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

• 7 night classic caribbean

  Starting in Basse-Terre with stops in St. Maarten/Saint Martin

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  2026 sails:

  Mar 21

  Dec 26

  2027 sails:

  Jan 09

  Jan 23

  Feb 06

  Feb 20

  Mar 06

  Mar 20

  Nov 28

  Dec 12

  Dec 27

  2028 sails:

  Jan 09

  Jan 23

  Feb 06

  Feb 20

  Mar 05

• 14 night star collector caribbean explorations

  Starting in St. Maarten/Saint Martin with stops in Basse-Terre

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  2026 sails:

  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

  Nov 28

  Dec 05

  2028 sails:

  Jan 09

  Jan 16

  Jan 23

  Jan 30

  Feb 06

  Feb 13

  Feb 20

  Feb 27

  Mar 05

• 7 night beach fun and sun a remote caribbean getaway

  Starting in St. Maarten/Saint Martin

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  2026 sails:

  Mar 28

  Dec 19

  2027 sails:

  Jan 02

  Jan 16

  Jan 30

  Feb 13

  Feb 27

  Mar 13

  Dec 05

  2028 sails:

  Jan 16

  Jan 30

  Feb 13

  Feb 27

  Mar 12

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

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

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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 Cadiz with stops in Málaga, Costa del Sol, St. Maarten/Saint Martin, Costa del Sol, Cartagena, Gibraltar, Lisbon

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  2026 sails:

  Apr 04

• 25 night star collector riviera rhapsody

  Starting in Portofino with stops in Venice, Gibraltar, Lisbon, Costa del Sol, Kotor, Cartagena, Málaga, Costa del Sol, Cadiz, Sorrento, Cannes, Rome, Dubrovnik

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  2026 sails:

  Apr 18

• 16 night star collector enchantment of the western mediterranean

  Starting in Málaga, Costa del Sol with stops in Gibraltar, Cartagena, Costa del Sol, Rome, Lisbon, Cannes, Cadiz, Portofino

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  2026 sails:

  Apr 18

  2027 sails:

  Apr 11

• 8 night spanish symphony

  Starting in Lisbon with stops in Cadiz, Gibraltar, Málaga, Costa del Sol, Costa del Sol, Cartagena

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  2026 sails:

  Apr 18

  Jun 14

  Jun 22

  Oct 30

  2027 sails:

  Apr 11

  Oct 28

• 8 night yachtsmans harbors of the rivieras

  Starting in Rome with stops in Cannes, Portofino

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  2026 sails:

  Apr 26

  2027 sails:

  Apr 19

• 9 night classic italy and dalmatian coast

  Starting in Sorrento with stops in Rome, Kotor, Dubrovnik, Venice

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  2026 sails:

  May 04

• 8 night classic italy and dalmatian coast

  Starting in Rome with stops in Venice, Sorrento, Dubrovnik, Kotor

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  2026 sails:

  May 13

  Jul 24

  Aug 18

  Sep 02

  Sep 19

• 21 night star collector iconic italy centerpiece of the mediterranean

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

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  2026 sails:

  May 13

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

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

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  2026 sails:

  May 13

  Sep 19

• 10 night sicilian splendors

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

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  2026 sails:

  May 21

  Sep 27

• 13 night historic harbors of italy and beyond

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

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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

• 8 night rome and the monaco grand prix

  Starting in Portofino with stops in St. Tropez, Rome

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  2026 sails:

  Jun 03

• 3 night quick getaway a taste of southern france

  Starting in Sete

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  2026 sails:

  Jun 11

• 11 night iberian icons and hidden french harbors

  Starting in Málaga, Costa del Sol with stops in Cartagena, Sete, Lisbon, Cadiz, Gibraltar, 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 Gibraltar, Lisbon, Rome, Portofino, Málaga, Costa del Sol, Cartagena, Cadiz, Costa del Sol, Marseille

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  2026 sails:

  Jun 22

  2027 sails:

  Oct 21

• 23 night star collector western mediterranean and adriatic discovery

  Starting in Venice with stops in Amalfi Coast, Rome, Portofino, Cannes, Cartagena, Costa del Sol, Málaga, Costa del Sol, Gibraltar, Cadiz, Lisbon

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  2026 sails:

  Jun 22

• 15 night star collector riviera and italian glamour

  Starting in Venice with stops in Amalfi Coast, Rome, Portofino, Cannes

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  2026 sails:

  Jun 30

• 7 night yachtsmans harbors of the rivieras

  Starting in Rome with stops in Portofino, Cannes, Marseille

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  2026 sails:

  Jun 30

  2027 sails:

  Oct 21

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

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

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  2026 sails:

  Jun 30

• 17 night star collector italian charms and croatian coastlines

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

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  2026 sails:

  Jul 07

  Aug 01

• 8 night bella italia a southern italian romance

  Starting in Amalfi Coast with stops in Rome, Venice

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

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  2026 sails:

  Jul 24

• 15 night star collector iconic italy and croatia

  Starting in Cannes with stops in Genoa, Portofino, Rome, Venice, Dubrovnik, Kotor, Sorrento

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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, Portofino, Cannes

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  2026 sails:

  Aug 26

• 18 night star collector italian charms and croatian coastlines

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

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  2026 sails:

  Sep 27

• 8 night james beard foundation and wine classic italy and dalmatian coast

  Starting in Rome with stops in Venice, Dubrovnik, Sorrento, Kotor

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  2026 sails:

  Oct 07

• 23 night star collector riviera rhapsody

  Starting in Venice with stops in Dubrovnik, Kotor, Sorrento, Rome, Portofino, Cartagena, Málaga, Costa del Sol, Costa del Sol, Gibraltar, Cadiz, Lisbon

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  2026 sails:

  Oct 15

• 15 night star collector italian trio

  Starting in Venice with stops in Dubrovnik, Kotor, Sorrento, Rome, Portofino

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  2026 sails:

  Oct 15

• 10 night classic italy and dalmatian coast

  Starting in Rome with stops in Sorrento, Venice, Dubrovnik, Kotor

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  2026 sails:

  Oct 15

• 13 night star collector enchantment of the western mediterranean

  Starting in Lisbon with stops in Portofino, Rome, Cadiz, Cartagena, Málaga, Costa del Sol, Gibraltar, Costa del Sol

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  2026 sails:

  Oct 25

• 5 night quick getaways yachtsmans harbors of the rivieras

  Starting in Rome with stops in Portofino

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  2026 sails:

  Oct 25

• 21 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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  2026 sails:

  Dec 05

• 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 Funchal, Madeira, Lisbon

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  2027 sails:

  Mar 27

  Nov 05

  2028 sails:

  Mar 19

• 23 night star collector spanish shores transatlantic crossing

  Starting in Cadiz with stops in Lisbon, Gibraltar, St. Maarten/Saint Martin, Cartagena, Funchal, Madeira, Costa del Sol, Málaga, Costa del Sol

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  2027 sails:

  Mar 27

• 15 night star collector riches of the rivieras romans and greeks

  Starting in Sorrento with stops in Rome, Portofino, Cannes

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  2027 sails:

  Apr 19

• 7 night treasures of the greek isles

  Starting in Santorini with stops in Mykonos

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  2027 sails:

  May 04

  May 11

  May 18

  May 25

  Jun 01

  Jun 08

  Jun 15

  Jun 22

  Jun 29

  Jul 13

  Jul 20

  Aug 05

  Aug 12

  Aug 26

  Sep 02

  Sep 09

  Sep 16

  Sep 23

  Sep 30

  Oct 07

• 14 night star collector greek classics and hidden gems unveiled

  Starting in Mykonos with stops in Santorini

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  2027 sails:

  Jul 06

  Aug 12

  Aug 19

• 9 night total solar eclipse with greece and malta

  Starting in Malta

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  2027 sails:

  Jul 27

• 7 night off the beaten path greek islands

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  2027 sails:

  Aug 19

• 14 night star collector riches of the rivieras romans and greeks

  Starting in Portofino with stops in Sorrento, Marseille, Cannes, Rome

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  2027 sails:

  Oct 14

• 7 night enchanting greece and the amalfi coast

  Starting in Rome with stops in Sorrento

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  2027 sails:

  Oct 14

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

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

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  2027 sails:

  Nov 05

• 8 night beach fun and sun a remote caribbean getaway

  Starting in St. Maarten/Saint Martin

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  2027 sails:

  Nov 20

  Dec 19

• 15 night star collector caribbean explorations

  Starting in St. Maarten/Saint Martin with stops in Basse-Terre

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  2027 sails:

  Nov 20

  Dec 12

  Dec 19

• 13 night star collector caribbean explorations

  Starting in St. Maarten/Saint Martin with stops in Basse-Terre

  Select

  2027 sails:

  Dec 27

  2028 sails:

  Jan 03

• 6 night beach fun and sun a remote caribbean getaway

  Starting in St. Maarten/Saint Martin

  Select

  2028 sails:

  Jan 03

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

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

  Select

  2028 sails:

  Mar 12