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2 Week Sailing Trips

Explore our 2 week sailing trips with 2 of the world's leading sailing trip operators. November, January and February are the most popular months to join a trip and we have 96 departures available and 4 unique itineraries to choose from.
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4 Trips (96 Trip Departures)
14 Day Highlights of Sri Lanka with Maldive Dhoni Cruise (West Coast) with Explore Worldwide
Tour + Cruise
 (1)

14 Days Negombo to Male
Operated By: Explore Worldwide
Departures: Nov 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$3,770
Save 210
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: Jun 2026 to Dec 2027
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$3,079
Save 830
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 2027 to Oct 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: Sri Lanka, Maldives
From
US$3,800
Per Person
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: Sep 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: India, Maldives
Exclusive Savings
From
US$2,699
Save 300
Per Person
View Trip
Results: 4 results

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Trip Lengths

7 Day 10 Day 2 Week

Departure Months

June July August September October November December January February March April

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