Home > Travel Styles > Adventure Tours > Sailing Trips > May 2024

Sailing Trips Starting In May 2024

Are you looking to embark on a sailing trip in May 2024? Choose from 36 unique trip itineraries and 993 departures from the world's leading touring operators.
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36 Trips (993 Trip Departures)
Featured8 Day Sail & Swim: Croatia (Moja Maja) with Topdeck
Cruise

8 Days (7 Nights) Split to Split
Operated By: Topdeck
Departures: Jun 2024 to Aug 2024
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
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8 Day Croatia Island Sail Plus with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: Jun 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: Jun 2024 to Sep 2024
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
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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
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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
Exclusive DealLimited Time Sale
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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: Jun 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: Jun 2024 to Oct 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: Oct 2024 to Apr 2025
Trip Styles: Adventure, Small Group, Sailing, Short Break, Walking & Hiking
Countries Visited: Australia
From 4,450
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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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8 Day Sailing Greece - Athens to Mykonos with G Adventures
Cruise

8 Days (7 Nights) Athens to Mykonos
Operated By: G Adventures
Departures: May 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
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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
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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: Jul 2024 to Jan 2026
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Maldives
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8 Day Sail Greece: Santorini to Mykonos with Intrepid Travel
Cruise

8 Days (7 Nights) Santorini to Mykonos
Operated By: Intrepid Travel
Departures: May 2024 to Oct 2024
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Greece
Limited Time Sale
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4 Day Sail Italy with Intrepid Travel
Cruise

4 Days (3 Nights) Procida to Amalfi
Operated By: Intrepid Travel
Departures: Jun 2024 to Sep 2024
Trip Styles: Group, Island Hopping, Sailing, Short Break
Countries Visited: Italy
Limited Time Sale
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18 Day Sri Lanka with Maldives Cruise: Spice Gardens & Seasides with G Adventures
Tour + Cruise

18 Days Negombo to Male
Operated By: G Adventures
Departures: Jun 2024 to Jan 2026
Trip Styles: Small Group, 18-30's, Sailing
Countries Visited: Sri Lanka, Maldives
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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: Jun 2024 to Sep 2024
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Italy
Limited Time Sale
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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
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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
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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
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8 Day Sardinia & Corsica Sailing Adventure with Intrepid Travel
Cruise

8 Days (7 Nights) Olbia to Olbia
Operated By: Intrepid Travel
Departures: May 2024 to Sep 2024
Trip Styles: Small Group, Cruise, Sailing
Countries Visited: Corsica, Sardinia
Limited Time Sale
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7 Day Maldives Dhoni Explorer with G Adventures
Cruise

7 Days (6 Nights) Male to Male
Operated By: G Adventures
Departures: Jun 2024 to Jan 2026
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Maldives
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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: Sep 2024 to Apr 2025
Trip Styles: Adventure, Small Group, Sailing, Short Break, Walking & Hiking
Countries Visited: Australia
From 3,164
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8 Day Croatia Island Sail with Contiki
Cruise

8 Days (7 Nights) Split to Split
Operated By: Contiki
Departures: May 2024 to Sep 2025
Trip Styles: Group, 18-30's, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive Savings
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From 1,867
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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: Jun 2024 to Sep 2024
Trip Styles: Small Group, Island Hopping, Sailing
Countries Visited: Greece
Limited Time Sale
Save 559
From 1,910
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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
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8 Day Sailing Greece - Mykonos to Athens with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Athens
Operated By: G Adventures
Departures: May 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive DealLast Minute Offer
Save 1,060
From 1,039
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8 Day Croatia Sailing Adventure: Dubrovnik to Split with Intrepid Travel
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: Intrepid Travel
Departures: Jun 2024 to Sep 2024
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
Limited Time Sale
Save 1,143
From 1,832
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8 Day Sailing Croatia with G Adventures
Cruise

8 Days (7 Nights) Dubrovnik to Split
Operated By: G Adventures
Departures: Jun 2024 to Oct 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Croatia
Exclusive DealLast Minute Offer
Save 1,494
From 1,465
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8 Day Sailing Greece - Mykonos to Santorini with G Adventures
Cruise

8 Days (7 Nights) Mykonos to Santorini
Operated By: G Adventures
Departures: May 2024 to Sep 2025
Trip Styles: Group, Island Hopping, Sailing
Countries Visited: Greece
Exclusive DealLast Minute Offer
Save 1,085
From 1,064
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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 1,242
From 1,817
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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
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