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Sailing Trips Starting In May 2026

Are you looking to embark on a sailing trip in May 2026? Choose from 24 unique trip itineraries and 808 departures from the world's leading touring operators.
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Departures (May 2026)
< April 2026 June 2026 >
Duration
7 Days
18 Days
Regions
Trip Styles
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Price
$800pp
$10,220pp
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24 Trips (808 Trip Departures)
8 Day Croatia Island Sail (Plus) with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: May 2025 to Aug 2026
Countries Visited: Croatia
Big Travel Sale
Save (per person) 665
From (per person) 2,306
View Trip
10 Day Croatia Sailing Adventure with Intro Travel
New ReleaseTour + Cruise
 (3)

10 Days Split to Split
Operated By: Intro Travel
Departures: May 2025 to Sep 2026
Trip Styles: 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive Savings
Save (per person) 76
From (per person) 3,037
View Trip
8 Day Turkish Sailing with Contiki
Cruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Contiki
Departures: Apr 2025 to Sep 2026
Countries Visited: Turkey
Exclusive Savings
Save (per person) 543
From (per person) 1,484
View Trip
10 Day Sailing Croatia to Italy with G Adventures
Cruise

10 Days (9 Nights) Zadar to Venice
Operated By: G Adventures
Departures: Apr 2025 to Sep 2026
Countries Visited: Slovenia, Italy, Croatia
Great Adventure Sale
Save (per person) 793
From (per person) 2,078
View Trip
10 Day Sailing Italy to Croatia with G Adventures
Cruise

10 Days (9 Nights) Venice to Zadar
Operated By: G Adventures
Departures: May 2025 to Sep 2026
Countries Visited: Slovenia, Italy, Croatia
Great Adventure Sale
Save (per person) 793
From (per person) 2,078
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: Apr 2025 to Oct 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 227
From (per person) 1,603
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: Feb 2025 to Dec 2026
Trip Styles: Small Group, 18-30's, Sailing
Countries Visited: Sri Lanka, Maldives
Great Adventure Sale
Save (per person) 1,287
From (per person) 3,229
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: Apr 2025 to Oct 2026
Countries Visited: Montenegro, Croatia
Great Adventure Sale
Save (per person) 716
From (per person) 1,915
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Feb 2025 to Jan 2027
Countries Visited: Maldives
Exclusive Savings
Save (per person) 61
From (per person) 2,547
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 2025 to Oct 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 229
From (per person) 1,647
View Trip
8 Day Croatia Island Sail with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: May 2025 to Sep 2026
Countries Visited: Croatia
Big Travel Sale
Save (per person) 592
From (per person) 1,836
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 2025 to Sep 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 327
From (per person) 2,316
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Jan 2025 to Dec 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: India, Maldives
Great Adventure Sale
Save (per person) 512
From (per person) 3,545
View Trip
15 Day Montenegro & Croatia Sailing with G Adventures
Cruise

15 Days (14 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Apr 2025 to Sep 2026
Countries Visited: Montenegro, Croatia
Great Adventure Sale
Save (per person) 1,401
From (per person) 3,786
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 2025 to Sep 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 312
From (per person) 2,432
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Dec 2024 to Jan 2027
Countries Visited: Maldives
Exclusive Savings
Save (per person) 70
From (per person) 2,939
View Trip
15 Day Sailing Greece - Athens to Santorini with G Adventures
Cruise

15 Days (14 Nights) Athens to Santorini
Operated By: G Adventures
Departures: May 2025 to Sep 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 452
From (per person) 3,527
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Apr 2025 to Oct 2026
Countries Visited: Croatia
Great Adventure Sale
Save (per person) 716
From (per person) 1,915
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 2025 to Sep 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 238
From (per person) 1,745
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: Feb 2025 to Dec 2026
Rivers: Nile
Countries Visited: Egypt
Exclusive Savings
Save (per person) 162
From (per person) 7,202
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: Jan 2025 to Jan 2027
Countries Visited: Maldives
Last Minute OfferGreat Adventure Sale
Save (per person) 1,080
From (per person) 1,930
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: Apr 2025 to Sep 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 215
From (per person) 1,710
View Trip
15 Day Dalmatian Coast & Montenegro Sailing with G Adventures
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Apr 2025 to Sep 2026
Countries Visited: Montenegro, Croatia
Great Adventure Sale
Save (per person) 1,401
From (per person) 3,786
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Apr 2025 to Oct 2026
Countries Visited: Croatia
Great Adventure Sale
Save (per person) 716
From (per person) 1,915
View Trip
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