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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 1,124 departures from the world's leading touring operators.
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42 Trips (1,124 Trip Departures)
10 Day Croatia Sail Adventure with Intro Travel
New ReleaseTour + Cruise
 (3)

10 Days Split to Split
Operated By: Intro Travel
Departures: Jun 2026 to Sep 2027
Trip Styles: 18-30's, Island Hopping, Sailing
Visit: Croatia
From
US$2,749
Per Person
View Trip
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$1,698
Save 546
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: May 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$2,172
Save 608
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$2,412
Save 127
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$2,754
Save 348
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: Jun 2026 to Sep 2027
Visit: Croatia, Montenegro
Exclusive Savings
From
US$3,880
Save 644
Per Person
View Trip
8 Day Family Greek Coast Caique Cruise with Explore Worldwide
Cruise

8 Days (7 Nights) Athens to Athens
Operated By: Explore Worldwide
Departures: Aug 2026 to Aug 2027
Visit: Greece
Exclusive Savings
From
US$1,790
Save 140
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$2,447
Save 510
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$2,185
Save 582
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$3,239
Save 810
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: May 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$1,724
Save 657
Per Person
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: May 2026 to Nov 2027
Visit: Indonesia
Exclusive Savings
From
US$1,575
Save 675
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: Apr 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$1,409
Save 940
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$1,553
Save 463
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 2027
Visit: Croatia
From
US$1,505
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$1,899
Save 107
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 Sep 2027
Visit: Croatia
Exclusive Savings
From
US$974
Save 975
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
Exclusive Savings
From
US$1,247
Save 832
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
Exclusive Savings
From
US$1,175
Save 504
Per Person
View Trip
8 Day Sail Maldives with Intrepid Travel
Cruise

8 Days (7 Nights) Male to Male
Operated By: Intrepid Travel
Departures: May 2026 to Dec 2027
Visit: Maldives
Exclusive Savings
From
US$2,763
Save 350
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$1,646
Save 656
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
Exclusive Savings
From
US$1,149
Save 1,150
Per Person
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: May 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,169
Save 780
Per Person
View Trip
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$2,412
Save 130
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$1,489
Save 504
Per Person
View Trip
6 Day Komodo & Flores Sail with Contiki
New ReleaseTour + Cruise

6 Days Sanur to Labuan Bajo
Operated By: Contiki
Departures: Jun 2026 to Oct 2026
Visit: Indonesia
Exclusive Savings
From
US$1,379
Save 138
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
Exclusive Savings
From
US$849
Save 850
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 Oct 2027
Visit: Montenegro, Croatia
Exclusive Savings
From
US$974
Save 975
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 2027
Visit: Greece
Exclusive Savings
From
US$1,760
Save 270
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
From
US$3,249
Per Person
View Trip
Results: 1-30 of 42

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