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Sailing Trips Starting In May 2027

Are you looking to embark on a sailing trip in May 2027? Choose from 35 unique trip itineraries and 932 departures from the world's leading touring operators.
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35 Trips (932 Departures)
35 Trips (932 Departures)
Departures
Duration
7 Days
26 Days
Regions
Trip Styles
Budget
Start & End Cities
Operators
Price
$900pp
$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: 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
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
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
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 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
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 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 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 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
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
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
18 Day Sri Lanka with Maldives Cruise: Spice Gardens & Seasides with G Adventures
Tour + Cruise

18 Days Negombo to Male
Operator: G Adventures
Departures: Sep 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 1,037
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 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 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 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 329
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
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Trip Lengths

7 Day 10 Day 2 Week

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June July August September October November December January February March April May

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