Home > Travel Styles > Adventure Tours > Sailing Trips > May 2026

Sailing Trips Starting In May 2026

Are you looking to embark on a sailing trip in May 2026? Choose from 27 unique trip itineraries and 955 departures from the world's leading touring operators.
Filter Results
Departures (May 2026)
< April 2026 June 2026 >
Duration
7 Days
18 Days
Regions
Trip Styles
Budget
Start & End Cities
Operators
Price
$800pp
$10,220pp
Countries
Show More...
Filter Results
27 Trips (955 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) 814
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
Intro Birthday Offer
Save (per person) 414
From (per person) 2,761
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 2025 to Sep 2026
Countries Visited: Greece
Great Adventure Sale
Save (per person) 327
From (per person) 2,432
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 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
Last Minute Offer
Save (per person) 1,689
From (per person) 6,430
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) 725
From (per person) 1,836
View Trip
8 Day Maldive Dhoni Cruise with Explore!
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore!
Departures: Feb 2025 to Dec 2026
Countries Visited: Maldives
Big Blue Sale
Save (per person) 603
From (per person) 3,077
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) 660
From (per person) 3,039
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
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) 351
From (per person) 1,519
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
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: May 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
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
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
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
Great Adventure Sale
Save (per person) 780
From (per person) 1,930
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2025 to Nov 2026
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Just Go Offer
Save (per person) 810
From (per person) 2,940
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Kuta to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2025 to Nov 2026
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Just Go Offer
Save (per person) 496
From (per person) 1,799
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) 2,182
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Mar 2025 to Jan 2027
Countries Visited: Maldives
Exclusive Savings
Save (per person) 61
From (per person) 2,547
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
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
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) 371
From (per person) 1,478
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Mar 2025 to Jan 2027
Countries Visited: Maldives
Exclusive Savings
Save (per person) 70
From (per person) 2,939
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 - 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) 374
From (per person) 1,647
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) 510
From (per person) 2,136
View Trip
Results: 27 results

No Results found. Try changing your search filters.




Trips found! Scroll up to view

Adventure Travel

Walking and Hiking Everest Base Camp Treks Sailing Trips Ski Trips Cycling Tours Kayaking Tours Camping Tours Rafting Tours Wildlife Tours & Cruises Gorilla Treks

Trip Lengths

7 Day 10 Day 2 Week

Departure Months

January 2025 February 2025 March 2025 April 2025 May 2025 June 2025 July 2025 August 2025 September 2025 October 2025 November 2025 December 2025 January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026 December 2026 January 2027

© 2010-2025. Global Journeys. You're viewing our site in Australian dollars.

    

About Us | View Your Booking | Terms & Conditions | Site Map

Global Journeys Pty Ltd. Accredited Member of The Australian Travel Industry Association (AITA). No. A11351.

Travel Industry Associations