9-Day England Self-Drive Road Trip With Itinerary from Liverpool traveling east to Chester, Windermere, York, and Whitby

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Liverpool city and cathedral, aerial shot
Photo of aerial view of the city of Liverpool in United Kingdom.
9-Day England Self-Drive Road Trip With Itinerary from Liverpool traveling east to Chester, Windermere, York, and Whitby
9-Day England Self-Drive Road Trip With Itinerary from Liverpool traveling east to Chester, Windermere, York, and Whitby
9-Day England Self-Drive Road Trip With Itinerary from Liverpool traveling east to Chester, Windermere, York, and Whitby
9-Day England Self-Drive Road Trip With Itinerary from Liverpool traveling east to Chester, Windermere, York, and Whitby
9-Day England Self-Drive Road Trip With Itinerary from Liverpool traveling east to Chester, Windermere, York, and Whitby
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Experience the freedom of the open road on an unforgettable 9-day road trip in England! Embark on a self-drive tour that caters to every traveler, featuring destinations like Liverpool, Chester, Near Sawrey, Rydal, Windermere, Grasmere, Keswick, York, Whitby, Hutton-le-Hole, Rievaulx, and Helmsley.

This perfectly planned road trip itinerary takes you through some of the best places to see in England. You will spend 3 nights in Liverpool, 1 night in Chester, 2 nights in Windermere, 1 night in York, and 1 night in Whitby. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in England. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have you covered.

Upon arriving in Liverpool, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover England on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in England. Royal Albert Dock Liverpool and Chester Zoo are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Liverpool, Chester, Near Sawrey, Rydal, Windermere, Grasmere, Keswick, York, Whitby, Hutton-le-Hole, Rievaulx, and Helmsley, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of England. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in England.

Throughout your road trip in England, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in England.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodations, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in England fill up quickly, so book your spot early. Select a date and start planning your road trip in England today!

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Driver’s age is 30 - 65
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Pick-up: 10:00
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Day1

Day 1

  • Liverpool - Arrival day
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  • Bold Street
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Your road trip adventure in England begins as soon as you reach Liverpool and pick up your car. You’ll stay here for 2 nights and explore what to see in Liverpool, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

Liverpool is a beautiful city with plenty to discover. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Liverpool. Make yourself at home and unwind before heading out again.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Liverpool, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at KURDINA RESTAURANT AND BAR, a top-rated dining destination in Liverpool. If you're in the mood to try something new, consider Rudy's Pizza Napoletana - Castle Street, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Quarter. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Liverpool this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Brass Monkey stands out as an excellent choice for a post-dinner cocktail. Alternatively, Sanctuary Bar offers an ideal atmosphere to enjoy the pleasures of the night. The Underground Gin Society is also a great option that provides a perfect setting for a relaxing evening.

Raise a toast to the start of your 9-day road trip in England!

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Day2

Day 2

  • Liverpool
  • More

Drive 11 km, 52 min

  • Liverpool Metropolitan Cathedral
  • The Liverpool Waterfront
  • Museum of Liverpool
  • The Beatles Story
  • Royal Albert Dock Liverpool
  • Wheel Of Liverpool
  • More

Day 2 offers an itinerary packed with the best things to see in Liverpool. You’ll stay in Liverpool for 1 night more, offering you enough time to explore at a relaxed pace.

No visit to Liverpool is complete without Liverpool Metropolitan Cathedral. This increasingly popular church is one of the top attractions in the city. Proceed to The Liverpool Waterfront, another must-visit attraction.

As you wander through the inviting streets of Liverpool, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Museum Of Liverpool. This captivating museum is a traveler-favorite. Not far away, you’ll find The Beatles Story, another key site on your sightseeing itinerary. Royal Albert Dock Liverpool is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at The Wheel Of Liverpool and uncover why it's recognized as one of the city's most underrated attractions.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in England. You can explore and select activities under each day of your itinerary.

After a day of adventure, treat yourself to an exquisite dinner at one of Liverpool's best restaurants.

Make sure to reserve a table at OH ME OH MY, an iconic dining spot in Liverpool. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Georgie Porgy Cafe, a popular restaurant in Liverpool. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Queens Wine Bar and Bistro, a hidden gem nestled in Liverpool. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Mcguffie & Co, where the evening is just getting started. In the same way, Ye Hole In Ye Wall offers a unique charm perfect for experiencing the local bar scene in Liverpool. Rox Cocktail Bar Liverpool is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Savor another day of unforgettable experiences in England!

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Day3

Day 3

  • Liverpool
  • Cheshire West and Chester
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Drive 45 km, 1 hour 16 min

  • Chester Zoo
  • The Grosvenor Museum
  • Chester Cathedral
  • Eastgate and Eastgate Clock
  • Chester Roman Amphitheatre
  • More

Your itinerary for day 3 of your road trip in England includes 1 stop and features some of the highlights of Chester. At the end of the day, enjoy the comforts of a top-rated hotel in Chester, where you'll spend 1 night.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Chester. This drive usually takes around 41 min, without any stops or traffic disruptions.

Spend your afternoon discovering Chester Zoo, a popular zoo known for its picture-perfect features. Next, continue your sightseeing at The Grosvenor Museum, an increasingly popular museum.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Chester Cathedral and uncover the details of this stunning church. Make sure to also explore Eastgate And Eastgate Clock, a frequently visited monument. For your last stop, consider Chester Roman Amphitheatre, a heritage-rich archeological site that many travelers find worth the detour.

When you’re done exploring for the day, you’ll drive to your hotel in Chester. Check in and relax before you head out to tour the city.

Indulge in a memorable dining experience at one of Chester's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a delicious meal at 1539 Restaurant and Bar, a highly-rated dining destination in Chester. If you're eager to try something different, consider The Church Chester Bar & Restaurant, another top spot with a tantalizing menu. You might also want to secure a reservation at BarLounge - Chester. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Chester this evening.

To truly maximize your evening out, consider visiting Prohibition after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Liquor And Co, another bar with an inviting ambiance. Similarly, Craft & Company also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Head back to your accommodation in Chester and get some rest to prepare for another magical day of your road trip in England.

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Day4

Day 4

  • Cheshire West and Chester
  • Near and Far Sawrey
  • Rydal
  • Bowness-on-Windermere
  • More

Drive 231 km, 3 hours 36 min

  • Ambleside Roman Fort
  • National Trust - Hill Top
  • Rydal Cave
  • More

Dive into day 4 of your remarkable road trip in England. Today you'll explore 3 destinations, including Clappersgate, Near Sawrey, and Rydal. At the end of the day, you’ll unwind at one of the finest accommodations in Windermere, where you'll spend 2 nights.

Fasten your seatbelt and make your way to your next stop — Clappersgate, home to many well-known sights in the region. Keep in mind that your travel time from Chester to Clappersgate may take around 2 hours 3 min without traffic disruptions. Upon arrival in Clappersgate, we highly recommend checking out some of the top attractions.

For a more meaningful self-guided tour of the hamlet's best attractions, visit Ambleside Roman Fort, an underrated archeological site that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

Continue your road trip and head to your next destination, Near Sawrey. This car ride takes around 18 min.

National Trust - Hill Top is a worthwhile museum we recommend visiting today. Discover its standout features before continuing your self-guided tour.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Rydal. This drive usually takes around 22 min, without any stops or traffic disruptions.

When you're ready for some sights, head to Rydal Cave, an increasingly popular cave in Rydal. Explore its eye-catching features at your own pace before you continue your journey.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Windermere. Windermere offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

After a day of adventure, treat yourself to an exquisite dinner at one of Windermere's best restaurants.

Savor another day of unforgettable experiences in England!

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Day5

Day 5

  • Bowness-on-Windermere
  • Grasmere
  • Keswick
  • More

Drive 88 km, 2 hours 13 min

  • Lake District National Park
  • National Trust - Allan Bank and Grasmere
  • Castlerigg stone circle
  • Friars Crag
  • Ashness Bridge
  • More

Greet day 5 of your road trip in England with a smile and start your day with a hearty breakfast. You have 1 night to stay in Windermere, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Grasmere and Keswick.

As you explore Grasmere’s charming streets, take in the lively atmosphere and get to know the character of the village.

Our first attraction recommendation in Grasmere is Lake District National Park, a notable national park that draws attention for its eye-catching features.

Continue your road trip and head to your next destination, Keswick. This car ride takes around 22 min.

Savor the day by heading to National Trust - Allan Bank And Grasmere, a worthwhile point of interest that draws visitors from near and far.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Keswick may take around 22 min. Upon your arrival in Keswick, you’ll be greeted with the opportunity to do some sightseeing and exploring.

One of our top recommendations for your sightseeing is Castlerigg Stone Circle. Spend some time admiring the historic features of the archeological site before you continue to your next stop. Then, head to Friars Crag. This increasingly popular park is a traveler-favorite in the village.

If you're keen to see more, continue to Ashness Bridge. Feed your curiosity by learning something new about the historical landmark.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Windermere.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Windermere, it's often a good idea to reserve a table in advance.

Raise your glass to another unforgettable day in England!

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Day6

Day 6

  • Bowness-on-Windermere
  • York
  • More

Drive 182 km, 3 hours 20 min

  • National Railway Museum York
  • York Minster
  • Shambles Market
  • Clifford's Tower, York
  • Rowntree Park
  • More

On day 6 of your exciting self-drive vacation in England, you’ll soak in the magnificence of 1 destination, including York. When you’re not sightseeing, take time to relax at your chosen hotel in York, where you’ll be staying for 1 night.

When you’re ready to jump back into the car and say goodbye to Windermere, you’ll hit the road in the direction of York. This drive usually takes around 2 hours 21 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to National Railway Museum, a locally renowned museum that everyone visiting York should see. Next, head to York Minster. This monumental church is one of the most interesting attractions in the region.

If you're keen to see more, don’t miss out on Shambles Market, a visually striking market popular among locals as well as travelers. Clifford's Tower, York is an excellent attraction to visit next. Spend some time learning more about this underrated castle before you continue your journey. Lastly, visit Rowntree Park, a romantic park and a top attraction in the city.

At the end of the day, you will drive to York, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in York, it's often a good idea to reserve a table in advance.

Treat yourself to a wonderful meal at Yakamoz, a top-rated dining spot in York. If you're in the mood for something new, try House Of The Trembling Madness, another premier location with a delectable menu. You might also want to book a table at Turtle Bay York. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in York.

Continue your evening by exploring the vibrant nightlife scene at The Habit Cafe Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Shambles Tavern, a bar that offers unique local touches. Likewise, Pivní York provides an excellent alternative for a fun evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in England.

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Day7

Day 7

  • York
  • Whitby
  • More

Drive 78 km, 1 hour 38 min

  • Whitby Abbey
  • 199 Steps
  • Captain Cook Memorial Museum
  • RNLI Whitby Museum
  • Whalebone Arch
  • More

Experience an unparalleled adventure on day 7 of your road trip in England. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Whitby. At the end of the day, you will retreat to the hotel of your choice in Whitby, where will spend 1 night.

Embrace the thrill of the open road as you wave goodbye to York and set your GPS to Whitby. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 13 min. Upon reaching Whitby, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Savor the day by heading to Whitby Abbey, a notable archeological site that draws visitors from near and far. When you're done, continue to 199 Steps, where you can soak in the history-steeped surroundings.

Next, explore Captain Cook Memorial Museum, yet another increasingly popular place to see in the area. After the museum, make time to go to Rnli Whitby Museum. Lastly, head to Whalebone Arch, an underrated monument you won’t want to miss.

When you’re done exploring for the day, you’ll drive to your hotel in Whitby. Check in and relax before you head out to tour the town.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Whitby. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delicious dinner at The Whitby Endeavour, an excellent option for tonight's dining.

Celebrate another amazing day of your road trip adventure in England!

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Day8

Day 8

  • Whitby
  • Hutton-le-Hole
  • Rievaulx
  • Helmsley
  • Liverpool
  • More

Drive 267 km, 3 hours 46 min

  • Ryedale Folk Museum
  • Rievaulx Abbey
  • Helmsley Castle
  • More

On day 8 of your road trip in England, your travel plans include 3 stops at the most scenic, wondrous, and interesting places in the region. Hutton-le-Hole, Rievaulx, and Helmsley are on today's agenda. In the evening, you’ll end up in Liverpool, where you will stay for 1 night.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Hutton-le-Hole may take around 45 min. Upon your arrival in Hutton-le-Hole, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you're ready for some sights, head to Ryedale Folk Museum, a curiosity-inducing museum in Hutton-le-Hole. Explore its respected features at your own pace before you continue your journey.

After soaking in Hutton-le-Hole’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Rievaulx. Expect your car journey to take a minimum of 21 min. When you arrive in Rievaulx, it's time to take a break from the road.

For a more meaningful self-guided tour of the village's best attractions, visit Rievaulx Abbey, an underrated monastery that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

Helmsley’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Rievaulx behind. This drive usually takes around 6 min. Helmsley welcomes you with a multitude of unique vacation experiences.

Set out on a self-guided sightseeing tour at Helmsley Castle and explore the gorgeous features.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Liverpool. Liverpool offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Liverpool is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Liverpool.

Enjoy a lovely dining experience at Mowgli Street Food, a popular restaurant in Liverpool. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Liverpool at Floating Grace, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Premier Inn Liverpool (West Derby) hotel. It’s yet another ideal choice to enhance your time in Liverpool tonight.

Continue the enjoyment post-dinner at Lady Of Mann, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Boom Battle Bar Liverpool offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Abditory. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Relax and recharge in preparation for another adventurous day in England!

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Day9

Day 9

  • Liverpool - Departure day
  • More
  • Chavasse Park
  • More

Day 9 of your road trip in England is your departure day. This is your chance to catch a last glimpse of Liverpool before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you're up for some more sightseeing, we recommend visiting Chavasse Park, a gorgeous park before you head out.

Make the most of your final day in England by visiting Liverpool’s iconic markets and shopping establishments in the buzzing St John's Shopping Centre. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing vacation.

Before you conclude your road trip in England, drop by another restaurant for a last chance at a memorable dining experience in Liverpool.

You’ll then say farewell to Liverpool. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in England!

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Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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