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Sailing Trips Starting In July 2026 and 2027

Are you looking to embark on a sailing trip in July 2026 or 2027? Choose from 42 unique trip itineraries and 1,132 departures from the world's leading touring operators.
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42 Trips (1,132 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$1,696
Save 489
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$2,877
Save 99
Per Person
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8 Day Greece: Sail & Swim with Topdeck
New ReleaseCruise

8 Days (7 Nights) Athens to Athens
Operated By: Topdeck
Departures: May 2026 to Oct 2026
Visit: Greece
Exclusive Savings
From
US$2,220
Save 320
Per Person
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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
G's February Sale
Exclusive Savings
From
US$1,657
Save 292
Per Person
View Trip
8 Day Croatia: Sail & Swim with Topdeck
Cruise

8 Days (7 Nights) Split to Split
Operated By: Topdeck
Departures: May 2026 to Aug 2026
Visit: Croatia
Exclusive Savings
From
US$1,745
Save 258
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$3,123
Save 102
Per Person
View Trip
8 Day Croatia: Sail & Swim (Plus) with Topdeck
Cruise

8 Days (7 Nights) Split to Split
Operated By: Topdeck
Departure: 20 June 2026
Visit: Croatia
Exclusive Savings
From
US$2,269
Save 270
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
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10 Day Sailing Greece - Santorini to Santorini with G Adventures
Cruise

10 Days (9 Nights) Santorini to Santorini
Operated By: G Adventures
Departures: Apr 2026 to Sep 2027
Visit: Greece
G's February Sale
Exclusive Savings
From
US$1,937
Save 456
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
G's February Sale
Exclusive Savings
From
US$1,444
Save 277
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: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$1,626
Save 504
Per Person
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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$3,088
Save 105
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
G's February Sale
Exclusive Savings
From
US$1,896
Save 447
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: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$2,066
Save 73
Per Person
View Trip
10 Day Sailing Italy to Croatia with G Adventures
Tour + Cruise

10 Days Venice to Zadar
Operated By: G Adventures
Departures: May 2026 to Sep 2026
Trip Styles: Island Hopping, Sailing, Scenic
Visit: Italy, Slovenia, Croatia
G's February Sale
Exclusive Savings
From
US$1,714
Save 400
Per Person
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 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,648
Save 54
Per Person
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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$2,619
Save 92
Per Person
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22 Day Sri Lanka in Depth with Maldive Dhoni Cruise (Horton Plains) with Explore Worldwide
Tour + Cruise

22 Days Negombo to Male
Operated By: Explore Worldwide
Departures: Jul 2026 to Dec 2026
Trip Styles: Adventure, Small Group, Sailing
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$5,170
Save 170
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
G's February Sale
Exclusive Savings
From
US$1,714
Save 400
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
Exclusive Savings
From
US$1,165
Save 116
Per Person
View Trip
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
From
US$1,250
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operated By: Intrepid Travel
Departures: Mar 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$2,978
Save 105
Per Person
View Trip
8 Day Sail Turkey: Fethiye to Bodrum (Turkish Gulet) with Intrepid Travel
New ReleaseCruise

8 Days (7 Nights) Fethiye to Bodrum
Operated By: Intrepid Travel
Departures: Jun 2026 to Aug 2027
Visit: Turkey
Exclusive Savings
From
US$3,123
Save 101
Per Person
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Mar 2026 to Dec 2027
Visit: Maldives
G's February Sale
Exclusive Savings
From
US$1,673
Save 626
Per Person
View Trip
8 Day Montenegro Sailing Adventure from Dubrovnik with Intrepid Travel
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: Intrepid Travel
Departures: Jun 2026 to Sep 2027
Visit: Croatia, Montenegro
Exclusive Savings
From
US$2,119
Save 71
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
Exclusive Savings
From
US$1,872
Save 62
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: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$2,158
Save 74
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
G's February Sale
Exclusive Savings
From
US$1,657
Save 292
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: Apr 2026 to Oct 2027
Visit: Greece
G's February Sale
Exclusive Savings
From
US$1,402
Save 270
Per Person
View Trip
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