35 days in Southern England Itinerary

35 days in Southern England Itinerary

Created using Inspirock Southern England trip itinerary planner

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Route & dates

35 days in Southern England Itinerary

Start: Chicago
Fly:  12​h
1
London
— 7 nights
train:  1​h
2
Canterbury
— 4 nights
Drive:  2​h
3
Eastbourne
— 5 nights
Drive:  1​h 30​min
4
Portsmouth
— 5 nights
Drive:  4​h
5
Newquay
— 6 nights
Drive:  4​h
6
Oxford
— 5 nights
train + Fly:  12​h 30​min
End: Chicago

7
nights
London

London ©
Vibrant and noisy, London is one of the world’s leading cities, an international capital of culture, education, fashion, music, finance, trade, and politics.
Step out of the city life by going to Speed Boats Tours and Tower Hamlets Cemetery Park. St. Paul's Cathedral and Westminster Abbey will appeal to history buffs. Explore the numerous day-trip ideas around London: Long Melford Church (in Long Melford) and The Animal Experience (in Stretham). The adventure continues: explore the historical opulence of Buckingham Palace, examine the collection at Madame Tussauds London, get engrossed in the history at Natural History Museum, and learn about all things military at Churchill War Rooms.

To see photos, other places to visit, where to stay, and other tourist information, use the London road trip planner .

Chicago, USA to London is an approximately 12-hour flight. You can also do a combination of bus and flight; or do a combination of train and flight. The time zone changes from Central Standard Time to Greenwich Mean Time, which is usually a 6 hour difference. Prepare for slightly colder weather when traveling from Chicago in May: high temperatures in London hover around 62°F and lows are around 46°F. Finish your sightseeing early on the 20th (Mon) so you can take a train to Canterbury.

Things to do in London

Historic Sites Museums Neighborhoods

Side Trips

Long Melford Church, The Animal Experience
Highlights from your plan
The British Museum ©
The British Museum
National Gallery ©
National Gallery
Natural History Museum ©
Natural History Museum

4
nights
Canterbury

Canterbury ©
Canterbury is a historic English cathedral city and UNESCO World Heritage Site, which lies at the heart of the City of Canterbury, a local government district of Kent, England. Museum-lovers will get to explore The Historic Dockyard Chatham and The Beaney House of Art & Knowledge. Dover Castle and Stelling Minnis Windmill and Museum are good opportunities to explore the local culture. Venture out of the city with trips to Camber Sands (in Camber), Rye (Rye Harbour Nature Reserve & St. Mary's Parish Church) and Sissinghurst Castle Garden (in Sissinghurst). It doesn't end there: identify plant and animal life at The Hawking Centre and take in the spiritual surroundings of Canterbury Cathedral.

To see more things to do, photos, ratings, and more tourist information, use the Canterbury road trip planning app .

Traveling by train from London to Canterbury takes an hour. Alternatively, you can drive; or take a bus. Finish your sightseeing early on the 24th (Fri) so you can drive to Eastbourne.

Things to do in Canterbury

Parks Historic Sites Wildlife

Side Trips

Rye, Stelling Minnis Windmill and Museum, Camber Sands, The Big Cat Sanctuary, The Hawking Centre
Highlights from your plan
The Big Cat Sanctuary ©
The Big Cat Sanctuary
Dover Castle ©
Dover Castle
The Hawking Centre ©
The Hawking Centre

5
nights
Eastbourne

Eastbourne ©
Eastbourne is a town, seaside resort and borough in the non-metropolitan county of East Sussex on the south coast of England, 19mi east of Brighton. Visiting East Sussex Falconry and Beachy Head will get you outdoors. Get some historical perspective at The Lanes and St Margaret's Church. Change things up with these side-trips from Eastbourne: Brighton (Kellie Miller Arts, Royal Pavilion, & more), De La Warr Pavilion (in Bexhill-on-Sea) and Newhaven Fort (in Newhaven). Next up on the itinerary: take in the exciting artwork at Farleys House & Gallery, admire the landmark architecture of Church of St Michael the Archangel, shop like a local with Henry Paddon Contemporary Art, and take an in-depth tour of Michelham Priory.

To see other places to visit, reviews, where to stay, and tourist information, read our Eastbourne online tour itinerary maker .

You can drive from Canterbury to Eastbourne in 2 hours. Other options are to take a train; or take a bus. May in Eastbourne sees daily highs of 60°F and lows of 46°F at night. Finish your sightseeing early on the 29th (Wed) to allow enough time to drive to Portsmouth.

Things to do in Eastbourne

Museums Parks Historic Sites

Side Trips

Brighton and Hove, Bexhill-on-Sea, Herstmonceux, Hastings, Church of St Michael the Archangel
Highlights from your plan
East Sussex Falconry ©
East Sussex Falconry
Nigel Greaves Gallery ©
Nigel Greaves Gallery
Beachy Head ©
Beachy Head

5
nights
Portsmouth

Portsmouth ©
Portsmouth is a port city and unitary authority in the ceremonial English county of Hampshire and is located south-west of London and south-east of Southampton. Let the collections at The Tank Museum and HMS Warrior 1860 capture your imagination. Visit Stonehenge and Salisbury Cathedral and Magna Carta for their historical value. Change things up with these side-trips from Portsmouth: Winchester Cathedral (in Winchester), Boscombe Down Aviation Collection (in Salisbury) and Bournemouth Beach (in Bournemouth). There's much more to do: admire the natural beauty at Longleat, examine the collection at HMS Victory, contemplate the long history of Osborne House, and explore the galleries of Royal Armouries - Fort Nelson.

To see where to stay, more things to do, reviews, and tourist information, you can read our Portsmouth trip planner .

You can drive from Eastbourne to Portsmouth in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 60°F in May, and nighttime lows around 46°F. Finish your sightseeing early on the 3rd (Mon) to allow enough time to drive to Newquay.

Things to do in Portsmouth

Historic Sites Museums Parks

Side Trips

Salisbury, Bournemouth Beach, The Tank Museum, Longleat, Winchester Cathedral
Highlights from your plan
Stonehenge ©
Stonehenge
The Tank Museum ©
The Tank Museum
Winchester Cathedral ©
Winchester Cathedral

6
nights
Newquay

Newquay ©
Known as the Surf Capital of the UK, Newquay is a vibrant city with youthful energy.
You'll explore and learn at Davidstow Airfield & Cornwall At War Museum and Polperro Heritage Museum of Smuggling & Fishing. Take a break from the city and head to St. Michael's Mount and Fistral Beach Bar. Explore Newquay's surroundings by going to Tintagel Castle (in Tintagel), Barbara Hepworth Museum and Sculpture Garden (in St Ives) and Marazion Museum (in Marazion). The adventure continues: kick back and relax at Woolacombe Beach, admire nature's wide array of creatures at Paignton Zoo Environmental Park, explore the historical opulence of Castle Drogo, and head outdoors with First Wave Adventures Activity Centre.

To see where to stay, traveler tips, and other tourist information, read our Newquay trip site .

Traveling by car from Portsmouth to Newquay takes 4 hours. Alternatively, you can do a combination of train and flight; or do a combination of train and flight. Finish your sightseeing early on the 9th (Sun) so you can drive to Oxford.

Things to do in Newquay

Parks Historic Sites Outdoors

Side Trips

Marazion, Eden Project, Woolacombe Beach, Lanhydrock House and Garden, Paignton Zoo Environmental Park
Highlights from your plan
St. Michael's Mount ©
St. Michael's Mount
Woolacombe Beach ©
Woolacombe Beach

5
nights
Oxford

Oxford ©
A busy, cosmopolitan city, Oxford is perhaps best known for its ancient university.
The Roman Baths and Bath Abbey will appeal to history buffs. Get in touch with nature at Head 4 Heights Ltd and The Cotswold Range. Get out of town with these interesting Oxford side-trips: Brunel's SS Great Britain (in Bristol), Warwick Castle (in Warwick) and Cotswolds Distillery (in Stourton). Next up on the itinerary: see the interesting displays at Mechanical Music Museum, step into the grandiose world of Sudeley Castle, stroll through Cotswold Wildlife Park & Gardens, and take in the architecture and atmosphere at St. Mary's Church.

To see ratings, where to stay, other places to visit, and tourist information, read our Oxford day trip planning app .

Getting from Newquay to Oxford by car takes about 4 hours. Other options: do a combination of flight and train; or do a combination of flight and train. June in Oxford sees daily highs of 68°F and lows of 49°F at night. Finish your sightseeing early on the 14th (Fri) so you can travel back home.

Things to do in Oxford

Historic Sites Museums Outdoors

Side Trips

Cirencester, Bath, Wells Cathedral, Cotswold Wildlife Park & Gardens, Cotswolds Distillery
Highlights from your plan
The Roman Baths ©
The Roman Baths
Wells Cathedral ©
Wells Cathedral
Cotswolds Distillery ©
Cotswolds Distillery