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

Sailing Trips Starting In September 2026 and 2027

Are you looking to embark on a sailing trip in September 2026 or 2027? Choose from 45 unique trip itineraries and 1,330 departures from the world's leading touring operators.
Filter Results
Departures
Duration
6 Days
26 Days
Regions
Trip Styles
Budget
Start & End Cities
Operators
Show More...
Price
$700pp
$5,950pp
Countries
Show More...
Filter Results
45 Trips (1,330 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
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$1,696
Save 489
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$2,877
Save 99
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
G's February Sale
Exclusive Savings
From
US$2,987
Save 862
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 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
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
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 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
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
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
G's February Sale
Exclusive Savings
From
US$3,174
Save 675
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$4,113
Save 139
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: Mar 2026 to Jan 2028
Visit: Maldives
Exclusive Savings
From
US$1,609
Save 690
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 Aug 2026
Visit: Greece
G's February Sale
Exclusive Savings
From
US$2,679
Save 570
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
G's February Sale
Exclusive Savings
From
US$1,427
Save 252
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
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 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 Egypt: Pyramids, Temples & the Nile with G Adventures
New ReleaseRiver Cruise

10 Days Cairo to Cairo
Operated By: G Adventures
Departures: Mar 2026 to Dec 2027
Rivers: Nile
Visit: Egypt
Exclusive Savings
From
US$4,190
Save 995
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
7 Day Egypt: Ancient Wonders & Temples of the Nile with G Adventures
New ReleaseTour

7 Days Cairo to Luxor
Operated By: G Adventures
Departures: Mar 2026 to Jan 2028
Trip Styles: Adventure, Small Group, Sailing
Visit: Egypt
G's February Sale
Exclusive Savings
From
US$2,473
Save 614
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$2,220
Save 320
Per Person
View Trip
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
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
View Trip
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$1,935
Save 68
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$3,088
Save 105
Per Person
View Trip
6 Day Komodo & Flores Sail with Contiki
New ReleaseTour + Cruise

6 Days Sanur to Labuan Bajo
Operated By: Contiki
Departures: May 2026 to Oct 2026
Visit: Indonesia
Exclusive Savings
From
US$1,262
Save 120
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
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
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
View Trip
Results: 1-30 of 45

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

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

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

    

About Us | View Your Booking | Operators | Terms & Conditions | Site Map | We're hiring!

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