Chat with us, powered by LiveChat Short City Tours for Solo Travelers | Winchester, England | Solos Holidays

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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.

Trip Reviews

Close to the Cathedral

Getting to know the other visitors. Being close to the Cathedral meant we could and did join in Cathedral activities

Keith

Tour leader was AMAZING!

Firstly, our tour leader was AMAZING!!! This was my first time with solo holidays and she made me feel so welcome and comfortable. The trip itself was brilliant. The hotel’s location couldn’t have been better. Very central to everything. Everything was organised perfectly and the whole weekend just flowed so well. I also had a lovely group of people to spend it with.

Priya

Making new friends

Making new friends, the tour leader was the best!!

Anne

Central location of hotel

I could just relax and leave arrangements to solo's. Nice bunch of people, I never felt alone, but could wander off on my own when I felt like it. There is no pressure and it all felt free and easy. Lovely guided tours of Winchester and Cathedral. Central location of hotel made it easy to walk around and explore the town.

Andrea

Accommodations

The Winchester Hotel & Spa

Perfectly situated, just a 10 minute walk from Winchester historic city centre and train station, the four-star Winchester Hotel & Spa is the perfect base whilst visiting this pretty and interesting city whilst offering great facilities where you can unwind after a day of sightseeing.
Facilities Include
The hotel offers great facilities such as:
  • Restaurant
  • Bar
  • Swimming Pool
  • Hot Tub
  • Spa * (Extra cost applies)
  • Outdoor Terrace
  • Complimentary WiFi
Room Includes
The comfortable rooms feature air-conditioning, WiFi, TV, tea & coffee making facilities, safe, hairdryer and private ensuite facilities.

Dates & Prices

Departure Return Nights Price from Other Info
Jul 16 2027 Jul 19 2027 3
$1149
  

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.
Check-in / Check-Out Times
Check-in is from 3pm and check-out is by 11am.
 
Early check-in / late check-out is subject to availability and extra charges may apply.
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
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.
 
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.
WhatsApp Group

Shortly before your holiday, you will be invited to join an optional WhatsApp group to connect with your fellow travellers and your Tour Leader.

Currency UK
£ - Sterling in London
Booking Information
It is important to consider whether this trip is suitable for your level of fitness, mobility, and any medical conditions. We are committed to making reasonable adjustments wherever possible. Please tell us about any disability, medical condition, or additional requirements before booking so we can assess whether we can safely and appropriately accommodate your needs. If you are unsure whether this trip is suitable for you, please contact us before booking. We will be happy to discuss the trip requirements and your individual circumstances.
Location & Transport
The hotel address is Worth Lane, Winchester, SO23 7AB which is located a 10 minute walk from Winchester Railway Station and not far from junctions 9 southbound / 11 northbound of the M3 or the Three Maids Hill junction of the A34. 
 
Parking is available for a fee. There are two car parks, one at the rear of the hotel through the barrier and a larger pay & display car park at the front of the hotel.

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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