Home > Travel Styles > Adventure Tours > Sailing Trips > August

Sailing Trips Starting In August 2026 and 2027

Are you looking to embark on a sailing trip in August 2026 or 2027? Choose from 44 unique trip itineraries and 1,166 departures from the world's leading touring operators.
Filter Results
Departures
Duration
6 Days
26 Days
Regions
Trip Styles
Start & End Cities
Operators
Show More...
Price
$500pp
$10,260pp
Countries
Show More...
Filter Results
44 Trips (1,166 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$2,398
Save 137
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$1,639
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: Jun 2026 to Sep 2027
Visit: Greece
Exclusive Savings
From
US$2,465
Save 99
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 104
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 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$1,439
Save 360
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$1,696
Save 489
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$1,274
Save 425
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$4,113
Save 139
Per Person
View Trip
8 Day Turkey: Sail & Swim with Topdeck
New ReleaseCruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Topdeck
Departures: Jun 2026 to Oct 2026
Visit: Turkey
Exclusive Savings
From
US$1,269
Save 52
Per Person
View Trip
14 Day Highlights of Sri Lanka with Maldive Dhoni Cruise (East Coast) with Explore Worldwide
Tour + Cruise

14 Days Negombo to Male
Operated By: Explore Worldwide
Departures: Aug 2026 to Oct 2026
Trip Styles: Adventure, Small Group, Sailing
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$3,599
Save 113
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$2,772
Save 105
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$2,340
Save 199
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$1,707
Save 223
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$1,462
Save 487
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 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$1,853
Save 74
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
Exclusive Savings
From
US$1,402
Save 360
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 132
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 Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Apr 2026 to Oct 2027
Visit: Croatia
Exclusive Savings
From
US$1,462
Save 487
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$1,842
Save 157
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: May 2026 to Oct 2027
Visit: Greece
Exclusive Savings
From
US$2,692
Save 94
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
Exclusive Savings
From
US$1,673
Save 716
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$2,463
Save 78
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$1,709
Save 640
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$1,462
Save 487
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
Exclusive Savings
From
US$2,800
Save 1,049
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$2,679
Save 623
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$1,479
Save 370
Per Person
View Trip
Results: 1-30 of 44

No trips found. Try adjusting the 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

March April May June July August September October November December January February

© 2010-2026. Global Journeys. You're viewing our site in US dollars.

    

Global Journeys | Terms & Conditions

Global Journeys Travel Inc. is a Member of the American Society of Travel Advisors (ASTA No: 900374670), CLIA (No. 00046729) & is TICO Accredited (No. 50027921).

Travel Industry Associations