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

• 7 night classic caribbean

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

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  2025 sails:

  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 Falmouth, Basse-Terre, Îles Des Saintes

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  2025 sails:

  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 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

• 14 night star collector leeward and windward caribbean havens

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

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  2026 sails:

  Jan 04

• 55 night star collector grand caribbean adventure

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

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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 antilles adventures

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

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  2026 sails:

  Jan 11

• 7 night lush and lovely islands of the lesser antilles

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

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  2026 sails:

  Jan 11

• 7 night jewels of the windward islands

  Starting in Castries with stops in Barbados

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  2026 sails:

  Jan 18

• 14 night star collector captivating caribbean

  Starting in Curacao with stops in Bonaire, Barbados, Castries

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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, Bonaire, Barbados

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

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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 St. Maarten/Saint Martin, Cozumel, Santo Domingo, Ocho Rios

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  2026 sails:

  Feb 17

• 11 night stars of the greater antilles

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

• 14 night knot your average crossing

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

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  2026 sails:

  Apr 04

• 22 night star collector atlantic interludes and iberian indulgences

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

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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

• 8 night spanish symphony

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

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  2026 sails:

  Apr 18

  Jun 14

  Jun 22

  Oct 30

• 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

• 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 Rome with stops in Dubrovnik, Kotor, Venice

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  2026 sails:

  May 04

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

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

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  2026 sails:

  May 13

  Sep 19

  Sep 27

• 21 night star collector iconic italy centerpiece of the mediterranean

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

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  2026 sails:

  May 13

• 8 night classic italy and dalmatian coast

  Starting in Rome with stops in Dubrovnik, Venice, Kotor

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  2026 sails:

  May 13

  Jul 24

  Aug 18

  Sep 02

  Sep 19

  Oct 07

• 10 night sicilian splendors

  Starting in Rome with stops in Malta, 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 Amalfi Coast, Malta

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

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  2026 sails:

  Jun 11

• 15 night star collector enchantment of the western mediterranean

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

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  2026 sails:

  Jun 22

• 15 night star collector riviera and italian glamour

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

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  2026 sails:

  Jun 30

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

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

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  2026 sails:

  Jun 30

• 7 night yachtsmans harbors of the rivieras

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

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  2026 sails:

  Jun 30

• 17 night star collector italian charms and croatian coastlines

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

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

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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

• 23 night star collector riviera rhapsody

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

• 15 night star collector italian trio

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

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  2026 sails:

  Oct 15

• 13 night star collector enchantment of the western mediterranean

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

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  2026 sails:

  Oct 25

• 5 night quick getaways yachtsmans harbors of the rivieras

  Starting in Rome with stops in Barcelona, Monte Carlo

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  2026 sails:

  Oct 25

• 14 night ocean crossing

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

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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