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Sailing Trips Starting In September 2026 and 2027

Are you looking to embark on a sailing trip in September 2026 or 2027? Choose from 42 unique trip itineraries and 808 departures from the world's leading touring operators.
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42 Trips (808 Departures)
42 Trips (808 Departures)
Departures
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7 Days
26 Days
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$1,300pp
$22,449pp
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10 Day Croatia Sail Adventure with Intro Travel
New ReleaseTour + Cruise
 (3)

10 Days Split to Split
Operator: Intro Travel
Departures: Aug 2026 to Sep 2027
Trip Styles: 18-30's, Island Hopping, Sailing
Visits: Croatia
Exclusive Savings
From (Per Person)
A$3,588
Save 120
Per Person
View Trip
8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise
 (1)

8 Days (7 Nights) Dubrovnik to Split
Operator: Intrepid
Departures: Sep 2026 to Oct 2026
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,138
Save 908
Per Person
View Trip
10 Day Greece Sailing Adventure: Cyclades Islands with Intrepid Travel
Cruise
 (1)

10 Days (9 Nights) Santorini to Santorini
Operator: Intrepid
Departures: Aug 2026 to Sep 2026
Visits: Greece
Exclusive Savings
From (Per Person)
A$3,096
Save 1,056
Per Person
View Trip
8 Day Sail Greece: Santorini to Mykonos with Intrepid Travel
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operator: Intrepid
Departures: Sep 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,107
Save 894
Per Person
View Trip
8 Day Greece Sailing Adventure: Kefalonia to Corfu with Intrepid Travel
Cruise

8 Days (7 Nights) Kefalonia to Corfu
Operator: Intrepid
Departures: Aug 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,771
Save 945
Per Person
View Trip
10 Day Egypt: Pyramids, Temples & the Nile with G Adventures
New ReleaseTour + River Cruise

10 Days Cairo to Cairo
Operator: G Adventures
Departures: Sep 2026 to Dec 2027
Rivers: Nile
Visits: Egypt
Exclusive Savings
From (Per Person)
A$7,202
Save 176
Per Person
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operator: TruTravels
Departures: Oct 2026 to Nov 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$2,252
Save 843
Per Person
View Trip
17 Day Signature: Egypt & Jordan's Ancient Wonders with G Adventures
New ReleaseTour + River Cruise

17 Days Cairo to Dead Sea
Operator: G Adventures
Departures: Mar 2027 to Mar 2028
Rivers: Nile
Visits: Egypt, Jordan
Exclusive Savings
From (Per Person)
A$19,893
Save 449
Per Person
View Trip
7 Day Egypt: Ancient Wonders & Temples of the Nile with G Adventures
New ReleaseTour

7 Days Cairo to Luxor
Operator: G Adventures
Departures: Sep 2026 to Jan 2028
Trip Styles: Adventure, Small Group, Sailing
Visits: Egypt
Exclusive Savings
From (Per Person)
A$4,297
Save 862
Per Person
View Trip
7 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

7 Days (6 Nights) Naples to Procida
Operator: Intrepid
Departures: Aug 2026 to Oct 2027
Visits: Italy
Exclusive Savings
From (Per Person)
A$3,284
Save 1,135
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operator: G Adventures
Departures: Aug 2026 to Oct 2027
Visits: Montenegro, Croatia
Exclusive Savings
From (Per Person)
A$2,132
Save 587
Per Person
View Trip
8 Day Sail Greece: Mykonos to Santorini with Intrepid Travel
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operator: Intrepid
Departures: Aug 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,456
Save 635
Per Person
View Trip
8 Day Croatia Sailing Adventure: Split to Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operator: Intrepid
Departures: Aug 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,138
Save 908
Per Person
View Trip
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operator: G Adventures
Departures: Oct 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Island Hopping, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$4,497
Save 1,335
Per Person
View Trip
18 Day Sri Lanka with Maldives Cruise: Spice Gardens & Seasides with G Adventures
Tour + Cruise

18 Days Negombo to Male
Operator: G Adventures
Departures: Oct 2026 to Dec 2027
Trip Styles: Small Group, 18-30's, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$3,762
Save 1,362
Per Person
View Trip
8 Day Montenegro Sailing Adventure from Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operator: Intrepid
Departures: Sep 2026 to Oct 2027
Visits: Croatia, Montenegro
Exclusive Savings
From (Per Person)
A$2,279
Save 767
Per Person
View Trip
8 Day Sailing Greece - Mykonos to Santorini with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operator: G Adventures
Departures: Aug 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,440
Save 1,009
Per Person
View Trip
8 Day Maldive Dhoni Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Male to Male
Operator: Explore
Departures: Aug 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$3,254
Save 340
Per Person
View Trip
15 Day Dalmatian Coast & Montenegro Sailing with G Adventures
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operator: G Adventures
Departures: Aug 2026 to Sep 2026
Visits: Montenegro, Croatia
Exclusive Savings
From (Per Person)
A$4,997
Save 107
Per Person
View Trip
8 Day Turkey: Sail & Swim with Topdeck
New ReleaseCruise

8 Days (7 Nights) Fethiye to Fethiye
Operator: Topdeck
Departures: Sep 2026 to Oct 2026
Visits: Turkey
Exclusive Savings
From (Per Person)
A$1,768
Save 131
Per Person
View Trip
7 Day Maldives Cruise: Indian Ocean Dhoni Life with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Oct 2026 to Jan 2028
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,057
Save 880
Per Person
View Trip
10 Day Sailing Greece - Santorini to Santorini with G Adventures
Cruise

10 Days (9 Nights) Santorini to Santorini
Operator: G Adventures
Departures: Aug 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,999
Save 1,400
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operator: G Adventures
Departures: Aug 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,865
Save 854
Per Person
View Trip
10 Day Sailing Italy to Croatia with G Adventures
Tour + Cruise

10 Days Venice to Zadar
Operator: G Adventures
Departure: 19 September 2026
Trip Styles: Island Hopping, Sailing, Scenic
Visits: Italy, Slovenia, Croatia
Exclusive Savings
From (Per Person)
A$2,278
Save 821
Per Person
View Trip
8 Day Sailing Greece - Athens to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Athens to Mykonos
Operator: G Adventures
Departures: Aug 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,842
Save 507
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operator: TruTravels
Departures: Sep 2026 to Nov 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$1,419
Save 531
Per Person
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Sep 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,057
Save 880
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operator: Intrepid
Departures: Sep 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$3,328
Save 1,010
Per Person
View Trip
8 Day Sailing Greece - Mykonos to Athens with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Athens
Operator: G Adventures
Departures: Aug 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,496
Save 853
Per Person
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operator: TruTravels
Departures: Oct 2026 to Oct 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$4,710
Save 685
Per Person
View Trip
Results: 1-30 of 42

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