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 28 unique trip itineraries and 928 departures from the world's leading touring operators.
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Departures (October 2025)
< September 2025 November 2025 >
Duration
4 Days
26 Days
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$800pp
$10,220pp
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28 Trips (928 Trip Departures)
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
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operated By: G Adventures
Departures: Mar 2025 to Dec 2026
Trip Styles: Adventure, Small Group, Island Hopping, Sailing, Scenic
Countries Visited: Sri Lanka, Maldives
Great Adventure Sale
Save (per person) 1,447
From (per person) 3,563
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: Feb 2025 to Dec 2026
Rivers: Nile
Countries Visited: Egypt
Last Minute Offer
Save (per person) 1,689
From (per person) 6,430
View Trip
4 Day Sailing Thailand with G Adventures
Cruise

4 Days (3 Nights) Phuket to Ko Phi Phi
Operated By: G Adventures
Departures: Feb 2025 to Apr 2026
Countries Visited: Thailand
Exclusive Savings
Save (per person) 31
From (per person) 1,322
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 2025
Countries Visited: Greece
Big Sale
Save (per person) 283
From (per person) 2,260
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 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
Great Adventure Sale
Save (per person) 716
From (per person) 1,915
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: May 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
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 Deal
Save (per person) 355
From (per person) 1,422
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
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
Great Adventure Sale
Save (per person) 1,287
From (per person) 3,229
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: Jan 2025 to Jan 2027
Countries Visited: Maldives
Great Adventure Sale
Save (per person) 780
From (per person) 1,930
View Trip
7 Day Sailing the Canary Islands with G Adventures
Cruise

7 Days (6 Nights) San Miguel de Abona to San Miguel de Abona
Operated By: G Adventures
Departures: Jan 2025 to Apr 2026
Countries Visited: Spain
Last Minute OfferGreat Adventure Sale
Save (per person) 989
From (per person) 970
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: Jul 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Big Blue SaleSolo Traveller Offer
Save (per person) 983
From (per person) 5,207
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 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Big Blue SaleSolo Traveller Offer
Save (per person) 948
From (per person) 7,474
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
Just Go Offer
Save (per person) 810
From (per person) 2,940
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
Just Go Offer
Save (per person) 496
From (per person) 1,799
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
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
Just Go Offer
Save (per person) 1,295
From (per person) 4,700
View Trip
8 Day Maldive Dhoni Cruise with Explore!
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore!
Departures: Feb 2025 to Dec 2026
Countries Visited: Maldives
Big Blue Sale
Save (per person) 603
From (per person) 2,643
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 2026
Countries Visited: Croatia
Great Adventure Sale
Save (per person) 716
From (per person) 1,915
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 2025
Countries Visited: Greece
Big Sale
Save (per person) 293
From (per person) 2,296
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
Great Adventure Sale
Save (per person) 371
From (per person) 1,478
View Trip
7 Day Maldives Dhoni Explorer 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) 70
From (per person) 2,939
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
Great Adventure Sale
Save (per person) 716
From (per person) 1,915
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
Great Adventure Sale
Save (per person) 374
From (per person) 1,647
View Trip
4 Day Sailing Thailand with G Adventures
Cruise

4 Days (3 Nights) Ko Phi Phi to Phuket
Operated By: G Adventures
Departures: Jan 2025 to Apr 2026
Countries Visited: Thailand
Exclusive Savings
Save (per person) 31
From (per person) 1,322
View Trip
7 Day Sailing Thailand - Phuket to Phuket with G Adventures
Cruise

7 Days (6 Nights) Phuket to Phuket
Operated By: G Adventures
Departures: Feb 2025 to Apr 2026
Countries Visited: Thailand
Exclusive Savings
Save (per person) 59
From (per person) 2,596
View Trip
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