BLACK FRIDAY IS HERE! 🌟 Up to 30% off your dream trip. Don't delay, SPOTS ARE LIMITED! 🔥

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

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

Available

Coordinator

Erica


Expected WeRoaders: 8

Total
$2,672
Private room included when booking for 2

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

Available

Expected WeRoaders: 12

Total
$823

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

Available

Expected WeRoaders: 8

Black Friday!
Total
$755
-7%
$ 813

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

Confirmed

Show
group info


Expected WeRoaders: 9

Black Friday!
Total
$905
-13%
$ 1,045

City Escape
02 Sep 2026
Wednesday
5 days
06 Sep 2026
Sunday

Available

Expected WeRoaders: 12

Total
$813
Private room included when booking for 2

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

Available

People interested: 3

Expected WeRoaders: 8

Black Friday!
Total
$2,288
-21%
$ 2,904
Private room included when booking for 2

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

Available

Expected WeRoaders: 8

Black Friday!
Total
$528
-23%
$ 689
Private room included when booking for 2

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

Available

Expected WeRoaders: 8

Black Friday!
Total
$539
-27%
$ 747
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

Black Friday!
Total
$1,242
-6%
$ 1,335
Private room included when booking for 2

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

Confirmed

Show
group info


Expected WeRoaders: 12

Black Friday!
Total
$1,951
-11%
$ 2,207
Private room included when booking for 2

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

Confirmed

Coordinator

Ali

Show
group info


Expected WeRoaders: 15

Total
$1,335
Private room included when booking for 2

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

Available

Expected WeRoaders: 10

Black Friday!
Total
$1,010
-20%
$ 1,277
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

Black Friday!
Total
$1,510
-7%
$ 1,626
Private room included when booking for 2

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

Available

Show
group info


People interested: 3

Expected WeRoaders: 9

Black Friday!
Total
$1,823
-10%
$ 2,033
Private room included when booking for 2

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

Confirmed

Coordinator

Andrea

Show
group info


Expected WeRoaders: 13

Black Friday!
Total
$1,010
-20%
$ 1,277
Private room included when booking for 2

360°, Art & Culture
04 Sep 2026
Friday
9 days
12 Sep 2026
Saturday

Available

People interested: 1

Expected WeRoaders: 8

Black Friday!
Total
$1,198
-20%
$ 1,498
Private room included when booking for 2

On the road
05 Sep 2026
Saturday
14 days
18 Sep 2026
Friday

Available

Expected WeRoaders: 8

Total
$3,141

360°
05 Sep 2026
Saturday
12 days
16 Sep 2026
Wednesday

Available

People interested: 3

Expected WeRoaders: 8

Black Friday!
Total
$1,921
-22%
$ 2,474
Private room included when booking for 2

City Escape
05 Sep 2026
Saturday
5 days
09 Sep 2026
Wednesday

Available

Expected WeRoaders: 12

Black Friday!
Total
$748
-7%
$ 806
Private room included when booking for 2

360°
05 Sep 2026
Saturday
11 days
15 Sep 2026
Tuesday

Confirmed

Show
group info


Expected WeRoaders: 10

Black Friday!
Total
$2,102
-7%
$ 2,265
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!