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Sailing Trips Starting In June 2026 and 2027

Are you looking to embark on a sailing trip in June 2026 or 2027? Choose from 45 unique trip itineraries and 1,303 departures from the world's leading touring operators.
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45 Trips (1,303 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 2027
Trip Styles: 18-30's, Island Hopping, Sailing
Visit: Croatia
Exclusive Savings
From
US$2,255
Save 130
Per Person
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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$1,711
Save 399
Per Person
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10 Day Greece Sailing Adventure: Cyclades Islands with Intrepid Travel
Cruise
 (1)

10 Days (9 Nights) Santorini to Santorini
Operated By: Intrepid Travel
Departures: Jun 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$2,464
Save 537
Per Person
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18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2026 to Nov 2027
Visit: Indonesia
Exclusive Savings
From
US$1,396
Save 599
Per Person
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6 Day Komodo & Flores Sail with Contiki
New ReleaseTour + Cruise

6 Days Sanur to Labuan Bajo
Operated By: Contiki
Departures: Apr 2026 to Oct 2026
Visit: Indonesia
Worldwide Sale
Exclusive Savings
From
US$1,262
Save 125
Per Person
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14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Apr 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: India, Maldives
Great Adventure Sale
Exclusive Savings
From
US$2,182
Save 940
Per Person
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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
Worldwide Sale
Exclusive Savings
From
US$1,320
Save 95
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: Jul 2026 to Sep 2026
Visit: Greece
Great Adventure Sale
Exclusive Savings
From
US$2,924
Save 451
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
Great Adventure Sale
Exclusive Savings
From
US$3,099
Save 750
Per Person
View Trip
7 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

7 Days (6 Nights) Naples to Procida
Operated By: Intrepid Travel
Departures: May 2026 to Oct 2027
Visit: Italy
Exclusive Savings
From
US$2,639
Save 595
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: May 2026 to Dec 2027
Trip Styles: Small Group, 18-30's, Sailing
Visit: Sri Lanka, Maldives
Great Adventure Sale
Exclusive Savings
From
US$2,364
Save 1,022
Per Person
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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
Great Adventure Sale
Exclusive Savings
From
US$1,237
Save 412
Per Person
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10 Day Egypt: Pyramids, Temples & the Nile with G Adventures
New ReleaseRiver Cruise

10 Days Cairo to Cairo
Operated By: G Adventures
Departures: Feb 2026 to Dec 2027
Rivers: Nile
Visit: Egypt
Exclusive Savings
From
US$4,655
Save 170
Per Person
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8 Day Croatia: Sail & Swim (Plus) with Topdeck
Cruise

8 Days (7 Nights) Split to Split
Operated By: Topdeck
Departures: Jun 2026 to Aug 2026
Visit: Croatia
Exclusive Savings
From
US$2,269
Save 270
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operated By: Intrepid Travel
Departures: Feb 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$2,680
Save 445
Per Person
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10 Day Sailing Italy to Croatia with G Adventures
Cruise

10 Days (9 Nights) Venice to Zadar
Operated By: G Adventures
Departures: May 2026 to Sep 2026
Visit: Slovenia, Italy, Croatia
Great Adventure Sale
Exclusive Savings
From
US$1,559
Save 621
Per Person
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7 Day Maldives Cruise: Indian Ocean Dhoni Life with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Feb 2026 to Jan 2028
Visit: Maldives
Great Adventure Sale
Exclusive Savings
From
US$1,499
Save 626
Per Person
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9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Lombok to Labuan Bajo
Operated By: TruTravels
Departures: Apr 2026 to Nov 2027
Visit: Indonesia
Exclusive Savings
From
US$875
Save 375
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
Worldwide Sale
Exclusive Savings
From
US$1,165
Save 85
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: Apr 2026 to Sep 2027
Visit: Greece
Great Adventure Sale
Exclusive Savings
From
US$1,274
Save 462
Per Person
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: Apr 2026 to Sep 2026
Visit: Montenegro, Croatia
Great Adventure Sale
Exclusive Savings
From
US$1,618
Save 331
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 2027
Visit: Turkey
Exclusive Savings
From
US$2,499
Save 765
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
Great Adventure Sale
Exclusive Savings
From
US$1,259
Save 462
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 2027
Visit: Croatia, Montenegro
Exclusive Savings
From
US$3,496
Save 783
Per Person
View Trip
8 Day Turkey: Sail & Swim with Topdeck
New ReleaseCruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Topdeck
Departures: May 2026 to Oct 2026
Visit: Turkey
Exclusive Savings
From
US$1,069
Save 200
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Apr 2026 to Oct 2026
Visit: Croatia
Great Adventure Sale
Exclusive Savings
From
US$1,618
Save 331
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Apr 2026 to Oct 2026
Visit: Croatia
Great Adventure Sale
Exclusive Savings
From
US$1,618
Save 331
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: Apr 2026 to Sep 2027
Visit: Greece
Great Adventure Sale
Exclusive Savings
From
US$1,673
Save 695
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: Apr 2026 to Dec 2027
Visit: Sri Lanka, Maldives
Great Adventure Sale
Exclusive Savings
From
US$3,099
Save 857
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$2,243
Save 515
Per Person
View Trip
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