Cruise ports Charlestown • Roseau, DM • Mayreau • Les Saintes • Basseterre, KN • Gustavia • Road Bay • Great Harbour • Virgin Gorda/prickly Pear • Sopers Hole

2 sailings · Dec 2027 – Jan 2028

▼ 2% below 90-day avg

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7 NIGHTSEastern Caribbean

Windstar

Wind Surf

66Deal scorelowest fare

from$2,275pp

View 9 dates → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports Gustavia • Jamaica • Road Bay • Sopers Hole • Great Harbour • Virgin Gorda/prickly Pear

9 sailings · Dec 2026 – Jan 2028

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7 NIGHTSEastern Caribbean

Windstar

Wind Surf

66Deal scorelowest fare

from$2,275pp

Top deal: 70 Ocean view · $2,485 pp

View 2 dates → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports St. John’s, AG • Road Bay • Sopers Hole • Great Harbour • Virgin Gorda/prickly Pear • Gustavia

2 sailings · Jan–Feb 2028

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14 NIGHTSEastern Caribbean

Windstar

Wind Surf

63Deal scorelowest fare

from$3,934pp

Top deal: 73 Ocean view · $4,130 pp

View 10 dates → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports Charlestown • Roseau, DM • Mayreau • Les Saintes • Basseterre, KN • Gustavia • Jamaica • Road Bay • Sopers Hole • Great Harbour • Virgin Gorda/prickly Pear

10 sailings · Feb 2027 – Feb 2028

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7 NIGHTSMediterranean

Windstar

Wind Surf

63Deal scorelowest fare

from$3,759pp

View 2 dates → Track itinerary

Roundtrip from Athens (Piraeus), GR

Cruise ports Ermoupoli • Kusadasi, TR • Pythagoreio • Naxos • Folegandros • Milos

2 sailings · Jul–Aug 2027

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5 NIGHTSMediterranean

Windstar

Wind Surf

60Deal scorelowest fare

from$1,325pp

Save $571 vs 90-day avg

Top deal: 75 Suite · $1,480 pp

View 1 date → Track itinerary

Roundtrip from Rome (Civitavecchia), IT

Cruise ports Portofino • Monte Carlo • Sanary-sur-mer • Palamos • Barcelona, ES • Palma De Mallorca • Cartagena • Almeria • Malaga • Gibraltar • Cadiz • Lisbon, PT

1 sailing · Oct 2026

▼ 30% below 90-day avg

View 1 date → Track itinerary

7 NIGHTSEastern Caribbean

Windstar

Wind Surf

58Deal scorelowest fare

from$2,359pp

Top deal: 75 Ocean view · $2,429 pp

View 14 dates → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports Gustavia • Charlestown • Roseau, DM • Mayreau • Les Saintes • Basseterre, KN

14 sailings · Dec 2026 – Feb 2028

View 14 dates → Track itinerary

16 NIGHTSMediterranean

Windstar

Wind Surf

53Deal scorelowest fare

from$4,736pp

View 1 date → Track itinerary

Roundtrip from Lisbon, PT

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

1 sailing · Apr 2027

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14 NIGHTSMediterranean

Windstar

Wind Surf

50Deal scorelowest fare

from$4,914pp

View 1 date → Track itinerary

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

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8 NIGHTSEastern Caribbean

Windstar

Wind Surf

50Deal scorelowest fare

from$3,032pp

Save $106 vs 90-day avg

Top deal: 63 Suite · $3,992 pp

View 1 date → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports St. John’s, AG • Gustavia • Road Bay • Sopers Hole • Great Harbour • Virgin Gorda/prickly Pear • Charlestown

1 sailing · Dec 2027

▼ 3% below 90-day avg

View 1 date → Track itinerary

6 NIGHTSEastern Caribbean

Windstar

Wind Surf

48Deal scorelowest fare

from$2,106pp

Top deal: 49 Suite · $2,826 pp

View 1 date → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports Road Bay • Gustavia • Great Harbour • Virgin Gorda/prickly Pear • Sopers Hole

1 sailing · Jan 2028

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8 NIGHTSEastern Caribbean

Windstar

Wind Surf

48Deal scorelowest fare

from$3,072pp

Save $190 vs 90-day avg

Top deal: 52 Suite · $4,032 pp

View 1 date → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports Gustavia • St. John’s, AG • Deshaies • Road Bay • Sopers Hole • Great Harbour • Virgin Gorda/prickly Pear

1 sailing · Nov 2027

▼ 6% below 90-day avgAt all-time low

View 1 date → Track itinerary

14 NIGHTSEastern Caribbean

Windstar

Wind Surf

25Deal scorelowest fare

from$4,312pp

Top deal: 70 Ocean view · $4,522 pp

View 4 dates → Track itinerary

Roundtrip from St. Maarten, SX

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

4 sailings · Jan–Feb 2028

View 4 dates → Track itinerary

15 NIGHTSEastern Caribbean

Windstar

Wind Surf

25Deal scorelowest fare

from$4,710pp

View 2 dates → Track itinerary

Roundtrip from St. Maarten, SX

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

2 sailings · Dec–Dec 2027

View 2 dates → Track itinerary

15 NIGHTSMediterranean

Windstar

Wind Surf

2Deal scorelowest fare

from$4,935pp

Top deal: 30 Suite · $6,015 pp

View 1 date → Track itinerary

Roundtrip from Tarragona

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

1 sailing · Apr 2027

View 1 date → Track itinerary

15 NIGHTSEastern Caribbean

Windstar

Wind Surf

2Deal scorelowest fare

from$4,965pp

View 1 date → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports Gustavia • St. John’s, AG • Deshaies • Road Bay • Sopers Hole • Great Harbour • Virgin Gorda/prickly Pear • Charlestown • Roseau, DM • Mayreau • Les Saintes • Basseterre, KN

1 sailing · Nov 2027

View 1 date → Track itinerary

8 NIGHTSMediterranean

Windstar

Wind Surf

2Deal scorelowest fare

from$3,224pp

View 1 date → Track itinerary

Roundtrip from Lisbon, PT

Cruise ports Cadiz • Gibraltar • Malaga • Almeria • Cartagena • Palma De Mallorca • Barcelona, ES

1 sailing · Apr 2027

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13 NIGHTSMediterranean

Windstar

Wind Surf

2Deal scorelowest fare

from$5,603pp

Save $221 vs 90-day avg

Top deal: 3 Suite · $6,539 pp

View 1 date → Track itinerary

Roundtrip from Barcelona, ES

Cruise ports Palma De Mallorca • Cartagena • Almeria • Malaga • Gibraltar • Cadiz • Lisbon, PT • Pestana Porto A Brasileira Hotel • Quinta Da Pacheca Hotel • Hotel Nh Sintra Centro

1 sailing · Oct 2026

▼ 4% below 90-day avgAt all-time low

View 1 date → Track itinerary

7 NIGHTSMediterranean

Windstar

Wind Surf

2Deal scorelowest fare

from$3,766pp

Top deal: 63 Ocean view · $3,766 pp

View 20 dates → Track itinerary

Roundtrip from Athens (Piraeus), GR

Cruise ports Mykonos, GR • Kusadasi, TR • Patmos • Santorini, GR • Monemvasia • Nafplio

20 sailings · May–Oct 2027

View 20 dates → Track itinerary

8 NIGHTSMediterranean

Windstar

Wind Surf

1Deal scorelowest fare

from$3,320pp

Top deal: 2 Suite · $4,400 pp

View 1 date → Track itinerary

Roundtrip from Barcelona, ES

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

1 sailing · Apr 2027

View 1 date → Track itinerary

23 NIGHTSEastern Caribbean

Windstar

Wind Surf

from$4,600pp

Save $22 vs 90-day avg

View 1 date → Track itinerary

Roundtrip from Lisbon, PT

Cruise ports Funchal • Great Harbour • St. Maarten, SX • Gustavia • St. John’s, AG • Deshaies • Road Bay • Sopers Hole • Virgin Gorda/prickly Pear

1 sailing · Nov 2027

▼ 0% below 90-day avg

View 1 date → Track itinerary

23 NIGHTSEastern Caribbean

Windstar

Wind Surf

from$5,221pp

View 1 date → Track itinerary

Roundtrip from St. Maarten, SX

Cruise ports Funchal • Porto Santo • Lisbon, PT • Cadiz • Gibraltar • Malaga • Almeria • Cartagena • Palma De Mallorca • Barcelona, ES

1 sailing · Mar 2027

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7 NIGHTSMediterranean

Windstar

Wind Surf

from$2,492pp

Save $188 vs 90-day avg

View 1 date → Track itinerary

Roundtrip from Rome (Civitavecchia), IT

Cruise ports Bastia • Cannes • Monte Carlo • Genoa, IT • Portofino • Porto Ercole

1 sailing · Aug 2026

▼ 7% below 90-day avg

View 1 date → Track itinerary

11 NIGHTSMediterranean

Windstar

Wind Surf

from$4,895pp

View 1 date → Track itinerary

Roundtrip from Rome (Civitavecchia), IT

Cruise ports Sorrento • Messina, IT • Gythion • Monemvasia • Athens (Piraeus), GR • Kalampaka • Divani Meteora Hotel

1 sailing · Apr 2027

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10 NIGHTSMediterranean

Windstar

Wind Surf

from$5,000pp

Save $18 vs 90-day avg

View 1 date → Track itinerary

Roundtrip from Venice, IT

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

1 sailing · Oct 2026

▼ 0% below 90-day avg

View 1 date → Track itinerary

9 NIGHTSMediterranean

Windstar

Wind Surf

from$4,752pp

View 1 date → Track itinerary

Roundtrip from Venice, IT

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

1 sailing · Sep 2026

View 1 date → Track itinerary

Departs	Nights	From	Region	Best Price	Score
Aug 26, 2026	7	Rome (Civitavecchia), IT	Mediterranean	$2,492	72	Price history →
Sep 2, 2026	8	Rome (Civitavecchia), IT	—	—	—	Price history →
Sep 10, 2026	9	Venice, IT	Mediterranean	$4,752	34	Price history →
Sep 19, 2026	8	Venice, IT	—	—	—	Price history →
Oct 7, 2026	8	Rome (Civitavecchia), IT	Mediterranean	$5,088	1	Price history →
Oct 15, 2026	13	Venice, IT	Mediterranean	$8,801	—	Price history →
Oct 15, 2026	23	Venice, IT	Mediterranean	$9,637	23	Price history →
Oct 15, 2026	10	Venice, IT	Mediterranean	$5,000	19	Price history →

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