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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.


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

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

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    2025 sails:
    Sep 14
  • 8 night classic italy and dalmatian coast

    Starting in Venice with stops in Dubrovnik, Kotor, Rome

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    2025 sails:
    Sep 14
    Oct 10
    Oct 18
    Oct 26
    2026 sails:
    May 13
    Jul 24
    Aug 18
    Sep 02
    Sep 19
    Oct 07
  • 18 night star collector culture and charms of italy and croatia

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

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    2025 sails:
    Sep 22
    2026 sails:
    May 13
    Sep 19
    Sep 27
  • 11 night sicilian splendors

    Starting in Rome with stops in Malta, Amalfi Coast

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    2025 sails:
    Sep 22
  • 7 night classic italy and dalmatian coast

    Starting in Rome with stops in Venice, Dubrovnik

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    2025 sails:
    Oct 03
  • 15 night star collector italian trio

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

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    2025 sails:
    Oct 26
    2026 sails:
    Oct 15
  • 15 night star collector enchantment of the western mediterranean

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

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    2025 sails:
    Nov 03
    2026 sails:
    Jun 22
  • 7 night wine yachtsmans harbors of the rivieras

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

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    2025 sails:
    Nov 03
  • 8 night spanish symphony

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

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    2025 sails:
    Nov 10
    2026 sails:
    Apr 18
    Jun 14
    Jun 22
    Oct 30
  • 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
  • 14 night knot your average crossing

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

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    2025 sails:
    Nov 18
    2026 sails:
    Apr 04
  • 5 night barefoot break in the british virgin islands

    Starting in St. Maarten/Saint Martin

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    2025 sails:
    Dec 02
  • 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
  • 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
    Dec 26
    2027 sails:
    Jan 09
    Jan 23
    Feb 06
    Feb 20
    Mar 06
    Mar 20
  • 14 night star collector caribbean explorations

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

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    2025 sails:
    Dec 07
    Dec 14
    Dec 21
    2026 sails:
    Feb 28
    Mar 14
    Mar 21
    Dec 19
    Dec 26
    2027 sails:
    Jan 02
    Jan 09
    Jan 16
    Jan 23
    Jan 30
    Feb 06
    Feb 13
    Feb 20
    Feb 27
    Mar 06
    Mar 13
  • 7 night beach fun and sun a remote caribbean getaway

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

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    2025 sails:
    Dec 14
    Dec 28
    2026 sails:
    Jan 04
    Mar 07
    Mar 14
    Mar 28
    Dec 19
    2027 sails:
    Jan 02
    Jan 16
    Jan 30
    Feb 13
    Feb 27
    Mar 13
  • 55 night star collector grand caribbean adventure

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

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    2026 sails:
    Jan 04
  • 28 night star collector the best of the windward and leeward isles

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

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    2026 sails:
    Jan 04
  • 21 night star collector a lesser antilles odyssey

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

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    2026 sails:
    Jan 04
  • 14 night star collector leeward and windward caribbean havens

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

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    2026 sails:
    Jan 04
  • 7 night lush and lovely islands of the lesser antilles

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

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    2026 sails:
    Jan 11
  • 14 night star collector antilles adventures

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

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    2026 sails:
    Jan 11
  • 14 night star collector captivating caribbean

    Starting in Barbados with stops in Castries, Bonaire, Curacao

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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 Colon with stops in Cartagena, Curacao, Bonaire, Barbados

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    2026 sails:
    Jan 25
  • 7 night windward ways and tobago cays

    Starting in Barbados with stops in Bonaire, Curacao

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    2026 sails:
    Jan 25
  • 8 night in the wake of the spanish armadas

    Starting in Colon with stops in Cartagena

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    2026 sails:
    Feb 01
  • 16 night star collector natural history meets ancient mystery latin america and beyond

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

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    2026 sails:
    Feb 01
  • 19 night star collector caribbean cultures latin america and the greater antilles

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

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    2026 sails:
    Feb 09
  • 8 night mayan legacies

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

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    2026 sails:
    Feb 09
  • 18 night star collector deep dive into the blue underwater worlds of the caribbean

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

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    2026 sails:
    Feb 17
  • 11 night stars of the greater antilles

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

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

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    2026 sails:
    Apr 04
  • 25 night star collector riviera rhapsody

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

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    2026 sails:
    Apr 18
  • 16 night star collector enchantment of the western mediterranean

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

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    2026 sails:
    Apr 18
  • 8 night yachtsmans harbors of the rivieras

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

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    2026 sails:
    Apr 26
  • 9 night classic italy and dalmatian coast

    Starting in Venice with stops in Rome, Dubrovnik, Kotor

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    2026 sails:
    May 04
  • 21 night star collector iconic italy centerpiece of the mediterranean

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

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    2026 sails:
    May 13
  • 10 night sicilian splendors

    Starting in Malta with stops in Rome, Amalfi Coast

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    2026 sails:
    May 21
    Sep 27
  • 13 night historic harbors of italy and beyond

    Starting in Rome with stops in Malta, Amalfi Coast

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    2026 sails:
    May 21
  • 3 night quick getaway la dolce vita in italy and france

    Starting in Rome

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    2026 sails:
    May 31
  • 11 night iberian icons and hidden french harbors

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

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    2026 sails:
    Jun 11
  • 3 night quick getaway a taste of southern france

    Starting in Barcelona

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    2026 sails:
    Jun 11
  • 7 night yachtsmans harbors of the rivieras

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

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    2026 sails:
    Jun 30
  • 24 night star collector europes classical coastlines from the riviera to the adriatic

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

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    2026 sails:
    Jun 30
  • 15 night star collector riviera and italian glamour

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

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    2026 sails:
    Jun 30
  • 8 night bella italia a southern italian romance

    Starting in Venice with stops in Amalfi Coast, Rome

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    2026 sails:
    Jul 07
    Aug 01
  • 17 night star collector italian charms and croatian coastlines

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

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    2026 sails:
    Jul 07
    Aug 01
  • 9 night adriatic icons and venetian treasures

    Starting in Venice with stops in Dubrovnik, Kotor, Hvar

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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 Venice, Rome, Kotor, Dubrovnik

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    2026 sails:
    Jul 24
  • 15 night star collector iconic italy and croatia

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

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    2026 sails:
    Aug 18
    Aug 26
  • 7 night jewels of the italian and french rivieras

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

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    2026 sails:
    Aug 26
  • 23 night star collector riviera rhapsody

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

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    2026 sails:
    Oct 15
  • 10 night classic italy and dalmatian coast

    Starting in Rome with stops in Venice, Dubrovnik, Kotor

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    2026 sails:
    Oct 15
  • 5 night quick getaways yachtsmans harbors of the rivieras

    Starting in Barcelona with stops in Monte Carlo, Rome

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    2026 sails:
    Oct 25
  • 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, Monte Carlo, Rome

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    2026 sails:
    Oct 25
  • 14 night ocean crossing

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

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    2026 sails:
    Dec 05
  • 15 night ocean crossing

    Starting in St. Maarten/Saint Martin with stops in Lisbon, Funchal, Madeira

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    2027 sails:
    Mar 27