Comprehensive Two Week England Itinerary: Heathrow to Northampton, Gloucester, Keswick, Nottingham, Oakham & Wimbledon

Day 1: Arrival and Northampton

Northampton, England on October 9, 2025

9:00am

Arrive at Heathrow Airport

Land at Heathrow and collect your luggage, then prepare for transfer to Northampton.
Variable, 1h

10:30am

Travel from Heathrow to Northampton

Take a direct coach or train from Heathrow to Northampton. The journey typically takes around 2 hours.
GBP25, 2h

12:30pm

Check-in and lunch at The Phipps Northampton

Settle into your hotel and enjoy a lunch featuring locally sourced British dishes at this popular pub.
GBP15, 1h

2:00pm

Visit Northampton Museum and Art Gallery

Explore Northampton’s rich shoemaking heritage and art collection in this engaging free museum, open 10am–5pm.
Free, 2h

5:00pm

Walk in Delapré Abbey Park

Relax with an afternoon stroll around the scenic abbey parkland and gardens. The park closes at dusk.
Free, 1.5h

7:00pm

Dinner at Little Sisters Café Bar & Kitchen

Dine on sophisticated British cuisine with a cosy atmosphere to finish your first day in Northampton.
GBP25, 1.5h
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Day 2: Explore Northampton

Northampton, England on October 10, 2025

8:30am

Breakfast at Brew and Brownie

Enjoy artisan coffee and fresh pastries to start your day.
GBP8, 1h

9:30am

Visit Northampton Guildhall

Admire the Gothic Revival architecture and learn about the town’s history. Open 9am–5pm.
Free, 1.5h

11:30am

Tour St Peter’s Church

Visit this beautiful church known for its stained glass and local significance.
Free, 1h

1:00pm

Lunch at The Old Mill

Traditional English pub fare served in a riverside setting.
GBP18, 1h

2:30pm

Shopping at Northampton Market

Browse antiques, crafts, and food stalls at the vibrant local market.
Variable, 2h

6:30pm

Dinner at O’Neill’s Bar & Grill

Enjoy a varied pub menu before preparing for your next destination.
GBP22, 1.5h
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Day 3: Northampton to Gloucester

Gloucester, England on October 11, 2025

8:00am

Breakfast at The Troubadour Café Northampton

Have a hearty breakfast to prepare for your journey to Gloucester.
GBP10, 1h

9:00am

Travel from Northampton to Gloucester

Take the train via Birmingham or direct route; journey around 3 hours.
GBP35, 3h

12:30pm

Check-in and lunch at The Lion, Gloucester

Settle into your Gloucester accommodation and enjoy traditional British lunch nearby.
GBP18, 1h

2:00pm

Visit Gloucester Cathedral

Explore the breathtaking medieval cathedral, famous for its architecture and film appearances. Open 9am–5pm.
GBP10, 2h

4:30pm

Walk around Gloucester Docks

Discover the historic docks area with shops, museums and cafes along the waterfront.
Free, 2h

7:00pm

Dinner at The Stable

Enjoy excellent pizzas and ciders in a lively dockside location.
GBP22, 1.5h
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Day 4: Explore Gloucester

Gloucester, England on October 12, 2025

8:30am

Breakfast at Honey & White

Start with coffee and pastries at this stylish café.
GBP10, 1h

9:30am

Visit The Museum of Gloucester

Discover local history and archaeology exhibits. Open 10am–4pm.
Free, 2h

12:00pm

Lunch at New County Wine Vaults

Enjoy traditional British pub dishes in a historic inn.
GBP18, 1h

1:30pm

Walk in Robinswood Hill Country Park

Relax amid woodlands with panoramic views of Gloucester. Open all day.
Free, 3h

6:30pm

Dinner at The Wharf Restaurant & Bar

Dine on seasonal British cuisine with picturesque waterside views.
GBP35, 2h
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Day 5: Gloucester to Keswick

Keswick, England on October 14, 2025

7:00am

Breakfast at your accommodation

Enjoy a filling breakfast before your journey to Keswick.
Included, 0.5h

7:30am

Travel from Gloucester to Keswick

Journey by train and bus through scenic countryside; approx. 5 hours.
GBP50, 5h

12:30pm

Check-in and lunch at The Square Orange Café

Relax and enjoy fresh local ingredients in this popular Keswick café.
GBP15, 1h

2:00pm

Visit Keswick Museum and Art Gallery

Learn about the Lake District’s culture and history. Open 10am–5pm.
GBP5, 1.5h

4:00pm

Walk by Derwentwater

Take a refreshing walk along Keswick’s beautiful lake shore.
Free, 2h

7:00pm

Dinner at The Chalet Restaurant

Enjoy fine British dining in a welcoming Keswick establishment.
GBP30, 1.5h
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Day 6: Explore Keswick

Keswick, England on October 15, 2025

8:00am

Breakfast at Rawnsley’s Café & Bistro

Enjoy a delicious breakfast featuring local produce.
GBP10, 1h

9:00am

Guided hike up Catbells

Join a moderate hike with spectacular views of Derwentwater. Approx 4 hours; dress appropriately.
GBP15, 4h

1:30pm

Lunch at The Pheasant Inn

Refuel with hearty local dishes at a nearby traditional inn.
GBP20, 1h

3:00pm

Visit artist studios and galleries in Keswick town centre

Explore local arts and crafts, supporting the creative community.
Free, 2h

6:30pm

Dinner at The George Hotel Restaurant

Dine on seasonal British dishes in Keswick’s historic George Hotel.
GBP35, 1.5h
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Day 7: Keswick to Nottingham to Oakham to Wimbledon

Wimbledon, England on October 16, 2025

7:00am

Breakfast at your accommodation

Prepare for a travel-intensive day with a wholesome breakfast.
Included, 0.5h

7:30am

Travel from Keswick to Nottingham

Start with a train journey, approx 2.5 hours; enjoy scenic views along the way.
GBP30, 2.5h

10:30am

Short visit in Nottingham

Briefly explore Nottingham city centre or grab a coffee before continuing your journey.
Variable, 1h

11:30am

Travel from Nottingham to Oakham

Take a short train or taxi ride (approx 45 minutes) to charming Oakham.
GBP10, 45m

12:15pm

Lunch in Oakham at The Peacock Inn

Enjoy a pleasant meal at this well-regarded local inn with traditional dishes.
GBP18, 1h

1:30pm

Explore Oakham briefly

Take a short stroll to see Oakham Castle and the market town atmosphere.
Free, 1h

2:30pm

Travel to Wimbledon

Continue your journey by train or car to Wimbledon, approx 2 hours travel time.
GBP25, 2h

4:30pm

Check-in to Wimbledon accommodation

Settle in and relax after your long travel day.
Variable, 1h

6:00pm

Dinner at The Alexandra

Enjoy classic British dishes in a friendly neighbourhood restaurant.
GBP25, 1.5h
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Day 8: Explore Wimbledon

Wimbledon, England on October 17, 2025

8:30am

Breakfast at Gails Bakery Wimbledon

Start with fresh croissants and excellent coffee.
GBP7, 1h

9:30am

Explore Wimbledon Common

Enjoy walking or cycling around the beautiful Wimbledon Common with woodlands and ponds.
Free, 2h

12:00pm

Lunch at The Greenhouse Bar & Grill

Seasonal British dishes in a relaxed gastropub environment close to the Common.
GBP18, 1h

1:30pm

Visit Wimbledon Lawn Tennis Museum

Discover the history of the famous tennis championships with interactive exhibits. Open 10am–5pm.
GBP20, 1.5h

4:00pm

Stroll around Wimbledon Village

Explore boutiques, galleries and cafes in this charming village area.
Free, 2h

7:00pm

Dinner at Hudsons London

Enjoy contemporary European cuisine and cocktails in a stylish setting.
GBP30, 1.5h
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Day 9: Wimbledon Leisure Day

Wimbledon, England on October 18, 2025

9:00am

Breakfast at The Original Maids of Honour

Taste famous traditional tarts and pastries with fresh coffee.
GBP8, 1h

10:00am

Visit Polesden Lacey

Drive or take a short trip to this Edwardian mansion and gardens. Opens at 10am.
GBP13, 3h

1:30pm

Lunch at Polesden Lacey café

Light refreshments in charming garden surroundings.
GBP12, 1h

2:45pm

Relax or explore local shops

Spend the afternoon wandering Wimbledon Village shops or relaxing at a café.
Free, 3h

7:00pm

Dinner at The Alexandra

Return to one of Wimbledon’s favourite restaurants for classic comfort food.
GBP25, 1.5h
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Day 10: Wimbledon Relaxation

Wimbledon, England on October 19, 2025

8:30am

Breakfast at Gails Bakery Wimbledon

Start your day with fresh bakery delights.
GBP7, 1h

9:30am

Wimbledon Park

Enjoy a peaceful walk or rent a bike at Wimbledon Park, open all day.
Free, 2h

12:00pm

Lunch at L'ho Tea Room

Enjoy homemade light lunches and good teas in a cosy setting.
GBP15, 1h

1:30pm

Visit Wimbledon Library or local galleries

Explore local cultural spots or attend an event if available.
Free, 3h

6:30pm

Dinner at Hudsons London

Enjoy an evening meal with contemporary European flavours.
GBP30, 1.5h
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Day 11: Wimbledon Cultural Day

Wimbledon, England on October 20, 2025

8:30am

Breakfast at The Original Maids of Honour

Indulge in traditional pastries and tea to start your day.
GBP8, 1h

9:30am

Visit Wimbledon Windmill Museum

Explore the local history at the charming windmill museum. Opens at 10am on weekdays.
GBP5, 1.5h

11:30am

Coffee break at Story Coffee

Recharge with excellent specialty coffee in a friendly café.
GBP5, 1h

12:30pm

Lunch at The Greenhouse Bar & Grill

Enjoy fresh British seasonal lunch options nearby.
GBP18, 1h

2:00pm

Visit Cannizaro Park

Relax in beautiful landscaped gardens open until dusk.
Free, 2h

5:00pm

Early Dinner at The Alexandra

Savour classic dishes in a welcoming neighbourhood setting.
GBP25, 1.5h
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Day 12: Wimbledon Leisure & Departure Prep

Wimbledon, England on October 21, 2025

8:30am

Breakfast at Gails Bakery

Enjoy fresh baked goods one last time.
GBP7, 1h

9:30am

Free morning for last-minute shopping or relaxing walks

Spend your final morning exploring any missed spots or relaxing before your departure.
Free, 3h

12:30pm

Lunch at your choice of local café

Enjoy your choice of meal from Wimbledon’s many excellent options before preparing to leave.
GBP15, 1h

2:00pm

Return to accommodation and pack

Prepare for your departure the following day.
Free, 2h

6:30pm

Dinner at a favourite local restaurant

Enjoy a final meal in Wimbledon celebrating your trip.
GBP25-30, 1.5h
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