Relaxed Southern England & Wales Road Trip: Cities, Countryside, Castles & Coast - 15 Days

Day 1: Arrive in London (England), Twilight Soho Food & Drinks Tour

Welcome to England! Upon arrival at the airport, you'll be met by your driver and whisked to your central hotel in the capital, London. A historic city with a timeline stretching back almost 2,000 years, this thriving metropolis has world-class museums, ornate architecture, and an exceptional dining scene. 

After settling in at your hotel, it's off to the legendary Soho district to fill up on gastronomic delights. In the company of an experienced and food-obsessed local guide, you'll discover hidden gems and famous haunts across Soho, Chinatown, and Seven Dials in Covent Garden to taste a variety of international dishes. Visit a former banana warehouse turned culinary start-up and devour the city's best bao buns while learning about the neighborhood venues that hosted legends, including Jimi Hendrix and David Bowie. You'll finish at a local bar, where you'll sample an unbeatable combination of cocktails and dessert.

Day 2: London by Vintage Bike, Shakespeare's Globe Theatre Production

After breakfast at your hotel, you'll spend the morning touring London's streets by bike. This is no ordinary cycling tour—you'll be cruising around on a vintage Pashley bicycle, the epitome of British cycling. From the grandeur of Big Ben to the cobbled streets of East London, you'll ride along atmospheric back streets and cycle lanes to discover a side of the capital beyond the guidebooks. Pedal through elegant royal parks to urban squares and witness London's dynamic street art scene before finishing at one of the city's historic pubs, where you'll toast your fellow cyclists with real ale or craft gin.

Later on, you'll be transported back in time to Shakespeare's London to see a performance at the iconic Globe Theatre, painstakingly built to replicate the original and completed in 1997. Step inside, and you'll find a 360-degree auditorium built from oak beams, lime-plaster walls, and a water-reed thatched roof. You'll follow in the footsteps of 17th-century Londoners and watch one of Bard's best-loved plays in the open-air theater (just like the original, there's no roof over the center yard, so be sure to dress for the weather).

Afterward, cap your day off with a post-theater dinner next door at The Swan London, which offers contemporary British dining with views over the River Thames. Your location in the heart of the city means you're well placed to explore some of the capital's iconic landmarks, such as St Paul's Cathedral, the Millennium Bridge and the Tower of London, and the city's some 4,000 pubs.

Day 3: Drive to Oxford, Chauffeured River Punt, Bodleian Library Tour, Oxford's Pubs

Today, you'll pick up your rental car and leave the city behind for a two-hour drive west to Oxford. Dubbed the "City of Dreaming Spires," the town is home to one of England's oldest and most prestigious universities (the other being Cambridge.) Once you've checked in to your hotel, you'll head down to the riverbank for a relaxing tour of the city along the River Cherwell. You'll travel on a chauffeured punt (flat-bottomed riverboat), where you'll gently glide along the water and see sights including the Botanic Gardens, the playing fields of Magdalen College, and the college gardens of St Hilda's and Christ Church.

Return to dry land, and it's time to explore Oxford's 11th-century university for a tour of one of the highlights, the Bodleian Library. Oxford's main research library, the Bodleian, is home to over 13 million books. You'll find some of these on a visit to the 15th-century Divinity School, Convocation House, Chancellor's Court, the medieval Duke Humfrey's Library, and Radcliffe Camera, which houses the science library. 

Your final immersion into Oxford life, and the best way to get a feel for the city's past and present, is a self-guided tour of the town's historic pubs. Literary fans should head to the Eagle and Child, the well-known haunt of C.S. Lewis and J.R.R. Tolkien, while the Turf Tavern, established in 1381, is known for its historic charm and as the watering hole for the "Harry Potter" cast. When it's time for dinner, the King's Arms serves hearty English pub classics alongside a selection of cask beers, which can be enjoyed on the pub's riverside terrace.

Day 4: Drive to Chipping Campden via the Cotswolds

England's famous Cotswolds is a rural area that encompasses six southern counties and enjoys Area of Outstanding Natural Beauty (AONB) conservation status. The region lies just over an hour's drive west of Oxford. Today, you'll drive north to Chipping Camden via a scenic detour to discover the northern loop of the Cotswolds. There's plenty to see en route, and you'll notice the local limestone used in the region's architecture gradually change from light cream to a deep golden honey-colored hue.

Stop to stretch your legs and soak up quintessential English village life as you pass by the small towns of Chipping Norton and then Burford, whose wide streets, flanked by medieval buildings and independent boutiques, are worth a potter. Continue to Bourton-on-the-Water, known for its bridges that cross the River Windrush and run gently through the town. Pass through Stow-on-the-Wold, where you'll find excellent options for a delicious lunch, and pass through The Slaughters until you arrive at Chipping Campden.

Check into your hotel, and once you've settled in, head out to explore. Alongside the beautifully preserved golden limestone buildings, you'll find a long and wide High Street that sweeps through the town center and dates from the 14th century to the 17th century, filled with tempting restaurants and bistros.

Day 5: Visit Warwick Castle & Explore Stratford-upon-Avon

The UK has its fair share of castles, 4,000 to be precise, and Warwick Castle regularly makes the top 10 list. Built by William the Conqueror in 1068, the medieval fortress is a fantastic place to explore and understand England's medieval history. After a quick 40-minute drive north, you'll reach the castle and have as much time as you like to visit the Great Hall, walk the castle's ramparts, and head down to the dungeons. Meanwhile, there are plenty of interactive shows on the castle grounds to enjoy, whether it's falconry, jousting, or archery.

Once you've explored all the castle has to offer, return to Chipping Camden via Stratford-upon-Avon, a bustling town on the banks of the River Avon and famous as the birthplace of William Shakespeare. Spend a few hours seeing the many Shakespearean sights such as the Royal Shakespeare Theatre or Shakespeare's Birthplace. If you can, squeeze in a visit to Anne Hathaway's Cottage, a charming 15th-century thatched cottage and childhood home of Shakespeare's wife. It's a great place to wander through the extensive gardens and follow the sculpture trail inspired by the Bard's works.

Afterward, either stop in for dinner, drinks, or both at The Coach House, a historic, award-winning pub with an almost 500-year-old heritage.

Afterward, drive half an hour to the Cotswolds Riding equestrian center in the picturesque village of Stanton. Here, you'll saddle up and set off on a relaxed countryside "hack," spending the next few hours trotting the miles of local scenic paths and bridleways, with lookout points in the hills offering fabulous views over southern England. Your pace and route will be decided by your experience level, with everyone from beginners to well-seasoned riders catered to. 

Post-ride, you can complete your Cotswolds immersion with a tour of the southern loop portion of the Cotswolds. Drive south to Bibury, a picture-perfect village along the River Coln and one of the most photographed places in the area. Stroll the photogenic Arlington Row of Weaver's Cottages, then hop back in the car and follow the river through a series of postcard-worthy villages along the Coln Valley. Your last stop is the village of Painswick, dubbed the "Queen of the Cotswolds," where you could stop for dinner before returning to Chipping Campden.

Day 10: Explore the Gower Peninsula, Drive to Cardiff, City Food Tour

You'll continue your Wales exploration this morning as you drive east toward Cardiff, the country's capital, with a scenic detour along the Gower Peninsula. In 1956, the peninsula in southwest Wales became the first area in the UK to be designated an Area of Outstanding Natural Beauty. Drive across pretty hills and an unspoiled coastline to see views from Three Cliff's Bay and Worm's Head. Reach Swansea, the birthplace of the writer Dylan Thomas, and you're an hour from Cardiff, the nation's largest city, whose regeneration over the last two decades has resulted in a dynamic, revitalized town.

Once you've had a chance to settle in at your hotel, it's time to head out and explore Cardiff's multicultural culinary scene on a food tour. On a guided stroll through the city with an experienced guide, you'll sample warm Welsh cakes, tuck into crumbly, buttery pies, and browse the stalls at the Riverside Food Market. You'll also hear tales of local life from your guide, admire the city's grand buildings, including Cardiff Castle and the Principality Stadium (the home of Welsh rugby), and even learn a few key words of Welsh. Lechyd da (cheers)!

Day 11: Drive to Bath (England) via Tintern Abbey, Afternoon Tea & Roman Baths

Wave goodbye to Wales this morning and get back behind the wheel to drive a couple of hours east to Bath, a small city whose elegant Georgian architecture has earned it UNESCO World Heritage Status. Just before you cross the border into England, you'll stop at Tintern Abbey. Once a thriving monastery founded by Cistercian monks in 1131, it was immortalized in the early writings of poet William Wordsworth. Now ruins, you'll still be able to make out its fragile architecture with soaring Gothic arches and the gaps for once-magnificent windows.

Arrive in Bath, and after checking into your hotel, You'll follow in the footsteps of Jane Austen and Charles Dickens with a sumptuous afternoon tea at The Pump Rooms. This Bath institution has been the social heart of the city for over 200 years. Enjoy an array of sweet and savory delicacies and, of course, homemade scones with clotted cream and jam. Afterward, head next door to visit one of the best-preserved religious spas in the world, the Roman Baths, whose thermal springs still flow with natural hot water.

Day 12: Discover Literary Bath, Food Heroes Walking & Tasting Tour

Spend the morning exploring Bath's Regency history and centuries-old connection to author Jane Austen, who called the city home in the early 1800s, at a time when it was a destination spot for fashionable society. Walk in the footsteps of Austen with a 2.5-hour tour that reveals the nuances of life in Regency England as you explore the elegant Georgian architecture of the Royal Crescent, Sydney Gardens, and the Jane Austen Centre, where guides in period costumes help bring the era to life.

If walking Bath's hilly cobbled streets has helped work up an appetite, you're in luck. This afternoon is dedicated to the city's excellent culinary reputation where, in the company of an enthusiastic local foodie, you'll take a guided walking tour that introduces you to the town's leading artisan food producers while seeing Bath's landmarks. Discover tasty morsels, such as fennel salami and fresh sheep's ricotta, at a selection of the city's leading independent cafés and street food sellers while you hear directly from the innovative individuals driving the current culinary scene.

Day 13: Self-Guided E-Bike Tour to Bradford-on-Avon, Free Time in Bath

Discover the gorgeous Wiltshire countryside this morning with a relaxed cycle along the Kennet and Avon Towpath to Bradford-upon-Avon. Let your e-bike take the strain as you weave through the Avon Valley, passing colorful, narrow boats and old stone bridges as you go. Talking of bridges, don't miss the ancient bridge in the town center, which still retains two of its original 13th-century arches. Then, see the 19th-century former cloth mills that flank the riverside and stroll The Shambles, where you'll find independent boutiques and excellent places to stop for tea and cake.

Return to Bath, and you'll cycle through the Two Tunnels Path, a Victorian railway tunnel and the longest cycling tunnel in Britain. You'll be accompanied on your ride through the tunnel with an interactive light and sound installation created in collaboration with the award-winning composer Mira Calix. Eventually, you'll emerge from the tunnel to wonderful views overlooking Bath and a gentle pedal downhill and back into the city.

Return your bike, and spend the rest of the afternoon at your own pace. Bath is filled with plenty of tempting, beautifully curated independent stores, so if you're looking for something special to commemorate your trip to the Cotswolds, you'll find it here. Later, when hunger bites, you'll be spoiled for choice. The city's eateries range from retro cafés, Lebanese restaurants, European brasserie fare, and a crop of excellent quality gastropubs, not to mention historic pubs and quirky microbreweries.

Day 14: Drive to London via Lacock, Castle Combe & Avebury

 It's time to wave goodbye to Bath and head back east to the capital. Set off, and around half an hour into your journey, detour to visit a few of the area's most notable villages and sights. The first is Castle Combe, known as one of England's most beautiful villages. With no new houses built since the 1600s, the town's charming cottages adorned with ivy make it a serene spot for a stretch of the legs and watching the world go by. 

Lacock, a 15-minute drive away, is another perfectly preserved village with only four streets and whose historic architecture has made it a go-to film location for shows such as "Downton Abbey" and the BBC's "Pride and Prejudice." The main attraction here is the 13th-century Lacock Abbey, built from the beautiful, golden Cotswold stone. "Harry Potter" fans will enjoy exploring the cloisters and abbey rooms, which served as Hogwarts School cloisters in the films.

If you have time, another nearby landmark worth seeing is Avebury, whose extraordinary set of Neolithic and Bronze Age ceremonial sites, together with Stonehenge, form a UNESCO World Heritage site. Explore the stones and perhaps stop for lunch in the local village pub, then hop back in the car. In around two hours, you'll arrive back in London, where you can drop off your rental car, check back into your hotel, and get ready for your final evening in the capital.

Day 15: Hyde Park & Kensington Gardens, Depart London

It's your last morning in the capital, and before you transfer to the airport, you could head to Hyde Park, central London's green lung and a vast open space adored by locals who go to jog, dog-walk, swim, or unwind. Leave behind the hustle and bustle for a few hours and brave an open-air swim in the Serpentine, or opt for a gentle row aboard one of the river boats available for hire. If the weather's fine, grab a second takeaway breakfast and coffee, spot the squirrels and swans, or admire the views across the lake from a waterside café.

Just next door to Hyde Park on its western side is Kensington Gardens, another of London's eight Royal Parks. Once the preserve of royalty, the park's palace has been the childhood home of Queen Victoria and more recently home to Diana, Princess of Wales, Princess Margaret, and the London home of the Duke and Duchess of Cambridge. Depending on your timings for the day, wander the historic tree avenues, see the cascading fountains in the Italian Gardens, or go in search of Peter Pan (you'll find a bronze sculpture dedicated to J.M. Barrie's literary hero down by the Long Water).

When you're ready, transfer to the airport in time to make your flight home or continue your European adventure. Safe travels!

More Great England Itineraries

Looking for more inspiration for your trip to England? Check out these other England itineraries, explore different ways to spend 15 days in England, or discover the best time of year to visit England.