT our UK Breaks, regardless if you book your own flights or if we book them for you. To learn more about flight options, payments, and transfers, click here.

 
Travel Insurance
We strongly recommend purchasing travel insurance before any trip — it safeguards you against unexpected issues like illness, cancellations, or lost luggage. It also protects your health and travel investment, giving you peace of mind to fully enjoy your journey. Click here. to learn more.
Check-in / Check-Out Times
Check-in time is 3pm and check-out time is 11am.
Luggage storage will be available.
Early check-in / late check-out will be on request and subject to availability at check-in.

Rated as Excellent (4.8/5) by our customers

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Fantastic time

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

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Highly Recommended

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

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Brilliant Week!

We laughed until our bellies ached. It was such a brilliant week.
-Janev

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Go for it!

I still get a bit nervous but this will be my third time with Solos and its one of the best decisions I have ever made- everyone is so friendly, just go for it!!
-Jane

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