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Sailing Trips Starting In May 2024

Are you looking to embark on a sailing trip in May 2024? Choose from 40 unique trip itineraries and 1,108 departures from the world's leading touring operators.
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40 Trips (1,108 Trip Departures)
8 Day Croatia Island Sail Plus with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: May 2024 to Aug 2025
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
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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 2024 to Sep 2024
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
Limited Time Sale
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5 Day Sail Italy: Amalfi to Procida with Intrepid Travel
Cruise

5 Days (4 Nights) Amalfi to Procida
Operated By: Intrepid Travel
Departures: May 2024 to Oct 2024
Trip Styles: Small Group, Island Hopping, Sailing, Short Break
Countries Visited: Italy
Limited Time Sale
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8 Day Croatia Sailing Adventure with TruTravels
New ReleaseCruise
 (1)

8 Days (7 Nights) Split to Split
Operated By: TruTravels
Departures: May 2024 to Sep 2024
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
Europe Summer Sale
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From 1,558
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10 Day Croatia Sailing Adventure with Intro Travel
New ReleaseTour + Cruise
 (3)

10 Days Split to Split
Operated By: Intro Travel
Departures: May 2024 to Sep 2025
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
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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 2024 to Sep 2024
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Greece
Limited Time Sale
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6 Day Wineglass Bay (Signature Walk) with Tasmanian Walking Co
New ReleaseTour + Cruise
 (1)

6 Days Hobart to Hobart
Operated By: Tasmanian Walking Co
Departures: May 2024 to May 2025
Trip Styles: Adventure, Small Group, Sailing, Short Break, Walking & Hiking
Countries Visited: Australia
From 4,450
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9 Day Komodo Island Hopper with TruTravels
New ReleaseTour + Cruise

9 Days Kuta to Labuan Bajo
Operated By: TruTravels
Departures: May 2024 to Nov 2025
Trip Styles: Adventure, Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Exclusive Deal
Save 721
From 1,574
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10 Day Sailing Greece - Santorini to Santorini with G Adventures
Cruise

10 Days (9 Nights) Santorini to Santorini
Operated By: G Adventures
Departures: May 2024 to Sep 2025
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Greece
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From 2,743
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15 Day Dalmatian Coast & Montenegro Sailing with G Adventures
Cruise

15 Days (14 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: May 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Montenegro, Croatia
Exclusive Savings
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From 4,801
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7 Day Maldives Cruise: Indian Ocean Dhoni Life with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: May 2024 to Jan 2026
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Maldives
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18 Day Bali & Beyond with TruTravels
New ReleaseTour + Cruise

18 Days Canggu to Labuan Bajo
Operated By: TruTravels
Departures: May 2024 to Nov 2025
Trip Styles: Small Group, 18-30's, Island Hopping, Sailing, Scenic
Countries Visited: Indonesia
Exclusive Deal
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7 Day Maldives Dhoni Cruise with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: May 2024 to Dec 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Maldives
Exclusive Deal
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8 Day Montenegro Sailing with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Dubrovnik
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Montenegro, Croatia
Exclusive Deal
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8 Day Sail & Swim: Turkey with Topdeck
New ReleaseCruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Topdeck
Departures: May 2024 to Oct 2024
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Turkey
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10 Day Sailing Greece - Mykonos to Mykonos with G Adventures
Cruise

10 Days (9 Nights) Mykonos to Mykonos
Operated By: G Adventures
Departures: May 2024 to Sep 2025
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive DealLast Minute Offer
Save 1,413
From 1,386
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8 Day Amalfi Coast Sailing Adventure with Intrepid Travel
Cruise

8 Days (7 Nights) Procida to Procida
Operated By: Intrepid Travel
Departures: May 2024 to Sep 2024
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Italy
Limited Time Sale
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From 2,656
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10 Day Sailing Italy to Croatia with G Adventures
Cruise

10 Days (9 Nights) Venice to Zadar
Operated By: G Adventures
Departures: May 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Slovenia, Italy, Croatia
Exclusive DealLast Minute Offer
Save 1,293
From 1,546
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8 Day Sail & Swim: Greece with Topdeck
New ReleaseCruise

8 Days (7 Nights) Athens to Athens
Operated By: Topdeck
Departures: Jun 2024 to Sep 2024
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Greece
Exclusive Deal
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15 Day Sailing Greece - Athens to Santorini with G Adventures
Cruise

15 Days (14 Nights) Athens to Santorini
Operated By: G Adventures
Departures: May 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive Savings
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From 4,213
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15 Day Montenegro & Croatia Sailing with G Adventures
Cruise

15 Days (14 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: May 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Montenegro, Croatia
Exclusive Savings
Save 110
From 4,801
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4 Day Sail Italy with Intrepid Travel
Cruise

4 Days (3 Nights) Procida to Amalfi
Operated By: Intrepid Travel
Departures: May 2024 to Sep 2024
Trip Styles: Group, Island Hopping, Sailing, Short Break
Countries Visited: Italy
Limited Time Sale
Save 513
From 1,170
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8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Split to Dubrovnik
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive DealLast Minute Offer
Save 1,262
From 1,237
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4 Day Wineglass Bay (Signature Walk) with Tasmanian Walking Co
New ReleaseTour + Cruise

4 Days Hobart to Hobart
Operated By: Tasmanian Walking Co
Departures: May 2024 to May 2025
Trip Styles: Adventure, Small Group, Sailing, Short Break, Walking & Hiking
Countries Visited: Australia
From 3,164
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8 Day Sail & Swim: Croatia (Moja Maja) with Topdeck
Cruise

8 Days (7 Nights) Split to Split
Operated By: Topdeck
Departures: May 2024 to Aug 2024
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive Deal
Save 460
From 1,817
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10 Day Sailing Croatia to Italy with G Adventures
Cruise

10 Days (9 Nights) Zadar to Venice
Operated By: G Adventures
Departures: Jun 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Slovenia, Italy, Croatia
Exclusive Deal
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From 1,827
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8 Day Sailing Greece - Santorini to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive Deal
Save 724
From 1,635
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8 Day Sail Greece: Mykonos to Santorini with Intrepid Travel
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operated By: Intrepid Travel
Departures: May 2024 to Sep 2024
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Greece
Limited Time Sale
Save 241
From 2,128
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8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive DealLast Minute Offer
Save 1,262
From 1,237
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8 Day Turkish Sailing with Contiki
Cruise

8 Days (7 Nights) Fethiye to Fethiye
Operated By: Contiki
Departures: May 2024 to Oct 2025
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Turkey
Exclusive Savings
Save 373
From 1,488
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