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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139 trips found
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$ 698
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$ 1,012
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360°, Active, Trekking & Hiking
9 days
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$ 826
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$ 814
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$ 1,165
winter trend
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$ 1,747
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$ 585
$ 644
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City Escape, Food & Wine, Relax & Wellbeing, Spa & Wellness
3 days
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$ 457
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$ 872
$ 1,162
-24%
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$ 2,621
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$ 814
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$ 2,504
Art & Culture, History, Multi country
13 days
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$ 2,330
$ 2,644
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$ 1,106
$ 1,222
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$ 2,073
$ 2,330
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$ 1,420
$ 1,630
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$ 1,173
Active, Relax & Wellbeing, Ski & Snowboard, Spa & Wellness
5 days
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$ 2,796
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$ 1,327
$ 1,397
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$ 995
$ 1,054
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$ 349
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$ 2,155
Active, On the road, Trekking & Hiking
14 days
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$ 5,768
Active, Expedition, Trekking & Hiking
14 days
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$ 1,770
$ 1,863
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