Top 3 Itineraries in Winchester

No matter how long you plan to stay, there’s a perfect trip to Winchester.

If you only have a few days, Winchester weekend getaways are the perfect option. A 3 to 5-day stay in Winchester offers just enough time to soak in the highlights

For a balanced mix of sightseeing and relaxation, city breaks in Winchester are ideal. With a few extra days, you can dive deeper into Winchester’s most iconic landmarks, stroll through charming neighborhoods, and savor local cuisine at a leisurely pace.

For those who crave freedom and discovery, road trips through Winchester offer the perfect opportunity to explore beyond the city. With the open road ahead, you’ll uncover England's most scenic landscapes, visit charming towns, and discover hidden gems along the way.

Explore all the best trips for every travel style below and make your next trip to Winchester truly unforgettable!

If you’re as convinced as we are that Winchester belongs on your bucket list, you're in luck. The best trips to Winchester are just a quick search away.

Enter your dates below to discover the best travel packages in Winchester and start planning your next trip!

Discover the perfect Winchester itinerary with our handpicked list. Whether you're in Winchester for a short stay or a longer visit, there's an itinerary for you.

With detailed routes, top attractions, and insider tips, these 3 itineraries will help you experience the best of Winchester without missing a thing. Dive into our list and learn how to plan the ultimate trip to Winchester!

A scenic 9-day road trip through London, Bath, Norwich, Watford, and Greenwich is one of the best ways to experience England. With the freedom to travel at your own pace, you’ll have plenty of opportunities to make spontaneous stops between the planned activities on your itinerary.

A 9-day itinerary means that Winchester can easily be combined with other top destinations in England without stress. While it’s possible to travel between London, Bath, Norwich, Watford, and Greenwich by public transport, renting a car in England opens up a whole new level of freedom!

So, with 9 days to spend, all you need is a rental car, some hotel reservations, and this iconic road trip itinerary:

Day 1: Arrive in Norwich

• Arrival city: Norwich
• Accommodation: 4-star hotel in Norwich, e.g., Maids Head Hotel
• Sightseeing: Gravity Active Norwich

Begin your road trip adventure by picking up your rental car at the airport upon arrival in Norwich. Drive to your centrally located hotel, which offers convenient access to local attractions. Spend the day exploring nearby sights, and in the evening, enjoy dinner at a local restaurant, sampling regional flavors and soaking up the atmosphere.

Day 2: Explore Norwich

• Destinations: Norwich
• Driving distance: 104.83 km, approx. 1 hour and 47 minutes
• Accommodation: 2-star hotel in Cambridge, e.g., West Court
• Sightseeing: Norwich Market, Norwich Cathedral, and The Museum of Norwich at the Bridewell
• Recommended tour: Cambridge University Tour with Optional Entrance to Kings College

Set out on a day of discovery and visit Norwich Market, Norwich Cathedral, and The Museum of Norwich at the Bridewell. Take time to enjoy the scenery and local highlights of Norwich, with the freedom to stop at whatever sight catches your interest. By the end of the day, check-in at a new hotel, located in central Cambridge.

Day 3: Discover Watford, Leavesden, Winchester, and Cambridge

• Destinations: Watford, Leavesden, Winchester, and Cambridge
• Driving distance: 222.25 km, approx. 3 hours and 20 minutes
• Accommodation: 4-star hotel in Southampton, e.g., Moxy Southampton
• Sightseeing: Winchester Cathedral, Warner Bros. Studio Tour London, and Cassiobury Park
• Recommended tour: Southampton Cruise Port To Heathrow Airport private transfer

Spend the day exploring Winchester Cathedral, Warner Bros. Studio Tour London, and Cassiobury Park. Take scenic drives or walking tours to experience the area’s charm at your own pace. End the day by checking into a new hotel, conveniently located in central Southampton.

Day 4: Experience Bath, Salisbury, and Southampton

• Destinations: Bath, Salisbury, and Southampton
• Driving distance: 296.45 km, approx. 4 hours and 39 minutes
• Accommodation: 5-star hotel in London, e.g., Intercontinental Hotel London - The O2
• Sightseeing: Stonehenge, Pulteney Bridge, The Roman Baths, and National Trust - Mompesson House
• Recommended tour: Historical Pub Walking Tour in London With a Small Group

Continue your journey through Bath, Salisbury, and Southampton, where you can explore Stonehenge, Pulteney Bridge, The Roman Baths, and National Trust - Mompesson House. Make time for a break at a cozy café or scenic picnic spot. Wrap up the day by checking in at a hotel in the heart of London.

Day 5: Enjoy Sightseeing in London, Brentford, and Eton

• Destinations: London, Brentford, and Eton
• Driving distance: 87.89 km, approx. 2 hours and 55 minutes
• Accommodation: 5-star hotel in London, e.g., Intercontinental Hotel London - The O2
• Sightseeing: Tower of London, Borough Market, Windsor Castle, Royal Botanic Gardens, Kew, and Tower Bridge
• Recommended tour: Day trip to Stonehenge, Windsor Castle, and Bath from London

Drive through London, Brentford, and Eton, stopping to visit Tower of London, Borough Market, Windsor Castle, Royal Botanic Gardens, Kew, and Tower Bridge. Don't forget to embrace the opportunity to explore smaller towns and hidden gems along the way.

Day 6: Embrace the Spirit of London

• Destinations: London
• Driving distance: 11.59 km, approx. 1 hour and 7 minutes
• Accommodation: 5-star hotel in London, e.g., Intercontinental Hotel London - The O2
• Sightseeing: Big Ben, The Regent's Park, The British Museum, lastminute.com London Eye, and Westminster Abbey
• Recommended tour: Changing of the Guard Guided Walking Tour in London

Spend time discovering Big Ben, The Regent's Park, The British Museum, lastminute.com London Eye, and Westminster Abbey, with plenty of opportunities to engage in outdoor activities or enjoy local culture.

Day 7: Spend Time in London and Kensington

• Destinations: London and Kensington
• Driving distance: 12.84 km, approx. 1 hour and 14 minutes
• Accommodation: 5-star hotel in London, e.g., Intercontinental Hotel London - The O2
• Sightseeing: Royal Albert Hall, Madame Tussauds London, Hyde Park, Science Museum, and Victoria and Albert Museum
• Recommended tour: London 30 Top Sights with Fun Local Guide

Explore Royal Albert Hall, Madame Tussauds London, Hyde Park, Science Museum, and Victoria and Albert Museum at a relaxed pace. Make spontaneous stops for sightseeing, photography, or lunch at a family-run restaurant.

Day 8: Explore London and Greenwich

• Destinations: London and Greenwich
• Driving distance: 198.26 km, approx. 3 hours and 26 minutes
• Accommodation: 4-star hotel in Norwich, e.g., Maids Head Hotel
• Sightseeing: Greenwich Park, The National Gallery, St James's Park, Trafalgar Square, and Buckingham Palace
• Recommended tour: Cruise Wells Next The Sea on Historic RNLI and Dunkirk Veteran Lifeboat

Continue your road trip through London and Greenwich, enjoying the flexibility to explore Greenwich Park, The National Gallery, St James's Park, Trafalgar Square, and Buckingham Palace and nearby points of interest. As the day winds down, arrive at a new hotel in central Norwich.

Day 9: Bid Farewell to Norwich

• Departure city: Norwich
• Driving distance: 6.49 km, approx. 16 minutes
• Sightseeing: Eaton Park

Savor an hour or two for souvenir shopping or revisiting a favorite spot before it’s time to say goodbye to Norwich. Drop off your rental car at the airport a couple of hours before departure for a seamless end to your trip.

The estimated cost for a rental car and accommodations for each night along this route is around 1201 EUR, providing a value-for-money way to experience what's beyond Winchester.

Looking for something different? Explore more road trips with a stop in Winchester for alternative itineraries, routes, and durations.

Enjoy a 6-day city break in Winchester with the perfect itinerary, designed to showcase the city’s top sights, local flavors, and hidden corners.

No need to stress over the details – we’ve curated the perfect 6-day itinerary to give you a seamless outline for your trip. Use this itinerary to capture the best of Winchester without the hassle of planning.

Day 1: Begin Your Journey in Winchester

Arrive in Winchester and start your trip with a relaxing walk through town, discovering highlights like Oram's Arbour.

Take in the local charm as you wander the streets, and as evening approaches, indulge in a delicious dinner at a local restaurant. The Bishop on the Bridge, Winchester is a top-rated recommendation. Say 'cheers' and set the tone for an amazing vacation ahead!

Day 2: Discover Winchester's Most Iconic Attractions

Enjoy your first full day in Winchester by heading out for some must-see sightseeing. Explore around town and visit popular attractions like the iconic Winchester Cathedral, Winchester City Museum, and Buttercross Monument.

Choose a walking tour to embrace a relaxed exploration. Alternatively, go for a tour by bus or bike to cover a larger part of Winchester in the same amount of time.

In the evening, head out for another lovely dinner and raise a glass to a fantastic day of exploring!

Day 6: Savor Your Final Moments in Winchester

Spend your last few hours in Winchester soaking up the charm of the city at your own pace. Stroll through favorite spots or revisit local markets before bidding farewell to the city.

For more inspiration, explore the complete selection of city breaks in Winchester, all including pre-planned itineraries you can customize to suit your style. Start with a ready-to-go Winchester travel plan and make it your own by selecting tours, accommodations, and more.

A 5-day weekend getaway in Winchester offers the perfect break from the hustle of daily life.

However, with a well-planned Winchester itinerary, you can effortlessly experience the best of the city in just a few days. Picture yourself exploring iconic landmarks, savoring local cuisine, and wandering charming neighborhoods—it's all within reach as long as you know how to plan your trip properly.

With 5 days to spend, this is the perfect Winchester weekend itinerary for your trip:

Day 1 - Arrive in Winchester

Arrive in Winchester around noon and head to your hotel for an early check-in.

• Morning: Take some time to relax and refresh after your journey, or get a head start by visiting a nearby landmark.
• Afternoon: Ease into your trip with some sightseeing, for example, visiting Winnall Moors Nature Reserve, and soak in the surroundings.
• Evening: Dine at a popular restaurant and celebrate the start of the vacation with some drinks.

Day 2 - Discover Winchester’s Famous Sights

Maximize your first full day in Winchester with sightseeing, food, and drinks.

• Morning: Visit Winchester Cathedral early to avoid crowds and enjoy the views.
• Afternoon: Continue to National Trust - Winchester City Mill, stopping by King Alfred the Great Statue for a break and some photos.
• Evening: Dine at a popular restaurant and cap off the day at a local bar.

Day 3 - Immerse in the Local Culture of Winchester

No itinerary in Winchester is complete without trying the city's top local delicacies and experiencing the culture.

• Morning: Start with a traditional breakfast to fuel up for the day and then head to St. Catherine's Hill.
• Afternoon: Explore Hockley Railway Viaduct, stopping at markets, boutiques, museums, or exhibitions along the way.
• Evening: Enjoy a dinner featuring regional specialties and finish with a night tour of the city’s illuminated landmarks.

Day 5 - Depart from Winchester

Make the most of your last few hours in Winchester before your departure.

• Morning: Grab a light breakfast at a local bakery or café and take a final stroll nearby.
• Afternoon: If you have time, do some last-minute sightseeing.

For more ideas, explore our complete selection of weekend trips to Winchester. Whether you’re looking for a quick getaway or want to extend the weekend, these trips all come with pre-planned but customizable Winchester itineraries, ensuring an effortless travel experience.

As you explore Winchester, you’ll find countless layers of history, art, and local charm waiting to be uncovered.

Finding the right place to stay is essential for a comfortable trip. This is why we've also gathered our top recommendations for the best places to stay in Winchester for you.

Wherever your journey takes you, we’re here to make every step memorable. From expert tips to local insights, count on us to help you experience Winchester in a way that feels truly unforgettable!