From clifftop castles to the busy streets of London, this 10-day road trip takes you to some of England's top highlights. Stops along the journey include the mysterious ruins of Stonehenge, historic Glastonbury, the idyllic villages of the Cotswolds, the hometowns of Jane Austen and William Shakespeare, and the gorgeous Welsh coastline, home to various castles. You'll finish up the adventure in London with a rooftop film screening and elegant tea service at the Savoy Hotel.


  • Discover the mysteries of Stonehenge on a guided tour
  • Hike between picturesque villages in the Cotswolds
  • Visit Shakespeare's hometown of Stratford-upon-Avon
  • Enjoy an elegant afternoon tea at the famed Savoy Hotel
  • See grand castles on the beautiful northern coast of Wales
  • Cruise around London on the Hop-on, Hop-off Bus

Brief Itinerary

Day Highlights Overnight
Day 1 Tour Stonehenge & Bath Bath
Day 2 "Bridgerton" Tour & Day-trip to Glastonbury Bath
Day 3 Hike on the Cotswolds Discovery Trail Chipping Campden
Day 4 Explore the Discovery Trail Independently Chipping Campden
Day 5 Enjoy One of England’s Most Inspiring Gardens Chipping Campden
Day 6 Shakespeare Tour in Stratford-upon-Avon, Transfer to Wales Conwy
Day 7 Discover the Northern Coast of Wales Ambleside
Day 8 Visit Shakespeare's Globe Theatre & Catch a Rooftop Film London
Day 9 London Bus Tour & High Tea at the Savoy Hotel London
Day 10 Depart London   

Detailed Itinerary

Day 1: Tour Stonehenge & Bath

Tour the Neolithic monument of Stonehenge
Welcome to England! Your adventure begins with a guided tour of the world-famous Stonehenge. Learn the secrets of the mysterious stone circle and take some time to wander around the site at your own pace.
Later in the day, enjoy a guided literary tour of Bath. Jane Austen made this city her home from 1801 to 1806, when it was a popular spa resort and a favorite haunt of fashionable society. Upper-class Brits came to Bath to relax and socialize in the Roman Baths, drink the requisite three glasses of water from the Pump Room, and stroll in Sydney Gardens and along the Royal Crescent. You'll overnight in Bath. 

Day 2: "Bridgerton" Tour & Day Trip to Glastonbury

A stone bridge across the River Avon in Bath
The popular Netflix series "Bridgerton" is set in London during the Regency Period. But many of the scenes were actually filmed in Bath to take advantage of the city's beautiful Georgian architecture. On a private walking tour around Bath, you'll see key locations from the series, including the residences of Lady Danbury and the Featheringtons, the Modiste dress shop, Gunter's tea shop, the street Daphne galloped down to save her love from a duel, and more.
In the afternoon, head to Glastonbury, a town steeped in history and famous for its legends relating to King Arthur. Tour the picturesque ruins of Glastonbury Abbey, once one of the richest abbeys in the country. On these grounds, monks discovered what they claimed to be the grave of King Arthur and Guinevere. During medieval times, the abbey was a popular pilgrimage destination.
Afterward, you can hike up the hill to Glastonbury Tor for panoramic views. Be sure to stop and see the White and Red Springs, which are said to have healing properties. Or you can spend some time browsing Glastonbury's unique occult shops. Head back to Bath in the evening to relax before continuing onward to the Cotswolds on day three.

Day 3: Hike on the Cotswolds Discovery Trail

Cotswolds Way
Sweeping views over the Cotswolds
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Today you'll hike around the famous Cotswolds region, a conservation area of southern England known for its medieval villages and beautiful countryside. Your journey on the Cotswolds Discovery Trail begins in Cirencester, originally a Roman settlement called Corinium. A military fort was first built here in the first century CE to help defend the then northwestern frontier of the Roman empire. From here, the trail takes you east to Bibury, a gorgeous Cotswold village on the River Coln. Follow the river through a series of idyllic villages before reaching Chedworth.
The trail then continues west, meandering through rolling hills to Painswick Beacon and the village of Painswick. You can take scenic walk to the top of the beacon offers, which will reward you with incredible 360-degree views. Continue on to Painswick, the "Queen of the Cotswolds," one of the most stunning places in the region. ​Leaving Painswick, you'll drive south to Minchinhampton and then to Chipping Camden, a historic market town where you'll spend the night.

Day 4: Explore the Discovery Trail Independently 

Visit the historic villages of the Cotswolds
Today you'll continue along the Cotswold Discovery Trail, this time on the northern loop. Guided by a trail map, you'll have the freedom to explore at your own pace and will hike and drive through gorgeous countryside and picture-postcard villages on a journey that harkens back to a bygone age. Along the way, depending on which route you take, you'll see Stone Age monuments, an Iron Age fort, a Roman amphitheater, and Anglo-Saxon settlements. 

Day 5: Enjoy One of England’s Most Inspiring Gardens

The gardens of Hidcote Manor

Situated in the beautiful Cotswold countryside, Hidcote Manor is home to one of England’s most inspiring gardens. Created by the talented American horticulturist Major Lawrence Johnston, this green space is characterized by colorful outdoor "rooms" that are full of surprises. Wander through a maze of narrow pathways and secret gardens blooming with exotic plants, many of which were collected during Johnston’s trips to faraway places.

Day 6: Shakespeare Tour in Stratford-upon-Avon, Transfer to Wales

Shakespeare's birthplace, in Stratford-upon-Avon
In the morning you'll travel to Stratford-upon-Avon, the one-time home of William Shakespeare. Walk in the Bard's footsteps from cradle to grave, learning about his life and times as you explore the noteworthy landmarks in the area. This includes the picturesque River Avon and the Royal Shakespeare Theatre. You'll also see a range of architectural gems like the Harvard House, the Guild Chapel, and Holy Trinity Church, where Shakespeare is buried.
Then continue on to Conwy, a port town on the coast of Wales. After checking into your hotel, you'll learn about traditional Welsh culture on a guided tour that will takes you to highlights like Conwy Castle, the Church of St Mary & All Saints, and the Smallest House in Great Britain. It stands a mere 122 inches tall and just 72 inches wide. 

Day 7: Discover the Northern Coast of Wales

Explore the beautiful Anglesey coastline
The beautiful Welsh coastline
Today is all about castles and coast! While exploring the area around Conwy, you'll encounter a group of 13th-century castles—Caernarfon, Conwy, and Beaumaris. This trio of fortresses is so historic that they've earned UNESCO World Heritage status.
There will also be time to explore more of Wales' famously beautiful coastline. In fact, this section near Conwy is nicknamed "the Queen of Welsh Resorts" for good reason. Its quiet appeal stands in stark contrast to the wilder Isle of Anglesey, where waves crash against the clifftops. Around here there are many opportunities for surfing, sailing, kayaking, windsurfing, and birding. 

Day 8: Visit Shakespeare's Globe Theatre & Catch a Rooftop Film

Globe Theatre London
Shakespeare's Globe in London
It's back to London today for a tour of Shakespeare's Globe, once known as the Globe Theatre. Hear the story of the original 1599 theatre and how it struggled to survive the plague, fires, and political unrest. Built with oak beams around a 360° auditorium, it is the only thatched-roof building in London. On your tour, imagine how thousands of Londoners once packed in to see the greatest actors of the day. 
Later you'll attend an open-air film screening with the Rooftop Film Club. Held at one of several venues around town, the screening features sunset views over the city skyline, comfortable deck chairs, gourmet food and drinks, and state-of-the-art wireless headphones so you don't miss any dialogue. Enjoy a cult classic or a new release with a local crowd.

Day 9: London Bus Tour & High Tea at the Savoy Hotel

Buckingham Palace

Board the famous Hop-On, Hop-Off Bus and explore the city at your own pace. The circuit includes a series of stops around London's landmarks and key attractions. Highlights include Buckingham Palace, the Houses of Parliament, Westminster Abbey, Big Ben, 10 Downing Street, Piccadilly Circus, the London Eye, Covent Garden, Tower Bridge, City Hall, Hyde Park Corner, Notting Hill, and many more. You'll have unlimited access to all routes for 24 hours. When you're ready to relax, head back to the hotel. 

Afterward, you'll go to the Savoy Hotel's world-famous High Tea, a feature of the hotel since it opened in 1889. Choose from an extensive range of over 30 teas, all accompanied by classic sandwiches, homemade scones with clotted cream, and the talented pastry team’s selection of pastries. The setting, in a stunning glass-domed atrium with live piano music, is enchanting. Afterward, enjoy one last night out in London.

Day 10: Depart London

London's famous skyline

Today the trip comes to an end. After breakfast, you'll head to the airport to catch a flight out. Safe travels! 

More England Itineraries

Looking for more inspiration for your trip to England? Check out these other England itineraries, with outdoor adventures, cultural trips, and family fun to hit the highlights. 


Map of Road Trip Around the Highlights of England & Wales - 10 Days
Map of Road Trip Around the Highlights of England & Wales - 10 Days