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 22 unique trip itineraries and 786 departures from the world's leading touring operators.
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Departures (October 2025)
< September 2025 November 2025 >
Duration
7 Days
26 Days
Regions
Trip Styles
Budget
Start & End Cities
Operators
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Price
$900pp
$9,400pp
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22 Trips (786 Trip Departures)
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: Apr 2025 to Oct 2025
Countries Visited: Montenegro, Croatia
Exclusive Savings
Save (per person) 56
From (per person) 2,527
View Trip
8 Day Maldive Dhoni Cruise with Explore!
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore!
Departures: Oct 2024 to Dec 2025
Countries Visited: Maldives
Exclusive Saving
Save (per person) 567
From (per person) 2,989
View Trip
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: Oct 2024 to Oct 2025
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Exclusive Saving
Save (per person) 461
From (per person) 5,802
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Kuta to Labuan Bajo
Operated By: TruTravels
Departures: Oct 2024 to Nov 2025
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Limited Time Sale
Save (per person) 721
From (per person) 1,574
View Trip
8 Day Sail & Swim: Turkey with Topdeck
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
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: Oct 2024 to Dec 2026
Trip Styles: Small Group, 18-30's, Sailing
Countries Visited: Sri Lanka, Maldives
Last Minute Offer
Save (per person) 1,153
From (per person) 3,326
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Oct 2024 to Jan 2027
Countries Visited: Maldives
Exclusive Savings
Save (per person) 70
From (per person) 2,939
View Trip
8 Day Sail Greece: Santorini to Mykonos with Intrepid Travel
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: Intrepid Travel
Departures: May 2025 to Oct 2026
Countries Visited: Greece
Exclusive Savings
Save (per person) 57
From (per person) 2,468
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 2025
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
8 Day Turkish Sailing with Contiki
Cruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Contiki
Departures: Apr 2025 to Oct 2026
Countries Visited: Turkey
Exclusive Savings
Save (per person) 560
From (per person) 1,463
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 2025
Countries Visited: Croatia
Exclusive Savings
Save (per person) 56
From (per person) 2,527
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Oct 2024 to Jan 2027
Countries Visited: Maldives
Exclusive Savings
Save (per person) 61
From (per person) 2,547
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 2025
Countries Visited: Greece
Exclusive Savings
Save (per person) 49
From (per person) 2,155
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: Oct 2024 to Jan 2027
Countries Visited: Maldives
Last Minute Offer
Save (per person) 700
From (per person) 2,019
View Trip
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operated By: G Adventures
Departures: Oct 2024 to Dec 2026
Trip Styles: Adventure, Small Group, Island Hopping, Sailing, Scenic
Countries Visited: Sri Lanka, Maldives
Exclusive Deal
Save (per person) 891
From (per person) 4,703
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: Oct 2024 to Dec 2026
Rivers: Nile
Countries Visited: Egypt
Exclusive DealLast Minute Offer
Save (per person) 1,972
From (per person) 5,687
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: May 2025 to Oct 2025
Countries Visited: Greece
Exclusive Savings
Save (per person) 49
From (per person) 2,204
View Trip
8 Day Sail Greece: Mykonos to Santorini with Intrepid Travel
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operated By: Intrepid Travel
Departures: May 2025 to Oct 2026
Countries Visited: Greece
Exclusive Savings
Save (per person) 58
From (per person) 2,507
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Apr 2025 to Oct 2025
Countries Visited: Croatia
Exclusive Savings
Save (per person) 56
From (per person) 2,527
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Oct 2024 to Nov 2025
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
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Nov 2024 to Dec 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: India, Maldives
Exclusive Savings
Save (per person) 94
From (per person) 3,899
View Trip
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: Sep 2025 to Nov 2025
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Exclusive Savings
Save (per person) 163
From (per person) 7,987
View Trip
Results: 22 results

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