May trips

May trips 2026

Skip the crowds and start your summer early

"I Was May for Lovin' You..."

Discover the season at its best

May trip: the sweet spot between spring's freshness and summer's sizzle. The days are longer, the sun shines brighter, and the world feels wide open. It's the perfect time to break free from routine and dive into new experiences with like-minded travellers in their 20s, 30s and 40s. May bring together curious people, just like you. No peak-season prices, no long lines — just epic journeys and real moments.

So, just for you, on this page we have a list of all our best trips in May - you just need to choose where to go!

All trips departing in May

5
200 departure dates found
May 2026
Beach Life
01 May 2026
Friday
8 days
08 May 2026
Friday

Planned

People interested: 1

Expected WeRoaders: 9

Total
$1,156

Art & Culture, City Escape, History
01 May 2026
Friday
5 days
05 May 2026
Tuesday

Planned

People interested: 1

Expected WeRoaders: 8

Total
$705
Private room included when booking for 2

City Escape
01 May 2026
Friday
5 days
05 May 2026
Tuesday

Confirmed

Show
group info


Expected WeRoaders: 12

Total
$873
Private room included when booking for 2

Art & Culture
01 May 2026
Friday
5 days
05 May 2026
Tuesday

Almost confirmed

Show
group info


People interested: 5

Expected WeRoaders: 13

Total
$815

City Escape
01 May 2026
Friday
5 days
05 May 2026
Tuesday

Almost confirmed

Coordinator

Veronica


Expected WeRoaders: 8

Total
$815

360°, Active, Trekking & Hiking
01 May 2026
Friday
9 days
09 May 2026
Saturday

Almost confirmed

Show
group info


People interested: 1

Expected WeRoaders: 8

Total
$1,340
Private room included when booking for 2

360°
01 May 2026
Friday
12 days
12 May 2026
Tuesday

Confirmed

Show
group info


Expected WeRoaders: 10

Total
$2,331
Private room included when booking for 2

360°, Beach Life
01 May 2026
Friday
13 days
13 May 2026
Wednesday

Almost confirmed

People interested: 1

Expected WeRoaders: 8

Total
$2,447
Private room included when booking for 2

City Escape
01 May 2026
Friday
5 days
05 May 2026
Tuesday

Almost confirmed

People interested: 1

Expected WeRoaders: 12

Total
$873
Private room included when booking for 2

360°, Safari
01 May 2026
Friday
13 days
13 May 2026
Wednesday

Planned

People interested: 2

Expected WeRoaders: 10

Total
$2,706
Private room included when booking for 2

360°
01 May 2026
Friday
10 days
10 May 2026
Sunday

Confirmed

Coordinator

Yaser

Show
group info


Expected WeRoaders: 8

Total
$2,156
Private room included when booking for 2

Collection
360°
01 May 2026
Friday
10 days
10 May 2026
Sunday

Almost confirmed

Expected WeRoaders: 8

Total
$4,314
Private room included when booking for 2

360°
01 May 2026
Friday
9 days
09 May 2026
Saturday

Almost confirmed

People interested: 1

Expected WeRoaders: 9

Total
$1,514
Private room included when booking for 2

360°, Beach Life
02 May 2026
Saturday
8 days
09 May 2026
Saturday

Confirmed

Coordinator

Renato

Show
group info


Expected WeRoaders: 15

Total
$873

On the road
02 May 2026
Saturday
14 days
15 May 2026
Friday

Almost confirmed

Expected WeRoaders: 8

Total
$2,914

360°
02 May 2026
Saturday
9 days
10 May 2026
Sunday

Almost confirmed

Show
group info


People interested: 4

Expected WeRoaders: 11

Total
$1,095
-6%
$ 1,165

360°
02 May 2026
Saturday
7 days
08 May 2026
Friday

Planned

Expected WeRoaders: 8

Total
$1,352
Private room included when booking for 2

Beach Life
02 May 2026
Saturday
11 days
12 May 2026
Tuesday

Almost confirmed

Show
group info


People interested: 3

Expected WeRoaders: 12

Total
$2,622
-5%
$ 2,769

Collection
Architecture, Art & Culture
02 May 2026
Saturday
5 days
06 May 2026
Wednesday

Almost confirmed

Expected WeRoaders: 8

Total
$1,340
Private room included when booking for 2

Multi country, On the road, Train
02 May 2026
Saturday
7 days
08 May 2026
Friday

Planned

Expected WeRoaders: 11

Total
$1,516

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!