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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 1,004 departures from the world's leading touring operators.
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35 Trips (1,004 Trip Departures)
8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise
 (1)

8 Days (7 Nights) Dubrovnik to Split
Operated By: Intrepid Travel
Departures: Jun 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,419
Save 681
Per Person
View Trip
10 Day Greece Sailing Adventure: Cyclades Islands with Intrepid Travel
Cruise
 (1)

10 Days (9 Nights) Santorini to Santorini
Operated By: Intrepid Travel
Departures: Jun 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,661
Save 1,080
Per Person
View Trip
8 Day Sail Greece: Mykonos to Santorini with Intrepid Travel
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operated By: Intrepid Travel
Departures: Jun 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,257
Save 844
Per Person
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jun 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$1,399
Save 600
Per Person
View Trip
8 Day Croatia Sailing Adventure: Split to Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: Intrepid Travel
Departures: Jun 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,450
Save 723
Per Person
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jul 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$1,724
Save 657
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: Jun 2026 to Oct 2027
Visit: Montenegro, Croatia
From
US$1,949
Per Person
View Trip
8 Day Maldive Dhoni Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore Worldwide
Departures: Aug 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$2,140
Save 170
Per Person
View Trip
8 Day Sailing Greece - Mykonos to Santorini with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operated By: G Adventures
Departures: Jun 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,109
Save 740
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operated By: TruTravels
Departures: Jul 2026 to Nov 2027
Visit: Indonesia
Exclusive Savings
From
US$937
Save 344
Per Person
View Trip
8 Day Greece Sailing Adventure: Kefalonia to Corfu with Intrepid Travel
Cruise

8 Days (7 Nights) Kefalonia to Corfu
Operated By: Intrepid Travel
Departures: Jun 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,668
Save 1,164
Per Person
View Trip
8 Day Sailing Greece - Athens to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Athens to Mykonos
Operated By: G Adventures
Departures: Jul 2026 to Sep 2027
Visit: Greece
From
US$1,699
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Jun 2026 to Sep 2027
Visit: Croatia
Exclusive Savings
From
US$1,657
Save 292
Per Person
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Jun 2026 to Nov 2027
Visit: Indonesia
Exclusive Savings
From
US$1,496
Save 563
Per Person
View Trip
10 Day Sailing Greece - Santorini to Santorini with G Adventures
Cruise

10 Days (9 Nights) Santorini to Santorini
Operated By: G Adventures
Departures: Jun 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,299
Save 1,300
Per Person
View Trip
8 Day Sail Greece: Santorini to Mykonos with Intrepid Travel
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: Intrepid Travel
Departures: Jun 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,317
Save 675
Per Person
View Trip
8 Day Sailing Greece - Santorini to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: G Adventures
Departures: Jun 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,202
Save 647
Per Person
View Trip
15 Day Croatia and Montenegro Sailing Adventure with Intrepid Travel
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operated By: Intrepid Travel
Departures: Jul 2026 to Sep 2027
Visit: Croatia, Montenegro
Exclusive Savings
From
US$3,237
Save 1,287
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operated By: Intrepid Travel
Departures: Jun 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$1,842
Save 1,228
Per Person
View Trip
8 Day Croatia Island Sail (Plus) with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: Jun 2026 to Aug 2027
Visit: Croatia
From
US$1,505
Per Person
View Trip
7 Day Egypt: Ancient Wonders & Temples of the Nile with G Adventures
New ReleaseTour

7 Days Cairo to Luxor
Operated By: G Adventures
Departures: Sep 2026 to Jan 2028
Trip Styles: Adventure, Small Group, Sailing
Visit: Egypt
Exclusive Savings
From
US$2,804
Save 495
Per Person
View Trip
9 Day Egypt Family Journey: Ancient Pyramids and the Mighty Nile with G Adventures
New ReleaseRiver Cruise

9 Days Cairo to Cairo
Operated By: G Adventures
Departures: Jul 2026 to Nov 2027
Rivers: Nile
Visit: Egypt
Exclusive Savings
From
US$2,549
Save 850
Per Person
View Trip
10 Day Sailing Greece - Mykonos to Mykonos with G Adventures
Cruise

10 Days (9 Nights) Mykonos to Mykonos
Operated By: G Adventures
Departures: Jun 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,529
Save 1,020
Per Person
View Trip
10 Day Egypt: Pyramids, Temples & the Nile with G Adventures
New ReleaseRiver Cruise

10 Days Cairo to Cairo
Operated By: G Adventures
Departures: Sep 2026 to Dec 2027
Rivers: Nile
Visit: Egypt
Exclusive Savings
From
US$4,049
Save 1,350
Per Person
View Trip
7 Day Maldives Cruise: Indian Ocean Dhoni Life with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Sep 2026 to Jan 2028
Visit: Maldives
Exclusive Savings
From
US$1,599
Save 400
Per Person
View Trip
10 Day Signature: Egypt's Cairo, Luxor & the Nile Valley with G Adventures
New ReleaseRiver Cruise

10 Days Cairo to Cairo
Operated By: G Adventures
Departures: Jan 2027 to Dec 2027
Rivers: Nile
Visit: Egypt
From
US$7,999
Per Person
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Sep 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: India, Maldives
Exclusive Savings
From
US$2,699
Save 300
Per Person
View Trip
17 Day Signature: Egypt & Jordan's Ancient Wonders with G Adventures
New ReleaseRiver Cruise

17 Days Cairo to Dead Sea
Operated By: G Adventures
Departures: Jan 2027 to Dec 2027
Rivers: Nile
Visit: Egypt, Jordan
From
US$13,499
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Jun 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,657
Save 307
Per Person
View Trip
8 Day Sailing Greece - Mykonos to Athens with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Athens
Operated By: G Adventures
Departures: Jun 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,402
Save 360
Per Person
View Trip
Results: 1-30 of 35

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7 Day 10 Day 2 Week

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