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Winter trips

Winter trips

Escape this winter: come on a WeRoad adventure and make friends for life!

No plans this winter? Whatever you do, don't stay in rainy Britain.

Are you ready for an epic winter adventure? Look no further! Discover unforgettable Winter trips with WeRoad. Imagine yourself surrounded by stunning snowy landscapes in Iceland, or lounging on the white sand beaches of the Maldives. And if exploring the vibrant culture and lush jungles of Thailand is more your style, we've got that too! WeRoad’s Winter trips are crafted for those who want more from their travel: real moments, shared laughter, and memories that outlast the season. So skip the routine. Come join us and embark on the adventure of a lifetime! Your next group trip - and your next great story - starts now.

Check out our departures over winter

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140 trips found
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Aerial view of a sandy peninsula stretching into shallow turquoise water, with mountains on the distant coastline under a blue sky.
Crete Beach Life
8 days
4.7
(860)
From$ 1,094
See trip
A wave splashes against the rocks of a sandy cove with turquoise water under a bright blue sky.
Italy Beach Life: North Sardinia
8 days
4.7
(956)
From$ 1,433
See trip
A pride of lions, including a lioness and cubs, walks through a field of tall, dry grass.
Kenya: Safari, Culture & Coast
9 days
From$ 2,752
$ 3,270
-15%
See trip
The exterior of Mr. D'z, a retro Route 66 diner, glows with colorful neon signs at twilight.
Route 66: on the road from Chicago to LA
15 days
4.8
(495)
From$ 2,982
See trip
A panoramic view of a long sandy beach along a calm blue sea, with a coastal city and mountains in the background.
Turkey Beach Life: Antalya & the Lycian Coast
10 days
From$ 1,375
$ 1,720
-20%
See trip
A woman with blonde dreadlocks in a red top, seen from behind, looking out over terraced salt evaporation ponds.
Peru: Inca Trail Trekking & Sacred Valley
7 days
From$ 905
See trip
A panoramic view of ancient stone ruins and terraces on a green mountainside with a prominent peak lit by sunlight.
Peru Trekking Express: Inca Trail
4 days
From$ 917
See trip
A large orange sand dune casts a deep shadow across itself in a rocky desert landscape under a clear blue sky.
Namibia 360°: Wildlife, Etosha Safari, and the Namib Desert
11 days
4.9
(210)
From$ 2,810
See trip
A wooden boat floats on a calm river that reflects the blue sky and clouds, with a dense green forest in the background.
Peru: Machu Picchu & the Amazon Experience
9 days
From$ 2,190
See trip
A yellow funicular tram travels up a steep, narrow cobblestone street lined with colorful buildings, with a view of the water in the distance.
Portugal Express: from Porto to Lisbon
5 days
4.7
(1173)
From$ 859
See trip
A WeRoad group trip of three women sitting on a clifftop, arms raised, overlooking a coastal village surrounded by mountains and sea.
Top seller
Norway 360°: discovering the Lofoten islands
8 days
4.9
(415)
From$ 1,949
See trip
A WeRoad group trip takes a smiling selfie on a narrow cobblestone street between colorful buildings.
Colombia 360°: Backpacking Edition
11 days
From$ 1,720
See trip
A panoramic view of a deep blue lake inside a volcanic caldera, surrounded by lush green mountains with the ocean in the distance.
Azores Trekking: adventures between volcanoes and ocean
8 days
5
(17)
From$ 1,662
See trip
A long reflecting pool leads to a large white marble mausoleum with minarets, surrounded by gardens where people are walking.
India: from Rajasthan to the Taj Mahal
9 days
4.8
(725)
From$ 1,605
See trip
A WeRoad group leader with blonde hair stands at a railing, looking out at a large, cascading waterfall under a clear blue sky.
Argentina and Brazil: A True South American Adventure
9 days
5
(20)
From$ 2,121
See trip
A pink vintage car parked on a narrow, sunlit street lined with colorful buildings, with a Cuban flag hanging from a balcony.
Cuba 360°: from Havana to Trinidad
12 days
4.7
(4326)
From$ 1,352
See trip
A volcano erupts at night, with glowing lava flowing down its dark slopes under a starry sky.
Guatemala and Belize: Volcanoes, Ruins, and Caribbean Vibes
13 days
5
(3)
From$ 2,144
$ 2,637
-18%
See trip
An aerial view of a narrow sandbar stretching into a turquoise sea, with a sailboat anchored offshore under a clear blue sky.
Ibiza and Formentera Beach Life: discovering the Balearics
8 days
5
(61)
From$ 1,720
See trip
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