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Star Pride
Windstar Cruises
Star Pride Sailing Dates and Sailing Calendar
For more information, prices, and detailed day-by-day Star Pride itineraries, please click one of the Star Pride sailing dates below.
Sail Date |
Itinerary Name and Ports |
Duration |
Save to Favorites |
Priced From(per person) |
|---|---|---|---|---|
|
Aug 31, 2026
(Monday) |
14 Night Greenland North Atlantic Odyssey Cruise
From Reykjavik, Iceland to Boston, Massachusetts Ports: Reykjavik, Cruising Prince Christian Sound, Narsaq, Qaqortoq, Nanortalik, Tasermiut Fjord, St Anthony, Woody Point, Halifax, Boston
Special Promotions
|
14 Nights
|
  Add to Favorites |
$4,384
Suite (double occupancy) Includes taxes & feesLearn More |
|
Aug 31, 2026
(Monday) |
25 Night Star Collector Greenland Fjords Canadian Maritimes Cruise
From Reykjavik, Iceland to Montreal, Canada Ports: Reykjavik, Cruising Prince Christian Sound, Narsaq, Qaqortoq, Nanortalik, Tasermiut Fjord, St Anthony, Woody Point, Halifax, Boston, Rockland, Portland, Halifax, Sydney, Cap-Aux-Meules, Gaspe, Quebec City, Cruising the St Lawrence River, Montreal |
25 Nights
|
Add to Favorites |
$12,443
Suite (double occupancy) Includes taxes & feesLearn More |
|
Sep 14, 2026
(Monday) |
11 Night Southeast Canadian Explorations Cruise
From Boston, Massachusetts to Montreal, Canada Ports: Boston, Rockland, Portland, Halifax, Sydney, Cap-Aux-Meules, Gaspe, Quebec City, Cruising the St Lawrence River, Montreal |
11 Nights
|
Add to Favorites |
$7,081
Suite (double occupancy) Includes taxes & feesLearn More |
|
Sep 14, 2026
(Monday) |
25 Night Star Collector Autumn in Newfoundland and New England Cruise
From Boston, Massachusetts to Montreal, Canada Ports: Boston, Rockland, Portland, Halifax, Sydney, Cap-Aux-Meules, Gaspe, Quebec City, Cruising the St Lawrence River, Montreal, Quebec City, Baie Comeau, Cap-Aux-Meules, St Pierre, St John's, St Anthony, Red Bay, Woody Point, Havre Saint Pierre, Cruising the St Lawrence River, Trois Rivieres, Montreal |
25 Nights
|
Add to Favorites |
$17,786
Suite (double occupancy) Includes taxes & feesLearn More |
|
Sep 25, 2026
(Friday) |
14 Night Quebec and Newfoundland Adventure Cruise
From Montreal, Canada to Montreal, Canada Ports: Montreal, Quebec City, Baie Comeau, Cap-Aux-Meules, St Pierre, St John's, St Anthony, Red Bay, Woody Point, Havre Saint Pierre, Cruising the St Lawrence River, Trois Rivieres, Montreal |
14 Nights
|
Add to Favorites |
$11,970
Suite (double occupancy) Includes taxes & feesLearn More |
|
Sep 25, 2026
(Friday) |
25 Night Star Collector Autumn in Newfoundland and New England Cruise
From Montreal, Canada to Boston, Massachusetts Ports: Montreal, Quebec City, Baie Comeau, Cap-Aux-Meules, St Pierre, St John's, St Anthony, Red Bay, Woody Point, Havre Saint Pierre, Cruising the St Lawrence River, Trois Rivieres, Montreal, Cruising the St Lawrence River, Quebec City, Gaspe, Cap-Aux-Meules, Sydney, Halifax, Portland, Rockland, Boston |
25 Nights
|
Add to Favorites |
$17,786
Suite (double occupancy) Includes taxes & feesLearn More |
|
Oct 9, 2026
(Friday) |
11 Night Southeast Canadian Explorations Cruise
From Montreal, Canada to Boston, Massachusetts Ports: Montreal, Cruising the St Lawrence River, Quebec City, Gaspe, Cap-Aux-Meules, Sydney, Halifax, Portland, Rockland, Boston |
11 Nights
|
Add to Favorites |
$7,081
Suite (double occupancy) Includes taxes & feesLearn More |
|
Oct 9, 2026
(Friday) |
19 Night Star Collector Fall Leaves and Caribbean Breezes Cruise
From Montreal, Canada to San Juan, Puerto Rico Ports: Montreal, Cruising the St Lawrence River, Quebec City, Gaspe, Cap-Aux-Meules, Sydney, Halifax, Portland, Rockland, Boston, Hamilton, St George, San Juan |
19 Nights
|
Add to Favorites |
$8,071
Suite (double occupancy) Includes taxes & feesLearn More |
|
Oct 20, 2026
(Tuesday) |
8 Night Mind Body and Spirit Collection Bermuda Bliss Cruise
From Boston, Massachusetts to San Juan, Puerto Rico Ports: Boston, Hamilton, St George, San Juan
Special Promotions
|
8 Nights
|
Add to Favorites |
$2,426
Suite (double occupancy) Includes taxes & feesLearn More |
|
Oct 28, 2026
(Wednesday) |
11 Night Masterpieces at Sea Gems of the Leeward Islands Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Falmouth Harbour, Iles des Saintes, Rodney Bay, St George's, Great Harbour, Prickly Pear British Virgin Islands, San Juan
Special Promotions
|
11 Nights
|
Add to Favorites |
$3,930
Suite (double occupancy) Includes taxes & feesLearn More |
|
Nov 8, 2026
(Sunday) |
7 Night Windward Islands Surf and Sunsets Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Special Promotions
|
7 Nights
|
Add to Favorites |
$2,411
Suite (double occupancy) Includes taxes & feesLearn More |
|
Nov 8, 2026
(Sunday) |
14 Night Star Collector Lovely Leewards Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan |
14 Nights
|
Add to Favorites |
$5,358
Suite (double occupancy) Includes taxes & feesLearn More |
|
Nov 15, 2026
(Sunday) |
7 Night San Juan and the Virgin Islands Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan
Special Promotions
|
7 Nights
|
Add to Favorites |
$2,218
Suite (double occupancy) Includes taxes & feesLearn More |
|
Nov 15, 2026
(Sunday) |
14 Night Star Collector Lovely Leewards Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan |
14 Nights
|
Add to Favorites |
$5,358
Suite (double occupancy) Includes taxes & feesLearn More |
|
Nov 22, 2026
(Sunday) |
7 Night Windward Islands Surf and Sunsets Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Special Promotions
|
7 Nights
|
Add to Favorites |
$2,411
Suite (double occupancy) Includes taxes & feesLearn More |
|
Nov 22, 2026
(Sunday) |
14 Night Star Collector Lovely Leewards Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan |
14 Nights
|
Add to Favorites |
$4,406
Suite (double occupancy) Includes taxes & feesLearn More |
|
Nov 29, 2026
(Sunday) |
7 Night San Juan and the Virgin Islands Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan
Special Promotions
|
7 Nights
|
Add to Favorites |
$1,966
Suite (double occupancy) Includes taxes & feesLearn More |
|
Nov 29, 2026
(Sunday) |
14 Night Star Collector Lovely Leewards Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan, St George's, Bequia, Mayreau, Deshaies, Marigot, San Juan |
14 Nights
|
Add to Favorites |
$4,966
Suite (double occupancy) Includes taxes & feesLearn More |
|
Dec 6, 2026
(Sunday) |
7 Night Windward Islands Surf and Sunsets Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, St George's, Bequia, Mayreau, Deshaies, Marigot, San Juan
Special Promotions
|
7 Nights
|
Add to Favorites |
$3,636
Suite (double occupancy) Includes taxes & feesLearn More |
|
Dec 6, 2026
(Sunday) |
14 Night Star Collector Lovely Leewards Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, St George's, Bequia, Mayreau, Deshaies, Marigot, San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan |
14 Nights
|
Add to Favorites |
$5,106
Suite (double occupancy) Includes taxes & feesLearn More |
