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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.

  • 11 night sicilian splendors

    Starting in Rome with stops in Malta, Amalfi Coast

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    2025 sails:
    Sep 22

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

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

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    2025 sails:
    Sep 22
    2026 sails:
    May 13
    Sep 19
    Sep 27

  • 7 night classic italy and dalmatian coast

    Starting in Venice with stops in Dubrovnik, Rome

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    2025 sails:
    Oct 03

  • 8 night classic italy and dalmatian coast

    Starting in Rome with stops in Kotor, Venice, Dubrovnik

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

  • 15 night star collector italian trio

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

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    2025 sails:
    Oct 26
    2026 sails:
    Oct 15

  • 15 night star collector enchantment of the western mediterranean

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

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    2025 sails:
    Nov 03
    2026 sails:
    Jun 22

  • 7 night wine yachtsmans harbors of the rivieras

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

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    2025 sails:
    Nov 03

  • 8 night spanish symphony

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

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    2025 sails:
    Nov 10
    2026 sails:
    Apr 18
    Jun 14
    Jun 22
    Oct 30

  • 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

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

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

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    2025 sails:
    Nov 18

  • 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 Basse-Terre, Îles Des Saintes

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

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    2026 sails:
    Jan 04

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

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

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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

  • 14 night star collector antilles adventures

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

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    2026 sails:
    Jan 11

  • 7 night lush and lovely islands of the lesser antilles

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

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    2026 sails:
    Jan 11

  • 7 night jewels of the windward islands

    Starting in Barbados with stops in Castries

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    2026 sails:
    Jan 18

  • 14 night star collector captivating caribbean

    Starting in Castries with stops in Barbados, Curacao, Bonaire

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    2026 sails:
    Jan 18

  • 7 night windward ways and tobago cays

    Starting in Curacao with stops in Bonaire, Barbados

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    2026 sails:
    Jan 25

  • 15 night star collector windward islands and spanish new world

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

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    2026 sails:
    Jan 25

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

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

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

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    2026 sails:
    Feb 09

  • 8 night mayan legacies

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

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    2026 sails:
    Feb 09

  • 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

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

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

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    2026 sails:
    Apr 04

  • 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

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    2026 sails:
    Apr 18

  • 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

  • 8 night yachtsmans harbors of the rivieras

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

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    2026 sails:
    Apr 26

  • 9 night classic italy and dalmatian coast

    Starting in Venice with stops in Rome, Kotor, Dubrovnik

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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, Amalfi Coast, Dubrovnik, Malta, Venice

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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

  • 3 night quick getaway a taste of southern france

    Starting in Barcelona

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    2026 sails:
    Jun 11

  • 11 night iberian icons and hidden french harbors

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

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    2026 sails:
    Jun 11

  • 7 night yachtsmans harbors of the rivieras

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

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    2026 sails:
    Jun 30

  • 15 night star collector riviera and italian glamour

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

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    2026 sails:
    Jun 30

  • 17 night star collector italian charms and croatian coastlines

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

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    2026 sails:
    Jul 07
    Aug 01

  • 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

  • 9 night adriatic icons and venetian treasures

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

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    2026 sails:
    Jul 24

  • 15 night star collector iconic italy and croatia

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

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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 Monte Carlo, Cannes, Genoa

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    2026 sails:
    Aug 26

  • 23 night star collector riviera rhapsody

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

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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

  • 13 night star collector enchantment of the western mediterranean

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

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    2026 sails:
    Oct 25

  • 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

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

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    2027 sails:
    Mar 27
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