Sail and rail to discover England’s prettiest towns and villages

"Many times the wrong train took me to the right place," the novelist Paulo Coelho once wrote, and from my own experience, that's certainly true. A last-minute change of plan to board an overnight train from Vienna with our children offered an unforgettable sunrise. From the sleeper window we watched Venice's skyline etched onto an orange, crimson and pale blue sky as the train glided across the lagoon. Another time, years earlier, I woke up in a tightly packed carriage to the offer of food and conversation from labourers on their way back home to Thessaloniki, because I had slept through a connection in Belgrade Central Station.

After two years of uncertainty around air travel, and growing awareness of its impact on the climate, there's no better time to rediscover the joy of travelling by train. Our own rail network in Ireland is limited, however, so the simplest way to try out a multi-destination rail holiday is take the ferry across the Irish Sea to England, to discover beautiful landscapes and picturesque towns and villages beyond the bright lights of London, Manchester or Liverpool.

As Inter Rail celebrates its 50th birthday this year, purchasing a flexi-rail pass with an agent such as International Rail offers a touch of nostalgia along with steep discounts – such as the £238 (€287) ticket for 15 non-consecutive days throughout England. You can reconnect with your inner student, with the liberty to stay longer in a location or move on at will. Such is the freedom of travelling by train.

This looped route explores some of the most beautiful towns, shires and hamlets in the English landscape.

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1. Cartmel, Cumbria

After arriving by ferry into Holyhead, discover the rhythm of train travel on a four-hour journey veering north to Cartmel, a small, leafy, medieval village and gateway to the Lake District. The village is as famous for horse racing as it is for its food – try the local speciality of sticky toffee pudding, or up it a notch at the Michelin-starred L’Enclume.

The journey: Train via Grange-over-Sands (three hours); bus (10 minutes) or cycle (15 minutes) to Cartmel

Stay: Priory Hall has lovely rooms in the centre of the village, from €120. prioryhotelcartmel.co.uk

2. Keswick, Cumbria

From Cartmel take the Cumbrian Coast Line before slipping off grid to the Lake District’s most northerly – and arguably prettiest – town of Keswick. Hillwalkers can embrace the fells of Skiddaw and Blencathra which surround the village, and the silver moon-shaped Derwentwater Lake, or just amble about waxing poetically about the backdrop to the place that Coleridge, Southey and Wordsworth called home.

The journey: Train to Workington (two hours); bus (one hour) or cycle (two hours) to Keswick

Stay: Rickerby Grange has been welcoming guests since the 1930s, now run by couple Phil and Charlotte with stylish rooms from €125. rickerbygrange.co.uk

3. Durham

Use Durham's Unesco-designated riverfront fairytale castle and cathedral – famous for its pivotal role in the Harry Potter movies – as landmarks to navigate the city's frustrating yet beautiful winding cobbled lanes. Cafés, bars and artisan food outlets line the streets; take a break at pink and pale blue rendered Tealicious for an extensive range of teas and snacks.

The journey: Bus to Wigton (40 minutes), Durham by train (two hours)

Stay: The Kingslodge Inn is a 10-minute walk from Durham, surrounded by the peaceful woodland of Flass Vale, with rooms from €130. inncollectiongroup.com/kingslodge-inn

4. Whitby, Yorkshire

Stay in this sweet little coastal village to discover the North York Moors with its tumbling dales aboard its excellent network of local buses and trains, including the Esk Valley Community Rail service. A museum in town explores the life of adventurer and cartographer Captain James Cook, and towering over the skyline from a cliff edge is the very atmospheric, very Gothic ruins of Whitby Abbey, which found its way onto the pages of Bram Stoker's Dracula. Pretty Robin Hood's Bay, south of Whitby, has tenuous links to the prince of thieves.

The journey: Train to Middlesbrough (two hours), bus to Whitby (50 minutes)

Stay: White Horse & Griffin is an historic in dating back to 1681, with rooms from €110. whitehorseandgriffin.com

5. York, Yorkshire

The very essence of a medieval town, York’s web of cobbled lanes is crammed with half-timbered buildings finished in stucco plaster, rich rustic handmade brick and casement windows. Head to The Shambles, one of the most Instagram-ed streets in the world, to get the full ye olde worlde vibe. The “House of Trembling Madness” in Stonegate has a wide selection of local beers on tap, but before you go down that road, be sure to catch a glimpse of Minster, York’s magnificent Gothic cathedral.

The journey: Train from Whitby to York (two hours)

Stay: The Hilton York has rooms from €115. hilton.com

6. Bakewell , Derbyshire

Right in the heart of the Peak District’s rolling hills and rocky outcrops, and set on the banks of the River Wye, is Bakewell, with its exquisite collection of independent bookshops and cafés lined along sandstone streets. A swooning heartbeat away is Chatsworth House, which doubled as Pemberley in the television and movie take on Jane Austin’s novel Pride and Prejudice. To promote sustainable tourism, visitors arriving at Chatsworth by bus, train or bicycle get £5 off tickets.

The journey: Train to Sheffield (one hour), onward bus to Bakewell (50 minutes)

Stay: The 200-year-old Peacock Inn offers colourful rooms with four-poster beds from €118. peacockbakewell.com

7. Rye, East Sussex

Arguably England's most beautiful town, Rye is a place where the clock stopped ticking sometime in the 15th century, with crooked timber overhangs, cast iron signage and lantern light that casts a ghostly reflection on its shiny cobbled alleyways. Head to Mermaid Street – a twisting lane that looks as if it belongs on a movie set – with eccentric buildings names such as The House Opposite. Tales of spirits, smugglers and pirates are aplenty, including the nightly apparitions at Lamb House, the one-time home of American author Henry James.

The journey: Train to Rye (four hours)

Stay: Willow Tree House offers luxurious bed & breakfast from €150 per room. willow-tree-house.com

8. Penzance, Cornwall

From Rye, take the Night Riviera Sleeper via London, which is only a short train trip away, to add a romantic twist to the adventure. Penzance's promenade has a rustic, Victorian charm, but stroll up to Chapel Street to see the town's impressive Georgian architecture, including the eccentric and outlandish Egyptian House or the little abode of Maria Branwell, mother of the Brontë siblings. From Penzance, ramble along the Cornish coast, first to beachfront St Ives by the scenic Bay Line. An eclectic panoply of roofs – belfries, slated or tiled – cluster around the white sand bay, and there's top-notch dining, too; linger at The Porthminster Beach Café for views. Then explore the coast by rail, dropping by places such as Mousehole or Saint Michael's Mount, before slow pacing it to Plymouth.

The journey: Sleeper train (10 hours) or day train (eight hours)

Stay: The Artist's Residence offers eccentric, charming rooms in a revived Georgian inn from €125. artistresidence.co.uk

9. Castle Combe, Wiltshire

Sleepy Castle Combe shows little sign of time passing, and so its winding streets have attracted the attention of movie producers from Steven Spielberg to the Downton Abbey team. It's definitely a slow-pace destination; stop by The Old Stables for a coffee, or make your way to Saint Andrew's Church to find the 15th century Faceless Clock. Castle Combe's location in the Cotswolds makes it the perfect base to explore the other golden villages in the region.

The journey: Train from Plymouth (three hours)

Stay: The 12th century Castle Inn has rooms from €120. exclusive.co.uk/the-castle-inn/

10. Stratford-Upon-Avon

The honey hues and spires of college city Oxford make it a worthy break on the journey to Shakespeare's country. Stratford is a handy last stop – most of the good stuff, including the great bard's home from the cradle to the grave at Holy Trinity Church – is within close walking distance of the station. Rest up for the final leg of the journey back to Holyhead by taking in a play at the Royal Shakespeare Company theatre.

The journey: Train from Castle Combe (three hours)

Stay: The Mercure Shakespeare Hotel has rooms from €110. all.accor.com