Home > Travel Styles > Adventure Tours > Sailing Trips > May 2025

Sailing Trips Starting In May 2025

Are you looking to embark on a sailing trip in May 2025? Choose from 29 unique trip itineraries and 886 departures from the world's leading touring operators.
Filter Results
Departures (May 2025)
< April 2025 June 2025 >
Duration
4 Days
26 Days
Regions
Trip Styles
Budget
Start & End Cities
Operators
Show More...
Price
$1,300pp
$14,645pp
Countries
Show More...
Filter Results
29 Trips (886 Trip Departures)
8 Day Croatia Island Sail Plus with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: Jun 2024 to Aug 2025
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive Deal
Save 690
From 2,334
View Trip
10 Day Croatia Sailing Adventure with Intro Travel
New ReleaseTour + Cruise
 (3)

10 Days Split to Split
Operated By: Intro Travel
Departures: Jun 2024 to Sep 2025
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive Savings
Save 70
From 3,233
View Trip
6 Day Wineglass Bay (Signature Walk) with Tasmanian Walking Co
New ReleaseTour + Cruise
 (1)

6 Days Hobart to Hobart
Operated By: Tasmanian Walking Co
Departures: Oct 2024 to Apr 2025
Trip Styles: Adventure, Small Group, Sailing, Short Break, Walking & Hiking
Countries Visited: Australia
From 4,450
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 2024 to Sep 2025
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive Savings
Save 66
From 2,743
View Trip
8 Day Turkish Sailing with Contiki
Cruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Contiki
Departures: Jun 2024 to Oct 2025
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Turkey
Exclusive Deal
Save 686
From 1,431
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: Jul 2024 to Jan 2026
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Maldives
Exclusive Deal
Save 835
From 1,884
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 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive DealLast Minute Offer
Save 933
From 1,366
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Jun 2024 to Nov 2025
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Exclusive Savings
Save 75
From 3,675
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jul 2024 to Jan 2026
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Maldives
Exclusive Deal
Save 772
From 2,227
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jun 2024 to Dec 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Maldives
Exclusive Savings
Save 59
From 2,547
View Trip
15 Day Montenegro & Croatia Sailing with G Adventures
Cruise

15 Days (14 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Jun 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Montenegro, Croatia
Exclusive Savings
Save 110
From 4,997
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Jun 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive Deal
Save 762
From 2,197
View Trip
9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Kuta to Labuan Bajo
Operated By: TruTravels
Departures: Jun 2024 to Nov 2025
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Exclusive Deal
Save 721
From 1,574
View Trip
8 Day Maldive Dhoni Cruise with Explore!
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore!
Departures: Jul 2024 to Dec 2025
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Maldives
Asia Sale
Save 455
From 3,322
View Trip
10 Day Sailing Italy to Croatia with G Adventures
Cruise

10 Days (9 Nights) Venice to Zadar
Operated By: G Adventures
Departures: Jun 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Slovenia, Italy, Croatia
Exclusive DealLast Minute Offer
Save 1,293
From 1,546
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 2024 to Sep 2025
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive DealLast Minute Offer
Save 1,242
From 1,817
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: Oct 2024 to Dec 2025
Rivers: Nile
Countries Visited: Egypt
Exclusive Savings
Save 162
From 7,202
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Jun 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
Last Minute Offer
Save 1,494
From 1,465
View Trip
4 Day Wineglass Bay (Signature Walk) with Tasmanian Walking Co
New ReleaseTour + Cruise

4 Days Hobart to Hobart
Operated By: Tasmanian Walking Co
Departures: Sep 2024 to Apr 2025
Trip Styles: Adventure, Small Group, Sailing, Short Break, Walking & Hiking
Countries Visited: Australia
From 3,164
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: Jun 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Montenegro, Croatia
Exclusive Deal
Save 1,055
From 1,904
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: Jun 2024 to Jan 2026
Trip Styles: Small Group, 18-30's, Sailing
Countries Visited: Sri Lanka, Maldives
Exclusive Deal
Save 1,289
From 2,910
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: Jul 2024 to Oct 2025
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Exclusive Savings
Save 120
From 5,875
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: Jun 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive Savings
Save 99
From 4,311
View Trip
10 Day Sailing Croatia to Italy with G Adventures
Cruise

10 Days (9 Nights) Zadar to Venice
Operated By: G Adventures
Departures: Jun 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Slovenia, Italy, Croatia
Exclusive DealLast Minute Offer
Save 1,205
From 1,686
View Trip
15 Day Dalmatian Coast & Montenegro Sailing with G Adventures
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Jun 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Montenegro, Croatia
Exclusive Savings
Save 112
From 4,997
View Trip
8 Day Croatia Island Sail with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: Jun 2024 to Sep 2025
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive Deal
Save 617
From 1,867
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 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive Deal
Save 724
From 1,635
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: Jun 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive Deal
Save 820
From 1,479
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 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive DealLast Minute Offer
Save 958
From 1,401
View Trip
Results: 29 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

June 2024 July 2024 August 2024 September 2024 October 2024 November 2024 December 2024 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

© 2010-2024. Global Journeys. You're viewing our site in Australian dollars.

    

About Us | View Your Booking | Terms & Conditions | Site Map | We're Hiring!

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

Travel Industry Associations