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Escorted City Breaks & Sightseeing Holidays by Rail

Across Europe and the UK, there's a magnificent wealth of cities to lose yourself in, each brimming with unique culture and unforgettable sights. Join us on an enticing city break and we'll take you to the cultural heart of each city, with carefully-planned itineraries that combine visits to must-see attractions with authentic local experiences, as well as free time to explore in a way that suits you.  

See how historic cities have developed into modern hubs while maintaining their one-of-a-kind charms, or step back in time in ancient cities seemingly unchanged in centuries; the best part of Europe is its rich diversity. Our holidays take you to your chosen city in the best way possible, with an efficient and comfortable rail journey that takes you straight into the centre of the action - and gives you the chance to admire some of Europe's stunning stations, often landmarks in themselves.

With us, you'll be expertly guided by our knowledgeable tour managers, who bring these amazing cities to life with their local insights and engaging stories. Whether you're a first-time visitor or a seasoned traveller, we'll show you a side of these cities that you've never seen before, and create memories that will last a lifetime.

Our recommended Cities & Sights holidays

ClassicClassic
Grand Imperial Cities
Save £100pp
4.6 stars(250 reviews)
2026AugSepOct
2027MarAprMayJunJul...
12 days from
£2,399 pp £2,299 pp
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ClassicClassic
Highlights of Tuscany
Double discount!
4.4 stars(297 reviews)
2026AugSepOct
2027AprMayJunAugSep...
10 days from
£2,099 pp £1,899 pp
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ClassicClassic
Lisbon
4.3 stars(99 reviews)
2026AugSepOct
2027AprMayJunAugSepOct
15 days from
£3,999 pp
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City break ideas from our blog

From what to get up to if you find yourself in Amsterdam for the day to the world's most beautiful railway stations, head over to the Journey Blog and let us inspire you with our unique city insights.

Why travel with us?

126 results matching: Cities & Sights Escorted Holidays

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ClassicClassic
Taj Mahal, AgraTaj Mahal, AgraTaj Mahal, AgraTaj Mahal, AgraTaj Mahal, Agra
Half price upgrade
4.8 stars(573 reviews)
2026SepOctNov
2027JanFebMarAprSep...

Follow in the footsteps of maharajas on our bestselling Indian holiday, uncovering the gems of northern India and visiting Shimla - the only tour operator to combine the Golden Triangle and the former summer capital of the British Raj. Embrace the many wonders of this mystical country on this unrivalled overland journey. Enjoy the bustle of...

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Half price upgrade
14 days from
£2,699 pp
per person
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DiscoveriesDiscoveries
DesenzanoDesenzanoDesenzanoDesenzanoDesenzano
Save £100pp
4.2 stars(357 reviews)
2026JulAugSepOct
2027MarAprMayJunJul...

A family-run hotel in the lakeside town of Desenzano is our charming base. With a panoramic terrace providing beautiful views of the lake, the hotel is perfectly positioned near to the characterful Old Town and train station. This holiday includes a cruise to enchanting Isola del Garda to explore the renowned Venetian Villa Borghese-Cavazza and...

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Save £100pp
10 days from
£1,699 pp £1,599 pp
per person
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ClassicClassic
Highlights of TuscanyHighlights of TuscanyHighlights of TuscanyHighlights of TuscanyHighlights of Tuscany
Double discount!
4.4 stars(297 reviews)
2026AugSepOct
2027AprMayJunAugSep...

Savour the glorious colours, aromas and flavours of Tuscany on a holiday highlighting the true beauty of this beloved region. Discover the great Renaissance city of Florence, visit a historic family estate for a tour and dinner, and marvel at the iconic monuments of Pisa, including the Leaning Tower. Explore the stunning sights of Siena, the...

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Double discount!
10 days from
£2,099 pp £1,899 pp
per person
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ClassicClassic
St Johann St Johann St Johann St Johann St Johann
4.2 stars(258 reviews)
2026JulAugSepOct
2027AprMayJunJulAug...

Explore the beautiful towns and landscapes of the Austrian Alps from your base in the charming town of St Johann, surrounded by rolling peaks and lush valleys. Marvel at views of Austria's tallest mountain on a journey across the Hochtor Pass on the Grossglockner High Alpine Road, viewing glaciers and gold-mining towns, before discovering the...

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9 days from
£2,199 pp
per person
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Carcassonne & the Canal du MidiCarcassonne & the Canal du MidiCarcassonne & the Canal du MidiCarcassonne & the Canal du MidiCarcassonne & the Canal du Midi
4.3 stars(276 reviews)
2026AugSepOct
2027AprMayJunJulAug...

Embark on an indulgent French holiday based in a riverside hotel in stunning Carcassonne, discovering the myths of hilltop Cathar castles and indulge in the region's renowned flavours. Stroll through Carcassonne's walled fortress on a guided tour of the city's medieval sights and uncover the mysterious history of the four hillside Châteaux de...

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7 days from
£1,999 pp
per person
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River CruiseRiver Cruise
Trier, GermanyTrier, GermanyTrier, GermanyTrier, GermanyTrier, Germany
4.7 stars(63 reviews)
2026Oct
2027AugSepOct

Join us as we uncover the Moselle and Rhine, where every bend of the river reveals breathtaking autumnal hues and every port beckons a new discovery. Ancient castles and Roman ruins sprinkle the red, gold, and orange landscape on this leisurely cruise as we sail by sloped vineyards and rolling hills ready for harvest. Visit charming towns like...

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8 days from
£1,899 pp
per person
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The Italian RivieraThe Italian RivieraThe Italian RivieraThe Italian RivieraThe Italian Riviera
Double discount!
2026AugSepOct
2027AprMayJunJulSepOct

Discover the towns and villages of the Italian Riviera which sparkle beside the Mediterranean Sea, as we explore the Cinque Terre and the harbour town of Portofino. Explore the pastel-hued fishing village of Camogli, a hidden gem, and relax in Sestri Levante - a town between two bays. Sail to San Fruttuoso abbey, set in a secluded cove and only...

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Double discount!
10 days from
£1,999 pp £1,799 pp
per person
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DiscoveriesDiscoveries
Nyhavn CanalNyhavn CanalNyhavn CanalNyhavn CanalNyhavn Canal
4.3 stars(141 reviews)
2026JulAugSepOct
2027AprMayJunJulAug...

Discover evocative Scandinavian landscapes on picturesque rail journeys between the cultured capitals of Norway, Sweden and Denmark. Starting in Oslo, uncover its stylish modernity and thousand-year history on a guided tour, before travelling by rail to Stockholm. In the Swedish capital, visit the colourful Gamla Stan, one of the best-preserved...

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8 days from
£2,199 pp
per person
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ClassicClassic
Senate Square, HelsinkiSenate Square, HelsinkiSenate Square, HelsinkiSenate Square, HelsinkiSenate Square, Helsinki
Save up to £500pp
2026JulAugSep
2027MayJunJulAugSep

Fly to Helsinki to begin a discovery of three unique countries on the shores of the Baltic Sea. Discover the charms of innovative Helsinki before sailing to Tallinn to uncover the fairytale sights of Estonia's timeless capital. This scenic exploration concludes amid the colourful cobbled streets of Riga, the picture-perfect capital of Latvia,...

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Save up to £500pp
8 days from
£1,699 pp £1,499 pp
per person
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River CruiseRiver Cruise
RegensburgRegensburgRegensburgRegensburgRegensburg
4.2 stars(35 reviews)
2026Sep
2027Aug

This nine-day river cruise featuring five-star dining and luxurious cabins, blends historical discovery with unparalleled onboard comfort. Experience Regensburg, visit Weltenburg Abbey, Bavaria's oldest Benedictine monastery and wander through the medieval streets of Rothenburg ob der Tauber. Sample fine wines in Würzburg's Baroque setting and...

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9 days from
£2,199 pp
per person
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ClassicClassic
Canada & the Rocky Mountaineer train tourCanada & the Rocky Mountaineer train tourCanada & the Rocky Mountaineer train tourCanada & the Rocky Mountaineer train tourCanada & the Rocky Mountaineer train tour
Half price upgrade
4.4 stars(84 reviews)
2026JulAugSepOct
2027MayJunJulAugSep

Delve into the remarkable landscapes of Canada, travelling through areas of outstanding beauty on world-famous trains. Beginning with a guided tour of beautiful Vancouver on the Pacific coast, the journey continues with two daytime trips on the amazing Rocky Mountaineer to the astonishing Canadian Rockies. Based in gorgeous Banff and Jasper,...

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Half price upgrade
14 days from
£6,499 pp
per person
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ClassicClassic
Glacier Bay National ParkGlacier Bay National ParkGlacier Bay National ParkGlacier Bay National ParkGlacier Bay National Park
Half price upgrade
4.7 stars(59 reviews)
2026AugSep
2027MayJunJulAug

A spectacular discovery of natural wonders awaits on this exploration by land and sea. From the mountain town of Banff in the Canadian Rockies, we marvel at the spellbinding beauty of Lake Louise before boarding the iconic Rocky Mountaineer. This fantastic rail journey transports us to Vancouver, where we set sail on an unforgettable cruise. ...

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Half price upgrade
16 days from
£6,199 pp
per person
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Our customers love our Cities & Sights tours
Oslo, Stockholm & Copenhagen
17/Jun
Martin Adams
5 stars
“As with my previous holidays with Great Rail this was very well organised with a good rep. We stayed in good hotels and the itinerary was well planned with good local guides in each city.
Collected by Trustpilot
Rocky Mountaineer & Alaska Cruise
15/Jun
Jennifer Aldred
5 stars
“Rocky Mountaineer was out of this world. Cruise ship was mega expensive
Collected by Trustpilot
Simply Lake Garda
15/Jun
James Parrish
5 stars
“Very well organised trip making use of a lovely traditional hotel in Desenzano. Francesca, the tour leader, was very professional and kept everyone on track with thorough organisation and calmness.
Collected by Trustpilot
India’s Golden Triangle, Tigers & Shimla
7/May
Rupert Lavers
5 stars
“Fantastic trip, enjoyed shimla most, followed by the national park and jaipur. Alot packed into 2 weeks, accommodation excellent
Collected by Trustpilot
Autumnal Colours of the Moselle & Rhine
05 Nov 2025
John Wood
5 stars
“A fantastic holiday. Cannot fault it but the highlights were excellent food, friendly, efficient staff and well run, interesting excursions.
Collected by Trustpilot
A Tale of Three Rivers: Danube, Main & Rhine
25 Sep 2025
Mr Smith
5 stars
“Excellent organisation, food, off-ship sightseeing tours and overall experience
Collected by Trustpilot
Tuscany: Florence, San Gimignano & Pisa
17/Jun
Philip Brown
4 stars
“Group was great - all good fun and Tour manager was great as well. Minor grumbles about lugging suitcases on and off trains but we knew that would be a feature and in hindsight should have gone for the luggage forwarding option. . A couple of the tour guides were...
Collected by Trustpilot
First-Class Carcassonne, Châteaux & Vineyards
17/Jun
Maureen Harding
4 stars
“Lovely itinerary, good hotel and excellent tour manager, but the train journey with our cases there and back was too long and tiring!… It might have been better to have flown direct to Carcassonne and then go on organised short rail journeys once there!!??….
Collected by Trustpilot
Classic Austrian Alps
13/Jun
Alan Thomson
4 stars
“Excellent trip. Our tour manager Martin was very professional and friendly. Our only disappointment was that this is sold as an all inclusive holiday which is not the case. Only drinks served at dinner in St Johann are included.
Collected by Trustpilot