Sailing Trips Starting In October 2025

Are you looking to embark on a sailing trip in October 2025? Choose from 18 unique trip itineraries and 607 departures from the world's leading touring operators.
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Departures (October 2025)
Duration
7 Days
26 Days
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$1,000pp
$14,645pp
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18 Trips (607 Trip Departures)
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore!
Departures: Jul 2024 to Dec 2025
Countries Visited: Maldives
Asia Sale
Save 738
From 3,322
Tour + Cruise

14 Days Negombo to Male
Operated By: G Adventures
Departures: Jul 2024 to Dec 2025
Countries Visited: Sri Lanka, Maldives
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Save 1,473
From 3,326
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jul 2024 to Jan 2026
Countries Visited: Maldives
Exclusive Deal
Save 835
From 1,884
Tour + Cruise

14 Days Negombo to Male
Operated By: Explore!
Departures: Jul 2024 to Oct 2025
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Asia Sale
Save 564
From 5,802
Cruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Contiki
Departures: Jun 2024 to Oct 2025
Countries Visited: Turkey
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Save 686
From 1,431
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18 Days Negombo to Male
Operated By: G Adventures
Departures: Jun 2024 to Jan 2026
Trip Styles: Small Group, 18-30's, Sailing
Countries Visited: Sri Lanka, Maldives
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Save 1,289
From 2,910
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: May 2024 to Nov 2025
Countries Visited: Indonesia
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Save 1,178
From 2,572
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Montenegro, Croatia
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Save 1,055
From 1,856
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
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Save 841
From 1,518
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22 Days Negombo to Male
Operated By: Explore!
Departures: Jul 2024 to Nov 2025
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Asia Sale
Save 571
From 7,987
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jun 2024 to Jan 2026
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Maldives
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Save 772
From 2,115
Cruise

8 Days (7 Nights) Mykonos to Athens
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive DealLast Minute Offer
Save 1,060
From 1,039
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Jun 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive DealLast Minute Offer
Save 1,494
From 1,465
New ReleaseRiver Cruise

10 Days Cairo to Cairo
Operated By: G Adventures
Departures: Oct 2024 to Dec 2025
Rivers: Nile
Countries Visited: Egypt
Exclusive Savings
Save 162
From 7,202
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9 Days Kuta to Labuan Bajo
Operated By: TruTravels
Departures: May 2024 to Nov 2025
Countries Visited: Indonesia
Exclusive Deal
Save 721
From 1,574
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: Jun 2024 to Oct 2025
Countries Visited: Indonesia
Exclusive Savings
Save 120
From 5,875
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jul 2024 to Dec 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Maldives
Exclusive Deal
Save 570
From 2,169
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive DealLast Minute Offer
Save 1,494
From 1,465
Results: 18 results

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