foto di gruppo WeRoad nel deserto del Wadi Rum in Giordania

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.

All trips departing in September

184 departure dates found
September 2026
360°, Beach Life
01 Sep 2026
Tuesday
13 days
13 Sep 2026
Sunday

Almost confirmed

Coordinator

Erica


Expected WeRoaders: 8

Total
$2,681

City Escape
01 Sep 2026
Tuesday
5 days
05 Sep 2026
Saturday

Planned

Expected WeRoaders: 8

Total
$761
Private room included when booking for 2

Art & Culture
01 Sep 2026
Tuesday
5 days
05 Sep 2026
Saturday

Planned

Expected WeRoaders: 12

Total
$823

360°
01 Sep 2026
Tuesday
13 days
13 Sep 2026
Sunday

Almost confirmed

Expected WeRoaders: 9

Total
$1,398
Private room included when booking for 2

Food & Wine
02 Sep 2026
Wednesday
5 days
06 Sep 2026
Sunday

Planned

Expected WeRoaders: 8

Total
$815

City Escape, On the road
02 Sep 2026
Wednesday
5 days
06 Sep 2026
Sunday

Confirmed

Show
group info


Expected WeRoaders: 8

Total
$1,048

360°
02 Sep 2026
Wednesday
14 days
15 Sep 2026
Tuesday

Planned

People interested: 1

Expected WeRoaders: 9

Total
$1,626
Private room included when booking for 2

360°, On the road
02 Sep 2026
Wednesday
15 days
16 Sep 2026
Wednesday

Planned

People interested: 2

Expected WeRoaders: 8

Total
$2,933
Private room included when booking for 2

Art & Culture, City Escape, History
03 Sep 2026
Thursday
5 days
07 Sep 2026
Monday

Planned

Expected WeRoaders: 8

Total
$703
Private room included when booking for 2

City Escape
03 Sep 2026
Thursday
5 days
07 Sep 2026
Monday

Planned

Expected WeRoaders: 8

Total
$760
Private room included when booking for 2

360°, Active, Trekking & Hiking
03 Sep 2026
Thursday
8 days
10 Sep 2026
Thursday

Confirmed

Show
group info


Expected WeRoaders: 15

Total
$1,339
Private room included when booking for 2

360°, Beach Life
04 Sep 2026
Friday
8 days
11 Sep 2026
Friday

Planned

Expected WeRoaders: 13

Total
$1,055

360°
04 Sep 2026
Friday
8 days
11 Sep 2026
Friday

Almost confirmed

Expected WeRoaders: 9

Total
$1,106
Private room included when booking for 2

360°
04 Sep 2026
Friday
12 days
15 Sep 2026
Tuesday

Confirmed

Show
group info


Expected WeRoaders: 10

Total
$2,214
Private room included when booking for 2

Beach Life
04 Sep 2026
Friday
8 days
11 Sep 2026
Friday

Almost confirmed

Expected WeRoaders: 11

Total
$1,048

360°
04 Sep 2026
Friday
12 days
15 Sep 2026
Tuesday

Planned

Expected WeRoaders: 8

Total
$1,348
Private room included when booking for 2

360°, Active, Trekking & Hiking
04 Sep 2026
Friday
8 days
11 Sep 2026
Friday

Confirmed

Show
group info


Expected WeRoaders: 15

Total
$1,339

360°
04 Sep 2026
Friday
8 days
11 Sep 2026
Friday

Planned

Expected WeRoaders: 9

Total
$1,290
Private room included when booking for 2

360°, Active
04 Sep 2026
Friday
10 days
13 Sep 2026
Sunday

Confirmed

Coordinator

Kerry Anne

Show
group info


Expected WeRoaders: 8

Total
$1,475
-9%
$ 1,631

360°
04 Sep 2026
Friday
12 days
15 Sep 2026
Tuesday

Almost confirmed

Show
group info


People interested: 2

Expected WeRoaders: 9

Total
$2,039
Private room included when booking for 2

Doubts? Questions? Contact our team!

Contact us!

Mon - Fri: 9:00 a.m. - 6:00 p.m.

Help with finding flights

Flights are not included in the price, but we'll be happy to help you find them!