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Drone image of Wind Surf anchored at Pigeon Island, St. Lucia.
JD Lasica / Special to Cruiseable

Wind Surf has following cruise itineraries. Contact us for more information.


  • 10 night ancient wonders of greece and ephesus

    Starting in Athens (Piraeus) with stops in Mykonos, Kusadasi (Ephesus), Rhodes, Santorini

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    2022 sails:
    Jun 27
    Sep 09
    2023 sails:
    Jun 26
    Sep 08
  • 19 night star collector adriatic and aegean sea adventures

    Starting in Athens (Piraeus) with stops in Mykonos, Kusadasi (Ephesus), Rhodes, Santorini, Greece, Kotor, Dubrovnik, Hvar, Venice

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    2022 sails:
    Jun 27
    Aug 31
    Sep 09
    2023 sails:
    Jun 17
    Jun 26
    Aug 30
    Sep 08
  • 17 night star collector stories of italy croatia and greece

    Starting in Venice with stops in Greece, Dubrovnik, Athens (Piraeus), Kotor, Rome, Hvar

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    2022 sails:
    Jul 07
    Aug 23
    Sep 19
    2023 sails:
    Jun 09
    Jul 06
    Aug 22
    Sep 18
  • 9 night adriatic archipelagos and greek goddesses

    Starting in Athens (Piraeus) with stops in Greece, Kotor, Dubrovnik, Hvar, Venice

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    2022 sails:
    Jul 07
    Aug 31
    Sep 19
    2023 sails:
    Jun 17
    Jul 06
    Aug 30
    Sep 18
  • 8 night classic italy and dalmatian coast

    Starting in Rome with stops in Venice, Kotor, Dubrovnik

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    2022 sails:
    Jul 16
    Aug 23
    Sep 28
    Oct 16
    Oct 24
    2023 sails:
    Apr 30
    May 08
    Jun 09
    Jul 15
    Aug 22
    Sep 27
    Oct 15
    Oct 23
  • 15 night star collector italian trio

    Starting in Venice with stops in Dubrovnik, Kotor, Rome, Monte Carlo, Cannes, Barcelona

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    2022 sails:
    Jul 16
    Aug 16
    2023 sails:
    Apr 23
    May 08
    Jul 15
    Aug 15
  • 23 night star collector riviera rhapsody

    Starting in Venice with stops in Dubrovnik, Kotor, Rome, Monte Carlo, Cannes, Barcelona, Mallorca (Majorca), Cartagena, Málaga, Costa del Sol, Cadiz, Lisbon, Gibraltar

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    2022 sails:
    Jul 16
    Aug 08
    2023 sails:
    Jul 15
    Aug 07
  • 7 night yachtsmans harbors of the rivieras

    Starting in Monte Carlo with stops in Rome, Cannes, Barcelona

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    2022 sails:
    Jul 24
    Aug 16
    Nov 11
    2023 sails:
    Apr 23
    May 16
    Jul 23
    Aug 15
    Nov 10
  • 15 night star collector enchantment of the western mediterranean

    Starting in Barcelona with stops in Mallorca (Majorca), Cartagena, Rome, Lisbon, Cannes, Cadiz, Gibraltar, Monte Carlo, Málaga, Costa del Sol

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    2022 sails:
    Jul 24
    Aug 08
    Nov 11
    2023 sails:
    Apr 15
    Jul 23
    Aug 07
    Nov 10
  • 8 night spanish symphony

    Starting in Málaga, Costa del Sol with stops in Barcelona, Gibraltar, Cartagena, Mallorca (Majorca), Cadiz, Lisbon

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    2022 sails:
    Aug 08
    Nov 18
    2023 sails:
    Apr 15
    Jul 30
    Aug 07
    Nov 17
  • 18 night star collector culture and charms of italy and croatia

    Starting in Kotor with stops in Malta, Venice, Amalfi Coast, Rome, Dubrovnik

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    2022 sails:
    Sep 28
    Oct 06
    Oct 24
    2023 sails:
    May 30
    Sep 27
    Oct 05
    Oct 23
  • 10 night sicilian splendors

    Starting in Rome with stops in Malta, Amalfi Coast

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    2022 sails:
    Oct 06
    Nov 01
    2023 sails:
    May 30
    Oct 05
    Oct 31
  • 17 night star collector cruising on the rivieras

    Starting in Barcelona with stops in Rome, Malta, Cannes, Amalfi Coast, Monte Carlo

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    2022 sails:
    Nov 01
    2023 sails:
    Oct 31
  • 14 night ocean crossing

    Starting in Lisbon with stops in St. Maarten/Saint Martin

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    2022 sails:
    Nov 26
    2023 sails:
    Nov 25
  • 7 night classic caribbean

    Starting in St. Maarten/Saint Martin with stops in Îles Des Saintes, Basse-Terre

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    2022 sails:
    Dec 10
    2023 sails:
    Jan 14
    Mar 25
    Dec 09
    Dec 23
    2024 sails:
    Jan 06
    Jan 20
    Feb 03
    Feb 17
    Mar 02
    Mar 16
  • 17 night star collector a leeward islands loop

    Starting in St. Maarten/Saint Martin with stops in Barbados, Îles Des Saintes, Basse-Terre, Falmouth, Castries

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    2022 sails:
    Dec 10
  • 10 night blue waters of the leeward islands

    Starting in Falmouth with stops in St. Maarten/Saint Martin, Castries, Barbados

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    2022 sails:
    Dec 17
  • 18 night star collector caribbean icons

    Starting in Îles Des Saintes with stops in St. Maarten/Saint Martin, Basse-Terre, Falmouth, Barbados

    Select
    2022 sails:
    Dec 27
  • 11 night caribbean pleasures

    Starting in Îles Des Saintes with stops in St. Maarten/Saint Martin, Barbados, Basse-Terre

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    2022 sails:
    Dec 27
  • 14 night star collector caribbean explorations

    Starting in St. Maarten/Saint Martin with stops in Falmouth, Îles Des Saintes, Basse-Terre

    Select
    2023 sails:
    Jan 07
    Jan 14
    Dec 09
    Dec 16
    Dec 23
    Dec 30
    2024 sails:
    Jan 06
    Jan 13
    Jan 20
    Jan 27
    Feb 03
    Feb 10
    Feb 17
    Feb 24
    Mar 02
    Mar 09
    Mar 16
  • 7 night yachtsmans caribbean

    Starting in St. Maarten/Saint Martin with stops in Falmouth

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    2023 sails:
    Jan 07
    Jan 21
    Feb 18
    Mar 18
  • 14 night star collector leeward and windward caribbean havens

    Starting in St. Maarten/Saint Martin with stops in Falmouth, Basse-Terre, Îles Des Saintes, Barbados

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    2023 sails:
    Jan 21
    Feb 11
    Feb 18
    Mar 11
  • 14 night star collector antilles adventures

    Starting in Îles Des Saintes with stops in Castries, Barbados, Basse-Terre, St. Maarten/Saint Martin

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    2023 sails:
    Jan 28
    Feb 04
    Feb 25
    Mar 04
  • 7 night lush and lovely islands of the lesser antilles

    Starting in St. Maarten/Saint Martin with stops in Basse-Terre, Îles Des Saintes, Barbados

    Select
    2023 sails:
    Jan 28
    Feb 11
    Feb 25
    Mar 11
  • 7 night jewels of the windward islands

    Starting in Barbados with stops in Castries

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    2023 sails:
    Feb 04
    Mar 04
  • 21 night star collector caribbean essence crossing

    Starting in St. Maarten/Saint Martin with stops in Lisbon, Basse-Terre, Îles Des Saintes

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    2023 sails:
    Mar 25
  • 14 night ocean crossing and ponta delgada azores

    Starting in Lisbon with stops in St. Maarten/Saint Martin

    Select
    2023 sails:
    Apr 01
    2024 sails:
    Mar 30
  • 22 night star collector atlantic interludes and iberian indulgences

    Starting in Cartagena with stops in Lisbon, Mallorca (Majorca), Cadiz, St. Maarten/Saint Martin, Barcelona, Gibraltar, Málaga, Costa del Sol

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    2023 sails:
    Apr 01
  • 14 night star collector racing for the grand prix along the rivieras

    Starting in Cannes with stops in Monte Carlo, Rome, Barcelona

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    2023 sails:
    May 16
  • 17 night star collector sicilian circumnavigation and monaco grand prix

    Starting in Rome with stops in Cannes, Barcelona, Monte Carlo, Malta, Amalfi Coast

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    2023 sails:
    May 23
  • 7 night rome and grand prix of monaco

    Starting in Monte Carlo with stops in Barcelona, Cannes, Rome

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    2023 sails:
    May 23
  • 7 night beach fun and sun a remote caribbean getaway

    Starting in Falmouth with stops in St. Maarten/Saint Martin

    Select
    2023 sails:
    Dec 16
    Dec 30
    2024 sails:
    Jan 13
    Jan 27
    Feb 10
    Feb 24
    Mar 09
    Mar 23