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Sailing Trips Starting In June 2027

Are you looking to embark on a sailing trip in June 2027? Choose from 34 unique trip itineraries and 909 departures from the world's leading touring operators.
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34 Trips (909 Departures)
34 Trips (909 Departures)
Departures
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7 Days
26 Days
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$900pp
$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: 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 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
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
8 Day Croatia Island Sail with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operator: Contiki
Departures: Jun 2026 to Sep 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,657
Save 55
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
7 Day Maldives Cruise: Indian Ocean Dhoni Life with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Sep 2026 to Jan 2028
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,057
Save 742
Per Person
View Trip
8 Day Croatia Island Sail (Plus) with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operator: Contiki
Departures: Jun 2026 to Aug 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,127
Save 61
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
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 Sail Turkey: Bodrum to Fethiye (Turkish Gulet) with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Bodrum to Fethiye
Operator: Intrepid
Departures: Jul 2026 to Aug 2027
Visits: Turkey
Exclusive Savings
From (Per Person)
A$2,929
Save 1,525
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok 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$1,419
Save 586
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 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$4,233
Save 1,257
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
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
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 742
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
8 Day Sailing Greece - Mykonos to Athens with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Athens
Operator: G Adventures
Departures: Jul 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,266
Save 1,083
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operator: G Adventures
Departures: Jun 2026 to Oct 2027
Visits: Montenegro, Croatia
Exclusive Savings
From (Per Person)
A$2,148
Save 454
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
8 Day Sail Turkey: Fethiye to Bodrum (Turkish Gulet) with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Fethiye to Bodrum
Operator: Intrepid
Departures: Jul 2026 to Aug 2027
Visits: Turkey
Exclusive Savings
From (Per Person)
A$2,898
Save 1,412
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
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operator: G Adventures
Departures: Jul 2026 to Sep 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,148
Save 454
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: Jul 2026 to Oct 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$1,411
Save 988
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: Jul 2026 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,885
Save 1,002
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: Jul 2026 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,195
Save 1,045
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: Aug 2026 to Oct 2027
Visits: Croatia, Montenegro
Exclusive Savings
From (Per Person)
A$2,138
Save 954
Per Person
View Trip
Results: 1-30 of 34

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