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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 is the most popular month to join a trip and we have 110 departures available and 4 unique itineraries to choose from.
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4 Trips (110 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: Mar 2026 to Dec 2026
Trip Styles: Adventure, Small Group, Sailing
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$3,967
Save 406
Per Person
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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
Departure: 03 August 2026
Trip Styles: Adventure, Small Group, Sailing
Visit: Sri Lanka, Maldives
Exclusive Savings
From
US$3,667
Save 113
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: Jun 2026 to Dec 2027
Trip Styles: Adventure, Small Group, Sailing
Visit: India, Maldives
Exclusive Savings
From
US$2,909
Save 103
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$3,734
Save 132
Per Person
View Trip
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Trip Lengths

7 Day 10 Day 2 Week

Departure Months

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

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