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Sailing Trips Starting In May 2027

Are you looking to embark on a sailing trip in May 2027? Choose from 42 unique trip itineraries and 1,185 departures from the world's leading touring operators.
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42 Trips (1,185 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: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,419
Save 874
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: May 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,916
Save 912
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$2,549
Save 450
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: May 2026 to Sep 2027
Visit: Greece
From
US$1,649
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: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,428
Save 874
Per Person
View Trip
18 Day Sri Lanka with Maldives Cruise: Spice Gardens & Seasides with G Adventures
Tour + Cruise

18 Days Negombo to Male
Operated By: G Adventures
Departures: Sep 2026 to Dec 2027
Trip Styles: Small Group, 18-30's, Sailing
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$2,974
Save 525
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$4,319
Save 1,080
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: May 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,174
Save 1,175
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
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: May 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$1,399
Save 600
Per Person
View Trip
10 Day Sailing Croatia to Italy with G Adventures
Cruise

10 Days (9 Nights) Zadar to Venice
Operated By: G Adventures
Departures: May 2026 to Sep 2026
Visit: Slovenia, Italy, Croatia
Exclusive Savings
From
US$1,039
Save 1,040
Per Person
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operated By: TruTravels
Departures: Jun 2026 to Nov 2027
Visit: Indonesia
Exclusive Savings
From
US$1,031
Save 344
Per Person
View Trip
10 Day Sailing Italy to Croatia with G Adventures
Tour + Cruise

10 Days Venice to Zadar
Operated By: G Adventures
Departures: May 2026 to Sep 2026
Trip Styles: Island Hopping, Sailing, Scenic
Visit: Italy, Slovenia, Croatia
Exclusive Savings
From
US$1,367
Save 912
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 Sail Greece: Mykonos to Santorini with Intrepid Travel
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,373
Save 695
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: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$989
Save 660
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: May 2026 to Sep 2027
Visit: Greece
From
US$1,699
Per Person
View Trip
8 Day Croatia Island Sail (Plus) with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: May 2026 to Aug 2027
Visit: Croatia
Exclusive Savings
From
US$1,441
Save 140
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: Jun 2026 to Nov 2027
Rivers: Nile
Visit: Egypt
Exclusive Savings
From
US$2,719
Save 680
Per Person
View Trip
8 Day Croatia Island Sail with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: May 2026 to Sep 2027
Visit: Croatia
Exclusive Savings
From
US$1,165
Save 114
Per Person
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: Jul 2026 to Oct 2027
Visit: Indonesia
Exclusive Savings
From
US$2,846
Save 949
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: May 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,926
Save 873
Per Person
View Trip
8 Day Turkey: Sail & Swim with Topdeck
New ReleaseCruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Topdeck
Departures: Jun 2026 to Oct 2026
Visit: Turkey
Exclusive Savings
From
US$1,269
Save 80
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: May 2026 to Oct 2027
Visit: Montenegro, Croatia
Exclusive Savings
From
US$1,462
Save 487
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: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,266
Save 806
Per Person
View Trip
13 Day Adriatic Adventure: Sail Croatia & Montenegro Discovery with G Adventures
New ReleaseTour

13 Days Split to Podgorica
Operated By: G Adventures
Departures: Aug 2026 to Oct 2026
Trip Styles: Adventure, Small Group, Sailing
Visit: Croatia, Montenegro
From
US$3,299
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: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,294
Save 555
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: May 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,657
Save 892
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: Jun 2026 to Sep 2027
Visit: Croatia, Montenegro
Exclusive Savings
From
US$3,202
Save 1,287
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
Results: 1-30 of 42

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7 Day 10 Day 2 Week

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