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Medieval Rye, Sussex, self-guided walking break

No of Nights: 1-3

Stay: Hotel

Grade: Easy-Moderate


Once an island, hilltop Rye has a rich history as an ‘Antient Town’ of the Cinque Ports. Today, with its cobbled streets and fine 16th-century timber-fronted houses, medieval Rye continues to enchant. It is perhaps not surprising that so many writers and artists were inspired to make Rye their home with the charm of its medieval winding streets, scarcely changed in centuries. Rye is beautifully situated, surrounded by tranquil countryside where you can experience peace, quiet, light and space and the biggest skies imaginable as well as extensive views across reclaimed marshes to the sea.


  • two days of relaxed walking in and around ancient Rye
  • peace, quiet, sea air and the isolated beauty that inspired artists from Van Dyck and Turner to Paul Nash and John Piper
  • visiting Henry James’s Lamb House, later home to EF Benson, famed for Mapp and Lucia comedies
  • self-guided tour of Rye
  • a luxurious 4-star hotel in the heart of Rye, surrounded by galleries, antique and craft shops; bed and breakfast accommodation also available
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Tour review scores and score breakdown

10 / 10

Based on 1 reviews

Guest reviews are written by our customers after their tour of Medieval Rye Sussex.

Guest reviews

  • Just a line to say how much I enjoyed the Rye holiday. The hotel and food were all up to your customary standard and the walks were varied and interesting. Rye and its surrounding countryside are spectacular. Thankfully we had good weather and were thus able to enjoy it all to the full. Please make it three or four nights next time!
    - John Tritton, Chelmsford, Essex


Day One: Arrival Day & Self-guided Walk around Rye
Explore the fascinating historical heart of Rye, wandering ancient streets and alleys and attractive little squares. Then enjoy fine dining in the hotel’s excellent restaurant. (Grade moderate: 2 miles/3 km)

Day Two: Rye Harbour & Romney Marsh – 5 miles
A great walk combining nature and history, visiting Rye Harbour, a fascinating Nature Reserve, a Site of Special Scientific Interest and a coastal wetland area full of shingle ridges with unique flora, sand dunes, marshland dissected by ditches, rivers and saltmarsh - the core of the Romney Marshes Living Landscape. Great flocks of sea birds fly overhead and arriving at one of the bird hides, you can perhaps spot a rare species. Picnic lunch today, beside the water. (Grade easy: 5 miles/8 km)

Day Three: Rye & Winchelsea – 6 miles
Following the River Tillingham and the Royal Military Canal, the towpath takes you easily across flat open peaceful countryside to historic Winchelsea, another ancient Cinque Port. Time here to visit the 14th-century Court Hall Museum and St Thomas' Church, noted for its ‘decorated' English Gothic architecture, the venue of John Wesley’s last open air sermon in 1790 and the last resting place of Spike Milligan. Lunch at The New Inn followed by a scenic return route below cliffs on easy paths lined with gorse. Back in Rye, a further explore this fascinating town and, of course, enjoy a cream tea! (Grade easy: 6 miles/9.6 km)

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Enjoy a luxury bedroom at The George, a former 16th century coaching inn, now wonderfully converted into a 4-star boutique hotel which retains much of its original 16th-century character.

The George is situated in the heart of historic Rye with its cobbled streets and fascinating shops.

Paul Gordon, the head chef who won acclaim at Qualia, is responsible for the hotel’s traditional English cuisine using local and seasonal ingredients.

We can also arrange B&B accommodation if preferred.

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Grade of the walks

The walks are easy and suitable for anyone of average fitness, able to walk up to 6 miles on flat terrain on two full days with breaks for lunch. The walks are flexible with opportunities for shortening the route if required or for taking a day off walking to further explore all the delights of Rye.

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Tour price and costs

Price per person:  from £279 for 2 people sharing a twin or double room

Price includes:

      • En-suite luxury accommodation with full English breakfasts (or B&B accommodation available)
      • Self-guided tour of Rye
      • Two full-day self-guided walks direct from the hotel
      • Comprehensive walks pack containing detailed route directions
      • Printed commentaries to accompany the route directions
      • Marked-up Ordnance Survey map and map case
      • Pocket guide
      • Travel information
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Rail Travel
With its high-speed rail service from St Pancras International, Rye is easily reached via Ashford International rail station in just over an hour. There are also services from London Charing Cross, London Bridge and Waterloo East.

Rye can also be easily reached via Eurostar's terminal.

Car Travel
The A21 and A268 roads provide easy access from London and the M25 motorway. Rye is also very easily reached from the Channel ferry terminals.

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