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Southern England & Isle of Wight in 8 Days

8 DAYS, 7 NIGHTS | Rye, Dover, Canterbury, Hastings, Portsmouth, Salisbury, Stonehenge & The Isle of Wight

This private tour of Southern England and the Isle of Wight offers a delightful journey to medieval Rye, with its abundance of historic cottages dating to the 1400-1500s, to the dramatic White Cliffs of Dover, to the charming towns of Canterbury and Salisbury and even to the Battle of Hastings, where the history of England was forever changed. You'll also visit the picturesque Isle of Wight with its Roman villa and a peaceful haven for Queen Victoria. This private tour gives you the best of Southern England along with the Isle of Wight. 

Day 1) Chartwell House & Rye

Depart from central London or London Heathrow Airport for a visit to Chartwell House, former home of Winston Churchill. Enjoy a visit to the house, his art studio and take some time to explore the enchanting gardens. Continue to Rye, a picturesque medieval town a short distance from the south coast, complete with crooked cottages, half-timbered houses and narrow cobbled lanes, for a three-night stay at the Mermaid Inn. Dinner tonight is included at the Mermaid Inn.


Day 2) Dover Castle & Canterbury

This morning, depart for St. Margaret’s Bay to admire the best views of the White Cliffs. Next, visit England’s largest and most significant fortification, Dover Castle. The site includes the Roman Lighthouse, the oldest building in England, the World War II war rooms and tunnels, not to mention the magnificent castle itself. This afternoon, enjoy a private-guided walking tour of Canterbury. Explore the magnificent cathedral, an important center of pilgrimage in medieval England and the site of the murder of Thomas Becket, the Archbishop of Canterbury in 1170. Tonight, you are free to choose from one of several excellent restaurants in Rye.


Day 3) Chapel Down Winery & Bodiam Castle

This morning, experience a guided tour at Chapel Down Winery, located in the beautiful Kent countryside, close to the picturesque market town of Tenterden followed by some wine tastings. The southeast coast of England is synonymous with the white cliffs of Dover with its iconic chalk soil, the same as that of Champagne, coupled with a cool climate all year long that enables Chapel Down to produce truly world-class wines. Afterwards, enjoy lunch at an award-winning village pub and then visit Bodiam Castle, a 14th-century moated castle with soaring towers.


Day 4) Battle of Hastings & Arundel

Today, depart Rye for the Battle of Hastings, which took place north of Hastings, close to the present day village of Battle. The Battle of Hastings, fought in 1066, saw the defeat of Saxon King Harold II by William the Conqueror, who then became King William I. This defeat was a dramatic turning point in British history. You will learn all about the battle and have an opportunity to walk the site of the battlefield. Next, continue to the picturesque market town of Arundel for lunch, where you may also visit Arundel Castle. Continue to Southampton to catch the ferry to Isle of Wight. Arrive Cowes for a two-night stay at a seafront hotel.


Day 5) Isle of Wight

Today, explore the unmissable highlights of the Isle of Wight. Visit Osborne House, the former retreat of Queen Victoria, and Brading Roman Villa, which offers unique insights into Roman life. After a stop for lunch in the seaside town of Shanklin, you will follow the coast around the southern half of the island to the Isle of Wight’s most beautiful natural wonder, the Needles. You will enjoy a boat ride out to Needles Battery—a Victorian coastal defense—which stands above three white, razer edge rocks strung out at sea leading to one of the Britain’s most photographed lighthouses. On your return to Cowes, visit the historic port of Yarmouth.


Day 6) Portsmouth

Today, depart the Isle of Wight by ferry from Fishbourne to Portsmouth. Visit Portsmouth Historic Shipyard, home to HMS Victory, Lord Nelson's flagship in his victory at the Battle of Trafalgar, and the Mary Rose, of the English Tudor Navy of Henry VIII and raised from the seas in 1982. You’ll also visit the D-Day Story, the only museum in the UK dedicated to the Allied Invasion of June 1944, and the Charles Dickens Birthplace Museum, home to the famous English author. Continue to Shrewton for a two-night stay at Rollestone Manor, a beautiful historic house near Stonehenge, where dinner is included tonight.


Day 7) Stonehenge & Salisbury

This morning, depart for nearby Stonehenge—a World Heritage Site and the best-known prehistoric monument in Europe—where you will walk in the footsteps of your Neolithic ancestors. If you want something extra special, please ask about our sunset/sunrise experiences where you walk between the stones on a private tour. This afternoon, visit the Cathedral City of Salisbury where you will enjoy a private-guided tour of Salisbury’s mediaeval quarter, Cathedral Close, the Cathedral itself and more. The Cathedral is famous for its rich lore and towering Gothic spire and includes one of four original copies of the Magna Carta, the 1215 document that first established that everyone was subject to the law. Dinner at Rollestone Manor.


Day 8) Heathrow Airport or London

Depart Shrewton with your driver for London Heathrow Airport or central London.

  Included with this private tour:
  • 7 nights' of hotel accommodation

  • 7 daily English breakfasts

  • 3 gourmet three-course dinners 

  • Your very own professional driver-guide and luxury vehicle

  • Airport meet and greet 

  • Entrance fees, tolls & taxes

  • Flexible itinerary

  Just a few tour highlights:

  • Medieval Rye

  • Dover Castle and the White Cliffs

  • Canterbury Cathedral

  • Salisbury

  • Stonehenge

  • Portsmouth

  • Winery tour & tastings

  • Arundel Castle

  • Isle of Wight


Superior Boutique

In this category we have hand-picked five-star guest houses or smaller luxury hotels. These lodgings are often family owned and offer a truly unique, authentic and welcome atmosphere where you are more likely to engage with local people than in a higher-end hotel. Some tours involve a mixture of both Superior and Luxury Boutique.

Luxury Boutique 

Through years of experience we have hand-picked luxury boutique hotels which are not only very comfortable in the traditional sense, but as importantly offer gourmet food, and an ambience of lasting memory. All our hotel choices are of unique character, range from 4-star to 5-star, and are either downtown, or enjoy a spectacular rural or village setting. 

Our detailed offer to you will specify the hotels recommended.


Subject to availability, you may choose your own travel dates. 

All prices are per person in US dollars includes hand-picked Luxury and Superior Boutique lodging and based on sharing a room for double occupancy.

    $3,980 per person (group of 6 people)

    $4,890 per person (group of 4 people)

    $6,490 per person (group of 2 people)

Want a luxury private tour? This tour can be customized to your wishes or offered with 5-star luxury accommodation. Simply call, or email us with your specifics and we'll plan a program that's right for you.


England's West Country in 11 days:

11 Days | 10 Nights | From $5,890

Why not add Cotswolds, Oxford and Blenheim Palace to your itinerary?

Click here for more details

England's West Country

Thank you so much for a truly wonderful trip in England's West Country. The Cornish coast was more beautiful and magical than I could have imagined, and the variety of experiences you provided gave this vacation dimensions we could never have found on our own. Thank you, too, for your patience with us, and all your insights, I will always treasure memories of this trip,

Kathy - Ohio

England's West County

Thank you so very for the most unforgettable holiday of a life. Each experience was perfect and your guidance and expertise exceptional. 

Karen - Halifax, Canada

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