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

Sailing Trips Starting In June 2026

Are you looking to embark on a sailing trip in June 2026? Choose from 39 unique trip itineraries and 737 departures from the world's leading touring operators.
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Departures (June 2026)
< May 2026 July 2026 >
Duration
6 Days
26 Days
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$700pp
$5,690pp
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39 Trips (737 Trip Departures)
10 Day Croatia Sail Adventure with Intro Travel
New ReleaseTour + Cruise
 (3)

10 Days Split to Split
Operated By: Intro Travel
Departures: May 2026 to Sep 2026
Trip Styles: 18-30's, Island Hopping, Sailing
Visit: Croatia
Exclusive Savings
From
US$2,279
Save 73
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: Sep 2025 to Sep 2026
Visit: Greece
Exclusive Savings
From
US$2,627
Save 331
Per Person
View Trip
15 Day Montenegro & Croatia Sailing with G Adventures
Cruise
 (1)

15 Days (14 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Sep 2025 to Sep 2026
Visit: Montenegro, Croatia
Exclusive Savings
From
US$3,821
Save 85
Per Person
View Trip
8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: Intrepid Travel
Departures: Sep 2025 to Oct 2026
Visit: Croatia
Exclusive Savings
From
US$1,965
Save 58
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: Nov 2025 to Jan 2027
Visit: Maldives
Exclusive Savings
From
US$1,954
Save 345
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: Sep 2025 to Oct 2026
Visit: Greece
Exclusive Savings
From
US$1,930
Save 508
Per Person
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Sep 2025 to Nov 2026
Visit: Indonesia
Exclusive Savings
From
US$1,935
Save 68
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: Apr 2026 to Sep 2026
Visit: Slovenia, Italy, Croatia
From
US$2,129
Per Person
View Trip
8 Day Greek Island Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Athens to Athens
Operated By: Explore Worldwide
Departures: Jun 2026 to Sep 2026
Visit: Greece
From
US$1,720
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: Sep 2025 to Oct 2026
Visit: Greece
From
US$1,529
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: Sep 2025 to Oct 2026
Visit: Greece
Exclusive Savings
From
US$1,109
Save 370
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Sep 2025 to Oct 2026
Visit: Croatia
Exclusive Savings
From
US$1,364
Save 735
Per Person
View Trip
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operated By: G Adventures
Departures: Jan 2026 to Dec 2026
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$3,664
Save 735
Per Person
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: Oct 2025 to Oct 2026
Visit: Indonesia
Exclusive Savings
From
US$3,443
Save 114
Per Person
View Trip
8 Day Greece Sailing Adventure: Corfu to Kefalonia with Intrepid Travel
Cruise

8 Days (7 Nights) Corfu to Kefalonia
Operated By: Intrepid Travel
Departures: Sep 2025 to Oct 2026
Visit: Greece
Exclusive Savings
From
US$2,582
Save 634
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 2026
Visit: Croatia
From
US$1,105
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: May 2026 to Sep 2026
Visit: Croatia, Montenegro
Exclusive Savings
From
US$3,739
Save 89
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: Sep 2025 to Sep 2026
Visit: Greece
Exclusive Savings
From
US$2,099
Save 52
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: Sep 2025 to Oct 2026
Visit: Greece
Exclusive Savings
From
US$2,015
Save 502
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: Sep 2025 to Sep 2026
Visit: Greece
Exclusive Savings
From
US$2,514
Save 63
Per Person
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 2026 to Sep 2026
Visit: Greece
Exclusive Savings
From
US$3,184
Save 71
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: Nov 2025 to Dec 2026
Trip Styles: Small Group, 18-30's, Sailing
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$3,123
Save 626
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 2026
Visit: Croatia
From
US$1,425
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Sep 2025 to Oct 2026
Visit: Croatia
Exclusive Savings
From
US$1,462
Save 487
Per Person
View Trip
10 Day Sailing Italy to Croatia with G Adventures
Cruise

10 Days (9 Nights) Venice to Zadar
Operated By: G Adventures
Departures: Sep 2025 to Sep 2026
Visit: Slovenia, Italy, Croatia
From
US$2,129
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: Sep 2025 to Sep 2026
Visit: Greece
From
US$1,599
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: Sep 2025 to Oct 2026
Visit: Croatia
Exclusive Savings
From
US$1,965
Save 882
Per Person
View Trip
6 Day Komodo & Flores Sail with Contiki
New ReleaseTour + Cruise

6 Days Sanur to Labuan Bajo
Operated By: Contiki
Departures: Oct 2025 to Oct 2026
Visit: Indonesia
Exclusive Savings
From
US$1,400
Save 138
Per Person
View Trip
8 Day Sail Turkey: Bodrum to Fethiye (Turkish Gulet) with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Bodrum to Fethiye
Operated By: Intrepid Travel
Departures: Jun 2026 to Aug 2026
Visit: Turkey
Exclusive Savings
From
US$3,156
Save 64
Per Person
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 2026 to Sep 2026
Visit: Montenegro, Croatia
Exclusive Savings
From
US$3,821
Save 85
Per Person
View Trip
Results: 1-30 of 39

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