Home > Travel Styles > Adventure Tours > Sailing Trips > September 2026

Sailing Trips Starting In September 2026

Are you looking to embark on a sailing trip in September 2026? Choose from 29 unique trip itineraries and 833 departures from the world's leading touring operators.
Filter Results
Departures (September 2026)
< August 2026 October 2026 >
Duration
7 Days
26 Days
Regions
Trip Styles
Budget
Start & End Cities
Operators
Price
$800pp
$5,690pp
Countries
Show More...
Filter Results
29 Trips (833 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 2025 to Sep 2026
Trip Styles: 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive Savings
Save (per person) 73
From (per person) 2,230
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: Jun 2025 to Sep 2026
Countries Visited: Greece
Last Minute OfferMay Sale
Save (per person) 880
From (per person) 1,319
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: Jul 2025 to Oct 2026
Countries Visited: Greece
May Sale
Save (per person) 247
From (per person) 1,402
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: Jun 2025 to Sep 2026
Countries Visited: Greece
Last Minute Offer
Save (per person) 252
From (per person) 1,427
View Trip
7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jun 2025 to Jan 2027
Countries Visited: Maldives
Last Minute OfferMay Sale
Save (per person) 740
From (per person) 1,109
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: Jun 2025 to Oct 2026
Countries Visited: Greece
Last Minute OfferMay Sale
Save (per person) 504
From (per person) 1,175
View Trip
15 Day Dalmatian Coast & Montenegro Sailing with G Adventures
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: Jun 2025 to Sep 2026
Countries Visited: Montenegro, Croatia
Last Minute OfferMay Sale
Save (per person) 2,090
From (per person) 2,009
View Trip
22 Day Sri Lanka in Depth with Maldive Dhoni Cruise (Horton Plains) with Explore!
Tour + Cruise

22 Days Negombo to Male
Operated By: Explore!
Departures: Sep 2025 to Nov 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Sign Up Savings
Save (per person) 671
From (per person) 4,481
View Trip
15 Day Montenegro & Croatia Sailing with G Adventures
Cruise

15 Days (14 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: May 2025 to Sep 2026
Countries Visited: Montenegro, Croatia
Last Minute OfferMay Sale
Save (per person) 1,963
From (per person) 1,886
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: Sep 2025 to Dec 2026
Rivers: Nile
Countries Visited: Egypt
Exclusive Savings
Save (per person) 106
From (per person) 4,703
View Trip
8 Day Greek Island Cruise with Explore!
Cruise

8 Days (7 Nights) Athens to Athens
Operated By: Explore!
Departures: Jun 2025 to Sep 2026
Countries Visited: Greece
Exclusive Deal
Save (per person) 170
From (per person) 1,590
View Trip
8 Day Turkish Sailing with Contiki
Cruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Contiki
Departures: Jun 2025 to Sep 2026
Countries Visited: Turkey
Last Minute Deal
Save (per person) 334
From (per person) 963
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: Jul 2025 to Sep 2026
Countries Visited: Greece
May Sale
Save (per person) 259
From (per person) 1,470
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: May 2025 to Oct 2026
Countries Visited: Croatia
Last Minute OfferMay Sale
Save (per person) 1,050
From (per person) 974
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 2025 to Sep 2026
Countries Visited: Greece
Exclusive Savings
Save (per person) 71
From (per person) 3,017
View Trip
8 Day Croatia Island Sail with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: Jun 2025 to Sep 2026
Countries Visited: Croatia
Last Minute Deal
Save (per person) 210
From (per person) 1,379
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: Jun 2025 to Sep 2026
Countries Visited: Greece
Last Minute OfferMay Sale
Save (per person) 920
From (per person) 1,379
View Trip
8 Day Maldive Dhoni Cruise with Explore!
Cruise

8 Days (7 Nights) Male to Male
Operated By: Explore!
Departures: Sep 2025 to Dec 2026
Countries Visited: Maldives
Exclusive Savings
Save (per person) 50
From (per person) 1,960
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Jun 2025 to Dec 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: India, Maldives
May Sale
Save (per person) 431
From (per person) 2,698
View Trip
8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: May 2025 to Oct 2026
Countries Visited: Croatia
Last Minute OfferMay Sale
Save (per person) 1,050
From (per person) 974
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: Jun 2025 to Jan 2027
Countries Visited: Maldives
Last Minute Offer
Save (per person) 740
From (per person) 1,109
View Trip
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operated By: G Adventures
Departures: Jun 2025 to Dec 2026
Trip Styles: Adventure, Small Group, Island Hopping, Sailing
Countries Visited: Sri Lanka, Maldives
Last Minute OfferMay Sale
Save (per person) 1,114
From (per person) 2,435
View Trip
10 Day Sailing Croatia to Italy with G Adventures
Cruise

10 Days (9 Nights) Zadar to Venice
Operated By: G Adventures
Departures: Jun 2025 to Sep 2026
Countries Visited: Slovenia, Italy, Croatia
Last Minute OfferMay Sale
Save (per person) 1,125
From (per person) 1,124
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: Oct 2025 to Dec 2026
Trip Styles: Small Group, 18-30's, Sailing
Countries Visited: Sri Lanka, Maldives
Exclusive Savings
Save (per person) 75
From (per person) 3,184
View Trip
26 Day Total Indonesia with TruTravels
New ReleaseTour + Cruise

26 Days Medan to Labuan Bajo
Operated By: TruTravels
Departures: Jun 2025 to Oct 2026
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Countries Visited: Indonesia
Exclusive Savings
Save (per person) 114
From (per person) 3,443
View Trip
7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jun 2025 to Jan 2027
Countries Visited: Maldives
Last Minute OfferMay Sale
Save (per person) 770
From (per person) 1,429
View Trip
10 Day Sailing Italy to Croatia with G Adventures
Cruise

10 Days (9 Nights) Venice to Zadar
Operated By: G Adventures
Departures: Jul 2025 to Sep 2026
Countries Visited: Slovenia, Italy, Croatia
Last Minute OfferMay Sale
Save (per person) 675
From (per person) 1,574
View Trip
8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: May 2025 to Oct 2026
Countries Visited: Montenegro, Croatia
Last Minute OfferMay Sale
Save (per person) 1,050
From (per person) 1,049
View Trip
18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: Jun 2025 to Nov 2026
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing
Countries Visited: Indonesia
Exclusive Savings
Save (per person) 68
From (per person) 1,935
View Trip
Results: 29 results

No Results found. Try changing your 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

May 2025 June 2025 July 2025 August 2025 September 2025 October 2025 November 2025 December 2025 January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026 December 2026 January 2027

© 2010-2025. Global Journeys. You're viewing our site in US dollars.

    

About Us | View Your Booking | Terms & Conditions | Site Map

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