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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) |
|---|---|---|---|---|
|
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 |
$2,442
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 |
$4,528
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 |
$2,506
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 |
$4,738
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 |
$2,442
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 |
$5,088
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 |
$2,856
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 |
$5,088
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 |
$2,442
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 |
$5,228
Suite (double occupancy) Includes taxes & feesLearn More |
|
Dec 13, 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 |
$3,276
Suite (double occupancy) Includes taxes & feesLearn More |
|
Dec 13, 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 |
$6,698
Suite (double occupancy) Includes taxes & feesLearn More |
|
Dec 20, 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 |
$3,702
Suite (double occupancy) Includes taxes & feesLearn More |
|
Dec 20, 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 |
$7,398
Suite (double occupancy) Includes taxes & feesLearn More |
|
Dec 27, 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 |
7 Nights
|
Add to Favorites |
$4,046
Suite (double occupancy) Includes taxes & feesLearn More |
|
Dec 27, 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 |
$6,208
Suite (double occupancy) Includes taxes & feesLearn More |
|
Jan 3, 2027
(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 |
$2,442
Suite (double occupancy) Includes taxes & feesLearn More |
|
Jan 3, 2027
(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, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan
Special Promotions
|
14 Nights
|
Add to Favorites |
$6,628
Suite (double occupancy) Includes taxes & feesLearn More |
|
Jan 10, 2027
(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 |
$4,466
Suite (double occupancy) Includes taxes & feesLearn More |
|
Mar 30, 2027
(Tuesday) |
16 Night Ocean Crossing Cruise
From San Juan, Puerto Rico to London, United Kingdom Ports: San Juan, Lisbon, London
Special Promotions
|
16 Nights
|
Add to Favorites |
$2,800
Suite (double occupancy) Includes taxes & feesLearn More |
