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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 45 unique trip itineraries and 1,083 departures from the world's leading touring operators.
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45 Trips (1,083 Departures)
45 Trips (1,083 Departures)
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26 Days
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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: Jun 2026 to Sep 2027
Trip Styles: 18-30's, Island Hopping, Sailing
Visits: Croatia
Exclusive Savings
From (Per Person)
A$3,685
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: Jul 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,843
Save 944
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: Jul 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,272
Save 1,470
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: Jul 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,502
Save 1,177
Per Person
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Jul 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,195
Save 1,004
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operator: G Adventures
Departures: Jul 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,769
Save 854
Per Person
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operator: G Adventures
Departures: Sep 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visits: India, Maldives
Exclusive Savings
From (Per Person)
A$3,370
Save 1,000
Per Person
View Trip
10 Day Signature: Egypt's Cairo, Luxor & the Nile Valley with G Adventures
New ReleaseTour + River Cruise

10 Days Cairo to Cairo
Operator: G Adventures
Departures: Jan 2027 to Dec 2027
Rivers: Nile
Visits: Egypt
Exclusive Savings
From (Per Person)
A$11,759
Save 270
Per Person
View Trip
7 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

7 Days (6 Nights) Naples to Procida
Operator: Intrepid
Departures: Jun 2026 to Oct 2027
Visits: Italy
Exclusive Savings
From (Per Person)
A$2,636
Save 1,412
Per Person
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operator: TruTravels
Departures: Jul 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 952
Per Person
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operator: TruTravels
Departures: Aug 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 736
Per Person
View Trip
14 Day Highlights of Sri Lanka with Maldive Dhoni Cruise (East Coast) with Explore Worldwide
Tour + Cruise

14 Days Negombo to Male
Operator: Explore
Departures: Aug 2027 to Oct 2027
Trip Styles: Adventure, Small Group, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$5,493
Save 415
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operator: Intrepid
Departures: Jul 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,912
Save 1,522
Per Person
View Trip
8 Day Greece Sailing Adventure: Corfu to Kefalonia with Intrepid Travel
Cruise

8 Days (7 Nights) Corfu to Kefalonia
Operator: Intrepid
Departures: Jun 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,335
Save 1,526
Per Person
View Trip
10 Day Sailing Italy to Croatia with G Adventures
Tour + Cruise

10 Days Venice to Zadar
Operator: G Adventures
Departures: Jul 2026 to Sep 2026
Trip Styles: Island Hopping, Sailing, Scenic
Visits: Italy, Slovenia, Croatia
Exclusive Savings
From (Per Person)
A$1,905
Save 1,334
Per Person
View Trip
10 Day Sailing Greece - Mykonos to Mykonos with G Adventures
Cruise

10 Days (9 Nights) Mykonos to Mykonos
Operator: G Adventures
Departures: Jun 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,631
Save 1,698
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: Jun 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,266
Save 1,083
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: Jan 2027 to Dec 2027
Rivers: Nile
Visits: Egypt, Jordan
Exclusive Savings
From (Per Person)
A$19,893
Save 449
Per Person
View Trip
22 Day Sri Lanka in Depth with Maldive Dhoni Cruise (Horton Plains) with Explore Worldwide
Tour + Cruise

22 Days Negombo to Male
Operator: Explore
Departures: Aug 2026 to Nov 2027
Trip Styles: Adventure, Small Group, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$7,699
Save 848
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: Jun 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,723
Save 942
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: Jul 2026 to Sep 2026
Visits: Montenegro, Croatia
Exclusive Savings
From (Per Person)
A$4,997
Save 107
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: Jul 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,611
Save 738
Per Person
View Trip
10 Day Sailing Croatia to Italy with G Adventures
Cruise

10 Days (9 Nights) Zadar to Venice
Operator: G Adventures
Departures: Jun 2026 to Sep 2026
Visits: Slovenia, Italy, Croatia
Exclusive Savings
From (Per Person)
A$1,587
Save 1,652
Per Person
View Trip
6 Day Komodo & Flores Sail with Contiki
New ReleaseTour + Cruise

6 Days Sanur to Labuan Bajo
Operator: Contiki
Departures: Aug 2026 to Oct 2026
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Short Break, Scenic
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$2,128
Save 45
Per Person
View Trip
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operator: G Adventures
Departures: Jul 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Island Hopping, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$3,968
Save 1,431
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: Jun 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,440
Save 1,009
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$3,606
Save 993
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$5,791
Save 2,088
Per Person
View Trip
8 Day Sailing Greece - Santorini to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operator: G Adventures
Departures: Jun 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,411
Save 988
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: Jul 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,999
Save 1,400
Per Person
View Trip
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