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Serving just 312 guests, Star Pride is the perfect size — small enough to offer unique experiences that set Windstar apart from other cruise lines (like our complimentary Signature Beach Party), yet large enough for you to make plenty of new connections on board — all without ever feeling crowded.
This intimate all-suite yacht features spacious, ocean-view accommodations, each with a walk-in closet and updated double-vanity bathroom. On board, you’ll find a fully equipped fitness center, a spa with complimentary sauna, an infinity pool, two full-service bars, on-deck hot tubs, a water-access marina platform, and so much more.
And did we mention all dining is included? From gourmet bites at our Yacht Club Café to 24-hour room service and even specialty restaurants like Basil + Bamboo (available April 7, 2026), Windstar’s award-winning cuisine is always complimentary, so you can indulge freely and enjoy every moment of your journey.
Ready to experience Star Pride for yourself? Join us on one of her voyages across the world — and get ready to sail beyond ordinary.
| 14th September 2026 for 25 nights | |
Boston, Massachusetts ~ Rockland, Maine ~ Isle of Portland ~ Halifax, Nova Scotia ~ Sydney, Nova Scotia ~ Cap-aux-Meules, Magdalen Islands, Québec ~ Gaspé, Québec ~ Quebec City, Québec ~ Portland, Ontario ~ Montréal, Québec ~ Quebec City, Québec ~ Baie Comeau, Québec ~ Cap-aux-Meules, Magdalen Islands, Québec ~ Saint Pierre ~ Saint-John, New Brunswick ~ Red Bay, Newfoundland and Labrador ~ Bonne Bay Canada, Newfoundland and Labrador ~ Havre-Saint-Pierre, Québec ~ Portland, Ontario ~ Trois-Rivieres (Three Rivers), Québec ~ Montréal, Québec | |
Cruise Only from Oceanview Suite £14,862pp Please Call for Flights |
| 14th September 2026 for 11 nights | |
Boston, Massachusetts ~ Rockland, Maine ~ Isle of Portland ~ Halifax, Nova Scotia ~ Sydney, Nova Scotia ~ Cap-aux-Meules, Magdalen Islands, Québec ~ Gaspé, Québec ~ Quebec City, Québec ~ Portland, Ontario ~ Montréal, Québec | |
Cruise Only from Oceanview Suite £7,172pp Please Call for Flights |
| 25th September 2026 for 25 nights | |
Montréal, Québec ~ Quebec City, Québec ~ Baie Comeau, Québec ~ Cap-aux-Meules, Magdalen Islands, Québec ~ Saint Pierre ~ Saint-John, New Brunswick ~ Red Bay, Newfoundland and Labrador ~ Bonne Bay Canada, Newfoundland and Labrador ~ Havre-Saint-Pierre, Québec ~ Portland, Ontario ~ Trois-Rivieres (Three Rivers), Québec ~ Montréal, Québec ~ Portland, Ontario ~ Quebec City, Québec ~ Gaspé, Québec ~ Cap-aux-Meules, Magdalen Islands, Québec ~ Sydney, Nova Scotia ~ Halifax, Nova Scotia ~ Isle of Portland ~ Rockland, Maine ~ Boston, Massachusetts | |
Cruise Only from Oceanview Suite £12,530pp Please Call for Flights |
| 25th September 2026 for 14 nights | |
Montréal, Québec ~ Quebec City, Québec ~ Baie Comeau, Québec ~ Cap-aux-Meules, Magdalen Islands, Québec ~ Saint Pierre ~ Saint-John, New Brunswick ~ Red Bay, Newfoundland and Labrador ~ Bonne Bay Canada, Newfoundland and Labrador ~ Havre-Saint-Pierre, Québec ~ Portland, Ontario ~ Trois-Rivieres (Three Rivers), Québec ~ Montréal, Québec | |
Cruise Only from Oceanview Suite £8,357pp Please Call for Flights |
| 9th October 2026 for 19 nights | |
Montréal, Québec ~ Portland, Ontario ~ Quebec City, Québec ~ Gaspé, Québec ~ Cap-aux-Meules, Magdalen Islands, Québec ~ Sydney, Nova Scotia ~ Halifax, Nova Scotia ~ Isle of Portland ~ Rockland, Maine ~ Boston, Massachusetts ~ Hamilton ~ Saint George ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £6,685pp Please Call for Flights |
| 9th October 2026 for 11 nights | |
Montréal, Québec ~ Portland, Ontario ~ Quebec City, Québec ~ Gaspé, Québec ~ Cap-aux-Meules, Magdalen Islands, Québec ~ Sydney, Nova Scotia ~ Halifax, Nova Scotia ~ Isle of Portland ~ Rockland, Maine ~ Boston, Massachusetts | |
Cruise Only from Oceanview Suite £4,751pp Please Call for Flights |
| 20th October 2026 for 8 nights | |
Boston, Massachusetts ~ Hamilton ~ Saint George ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £2,199pp Please Call for Flights |
| 28th October 2026 for 11 nights | |
San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Falmouth ~ Terre-de-Haut ~ Rodney Bay ~ Saint George's ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £3,736pp Please Call for Flights |
| 8th November 2026 for 7 nights | |
San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Terre-de-Haut ~ Marigot ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £2,346pp Please Call for Flights |
| 8th November 2026 for 14 nights | |
San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Terre-de-Haut ~ Marigot ~ San Juan (Puerto Rico) ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £5,502pp Please Call for Flights |
| 15th November 2026 for 7 nights | |
San Juan (Puerto Rico) ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £3,703pp Please Call for Flights |
| 15th November 2026 for 14 nights | |
San Juan (Puerto Rico) ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Terre-de-Haut ~ Marigot ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £5,032pp Please Call for Flights |
| 22nd November 2026 for 7 nights | |
San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Terre-de-Haut ~ Marigot ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £1,798pp Please Call for Flights |
| 22nd November 2026 for 14 nights | |
San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Terre-de-Haut ~ Marigot ~ San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £3,308pp Please Call for Flights |
| 29th November 2026 for 7 nights | |
San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £1,822pp Please Call for Flights |
| 29th November 2026 for 14 nights | |
San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Deshaies ~ Marigot ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £4,091pp Please Call for Flights |
| 6th December 2026 for 7 nights | |
San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Deshaies ~ Marigot ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £2,660pp Please Call for Flights |
| 6th December 2026 for 14 nights | |
San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Deshaies ~ Marigot ~ San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £4,248pp Please Call for Flights |
| 13th December 2026 for 7 nights | |
San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £1,979pp Please Call for Flights |
| 13th December 2026 for 14 nights | |
San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Deshaies ~ Marigot ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £3,726pp Please Call for Flights |
| 20th December 2026 for 14 nights | |
San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Deshaies ~ Marigot ~ San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £5,032pp Please Call for Flights |
| 20th December 2026 for 7 nights | |
San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Deshaies ~ Marigot ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £2,085pp Please Call for Flights |
| 27th December 2026 for 14 nights | |
San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Deshaies ~ Marigot ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £6,442pp Please Call for Flights |
| 27th December 2026 for 7 nights | |
San Juan (Puerto Rico) ~ Gustavia ~ Basseterre, Saint Kitts ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £3,154pp Please Call for Flights |
| 3rd January 2027 for 14 nights | |
San Juan (Puerto Rico) ~ Saint George's ~ Port Elizabeth, Bequia ~ Mayreau Island ~ Deshaies ~ Marigot ~ San Juan (Puerto Rico) ~ Basseterre, Saint Kitts ~ Gustavia ~ Philipsburg ~ Great Harbour, Jost Van Dyke ~ San Juan (Puerto Rico) | |
Cruise Only from Oceanview Suite £6,390pp Please Call for Flights |