Home > Travel Styles > Adventure Tours > Sailing Trips > October 2025

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 640 departures from the world's leading touring operators.
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Departures (October 2025)
< September 2025 November 2025 >
Duration
7 Days
26 Days
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Price
$1,100pp
$14,645pp
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18 Trips (640 Trip Departures)
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: May 2024 to Dec 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Maldives
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8 Day Sailing Greece - Mykonos to Athens with G Adventures
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
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22 Day Sri Lanka in Depth with Maldive Dhoni Cruise (Horton Plains) with Explore!
Tour + Cruise

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
Getaway Sale
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14 Day Highlights of Sri Lanka with Maldive Dhoni Cruise (East Coast) with Explore!
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
Getaway Sale
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8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
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8 Day Sailing Greece - Santorini to Mykonos with G Adventures
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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14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operated By: G Adventures
Departures: Jul 2024 to Dec 2025
Trip Styles: Adventure, Small Group, Island Hopping, Sailing, Scenic
Countries Visited: Sri Lanka, Maldives
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26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: May 2024 to Oct 2025
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
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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: May 2024 to Jan 2026
Trip Styles: Small Group, 18-30's, Sailing
Countries Visited: Sri Lanka, Maldives
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9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Kuta to Labuan Bajo
Operated By: TruTravels
Departures: May 2024 to Nov 2025
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
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10 Day Egypt: Pyramids, Temples & the Nile with G Adventures
New ReleaseRiver Cruise

10 Days Cairo to Cairo
Operated By: G Adventures
Departures: Oct 2024 to Dec 2025
Rivers: Nile
Countries Visited: Egypt
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8 Day Montenegro Sailing with G Adventures
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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18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2024 to Nov 2025
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
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8 Day Turkish Sailing with Contiki
Cruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Contiki
Departures: May 2024 to Oct 2025
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Turkey
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8 Day Sailing Croatia with G Adventures
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
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7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: May 2024 to Jan 2026
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Maldives
Exclusive Deal
Save 734
From 2,115
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8 Day Maldive Dhoni Cruise with Explore!
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore!
Departures: Jul 2024 to Dec 2025
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Maldives
Getaway Sale
Save 455
From 3,322
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7 Day Maldives Cruise: Indian Ocean Dhoni Life with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: May 2024 to Jan 2026
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Maldives
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