Home > Travel Styles > Adventure Tours > Sailing Trips > October 2027

Sailing Trips Starting In October 2027

Are you looking to embark on a sailing trip in October 2027? Choose from 16 unique trip itineraries and 683 departures from the world's leading touring operators.
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Departures (October 2027)
< September 2027 November 2027 >
Duration
7 Days
26 Days
Regions
Trip Styles
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Price
$800pp
$5,950pp
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16 Trips (683 Trip Departures)
8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise
 (1)

8 Days (7 Nights) Dubrovnik to Split
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$2,119
Save 69
Per Person
View Trip
7 Day Egypt: Ancient Wonders & Temples of the Nile with G Adventures
New ReleaseTour

7 Days Cairo to Luxor
Operated By: G Adventures
Departures: Feb 2026 to Jan 2028
Trip Styles: Adventure, Small Group, Sailing
Visit: Egypt
Exclusive Savings
From
US$2,909
Save 105
Per Person
View Trip
8 Day Croatia Sailing Adventure: Split to Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$2,119
Save 71
Per Person
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 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$2,066
Save 71
Per Person
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: Nov 2025 to Jan 2028
Visit: Maldives
Exclusive Savings
From
US$1,896
Save 403
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operated By: TruTravels
Departures: Nov 2025 to Nov 2027
Visit: Indonesia
From
US$1,250
Per Person
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 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$2,828
Save 92
Per Person
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: Dec 2025 to Dec 2027
Rivers: Nile
Visit: Egypt
Exclusive Savings
From
US$3,855
Save 1,444
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operated By: Intrepid Travel
Departures: Nov 2025 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$2,978
Save 409
Per Person
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 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$2,158
Save 71
Per Person
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Jan 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: India, Maldives
Exclusive Savings
From
US$2,909
Save 103
Per Person
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2026 to Oct 2027
Visit: Indonesia
Exclusive Savings
From
US$3,443
Save 114
Per Person
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18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2026 to Nov 2027
Visit: Indonesia
Exclusive Savings
From
US$1,935
Save 68
Per Person
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jan 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$1,939
Save 69
Per Person
View Trip
7 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

7 Days (6 Nights) Naples to Procida
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Italy
Exclusive Savings
From
US$3,243
Save 105
Per Person
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 2026 to Dec 2027
Trip Styles: Small Group, 18-30's, Sailing
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$3,091
Save 658
Per Person
View Trip
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