windstar Wind Surf

14 NIGHTSEastern Caribbean

Windstar

Wind Surf

from$3,808pp

Save $228 vs 90-day avg

View 6 dates → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports Charlestown • Roseau, DM • Mayreau • Les Saintes • Basseterre, KN • Gustavia • Jamaica • Road Bay • Sopers Hole • Vancouver, BC • Virgin Gorda / Prickly Pear

6 sailings · Feb–Dec 2027

▼ 6% below 90-day avgAt all-time low

View 6 dates → Track itinerary

15 NIGHTSEastern Caribbean

Windstar

Wind Surf

from$4,275pp

Save $143 vs 90-day avg

Roundtrip from St. Maarten, SX

Cruise ports Charlestown • Roseau, DM • Mayreau • Les Saintes • Basseterre, KN • Gustavia • St. John’s, AG • Road Bay • Sopers Hole • Vancouver, BC • Virgin Gorda / Prickly Pear

2 sailings · Dec–Dec 2027

▼ 3% below 90-day avgAt all-time low

15 NIGHTSMediterranean

Windstar

Wind Surf

from$4,320pp

Roundtrip from Tarragona

Cruise ports Palamos • Collioure • Toulon • Monte Carlo • Cannes • Portofino • Portoferraio • Rome (Civitavecchia), IT • Sorrento • Messina, IT • Gythion • Monemvasia • Athens (Piraeus), GR

1 sailing · Apr 2027

At all-time low

16 NIGHTSMediterranean

Windstar

Wind Surf

from$4,624pp

Roundtrip from Venice, IT

Cruise ports Rovinj • Split, HR • Dubrovnik, HR • Kotor • Giardini Naxos • Sorrento • Rome (Civitavecchia), IT • Amalfi Coast (Salerno), IT • Marina Velentia (vibo Valentia) • Reggio Calabria • Taranto • Otranto • Rab

1 sailing · Jul 2026

16 NIGHTSMediterranean

Windstar

Wind Surf

from$4,672pp

Roundtrip from Lisbon, PT

Cruise ports Cadiz • Gibraltar • Malaga • Almeria • Cartagena • Palma De Mallorca • Tarragona • Palamos • Collioure • Toulon • Monte Carlo • Cannes • Portofino • Portoferraio • Rome (Civitavecchia), IT

1 sailing · Apr 2027

At all-time low

5 NIGHTSMediterranean

Windstar

Wind Surf

from$1,480pp

Save $691 vs 90-day avg

Roundtrip from Rome (Civitavecchia), IT

Cruise ports Portofino • Monte Carlo • Sanary-sur-mer • Palamos • Barcelona, ES

1 sailing · Oct 2026

▼ 32% below 90-day avgAt all-time low

14 NIGHTSMediterranean

Windstar

Wind Surf

from$4,144pp

Save $42 vs 90-day avg

Roundtrip from Athens (Piraeus), GR

Cruise ports Monemvasia • Gythion • Messina, IT • Sorrento • Rome (Civitavecchia), IT • Portoferraio • Portofino • Monte Carlo • Cannes • Marseille, FR • Collioure • Barcelona, ES

1 sailing · Oct 2027

▼ 1% below 90-day avgAt all-time low

14 NIGHTSEastern Caribbean

Windstar

Wind Surf

from$4,200pp

Roundtrip from St. Maarten, SX

Cruise ports Charlestown • Roseau, DM • Mayreau • Les Saintes • Basseterre, KN • Gustavia • St. John’s, AG • Road Bay • Sopers Hole • Vancouver, BC • Virgin Gorda / Prickly Pear

1 sailing · Jan 2028

At all-time low

Windstar

Wind Surf

from$2,560pp

Roundtrip from Venice, IT

Cruise ports Rovinj • Split, HR • Dubrovnik, HR • Kotor • Giardini Naxos • Sorrento • Rome (Civitavecchia), IT

2 sailings · Jul–Aug 2026

Windstar

Wind Surf

from$2,568pp

Save $434 vs 90-day avg

Roundtrip from Rome (Civitavecchia), IT

Cruise ports Amalfi Coast (Salerno), IT • Marina Velentia (vibo Valentia) • Reggio Calabria • Taranto • Otranto • Rab • Venice, IT

1 sailing · Aug 2026

▼ 14% below 90-day avgAt all-time low

6 NIGHTSEastern Caribbean

Windstar

Wind Surf

from$2,040pp

Roundtrip from St. Maarten, SX

Cruise ports Road Bay • Gustavia • Vancouver, BC • Virgin Gorda / Prickly Pear • Sopers Hole

1 sailing · Jan 2028

At all-time low

Windstar

Wind Surf

from$2,880pp

Save $29 vs 90-day avg

Roundtrip from Tarragona

Cruise ports Palamos • Collioure • Toulon • Monte Carlo • Cannes • Portofino • Portoferraio • Rome (Civitavecchia), IT

1 sailing · Apr 2027

▼ 1% below 90-day avgAt all-time low

Windstar

Wind Surf

from$2,920pp

Roundtrip from Barcelona, ES

Cruise ports Palamos • Collioure • Toulon • Monte Carlo • Cannes • Portofino • Portoferraio • Rome (Civitavecchia), IT

1 sailing · Apr 2027

Windstar

Wind Surf

from$2,960pp

Save $12 vs 90-day avg

Roundtrip from Lisbon, PT

Cruise ports Cadiz • Gibraltar • Malaga • Almeria • Cartagena • Palma De Mallorca • Tarragona

1 sailing · Apr 2027

▼ 0% below 90-day avgAt all-time low

8 NIGHTSEastern Caribbean

Windstar

Wind Surf

from$2,960pp

Save $36 vs 90-day avg

Roundtrip from St. Maarten, SX

Cruise ports St. John’s, AG • Gustavia • Road Bay • Sopers Hole • Vancouver, BC • Virgin Gorda / Prickly Pear • Charlestown

1 sailing · Dec 2027

▼ 1% below 90-day avgAt all-time low

11 NIGHTSMediterranean

Windstar

Wind Surf

from$4,422pp

Roundtrip from Rome (Civitavecchia), IT

Cruise ports Sorrento • Messina, IT • Gythion • Monemvasia • Athens (Piraeus), GR • Delphi

1 sailing · Apr 2027

At all-time low

8 NIGHTSEastern Caribbean

Windstar

Wind Surf

from$3,440pp

Save $36 vs 90-day avg

Roundtrip from St. Maarten, SX

Cruise ports Gustavia • St. John’s, AG • Deshaies • Road Bay • Sopers Hole • Vancouver, BC • Virgin Gorda / Prickly Pear

1 sailing · Nov 2027

▼ 1% below 90-day avgAt all-time low

10 NIGHTSMediterranean

Windstar

Wind Surf

from$4,490pp

Roundtrip from Athens (Piraeus), GR

Cruise ports Delphi • Monemvasia • Gythion • Messina, IT • Sorrento • Rome (Civitavecchia), IT

1 sailing · Oct 2027

At all-time low

10 NIGHTSMediterranean

Windstar

Wind Surf

from$4,490pp

Roundtrip from Rome (Civitavecchia), IT

Cruise ports Portoferraio • Portofino • Monte Carlo • Cannes • Marseille, FR • Collioure • Barcelona, ES

1 sailing · Oct 2027

At all-time low

9 NIGHTSMediterranean

Windstar

Wind Surf

from$4,140pp

Roundtrip from Venice, IT

Cruise ports Rovinj • Zadar • Hvar • Kotor • Dubrovnik, HR • Piran

1 sailing · Aug 2026

10 NIGHTSMediterranean

Windstar

Wind Surf

from$4,780pp

Roundtrip from Tarragona

Cruise ports Palamos • Collioure • Toulon • Monte Carlo • Cannes • Portofino • Portoferraio • Rome (Civitavecchia), IT

1 sailing · Apr 2027

At all-time low

Windstar

Wind Surf

from$3,960pp

Roundtrip from Barcelona, ES

Cruise ports Palma De Mallorca • Cartagena • Almeria • Malaga • Gibraltar • Cadiz • Lisbon, PT

1 sailing · Oct 2027