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2 Week Sailing Trips

Explore our 2 week sailing trips with 2 of the world's leading sailing trip operators. August, September and October are the most popular months to join a trip and we have 121 departures available and 4 unique itineraries to choose from.
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4 Trips (121 Trip Departures)
14 Day Sri Lanka & Maldives Adventure with G Adventures
Tour + Cruise

14 Days Negombo to Male
Operated By: G Adventures
Departures: Mar 2025 to Dec 2026
Trip Styles: Adventure, Small Group, Island Hopping, Sailing, Scenic
Countries Visited: Sri Lanka, Maldives
Great Adventure Sale
Save (per person) 1,447
From (per person) 3,563
View Trip
14 Day Essential India & Maldives Sailing with G Adventures
Tour + Cruise

14 Days Delhi to Male
Operated By: G Adventures
Departures: May 2025 to Dec 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: India, Maldives
Great Adventure Sale
Save (per person) 512
From (per person) 3,545
View Trip
14 Day Highlights of Sri Lanka with Maldive Dhoni Cruise (West Coast) with Explore!
Tour + Cruise

14 Days Negombo to Male
Operated By: Explore!
Departures: Mar 2025 to Dec 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Big Blue SaleSolo Traveller Offer
Save (per person) 689
From (per person) 5,514
View Trip
14 Day Highlights of Sri Lanka with Maldive Dhoni Cruise (East Coast) with Explore!
Tour + Cruise

14 Days Negombo to Male
Operated By: Explore!
Departures: Jul 2025 to Oct 2026
Trip Styles: Adventure, Small Group, Sailing
Countries Visited: Sri Lanka, Maldives
Big Blue SaleSolo Traveller Offer
Save (per person) 983
From (per person) 5,207
View Trip
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Trip Lengths

7 Day 10 Day 2 Week

Departure Months

March 2025 April 2025 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

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