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 897 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 (897 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
Exclusive Savings
Save (per person) 76
From (per person) 3,371
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: Jan 2025 to Apr 2026
Countries Visited: Thailand
Exclusive Savings
Save (per person) 59
From (per person) 2,596
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 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) 227
From (per person) 1,603
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 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: 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
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
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
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Kuta to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2025 to Nov 2025
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
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
Exclusive Savings
Save (per person) 76
From (per person) 3,379
View Trip
7 Day Maldives Dhoni Cruise 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 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
Exclusive Savings
Save (per person) 55
From (per person) 2,468
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) 229
From (per person) 1,647
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: Dec 2024 to Apr 2026
Countries Visited: Spain
Last Minute OfferGreat Adventure Sale
Save (per person) 698
From (per person) 1,261
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 2025
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
4 Day Sailing Thailand with G Adventures
Cruise

4 Days (3 Nights) Phuket to Ko Phi Phi
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
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Jan 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 Maldive Dhoni Cruise with Explore!
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore!
Departures: Jan 2025 to Dec 2025
Countries Visited: Maldives
Exclusive Deal
Save (per person) 454
From (per person) 3,077
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Dec 2024 to Jan 2027
Countries Visited: Maldives
Exclusive Savings
Save (per person) 70
From (per person) 2,939
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) 174
From (per person) 8,222
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
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
Exclusive Savings
Save (per person) 162
From (per person) 7,202
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
Last Minute OfferGreat Adventure Sale
Save (per person) 1,080
From (per person) 1,930
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
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 2025
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Exclusive Savings
Save (per person) 124
From (per person) 5,968
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
Exclusive Savings
Save (per person) 57
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 2026
Countries Visited: Croatia
Great Adventure Sale
Save (per person) 716
From (per person) 1,915
View Trip
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