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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 sicilian splendors

    Starting in Rome with stops in Amalfi Coast, Malta

    Select
    2021 sails:
    Sep 29
    2022 sails:
    May 31
    Oct 06
    Nov 01
    2023 sails:
    May 30
    Oct 05
    Oct 31
  • 8 night classic italy and dalmatian coast

    Starting in Rome with stops in Kotor, Dubrovnik, Venice

    Select
    2021 sails:
    Oct 09
    Oct 17
    2022 sails:
    May 01
    May 09
    Jun 10
    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
  • 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, Gibraltar, Cadiz, Lisbon

    Select
    2021 sails:
    Oct 17
    2022 sails:
    Jul 16
    Aug 08
    2023 sails:
    Jul 15
    Aug 07
  • 15 night star collector italian trio

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

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    2021 sails:
    Oct 17
    2022 sails:
    Apr 24
    May 09
    Jul 16
    Aug 16
    2023 sails:
    Apr 23
    May 08
    Jul 15
    Aug 15
  • 15 night star collector enchantment of the western mediterranean

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

    Select
    2021 sails:
    Oct 25
    2022 sails:
    Apr 16
    Jul 24
    Aug 08
    Nov 11
    2023 sails:
    Apr 15
    Jul 23
    Aug 07
    Nov 10
  • 7 night yachtsmans harbors of the rivieras

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

    Select
    2021 sails:
    Oct 25
    2022 sails:
    Apr 24
    May 17
    Jul 24
    Aug 16
    Nov 11
    2023 sails:
    Apr 23
    May 16
    Jul 23
    Aug 15
    Nov 10
  • 8 night spanish symphony

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

    Select
    2021 sails:
    Nov 01
    2022 sails:
    Apr 16
    Aug 08
    Nov 18
    2023 sails:
    Apr 15
    Jul 30
    Aug 07
    Nov 17
  • 13 night ocean crossing

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

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    2021 sails:
    Nov 28
  • 7 night classic caribbean

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

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    2021 sails:
    Dec 11
    2022 sails:
    Mar 05
    Mar 19
    Dec 10
    2023 sails:
    Jan 14
    Mar 25
  • 17 night star collector a leeward island loop

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

    Select
    2021 sails:
    Dec 11
  • 10 night blue waters of the leeward islands

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

    Select
    2021 sails:
    Dec 18
    2022 sails:
    Dec 17
  • 18 night star collector caribbean icons

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

    Select
    2021 sails:
    Dec 28
    2022 sails:
    Dec 27
  • 11 night caribbean pleasures

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

    Select
    2021 sails:
    Dec 28
    2022 sails:
    Dec 27
  • 7 night yachtsmans caribbean

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

    Select
    2022 sails:
    Jan 08
    Mar 12
    Mar 26
    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

    Select
    2022 sails:
    Jan 08
    2023 sails:
    Jan 21
    Feb 11
    Feb 18
    Mar 11
  • 56 night star collector grand caribbean adventure

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

    Select
    2022 sails:
    Jan 08
  • 14 night star collector antilles adventures

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

    Select
    2022 sails:
    Jan 15
    2023 sails:
    Jan 28
    Feb 04
    Feb 25
    Mar 04
  • 7 night lush and lovely islands of the lesser antilles

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

    Select
    2022 sails:
    Jan 15
    2023 sails:
    Jan 28
    Feb 11
    Feb 25
    Mar 11
  • 14 night star collector captivating caribbean

    Starting in Barbados with stops in Curacao, Castries, Bonaire

    Select
    2022 sails:
    Jan 22
  • 15 night star collector captivating caribbean

    Starting in Curacao with stops in Bonaire, Barbados, Castries

    Select
    2022 sails:
    Jan 22
  • 7 night jewels of the windward islands

    Starting in Barbados with stops in Castries

    Select
    2022 sails:
    Jan 22
    2023 sails:
    Feb 04
    Mar 04
  • 7 night windward ways and tobago cays

    Starting in Barbados with stops in Bonaire, Curacao

    Select
    2022 sails:
    Jan 29
  • 8 night windward ways and tobago cays

    Starting in Barbados with stops in Bonaire, Curacao

    Select
    2022 sails:
    Jan 29
  • 16 night star collector windward islands and spanish new world

    Starting in Barbados with stops in Bonaire, Curacao, Cartagena, Colon

    Select
    2022 sails:
    Jan 29
  • 16 night star collector natural history meets ancient mystery latin america and beyond

    Starting in Cartagena with stops in Colon, Belize, Costa Maya, Cozumel

    Select
    2022 sails:
    Feb 06
  • 8 night in the wake of the spanish armadas

    Starting in Cartagena with stops in Colon

    Select
    2022 sails:
    Feb 06
  • 19 night star collector caribbean cultures latin america and the greater antilles

    Starting in St. Maarten/Saint Martin with stops in Costa Maya, Cozumel, Colon, Belize, Santo Domingo

    Select
    2022 sails:
    Feb 14
  • 11 night stars of the greater antilles

    Starting in Cozumel with stops in St. Maarten/Saint Martin, Santo Domingo

    Select
    2022 sails:
    Feb 22
  • 18 night star collector deep dive into the blue underwater worlds of the caribbean

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

    Select
    2022 sails:
    Feb 22
  • 14 night star collector caribbean explorations

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

    Select
    2022 sails:
    Mar 05
    Mar 12
    Mar 19
    2023 sails:
    Jan 07
    Jan 14
  • 14 night ocean crossing and ponta delgada azores

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

    Select
    2022 sails:
    Apr 02
    2023 sails:
    Apr 01
  • 14 night star collector racing for the grand prix along the rivieras

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

    Select
    2022 sails:
    May 17
    2023 sails:
    May 16
  • 7 night rome and grand prix of monaco

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

    Select
    2022 sails:
    May 24
    2023 sails:
    May 23
  • 17 night star collector sicilian circumnavigation and monaco grand prix

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

    Select
    2022 sails:
    May 24
    2023 sails:
    May 23
  • 18 night star collector culture and charms of italy and croatia

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

    Select
    2022 sails:
    May 31
    Sep 28
    Oct 06
    Oct 24
    2023 sails:
    May 30
    Sep 27
    Oct 05
    Oct 23
  • 17 night star collector stories of italy croatia and greece

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

    Select
    2022 sails:
    Jun 10
    Jul 07
    Aug 23
    Sep 19
    2023 sails:
    Jun 09
    Jul 06
    Aug 22
    Sep 18
  • 19 night star collector adriatic and aegean sea adventures

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

    Select
    2022 sails:
    Jun 18
    Jun 27
    Aug 31
    Sep 09
    2023 sails:
    Jun 17
    Jun 26
    Aug 30
    Sep 08
  • 9 night adriatic archipelagos and greek goddesses

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

    Select
    2022 sails:
    Jun 18
    Jul 07
    Aug 31
    Sep 19
    2023 sails:
    Jun 17
    Jul 06
    Aug 30
    Sep 18
  • 10 night ancient wonders of greece and ephesus

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

    Select
    2022 sails:
    Jun 27
    Sep 09
    2023 sails:
    Jun 26
    Sep 08
  • 17 night star collector cruising on the rivieras

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

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

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

    Select
    2022 sails:
    Nov 26
  • 17 night star collector a leeward islands loop

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

    Select
    2022 sails:
    Dec 10