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October Departures

All of our October travel destinations

Fall is finally here, and you can either spend these gloomy days dreaming about faraway destinations, or you can catch the first flight and spend an 'Autumn in New York' looking for Richard Gere - hopefully, you get the reference, if not, you're missing out on a great movie here! Moving on: whether you're looking for a beach getaway in October or a trip to Italy or maybe an adventure overseas... you're sure to find the perfect WeRoad for you here! Get inspired by the suggestions below (yes, New York is on the list indeed): maybe you fancy a camel ride at sunset on the Sahara in Morocco, or you'd like to have the first sight of season of the Northern Lights in Iceland? You can't go wrong, trust us!

All trips departing in October

5
149 departure dates found
October 2025
Food & Wine
01 Oct 2025
Wednesday
5 days
05 Oct 2025
Sunday

Almost confirmed

2 people interested

Total
$885
-5%
$ 937

01 Oct 2025
Wednesday
5 days
05 Oct 2025
Sunday

Almost confirmed

Group

1 WeRoader

Total
$989
-5%
$ 1,041

01 Oct 2025
Wednesday
5 days
05 Oct 2025
Sunday

Almost confirmed

Group

2 WeRoaders

Total
$676
-7%
$ 728
Private room included when booking for 2

01 Oct 2025
Wednesday
5 days
05 Oct 2025
Sunday

Almost confirmed

Group

1 WeRoader

Total
$739
-5%
$ 780
Private room included when booking for 2

02 Oct 2025
Thursday
5 days
06 Oct 2025
Monday

On request

Travel coordinator

Luke Thomas

Group

7 WeRoaders

Total
$732

360°, Art & Culture
03 Oct 2025
Friday
9 days
11 Oct 2025
Saturday

Planned

Total
$2,667
-5%
$ 2,813
Private room included when booking for 2

03 Oct 2025
Friday
9 days
11 Oct 2025
Saturday

Almost confirmed

7 people interested

Total
$885
-5%
$ 937
Private room included when booking for 2

360°
03 Oct 2025
Friday
13 days
15 Oct 2025
Wednesday

Almost confirmed

2 people interested

Total
$2,229
-4%
$ 2,344
Private room included when booking for 2

360°
03 Oct 2025
Friday
12 days
14 Oct 2025
Tuesday

Confirmed

Travel coordinator

Yaiza

Group

4 WeRoaders

Total
$1,083
-5%
$ 1,145
Private room included when booking for 2

360°
04 Oct 2025
Saturday
8 days
11 Oct 2025
Saturday

Almost confirmed

Group

1 WeRoader

Total
$1,062
-7%
$ 1,145

Beach Life
04 Oct 2025
Saturday
8 days
11 Oct 2025
Saturday

Almost confirmed

Group

1 WeRoader

Total
$1,135
-5%
$ 1,197

Art & Culture
04 Oct 2025
Saturday
5 days
08 Oct 2025
Wednesday

Almost confirmed

3 people interested

Total
$1,041
-4%
$ 1,093

360°
04 Oct 2025
Saturday
8 days
11 Oct 2025
Saturday

Confirmed

Group

4 WeRoaders

Total
$1,114
-6%
$ 1,197
Private room included when booking for 2

360°
04 Oct 2025
Saturday
9 days
12 Oct 2025
Sunday

Confirmed

Travel coordinator

Kerry Anne

Group

3 WeRoaders

Total
$1,083
-5%
$ 1,145
Private room included when booking for 2

360°
04 Oct 2025
Saturday
15 days
18 Oct 2025
Saturday

Almost confirmed

2 people interested

Total
$1,927
-11%
$ 2,188

04 Oct 2025
Saturday
8 days
11 Oct 2025
Saturday

Almost confirmed

Total
$1,333
-5%
$ 1,406
Private room included when booking for 2

360°, Art & Culture
05 Oct 2025
Sunday
9 days
13 Oct 2025
Monday

Planned

1 person interested

Total
$1,979
-5%
$ 2,084

Beach Life
05 Oct 2025
Sunday
8 days
12 Oct 2025
Sunday

Almost confirmed

1 person interested

Total
$728
-12%
$ 832
Private room included when booking for 2

360°
05 Oct 2025
Sunday
12 days
16 Oct 2025
Thursday

Almost confirmed

Group

1 WeRoader

Total
$1,854
-11%
$ 2,104

Yoga, Wellness & Spirituality
05 Oct 2025
Sunday
13 days
17 Oct 2025
Friday

Planned

Total
$2,988