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Intrepid Sailing Trips

Join Intrepid on one of 16 sailing trips around the islands of the Mediterranean, Asia & the Caribbean this season. June, July and August are the most popular months to begin your trip and Intrepid have 431 trips departing between May 2026 and December 2027.
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4 Days
15 Days
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$700pp
$4,869pp
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16 Sailing Trips (431 Sailing Trip Departures)
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$1,419
Save 874
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$1,916
Save 912
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$1,797
Save 1,120
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$3,202
Save 1,287
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$1,428
Save 874
Per Person
View Trip
7 Day Phuket Sailing Adventure with Intrepid Travel
Cruise

7 Days (6 Nights) Phuket to Phuket
Operated By: Intrepid Travel
Departures: Nov 2026 to Dec 2027
Visit: Thailand
Exclusive Savings
From
US$1,477
Save 633
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$2,117
Save 1,005
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$2,149
Save 1,050
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$1,926
Save 873
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$1,266
Save 806
Per Person
View Trip
4 Day Sail Phuket to Ko Phi Phi with Intrepid Travel
Cruise

4 Days (3 Nights) Phuket to Ko Phi Phi
Operated By: Intrepid Travel
Departures: Nov 2026 to Dec 2027
Visit: Thailand
Exclusive Savings
From
US$798
Save 363
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 Oct 2027
Visit: Croatia, Montenegro
Exclusive Savings
From
US$1,646
Save 689
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$1,373
Save 695
Per Person
View Trip
4 Day Sail Ko Phi Phi to Phuket with Intrepid Travel
Cruise

4 Days (3 Nights) Ko Phi Phi to Phuket
Operated By: Intrepid Travel
Departures: Nov 2026 to Dec 2027
Visit: Thailand
Exclusive Savings
From
US$724
Save 336
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$2,142
Save 1,043
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$2,033
Save 1,020
Per Person
View Trip
Results: 16 results

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