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Sailing Trips Starting In May 2027 and 2028

Are you looking to embark on a sailing trip in May 2027 or 2028? Choose from 36 unique trip itineraries and 805 departures from the world's leading touring operators.
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36 Trips (805 Departures)
36 Trips (805 Departures)
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7 Days
26 Days
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$1,100pp
$22,449pp
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8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise
 (1)

8 Days (7 Nights) Dubrovnik to Split
Operator: Intrepid
Departures: May 2027 to Oct 2028
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,740
Save 209
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operator: G Adventures
Departures: Apr 2027 to Oct 2027
Visits: Croatia, Montenegro
Exclusive Savings
From (Per Person)
A$1,803
Save 826
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operator: Intrepid
Departures: Dec 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$4,003
Save 584
Per Person
View Trip
8 Day Sail & Hike Greece: Athens to Mykonos with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Lavrio to Mykonos
Operator: Intrepid
Departures: Apr 2027 to Oct 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,647
Save 204
Per Person
View Trip
9 Day Egypt Family Journey: Ancient Pyramids and the Mighty Nile with G Adventures
New ReleaseTour + River Cruise

9 Days Cairo to Cairo
Operator: G Adventures
Departures: Mar 2027 to Nov 2027
Rivers: Nile
Visits: Egypt
Exclusive Savings
From (Per Person)
A$4,850
Save 105
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operator: TruTravels
Departures: Apr 2027 to Nov 2027
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Visits: Indonesia
Exclusive Savings
From (Per Person)
A$1,135
Save 899
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: May 2027 to Sep 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,559
Save 202
Per Person
View Trip
7 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

7 Days (6 Nights) Naples to Procida
Operator: Intrepid
Departures: May 2027 to Sep 2028
Visits: Italy
Exclusive Savings
From (Per Person)
A$3,958
Save 233
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operator: G Adventures
Departures: Apr 2027 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$1,803
Save 826
Per Person
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Nov 2026 to Jan 2029
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,790
Save 1,033
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operator: G Adventures
Departures: May 2027 to Oct 2027
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,319
Save 326
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: Apr 2027 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,297
Save 1,052
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$3,373
Save 2,422
Per Person
View Trip
8 Day Maldive Dhoni Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Male to Male
Operator: Explore
Departures: Nov 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$3,212
Save 410
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: Feb 2027 to Apr 2028
Rivers: Nile
Visits: Egypt
Exclusive Savings
From (Per Person)
A$11,759
Save 270
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: Dec 2026 to Jan 2028
Trip Styles: Adventure, Small Group, Sailing
Visits: Egypt
Exclusive Savings
From (Per Person)
A$4,056
Save 897
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$2,393
Save 177
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: Feb 2027 to Apr 2028
Rivers: Nile
Visits: Egypt, Jordan
Exclusive Savings
From (Per Person)
A$19,893
Save 449
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: Dec 2026 to Dec 2027
Rivers: Nile
Visits: Egypt
Exclusive Savings
From (Per Person)
A$6,482
Save 2,337
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$2,072
Save 311
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: May 2027 to Oct 2028
Visits: Croatia
Exclusive Savings
From (Per Person)
A$2,740
Save 211
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: May 2027 to Sep 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,657
Save 204
Per Person
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operator: G Adventures
Departures: Nov 2026 to Dec 2027
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,057
Save 942
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: Apr 2027 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,229
Save 1,020
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: May 2027 to Sep 2027
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,072
Save 309
Per Person
View Trip
8 Day Sail & Hike Greece: Mykonos to Athens with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Mykonos to Lavrio
Operator: Intrepid
Departures: Apr 2027 to Oct 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$2,647
Save 204
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: Dec 2026 to Jan 2028
Visits: Maldives
Exclusive Savings
From (Per Person)
A$2,114
Save 1,205
Per Person
View Trip
8 Day Sail Greece: Skiathos, Skopelos & Alonnisos (Catamaran) with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Skiathos to Skiathos
Operator: Intrepid
Departures: May 2027 to Sep 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$4,591
Save 244
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: May 2027 to Sep 2028
Visits: Greece
Exclusive Savings
From (Per Person)
A$3,441
Save 220
Per Person
View Trip
15 Day Croatia and Montenegro Sailing Adventure with Intrepid Travel
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operator: Intrepid
Departures: Jun 2027 to Sep 2028
Visits: Croatia, Montenegro
Exclusive Savings
From (Per Person)
A$5,705
Save 270
Per Person
View Trip
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