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Cruises by Wind Surf

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

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

  • 7 night yachtsmans harbors of the rivieras

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

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    2025 sails:
    Jul 20
    Aug 12
    2026 sails:
    Jun 30

  • 15 night star collector enchantment of the western mediterranean

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

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    2025 sails:
    Jul 20
    Aug 04
    Nov 03
    2026 sails:
    Jun 22

  • 8 night spanish symphony

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

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    2025 sails:
    Jul 27
    Aug 04
    Nov 10
    2026 sails:
    Apr 18
    Jun 14
    Jun 22
    Oct 30

  • 23 night star collector riviera rhapsody

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

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    2025 sails:
    Aug 04
    2026 sails:
    Oct 15

  • 15 night star collector italian trio

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

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    2025 sails:
    Aug 12
    Oct 26
    2026 sails:
    Oct 15

  • 17 night star collector stories of italy croatia and greece

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

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    2025 sails:
    Aug 19
    Sep 05

  • 8 night classic italy and dalmatian coast

    Starting in Dubrovnik with stops in Venice, Kotor, Rome

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    2025 sails:
    Aug 19
    Sep 14
    Oct 10
    Oct 18
    Oct 26
    2026 sails:
    May 13
    Jul 24
    Aug 18
    Sep 02
    Sep 19
    Oct 07

  • 9 night james beard foundation and wine adriatic archipelagos and greek goddesses

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

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    2025 sails:
    Aug 27

  • 9 night adriatic archipelagos and greek goddesses

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

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    2025 sails:
    Sep 05

  • 19 night star collector culture and charms of italy and croatia

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

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    2025 sails:
    Sep 14

  • 11 night sicilian splendors

    Starting in Amalfi Coast with stops in Rome, Malta

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    2025 sails:
    Sep 22

  • 18 night star collector culture and charms of italy and croatia

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

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    2025 sails:
    Sep 22
    2026 sails:
    Sep 19
    Sep 27

  • 7 night classic italy and dalmatian coast

    Starting in Dubrovnik with stops in Venice, Rome

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    2025 sails:
    Oct 03

  • 7 night wine yachtsmans harbors of the rivieras

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

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    2025 sails:
    Nov 03

  • 14 night ocean crossing

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

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    2025 sails:
    Nov 18

  • 19 night star collector hearty ports and rum punches a transatlantic crossing

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

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    2025 sails:
    Nov 18

  • 12 night star collector ivory beaches and sapphire seas of the caribbean

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

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    2025 sails:
    Dec 02

  • 5 night barefoot break in the british virgin islands

    Starting in St. Maarten/Saint Martin

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    2025 sails:
    Dec 02

  • 14 night star collector caribbean explorations

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

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    2025 sails:
    Dec 07
    Dec 14
    Dec 21
    2026 sails:
    Feb 28
    Mar 14
    Mar 21

  • 7 night classic caribbean

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

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    2025 sails:
    Dec 07
    Dec 21
    2026 sails:
    Feb 28
    Mar 21

  • 7 night beach fun and sun a remote caribbean getaway

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

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    2025 sails:
    Dec 14
    Dec 28
    2026 sails:
    Jan 04
    Mar 07
    Mar 14
    Mar 28

  • 55 night star collector grand caribbean adventure

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

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    2026 sails:
    Jan 04

  • 14 night star collector leeward and windward caribbean havens

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

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    2026 sails:
    Jan 04

  • 21 night star collector a lesser antilles odyssey

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

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    2026 sails:
    Jan 04

  • 28 night star collector the best of the windward and leeward isles

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

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    2026 sails:
    Jan 04

  • 14 night star collector antilles adventures

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

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    2026 sails:
    Jan 11

  • 7 night lush and lovely islands of the lesser antilles

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

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    2026 sails:
    Jan 11

  • 14 night star collector captivating caribbean

    Starting in Barbados with stops in Bonaire, Curacao, Castries

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    2026 sails:
    Jan 18

  • 7 night jewels of the windward islands

    Starting in Barbados with stops in Castries

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    2026 sails:
    Jan 18

  • 15 night star collector windward islands and spanish new world

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

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    2026 sails:
    Jan 25

  • 7 night windward ways and tobago cays

    Starting in Curacao with stops in Barbados, Bonaire

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    2026 sails:
    Jan 25

  • 16 night star collector natural history meets ancient mystery latin america and beyond

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

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    2026 sails:
    Feb 01

  • 8 night in the wake of the spanish armadas

    Starting in Colon with stops in Cartagena

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    2026 sails:
    Feb 01

  • 19 night star collector caribbean cultures latin america and the greater antilles

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

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    2026 sails:
    Feb 09

  • 8 night mayan legacies

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

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    2026 sails:
    Feb 09

  • 11 night stars of the greater antilles

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

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    2026 sails:
    Feb 17

  • 18 night star collector deep dive into the blue underwater worlds of the caribbean

    Starting in St. Maarten/Saint Martin with stops in Cozumel, Basse-Terre, Santo Domingo, Ocho Rios

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    2026 sails:
    Feb 17

  • 21 night star collector spectacular transatlantic journey caribbean to the azores

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

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    2026 sails:
    Mar 28

  • 22 night star collector atlantic interludes and iberian indulgences

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

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    2026 sails:
    Apr 04

  • 14 night ocean crossing and ponta delgada azores

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

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    2026 sails:
    Apr 04

  • 25 night star collector riviera rhapsody

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

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    2026 sails:
    Apr 18

  • 16 night star collector enchantment of the western mediterranean

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

    Select
    2026 sails:
    Apr 18

  • 8 night yachtsmans harbors of the rivieras

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

    Select
    2026 sails:
    Apr 26

  • 9 night classic italy and dalmatian coast

    Starting in Rome with stops in Venice, Dubrovnik, Kotor

    Select
    2026 sails:
    May 04

  • 10 night sicilian splendors

    Starting in Rome with stops in Malta, Amalfi Coast

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    2026 sails:
    May 21
    Sep 27

  • 8 night rome and the monaco grand prix

    Starting in Rome with stops in Monte Carlo, Barcelona, St. Tropez

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    2026 sails:
    Jun 03

  • 15 night star collector riviera and italian glamour

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

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    2026 sails:
    Jun 30

  • 24 night star collector europes classical coastlines from the riviera to the adriatic

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

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    2026 sails:
    Jun 30

  • 8 night bella italia a southern italian romance

    Starting in Venice with stops in Rome, Amalfi Coast

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    2026 sails:
    Jul 07
    Aug 01

  • 17 night star collector italian charms and croatian coastlines

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

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    2026 sails:
    Jul 07
    Aug 01

  • 9 night adriatic icons and venetian treasures

    Starting in Venice with stops in Hvar, Dubrovnik, Kotor

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    2026 sails:
    Jul 15
    Aug 09
    Sep 10

  • 16 night star collector southern italian enchantment and balkan beaches

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

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    2026 sails:
    Jul 24

  • 15 night star collector iconic italy and croatia

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

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    2026 sails:
    Aug 18
    Aug 26

  • 7 night jewels of the italian and french rivieras

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

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    2026 sails:
    Aug 26

  • 10 night classic italy and dalmatian coast

    Starting in Venice with stops in Dubrovnik, Kotor, Rome

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    2026 sails:
    Oct 15

  • 13 night star collector enchantment of the western mediterranean

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

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    2026 sails:
    Oct 25

  • 5 night yachtsmans harbors of the rivieras

    Starting in Barcelona with stops in Rome, Monte Carlo

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    2026 sails:
    Oct 25
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