September Trips 2026
It's not the end of summer
September holidays are calling your name
The heat eases, the crowds disappear, and the world opens up for a different kind of adventure
Isn't September the hardest and most challenging month of the year? Maybe it's because summer is coming to an end, maybe it's that feeling that vacations are gone... what if we fight against that by planning a trip in September? One thing is sure: places are less crowded, prices are lower, and you'll be sure to enjoy and unforgettable adventure with new friends - well, that works all-year long with WeRoad, but we're not here to brag. So, now the question is: Peru for epic hikes, Italy for some great food, Jordan to feel like in another planet, or New York to enjoy some city vibes? On this page, you’ll find all our best group adventures departing in September.
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134 trips found
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Top seller
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$ 523
$ 756
-30%
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$ 1,047
$ 1,105
-5%
Top seller
360°, Active, Trekking & Hiking
9 days
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$ 825
$ 930
-11%
Top seller
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$ 860
$ 1,012
-14%
Top seller
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$ 686
$ 814
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$ 1,582
$ 1,745
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$ 779
$ 826
-5%
Top seller
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$ 639
$ 697
-8%
winter trend
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$ 1,547
$ 1,745
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$ 332
$ 349
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$ 815
$ 1,163
-29%
Top seller
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$ 651
$ 698
-6%
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$ 411
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$ 757
$ 814
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$ 2,248
$ 2,551
-11%
Art & Culture, History, Multi country
13 days
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$ 2,176
$ 2,642
-17%
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$ 2,118
$ 2,328
-9%
From
$ 1,281
Active, Relax & Wellbeing, Ski & Snowboard, Spa & Wellness
5 days
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$ 1,163
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$ 662
$ 697
-5%
City Escape, Food & Wine, Relax & Wellbeing, Spa & Wellness
3 days
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$ 457
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$ 1,233
$ 1,396
-11%
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$ 1,151
$ 1,221
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$ 2,543
$ 2,677
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$ 1,454
$ 1,629
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$ 1,326
$ 1,396
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$ 406
From
$ 349
Active, Expedition, Trekking & Hiking
14 days
From
$ 1,769
$ 1,862
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$ 1,908
$ 2,037
-6%
360°, Architecture, Art & Culture, History
12 days
From
$ 2,522
Top seller
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$ 2,095
$ 2,514
-16%
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$ 2,096
$ 2,388
-12%
From
$ 686
$ 989
-30%
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$ 2,351
$ 2,619
-10%
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$ 1,629
$ 1,745
-6%
Top seller
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$ 1,910
$ 2,127
-10%
Top seller
From
$ 1,385
$ 1,455
-4%
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