Sailing Trips Starting In May 2025

Are you looking to embark on a sailing trip in May 2025? Choose from 42 unique trip itineraries and 1,076 departures from the world's leading touring operators.
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Departures (May 2025)
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4 Days
26 Days
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$10,220pp
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42 Trips (1,076 Trip Departures)
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: May 2025 to Aug 2026
Countries Visited: Croatia
Big Travel Sale
Save (per person) 665
From (per person) 2,306
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Croatia
Exclusive Savings
Save (per person) 74
From (per person) 3,095
Cruise
 (1)

10 Days (9 Nights) Santorini to Santorini
Operated By: Intrepid Travel
Departures: May 2025 to Oct 2025
Countries Visited: Greece
Exclusive Savings
Save (per person) 76
From (per person) 3,371
New ReleaseTour + Cruise
 (3)

10 Days Split to Split
Operated By: Intro Travel
Departures: May 2025 to Sep 2026
Trip Styles: 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive Savings
Save (per person) 76
From (per person) 3,037
New ReleaseTour + Cruise
 (1)

6 Days Hobart to Hobart
Operated By: Tasmanian Walking Co
Departures: Jan 2025 to Apr 2025
Countries Visited: Australia
From (per person) 4,846
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Croatia, Montenegro
Exclusive Savings
Save (per person) 70
From (per person) 3,144
Cruise

10 Days (9 Nights) Zadar to Venice
Operated By: G Adventures
Departures: Apr 2025 to Sep 2026
Countries Visited: Slovenia, Italy, Croatia
Great Adventure Sale
Save (per person) 793
From (per person) 2,078
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Croatia
Exclusive Savings
Save (per person) 72
From (per person) 3,159
Cruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Contiki
Departures: Apr 2025 to Sep 2026
Countries Visited: Turkey
Exclusive Savings
Save (per person) 543
From (per person) 1,463
Cruise

8 Days (7 Nights) Kefalonia to Corfu
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Greece
Exclusive Savings
Save (per person) 76
From (per person) 3,379
Cruise

10 Days (9 Nights) Venice to Zadar
Operated By: G Adventures
Departures: May 2025 to Sep 2026
Countries Visited: Slovenia, Italy, Croatia
Great Adventure Sale
Save (per person) 793
From (per person) 2,078
Cruise

8 Days (7 Nights) Mykonos to Athens
Operated By: G Adventures
Departures: Apr 2025 to Oct 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 227
From (per person) 1,603
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2025 to Oct 2025
Countries Visited: Indonesia
Just Go Offer
Save (per person) 1,295
From (per person) 4,700
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: May 2025 to Sep 2026
Countries Visited: Croatia
Big Travel Sale
Save (per person) 592
From (per person) 1,794
Cruise

8 Days (7 Nights) Split to Split
Operated By: Topdeck
Departures: May 2025 to Aug 2025
Countries Visited: Croatia
Exclusive Savings
Save (per person) 54
From (per person) 2,665
New ReleaseCruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Topdeck
Departures: May 2025 to Oct 2025
Countries Visited: Turkey
Exclusive Savings
Save (per person) 45
From (per person) 1,655
Tour + Cruise

18 Days Negombo to Male
Operated By: G Adventures
Departures: Feb 2025 to Dec 2026
Trip Styles: Small Group, 18-30's, Sailing
Countries Visited: Sri Lanka, Maldives
Great Adventure Sale
Save (per person) 1,287
From (per person) 3,229
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: Apr 2025 to Oct 2026
Countries Visited: Montenegro, Croatia
Great Adventure Sale
Save (per person) 716
From (per person) 1,915
New ReleaseTour + Cruise

9 Days Kuta to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2025 to Nov 2025
Countries Visited: Indonesia
Just Go Offer
Save (per person) 496
From (per person) 1,799
Cruise

8 Days (7 Nights) Corfu to Kefalonia
Operated By: Intrepid Travel
Departures: May 2025 to Oct 2025
Countries Visited: Greece
Exclusive Savings
Save (per person) 76
From (per person) 3,379
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Feb 2025 to Jan 2027
Countries Visited: Maldives
Exclusive Savings
Save (per person) 61
From (per person) 2,547
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: Intrepid Travel
Departures: May 2025 to Oct 2025
Countries Visited: Greece
Exclusive Savings
Save (per person) 55
From (per person) 2,468
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: G Adventures
Departures: Jun 2025 to Oct 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 229
From (per person) 1,647
Cruise

8 Days (7 Nights) Olbia to Olbia
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Corsica, Sardinia
Exclusive Savings
Save (per person) 74
From (per person) 3,320
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2025 to Nov 2025
Countries Visited: Indonesia
Just Go Offer
Save (per person) 810
From (per person) 2,940
Cruise

10 Days (9 Nights) Santorini to Santorini
Operated By: G Adventures
Departures: May 2025 to Sep 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 327
From (per person) 2,316
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Jan 2025 to Dec 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: India, Maldives
Great Adventure Sale
Save (per person) 512
From (per person) 3,545
Cruise

15 Days (14 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Apr 2025 to Sep 2026
Countries Visited: Montenegro, Croatia
Great Adventure Sale
Save (per person) 1,401
From (per person) 3,786
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore!
Departures: Jan 2025 to Dec 2025
Countries Visited: Maldives
Exclusive Deal
Save (per person) 454
From (per person) 3,077
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Croatia, Montenegro
Exclusive Savings
Save (per person) 139
From (per person) 6,063
Results: 1-30 of 42

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