Top 3 Itineraries in Chester

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

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

For a balanced mix of sightseeing and relaxation, city breaks in Chester are ideal. With a few extra days, you can dive deeper into Chester’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 Chester 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 Chester truly unforgettable!

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

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

Discover the perfect Chester itinerary with our handpicked list. Whether you're in Chester 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 Chester without missing a thing. Dive into our list and learn how to plan the ultimate trip to Chester!

A scenic 12-day road trip through London, Bath, Chester, Christchurch, and Bournemouth 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 12-day itinerary means that Chester can easily be combined with other top destinations in England without stress. While it’s possible to travel between London, Bath, Chester, Christchurch, and Bournemouth by public transport, renting a car in England opens up a whole new level of freedom!

So, with 12 days to spend, all you need is a rental car, some hotel reservations, and this iconic road trip itinerary:

Day 1: Arrive in Bournemouth

• Arrival city: Bournemouth
• Accommodation: hotel in Bournemouth, e.g., Derby Manor Hotel & Restaurant
• Sightseeing: Bournemouth Parks - Lower Gardens

Begin your road trip adventure by picking up your rental car at the airport upon arrival in Bournemouth. 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 Christchurch, Bournemouth, and Bournemouth, Christchurch and Poole

• Destinations: Christchurch, Bournemouth, and Bournemouth, Christchurch and Poole
• Driving distance: 48.31 km, approx. 1 hour and 38 minutes
• Accommodation: hotel in Bournemouth, e.g., Derby Manor Hotel & Restaurant
• Sightseeing: Boscombe Chine Gardens, Canford Heath Nature Reserve, Bournemouth Beach, Boscombe Pier, and Mudeford Quay

Set out on a day of discovery and visit Boscombe Chine Gardens, Canford Heath Nature Reserve, Bournemouth Beach, Boscombe Pier, and Mudeford Quay. Take time to enjoy the scenery and local highlights of Christchurch, Bournemouth, and Bournemouth, Christchurch and Poole, with the freedom to stop at whatever sight catches your interest.

Day 3: Discover Bath and Salisbury

• Destinations: Bath and Salisbury
• Driving distance: 140.13 km, approx. 2 hours and 58 minutes
• Accommodation: 4-star hotel in Bristol, e.g., Clayton Hotel Bristol City
• Sightseeing: Thermae Bath Spa, Stonehenge, Pulteney Bridge, The Roman Baths, and Salisbury Cathedral
• Recommended tour: Blackbeard to Banksy - The Ultimate Walking Tour of Bristol

Spend the day exploring Thermae Bath Spa, Stonehenge, Pulteney Bridge, The Roman Baths, and Salisbury Cathedral. 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 Bristol.

Day 4: Experience Liverpool and Featherstone

• Destinations: Liverpool and Featherstone
• Driving distance: 299.04 km, approx. 3 hours and 47 minutes
• Accommodation: 4-star hotel in Liverpool, e.g., Titanic Hotel Liverpool
• Sightseeing: National Trust - Moseley Old Hall, Royal Albert Dock Liverpool, Museum of Liverpool, and The Liverpool Waterfront
• Recommended tour: A Walk Through Time: History of Liverpool Walking Tour

Continue your journey through Liverpool and Featherstone, where you can explore National Trust - Moseley Old Hall, Royal Albert Dock Liverpool, Museum of Liverpool, and The Liverpool Waterfront. 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 Liverpool.

Day 5: Enjoy Sightseeing in Chester and Edensor

• Destinations: Chester and Edensor
• Driving distance: 270.26 km, approx. 4 hours and 22 minutes
• Accommodation: 4-star hotel in Birmingham, e.g., Leonardo Royal Hotel Birmingham
• Sightseeing: Peak District National Park, Chester Zoo, and Chatsworth House
• Recommended tour: From Canals and Victorians to Today's City: Birmingham Walking Tour

Drive through Chester and Edensor, stopping to visit Peak District National Park, Chester Zoo, and Chatsworth House. Don't forget to embrace the opportunity to explore smaller towns and hidden gems along the way. Conclude your day by settling into a centrally located hotel in Birmingham.

Day 6: Embrace the Spirit of Warwick, Leavesden, and Stratford-upon-Avon

• Destinations: Warwick, Leavesden, and Stratford-upon-Avon
• Driving distance: 260.15 km, approx. 3 hours and 49 minutes
• Accommodation: 5-star hotel in London, e.g., Intercontinental Hotel London - The O2
• Sightseeing: Stratford Butterfly Farm, Shakespeare's Birthplace, Warwick Castle, and Warner Bros. Studio Tour London
• Recommended tour: Walking Tour for Muggles in London

Spend time discovering Stratford Butterfly Farm, Shakespeare's Birthplace, Warwick Castle, and Warner Bros. Studio Tour London, with plenty of opportunities to engage in outdoor activities or enjoy local culture. After a day of exploring, check into a hotel in London.

Day 7: Spend Time in London and Greenwich

• Destinations: London and Greenwich
• Driving distance: 35.1 km, approx. 2 hours and 18 minutes
• Accommodation: 5-star hotel in London, e.g., Intercontinental Hotel London - The O2
• Sightseeing: Greenwich Park, The Regent's Park, St James's Park, Madame Tussauds London, and Buckingham Palace
• Recommended tour: London 30 Top Sights with Fun Local Guide

Explore Greenwich Park, The Regent's Park, St James's Park, Madame Tussauds London, and Buckingham Palace at a relaxed pace. Make spontaneous stops for sightseeing, photography, or lunch at a family-run restaurant.

Day 8: Explore London

• Destinations: London
• Driving distance: 7.84 km, approx. 54 minutes
• Accommodation: 5-star hotel in London, e.g., Intercontinental Hotel London - The O2
• Sightseeing: Big Ben, lastminute.com London Eye, Borough Market, Tate Modern, and London Bridge
• Recommended tour: Historical Pub Walking Tour in London With a Small Group

Continue your road trip through London, enjoying the flexibility to explore Big Ben, lastminute.com London Eye, Borough Market, Tate Modern, and London Bridge and nearby points of interest.

Day 9: Wander Through London, Brentford, and Kensington

• Destinations: London, Brentford, and Kensington
• Driving distance: 32.28 km, approx. 1 hour and 46 minutes
• Accommodation: 5-star hotel in London, e.g., Intercontinental Hotel London - The O2
• Sightseeing: Royal Albert Hall, Hyde Park, Science Museum, Royal Botanic Gardens, Kew, and Victoria and Albert Museum
• Recommended tour: Changing of the Guard Guided Walking Tour in London

Visit Royal Albert Hall, Hyde Park, Science Museum, Royal Botanic Gardens, Kew, and Victoria and Albert Museum as you navigate scenic routes. Take time to enjoy local markets, trails, or viewpoints that catch your eye.

Day 10: Uncover London

• Destinations: London
• Driving distance: 12.56 km, approx. 1 hour and 3 minutes
• Accommodation: 5-star hotel in London, e.g., Intercontinental Hotel London - The O2
• Sightseeing: Tower of London, The British Museum, The National Gallery, Trafalgar Square, and Tower Bridge
• Recommended tour: Day trip to Stonehenge, Windsor Castle, and Bath from London

Continue your exploration of Tower of London, The British Museum, The National Gallery, Trafalgar Square, and Tower Bridge, taking your time to enjoy scenic drives or leisurely strolls that add to the adventure.

Day 11: Journey Through Windsor, Eton, and Cheapside

• Destinations: Windsor, Eton, and Cheapside
• Driving distance: 184.76 km, approx. 3 hours and 1 minute
• Accommodation: hotel in Bournemouth, e.g., Derby Manor Hotel & Restaurant
• Sightseeing: Windsor Castle, LEGOLAND® Windsor Resort, and Windsor Great Park
• Recommended tour: E-Bike Half-Day Trip to Harrys Rock or Corfé Castle

Take in the highlights of Windsor Castle, LEGOLAND® Windsor Resort, and Windsor Great Park, with plenty of opportunities to pause for a break in charming villages or serene natural settings. Conclude your day with a stay at a different hotel in the heart of Bournemouth.

Day 12: Bid Farewell to Bournemouth

• Departure city: Bournemouth
• Driving distance: 4.45 km, approx. 28 minutes
• Sightseeing: Bournemouth Upper Gardens

Savor an hour or two for souvenir shopping or revisiting a favorite spot before it’s time to say goodbye to Bournemouth. 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 1591 EUR, providing a value-for-money way to experience what's beyond Chester.

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

Enjoy a 7-day city break in Chester 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 7-day itinerary to give you a seamless outline for your trip. Use this itinerary to capture the best of Chester without the hassle of planning.

Day 1: Begin Your Journey in Chester

Arrive in Chester and start your trip with a relaxing walk through town, discovering highlights like Eastgate Clock.

Take in the local charm as you wander the streets, and as evening approaches, indulge in a delicious dinner at a local restaurant. 1539 Restaurant and Bar is a top-rated recommendation. Say 'cheers' and set the tone for an amazing vacation ahead!

Day 2: Discover Chester's Most Iconic Attractions

Enjoy your first full day in Chester by heading out for some must-see sightseeing. Explore around town and visit popular attractions like the iconic The Grosvenor Museum and Cheshire Military Museum.

One of the best ways to quickly learn how to navigate the city is to join one of the many great city sightseeing tours in Chester. Choose a walking tour to embrace a relaxed exploration. Alternatively, go for a tour by bus or bike to cover a larger part of Chester 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: Connect With the Local Culture in Chester

No Chester itinerary is complete without learning something about the local culture. The large selection of cultural tours in Chester has something for every traveler.

If you prefer sightseeing on your own, head out to explore Chester Zoo and Countess of Chester Country Park, other popular attractions in Chester.

End the day with a sunset walk and dinner around Chester Zoo.

Day 7: Savor Your Final Moments in Chester

Spend your last few hours in Chester 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.

We recommend booking your transfers from Chester in advance.

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

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

However, with a well-planned Chester 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 Chester weekend itinerary for your trip:

Day 1 - Arrive in Chester

Arrive in Chester 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 Escapism Chester, and soak in the surroundings.
• Evening: Dine at a popular restaurant and celebrate the start of the vacation with some drinks.

Day 2 - Discover Chester’s Famous Sights

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

• Morning: Visit Chester Cathedral early to avoid crowds and enjoy the views.
• Afternoon: Continue to Eastgate Clock, stopping by Chester Cross for a break and some photos.
• Evening: Dine at a popular restaurant and cap off the day at a local bar.
• Tip: Use part of the morning to join one of the many city sightseeing tours in Chester and get a guided journey through the top attractions in the city.

Day 3 - Immerse in the Local Culture of Chester

No itinerary in Chester 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 Queens Park Bridge.
• Afternoon: Explore Chester Roman Gardens, 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 Chester

Make the most of your last few hours in Chester 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 Chester. Whether you’re looking for a quick getaway or want to extend the weekend, these trips all come with pre-planned but customizable Chester itineraries, ensuring an effortless travel experience.

As you explore Chester, 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 Chester 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 Chester in a way that feels truly unforgettable!