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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 1,110 departures from the world's leading touring operators.
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Departures (May 2025)
< April 2025 June 2025 >
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26 Days
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42 Trips (1,110 Trip Departures)
8 Day Croatia Island Sail (Plus) with Contiki
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) 814
From (per person) 2,306
View Trip
8 Day Croatia Sailing Adventure: Split to Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Croatia
Big Sale
Save (per person) 723
From (per person) 2,533
View Trip
10 Day Croatia Sailing Adventure with Intro Travel
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) 72
From (per person) 3,037
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10 Day Greece Sailing Adventure: Cyclades Islands with Intrepid Travel
Cruise
 (1)

10 Days (9 Nights) Santorini to Santorini
Operated By: Intrepid Travel
Departures: May 2025 to Oct 2025
Countries Visited: Greece
Big Sale
Save (per person) 577
From (per person) 2,921
View Trip
6 Day Wineglass Bay (Signature Walk) with Tasmanian Walking Co
New ReleaseTour + Cruise
 (1)

6 Days Hobart to Hobart
Operated By: Tasmanian Walking Co
Departure: 22 February 2025
Trip Styles: Adventure, Small Group, Sailing, Short Break, Walking & Hiking
Countries Visited: Australia
From (per person) 4,846
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8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: Apr 2025 to Oct 2026
Countries Visited: Montenegro, Croatia
Latest Offer
Save (per person) 409
From (per person) 2,170
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Kuta to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2025 to Nov 2026
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Exclusive Savings
Save (per person) 46
From (per person) 2,249
View Trip
10 Day Sailing Greece - Santorini to Santorini with G Adventures
Cruise

10 Days (9 Nights) Santorini to Santorini
Operated By: G Adventures
Departures: Jun 2025 to Sep 2026
Countries Visited: Greece
Exclusive Savings
Save (per person) 60
From (per person) 2,547
View Trip
18 Day Sri Lanka with Maldives Cruise: Spice Gardens & Seasides with G Adventures
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
Exclusive Savings
Save (per person) 100
From (per person) 4,262
View Trip
4 Day Wineglass Bay (Signature Walk) with Tasmanian Walking Co
New ReleaseTour + Cruise

4 Days Hobart to Hobart
Operated By: Tasmanian Walking Co
Departures: Mar 2025 to Apr 2025
Trip Styles: Adventure, Small Group, Sailing, Short Break, Walking & Hiking
Countries Visited: Australia
From (per person) 3,460
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8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Croatia
Big Sale
Save (per person) 719
From (per person) 2,621
View Trip
15 Day Montenegro & Croatia Sailing with G Adventures
Cruise

15 Days (14 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Apr 2025 to Sep 2026
Countries Visited: Montenegro, Croatia
Latest Offer
Save (per person) 808
From (per person) 4,291
View Trip
10 Day Sailing Italy to Croatia with G Adventures
Cruise

10 Days (9 Nights) Venice to Zadar
Operated By: G Adventures
Departures: May 2025 to Sep 2026
Countries Visited: Slovenia, Italy, Croatia
Latest Offer
Save (per person) 488
From (per person) 2,591
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2025 to Oct 2026
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Exclusive Savings
Save (per person) 120
From (per person) 5,875
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Mar 2025 to Jan 2027
Countries Visited: Maldives
Exclusive Savings
Save (per person) 61
From (per person) 2,547
View Trip
8 Day Greece Sailing Adventure: Kefalonia to Corfu with Intrepid Travel
Cruise

8 Days (7 Nights) Kefalonia to Corfu
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Greece
Big Sale
Save (per person) 564
From (per person) 2,926
View Trip
15 Day Sailing Greece - Athens to Santorini with G Adventures
Cruise

15 Days (14 Nights) Athens to Santorini
Operated By: G Adventures
Departures: May 2025 to Sep 2026
Countries Visited: Greece
Exclusive Savings
Save (per person) 83
From (per person) 3,625
View Trip
8 Day Croatia Island Sail with Contiki
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) 1,870
View Trip
7 Day Maldives Cruise: Indian Ocean Dhoni Life with G Adventures
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
View Trip
8 Day Turkish Sailing with Contiki
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
View Trip
8 Day Greece Sailing Adventure: Corfu to Kefalonia with Intrepid Travel
Cruise

8 Days (7 Nights) Corfu to Kefalonia
Operated By: Intrepid Travel
Departures: May 2025 to Oct 2025
Countries Visited: Greece
Big Sale
Save (per person) 582
From (per person) 2,926
View Trip
8 Day Sardinia & Corsica Sailing Adventure with Intrepid Travel
Cruise

8 Days (7 Nights) Olbia to Olbia
Operated By: Intrepid Travel
Departures: May 2025 to Sep 2025
Countries Visited: Corsica, Sardinia
Big Sale
Save (per person) 560
From (per person) 2,876
View Trip
8 Day Sailing Greece - Santorini to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: G Adventures
Departures: Jun 2025 to Oct 2026
Countries Visited: Greece
Exclusive Savings
Save (per person) 42
From (per person) 1,812
View Trip
8 Day Sailing Greece - Athens to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Athens to Mykonos
Operated By: G Adventures
Departures: May 2025 to Sep 2026
Countries Visited: Greece
Exclusive Savings
Save (per person) 44
From (per person) 1,763
View Trip
10 Day Sailing Greece - Mykonos to Mykonos with G Adventures
Cruise

10 Days (9 Nights) Mykonos to Mykonos
Operated By: G Adventures
Departures: May 2025 to Sep 2026
Countries Visited: Greece
Exclusive Savings
Save (per person) 57
From (per person) 2,547
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2025 to Nov 2026
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Exclusive Savings
Save (per person) 75
From (per person) 3,675
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Apr 2025 to Oct 2026
Countries Visited: Croatia
Latest Offer
Save (per person) 409
From (per person) 2,170
View Trip
8 Day Sail & Swim: Croatia (Toma) with Topdeck
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
View Trip
8 Day Sailing Greece - Mykonos to Athens with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Athens
Operated By: G Adventures
Departures: Apr 2025 to Oct 2026
Countries Visited: Greece
Exclusive Savings
Save (per person) 42
From (per person) 1,763
View Trip
10 Day Egypt: Pyramids, Temples & the Nile with G Adventures
New ReleaseRiver Cruise

10 Days Cairo to Cairo
Operated By: G Adventures
Departures: Mar 2025 to Dec 2026
Rivers: Nile
Countries Visited: Egypt
Last Minute OfferLatest Offer
Save (per person) 1,689
From (per person) 6,430
View Trip
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