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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 beach fun and sun a remote caribbean getaway

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

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    2025 sails:
    Jan 25
    Feb 01
    Feb 15
    Mar 01
    Mar 08
    Mar 22
    Dec 14
    Dec 28
    2026 sails:
    Jan 04
    Mar 28

  • 14 night star collector caribbean explorations

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

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    2025 sails:
    Feb 01
    Feb 08
    Feb 15
    Feb 22
    Mar 08
    Mar 15
    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 Basse-Terre, Îles Des Saintes

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    2025 sails:
    Feb 08
    Feb 22
    Mar 15
    Dec 07
    Dec 21
    2026 sails:
    Feb 28
    Mar 21

  • 22 night star collector atlantic interludes and iberian indulgences

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

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    2025 sails:
    Mar 29
    2026 sails:
    Apr 04

  • 14 night ocean crossing and ponta delgada azores

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

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    2025 sails:
    Mar 29
    2026 sails:
    Apr 04

  • 23 night star collector riviera rhapsody

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

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    2025 sails:
    Apr 12
    Aug 04
    2026 sails:
    Oct 15

  • 15 night star collector enchantment of the western mediterranean

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

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    2025 sails:
    Apr 12
    Jul 20
    Aug 04
    Nov 03
    2026 sails:
    Jun 07
    Jun 22

  • 8 night james beard foundation and wine spanish symphony

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

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    2025 sails:
    Apr 12

  • 7 night yachtsmans harbors of the rivieras

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

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    2025 sails:
    Apr 20
    May 13
    Jul 20
    Aug 12
    2026 sails:
    Jun 07
    Jun 30

  • 15 night star collector italian trio

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

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    2025 sails:
    Apr 20
    May 05
    Aug 12
    Oct 26
    2026 sails:
    Oct 15

  • 8 night classic italy and dalmatian coast

    Starting in Dubrovnik with stops in Venice, Rome, Kotor

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    2025 sails:
    Apr 27
    May 05
    Jun 06
    Jul 02
    Aug 19
    Sep 14
    Oct 10
    Oct 18
    Oct 26
    2026 sails:
    May 13
    Jul 24
    Aug 18
    Sep 02
    Sep 19
    Oct 07

  • 14 night star collector racing for the prix du monde along the rivieras

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

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    2025 sails:
    May 13

  • 17 night star collector sicilian circumnavigation and monaco

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

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    2025 sails:
    May 20
    2026 sails:
    May 21

  • 7 night rome and the monaco grand prix

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

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    2025 sails:
    May 20
    2026 sails:
    May 21

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

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

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

  • 10 night sicilian splendors

    Starting in Rome with stops in Malta, Amalfi Coast

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    2025 sails:
    May 27
    Jul 10
    2026 sails:
    May 28
    Sep 27

  • 17 night star collector stories of italy croatia and greece

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

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    2025 sails:
    Jun 06
    Aug 19
    Sep 05

  • 9 night adriatic archipelagos and greek goddesses

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

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    2025 sails:
    Jun 14
    Jun 23
    Sep 05

  • 17 night star collector cruising on the rivieras

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

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    2025 sails:
    Jul 10
    2026 sails:
    May 28

  • 8 night spanish symphony

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

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

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

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

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    2025 sails:
    Aug 27

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

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

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    2025 sails:
    Sep 14

  • 11 night sicilian splendors

    Starting in Rome with stops in Amalfi Coast, Malta

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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

  • 7 night wine yachtsmans harbors of the rivieras

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

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    2025 sails:
    Nov 03

  • 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 Basse-Terre, Îles Des Saintes

    Select
    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

  • 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

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

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

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    2026 sails:
    Jan 04

  • 55 night star collector grand caribbean adventure

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

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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 Falmouth, Basse-Terre, Îles Des Saintes, Barbados

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    2026 sails:
    Jan 04

  • 14 night star collector antilles adventures

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

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    2026 sails:
    Jan 11

  • 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

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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, Bonaire, Curacao

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    2026 sails:
    Jan 18

  • 7 night windward ways and tobago cays

    Starting in Barbados with stops in Bonaire, Curacao

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

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

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    2026 sails:
    Feb 09

  • 8 night mayan legacies

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

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    2026 sails:
    Feb 09

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

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

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    2026 sails:
    Feb 17

  • 11 night stars of the greater antilles

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

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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

  • 25 night star collector riviera rhapsody

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

    Select
    2026 sails:
    Apr 18

  • 16 night star collector enchantment of the western mediterranean

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

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    2026 sails:
    Apr 18

  • 8 night yachtsmans harbors of the rivieras

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

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    2026 sails:
    Apr 26

  • 9 night classic italy and dalmatian coast

    Starting in Venice with stops in Kotor, Rome, Dubrovnik

    Select
    2026 sails:
    May 04

  • 15 night star collector the adriatic italy and monacos grand prix

    Starting in Rome with stops in St. Tropez, Monte Carlo, Kotor, Dubrovnik, Venice

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    2026 sails:
    May 13

  • 25 night star collector sicilian and andalusian sunshine

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

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    2026 sails:
    May 28

  • 15 night star collector riviera and italian glamour

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

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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 Kotor, Venice, Rome, Dubrovnik, Monte Carlo, Cannes, Hvar, Amalfi Coast

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    2026 sails:
    Jun 30

  • 8 night bella italia a southern italian romance

    Starting in Rome with stops in Venice, Amalfi Coast

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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 Amalfi Coast, Rome, Kotor, Dubrovnik, Hvar

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

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    2026 sails:
    Jul 24

  • 15 night star collector iconic italy and croatia

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

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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 Cannes, Monte Carlo, Genoa

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    2026 sails:
    Aug 26

  • 10 night classic italy and dalmatian coast

    Starting in Rome with stops in Dubrovnik, Venice, Kotor

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    2026 sails:
    Oct 15

  • 13 night star collector enchantment of the western mediterranean

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

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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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