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Sailing Trips Starting In August 2027 and 2028

Are you looking to embark on a sailing trip in August 2027 or 2028? Choose from 29 unique trip itineraries and 670 departures from the world's leading touring operators.
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29 Trips (670 Departures)
29 Trips (670 Departures)
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Duration
7 Days
26 Days
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$1,200pp
$22,449pp
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7 Day Amalfi Coast Sailing Adventure with Intrepid Travel Featured
Cruise

7 Days (6 Nights) Naples to Procida
Operator: Intrepid
Departures: Sep 2026 to Oct 2027
Visits: Italy
Exclusive Savings
From (Per Person)
A$3,284
Save 1,135
Per Person
View Trip
10 Day Croatia Sail Adventure with Intro Travel
New ReleaseTour + Cruise
 (3)

10 Days Split to Split
Operator: Intro Travel
Departures: Sep 2026 to Sep 2027
Trip Styles: 18-30's, Island Hopping, Sailing
Visits: Croatia
Exclusive Savings
From (Per Person)
A$3,879
Save 120
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$1,891
Save 65
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: Oct 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,580
Save 569
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 Croatia Island Sail with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operator: Contiki
Departures: May 2027 to Sep 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,726
Save 48
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: Sep 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,410
Save 869
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operator: G Adventures
Departures: Sep 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,896
Save 683
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 2028
Trip Styles: Adventure, Small Group, Island Hopping, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$4,277
Save 1,542
Per Person
View Trip
8 Day Family Greek Coast Caique Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Athens to Athens
Operator: Explore
Departures: May 2027 to Aug 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,401
Save 659
Per Person
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operator: TruTravels
Departures: Apr 2027 to Oct 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$5,233
Save 174
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operator: G Adventures
Departures: Sep 2026 to Oct 2027
Visits: Montenegro, Croatia
Exclusive Savings
From (Per Person)
A$2,576
Save 55
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: May 2027 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,449
Save 56
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: Apr 2027 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,498
Save 56
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: Jul 2027 to Nov 2027
Trip Styles: Adventure, Sailing
Visits: Sri Lanka, Maldives
Exclusive Savings
From (Per Person)
A$7,662
Save 632
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 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$2,524
Save 477
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: Sep 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,351
Save 848
Per Person
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Oct 2026 to Jan 2029
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,667
Save 970
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: Sep 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,279
Save 767
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: Maldives, Sri Lanka
Exclusive Savings
From (Per Person)
A$5,465
Save 412
Per Person
View Trip
8 Day Croatia Island Sail (Plus) with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operator: Contiki
Departures: May 2027 to Aug 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,220
Save 52
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: Sep 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$3,274
Save 627
Per Person
View Trip
8 Day Greek Island Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Athens to Athens
Operator: Explore
Departures: Sep 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,401
Save 659
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: Sep 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,657
Save 361
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: Sep 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,175
Save 55
Per Person
View Trip
8 Day Maldive Dhoni Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Male to Male
Operator: Explore
Departures: Oct 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$3,254
Save 388
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$3,002
Save 105
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operator: G Adventures
Departures: Sep 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,896
Save 721
Per Person
View Trip
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