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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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186 trips found
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Aerial view of a rocky shoreline with clear, turquoise water showing submerged boulders beside a dense pine forest.
Lake Tahoe Weekend: Alpine Lakes & Mountain Trails
3 days
From$ 655
$ 936
-30%
See trip
A man on a bicycle carries a surfboard along a wide, paved path lined with tall palm trees on a sunny day.
Los Angeles Weekend: from Venice Beach to Joshua Tree Park
3 days
From$ 492
$ 703
-30%
See trip
A panoramic aerial view of a rugged, green coastline and deep blue sea, with a large sailing ship and other boats.
Madeira 360°: trekking and canyoning
8 days
4.8(596)
From$ 1,171
$ 1,465
-20%
See trip
A dry, rocky wash with yellow grass and yucca plants winds through a desert landscape toward distant mountains under a cloudy sky.
Marfa & Big Bend Weekend: Desert, Art & Stargazing
3 days
From$ 491
$ 702
-30%
See trip
A stack of wooden barrels decorated with red flowers sits on a patio overlooking a vast vineyard on a rolling hill.
Napa Valley & San Fran Weekend: Wine, Food & Rolling Hills
3 days
From$ 655
$ 936
-30%
See trip
The back of a bronze boxer statue with arms raised in victory, overlooking a modern city skyline under an overcast sky.
Philadelphia Weekend: History, Food & Street Art
3 days
From$ 573
$ 820
-30%
See trip
A red and white lighthouse with an adjacent building sits atop a grassy hill under a clear teal sky, with a path leading up to it.
The Hamptons Weekend: Beaches, Vineyards & Montauk
3 days
From$ 655
$ 937
-30%
See trip
A rocky river flows through a pine forest with misty mountains in the background under a sunset sky.
Yosemite Weekend: Waterfalls, Granite Cliffs & Stargazing
3 days
From$ 444
$ 643
-30%
See trip
Lush green mountains rise above a thick blanket of fog in a valley under a golden sunrise sky.
Nashville & Great Smoky Mountains Express
6 days
From$ 1,406
$ 1,993
-29%
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(1180)
From$ 751
$ 939
-20%
See trip
A WeRoad group trip of three women sitting on a clifftop, arms raised, overlooking a coastal village surrounded by mountains and sea.
Norway 360°: discovering the Lofoten islands
8 days
4.9(415)
From$ 1,691
$ 1,997
-15%
See trip
Four women in traditional clothing walk through a terraced rice field, with lush green mountains in the background.
Vietnam 360°: from Hanoi to Ho Chi Minh City
13 days
4.8(2452)
From$ 1,265
$ 1,582
-20%
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$ 1,409
$ 1,762
-20%
See trip
A waterfall cascades into a turquoise pool surrounded by a lush green rainforest.
Costa Rica 360°: between jungle, beaches and volcanoes
13 days
4.7(807)
From$ 1,832
$ 2,291
-20%
See trip
A coastal city with a church dome and spire overlooks the blue sea under a partly cloudy sky.
Malta Beach Life Weekend: relax and adventure in the Maltese coast
3 days
4.9(11)
From$ 398
$ 422
-5%
See trip
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