Cruise ports St. George’s, GD • Bequia • Mayreau • Les Saintes • Marigot Bay • Cruz Bay • Basseterre, KN • Gustavia • St. Maarten, SX • Great Harbour • Virgin Gorda/prickly Pear

6 sailings · Nov 2026 – Nov 2027

▼ 22% below 90-day avg

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7 NIGHTSEastern Caribbean

Windstar

Star Pride

63Deal scorelowest fare

from$2,415pp

Top deal: 75 Suite · $2,863 pp

View 1 date → Track itinerary

Roundtrip from San Juan, PR

Cruise ports Isla Catalina • Santo Domingo, DO • Cartagena • San Diego, CA • Colon

1 sailing · Nov 2027

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11 NIGHTSNorthern Europe

Windstar

Star Pride

63Deal scorelowest fare

from$4,752pp

Save $401 vs 90-day avg

Top deal: 90 Suite · $5,500 pp

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Roundtrip from London

Cruise ports London / Hms Belfast • Stavanger • Molde • Andalsnes • Trondheim • Froya / Sistranda Liggeka • Olden / Loen • Bergen • Copenhagen, DK

1 sailing · May 2027

▼ 8% below 90-day avg

View 1 date → Track itinerary

7 NIGHTSNorthern Europe

Windstar

Star Pride

60Deal scorelowest fare

from$3,773pp

Save $20 vs 90-day avg

Top deal: 75 Suite · $5,495 pp

View 2 dates → Track itinerary

Roundtrip from Reykjavik

Cruise ports Grundarfjordur • Isafjordur • Husavik • Seydisfjordur • Heimaey Island

2 sailings · Jul–Aug 2027

▼ 1% below 90-day avg

View 2 dates → Track itinerary

7 NIGHTSNorthern Europe

Windstar

Star Pride

59Deal scorelowest fare

from$3,780pp

Save $60 vs 90-day avg

Top deal: 76 Suite · $5,474 pp

View 5 dates → Track itinerary

Roundtrip from Reykjavik

Cruise ports Grundarfjordur • Isafjordur • Akureyri • Seydisfjordur • Heimaey Island

5 sailings · Jul–Aug 2027

▼ 2% below 90-day avg

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14 NIGHTSEastern Caribbean

53Deal scorelowest fare

from$2,768pp

View 1 date → Track itinerary

Roundtrip from San Juan, PR

Cruise ports Lisbon, PT • London / Hms Belfast

1 sailing · Mar 2027

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14 NIGHTSEastern Caribbean

Windstar

Star Pride

52Deal scorelowest fare

from$4,970pp

Save $974 vs 90-day avg

Top deal: 75 Suite · $5,054 pp

View 5 dates → Track itinerary

Roundtrip from San Juan, PR

Cruise ports Cruz Bay • Gustavia • Basseterre, KN • St. Maarten, SX • Great Harbour • Virgin Gorda/prickly Pear • St. George’s, GD • Bequia • Mayreau • Deshaies • Marigot Bay

5 sailings · Nov–Dec 2026

▼ 16% below 90-day avg

View 5 dates → Track itinerary

21 NIGHTSEastern Caribbean

Windstar

Star Pride

50Deal scorelowest fare

from$6,426pp

Top deal: 79 Suite · $7,665 pp

View 1 date → Track itinerary

Roundtrip from San Juan, PR

Cruise ports St. George’s, GD • Bequia • Mayreau • Les Saintes • Marigot Bay • Isla Catalina • Santo Domingo, DO • Cartagena • San Diego, CA • Colon • Panama Canal Transit • Fuerte Amador • Isla Parida • Puerto Jimenez • Quepos • Puerto Caldera

1 sailing · Nov 2027

View 1 date → Track itinerary

7 NIGHTSEastern Caribbean

Windstar

Star Pride

50Deal scorelowest fare

from$2,408pp

Top deal: 89 Suite · $2,772 pp

View 4 dates → Track itinerary

Roundtrip from San Juan, PR

Cruise ports St. George’s, GD • Bequia • Mayreau • Les Saintes • Marigot Bay

4 sailings · Nov 2026 – Nov 2027

View 4 dates → Track itinerary

7 NIGHTSCentral America

Windstar

Star Pride

50Deal scorelowest fare

from$2,877pp

Top deal: 83 Suite · $2,877 pp

View 5 dates → Track itinerary

Roundtrip from Puerto Caldera

Cruise ports Puerto Jimenez • Quepos • Isla Parida • Fuerte Amador • Panama Canal Transit • Colon

5 sailings · Dec 2027 – Feb 2028

View 5 dates → Track itinerary

11 NIGHTSSouth Pacific

Windstar

Star Pride

50Deal scorelowest fare

from$5,654pp

Save $320 vs 90-day avg

Top deal: 74 Suite · $6,402 pp

View 1 date → Track itinerary

Roundtrip from Montreal

Cruise ports Quebec City • Gaspe • Sydney • Halifax • Bar, ME • Portland • Boston, MA

1 sailing · Oct 2027

▼ 5% below 90-day avgAt all-time low

View 1 date → Track itinerary

7 NIGHTSEastern Caribbean

Windstar

Star Pride

49Deal scorelowest fare

from$2,961pp

Save $219 vs 90-day avg

Top deal: 75 Suite · $3,423 pp

View 3 dates → Track itinerary

Roundtrip from San Juan, PR

Cruise ports St. George’s, GD • Bequia • Mayreau • Deshaies • Marigot Bay

3 sailings · Dec 2026 – Jan 2027

▼ 7% below 90-day avg

View 3 dates → Track itinerary

14 NIGHTSSouthern Caribbean

Windstar

Star Pride

47Deal scorelowest fare

from$4,662pp

Top deal: 74 Suite · $5,586 pp

View 1 date → Track itinerary

Roundtrip from Puerto Caldera

Cruise ports Playa Flamingo • Punta Leona • Quepos • Puerto Jimenez • Isla Parida • Fuerte Amador • Panama Canal Transit • Bocas Del Toro • San Diego, CA • Cartagena • Aruba, AW

1 sailing · Feb 2028

View 1 date → Track itinerary

21 NIGHTSEastern Caribbean

Windstar

Star Pride

19Deal scorelowest fare

from$6,615pp

Top deal: 75 Suite · $7,959 pp

View 1 date → Track itinerary

Roundtrip from Puerto Caldera

Cruise ports Playa Flamingo • Punta Leona • Quepos • Puerto Jimenez • Isla Parida • Fuerte Amador • Panama Canal Transit • Bocas Del Toro • San Diego, CA • Cartagena • Aruba, AW • Curacao, CW • Kralendijk, BQ • Gustavia • Great Harbour • Virgin Gorda/prickly Pear • San Juan, PR

1 sailing · Feb 2028

View 1 date → Track itinerary

11 NIGHTSCanada/New England

Windstar

Star Pride

1Deal scorelowest fare

from$7,084pp

Top deal: 73 Suite · $8,052 pp

View 1 date → Track itinerary

Roundtrip from Boston, MA

Cruise ports Portland • Bar, ME • Halifax • Transit Canso Canal • Charlottetown • Gaspe • Quebec City • Montreal

1 sailing · Sep 2027

View 1 date → Track itinerary

9 NIGHTSEastern Caribbean

Windstar

Star Pride

from$2,547pp

View 1 date → Track itinerary

Roundtrip from San Juan, PR

Cruise ports Virgin Gorda/prickly Pear • Soufriere • Jamaica • Basseterre, KN • Gustavia

1 sailing · Jan 2027

View 1 date → Track itinerary

8 NIGHTSEastern Caribbean

Windstar

Star Pride

from$2,424pp

Save $249 vs 90-day avg

View 1 date → Track itinerary

Roundtrip from Boston, MA

Cruise ports Hamilton • St. George’s, GD • San Juan, PR

1 sailing · Oct 2026

▼ 9% below 90-day avg

View 1 date → Track itinerary

19 NIGHTSEastern Caribbean

Windstar

Star Pride

from$6,726pp

View 1 date → Track itinerary

Roundtrip from Montreal

Cruise ports Quebec City • Gaspe • Capaux Meules • Sydney • Halifax • Portland • Rockland • Boston, MA • Hamilton • St. George’s, GD • San Juan, PR

1 sailing · Oct 2026

View 1 date → Track itinerary

4 NIGHTSCruise

Windstar

Star Pride

from$1,820pp

Save $249 vs 90-day avg

View 1 date → Track itinerary

Roundtrip from London

Cruise ports London / Hms Belfast • St Malo

1 sailing · May 2027

▼ 12% below 90-day avgAt all-time low

View 1 date → Track itinerary

10 NIGHTSEastern Caribbean

from$5,160pp

Save $299 vs 90-day avg

View 1 date → Track itinerary

Roundtrip from Amsterdam

Cruise ports Oudeschild / Texel • Harlingen • Oostende • Antwerp • London / Hms Belfast

1 sailing · Apr 2027

▼ 5% below 90-day avg

View 1 date → Track itinerary

10 NIGHTSNorthern Europe

Windstar

Star Pride

from$6,950pp

Save $500 vs 90-day avg

View 1 date → Track itinerary

Roundtrip from Copenhagen, DK

Cruise ports Stavanger • Alesund • Andalsnes • Trondheim • Froya / Sistranda Liggeka • Olden / Loen • Bergen

1 sailing · Jun 2027

▼ 7% below 90-day avgAt all-time low

View 1 date → Track itinerary

3 NIGHTSNorthern Europe

Windstar

Star Pride

from$2,628pp

Save $508 vs 90-day avg

View 1 date → Track itinerary

Roundtrip from London

Cruise ports London / Hms Belfast • Antwerp • Oostende

1 sailing · May 2027

▼ 16% below 90-day avg

View 1 date → Track itinerary

8 NIGHTSNorthern Europe

Windstar

Star Pride

from$7,224pp

Save $2,368 vs 90-day avg

View 1 date → Track itinerary

Roundtrip from Copenhagen, DK

Cruise ports Gudhjem • Gdansk • Klaipeda • Riga • Stockholm • Tallinn • Helsinki

1 sailing · Jun 2027

▼ 25% below 90-day avgAt all-time low

View 1 date → Track itinerary

Departs	Nights	From	Region	Best Price	Score
Aug 24, 2026	7	Reykjavik	Northern Europe	$4,648	21	Price history →
Aug 31, 2026	14	Reykjavik	Canada/New England	$4,382	68	Price history →
Aug 31, 2026	25	Reykjavik	Canada/New England	$8,125	—	Price history →
Sep 14, 2026	11	Boston, MA	Canada/New England	$7,414	1	Price history →
Sep 25, 2026	14	Montreal	Caribbean	$6,398	—	Price history →
Oct 9, 2026	19	Montreal	Canada/New England	$6,726	—	Price history →
Oct 9, 2026	11	Montreal	Canada/New England	$5,203	75	Price history →
Oct 20, 2026	8	Boston, MA	Canada/New England	$2,424	—	Price history →

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