Star Seeker
Windstar Cruises
Star Seeker Sailing Dates and Sailing Calendar
For more information, prices, and detailed day-by-day Star Seeker itineraries, please click one of the Star Seeker sailing dates below.
Sail Date |
Itinerary Name and Ports |
Duration |
Save to Favorites |
Priced From(per person) |
|---|---|---|---|---|
|
Dec 28, 2025
(Sunday) |
16 Night Star Seeker Maiden Voyage Cruise
From Malaga, Spain to Miami, Florida Ports: Malaga, Santa Cruz de Tenerife, Freeport, Miami |
16 Nights
|
  Add to Favorites |
$5,215
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Jan 15, 2026
(Thursday) |
8 Night Star Seeker Christening Sailing Cruise
From Miami, Florida to San Juan, Puerto Rico Ports: Miami, Puerto Plata, Samana, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, San Juan |
8 Nights
|
Add to Favorites |
$7,996
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Jan 23, 2026
(Friday) |
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 |
7 Nights
|
Add to Favorites |
$6,862
Balcony (double occupancy) Includes taxes & feesLearn More |
|
Jan 23, 2026
(Friday) |
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, Bequia, Mayreau, Soufriere , Iles des Saintes, Marigot, San Juan
Special Promotions
|
14 Nights
|
Add to Favorites |
Call
For Price Inside (double occupancy) Learn More |
|
Jan 30, 2026
(Friday) |
7 Night Windward Islands Surf and Sunsets Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Bequia, Mayreau, Soufriere , Iles des Saintes, Marigot, San Juan |
7 Nights
|
Add to Favorites |
$5,127
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Jan 30, 2026
(Friday) |
14 Night Star Collector Lovely Leewards Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Bequia, Mayreau, Soufriere , Iles des Saintes, 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 |
Call
For Price Inside (double occupancy) Learn More |
|
Feb 6, 2026
(Friday) |
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 |
7 Nights
|
Add to Favorites |
$6,612
Balcony (double occupancy) Includes taxes & feesLearn More |
|
Feb 6, 2026
(Friday) |
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, Bequia, Mayreau, Soufriere , Iles des Saintes, Marigot, San Juan
Special Promotions
|
14 Nights
|
Add to Favorites |
Call
For Price Inside (double occupancy) Learn More |
|
Feb 13, 2026
(Friday) |
7 Night Windward Islands Surf and Sunsets Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Bequia, Mayreau, Soufriere , Iles des Saintes, Marigot, San Juan |
7 Nights
|
Add to Favorites |
$5,227
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Feb 13, 2026
(Friday) |
14 Night Star Collector Lovely Leewards Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Bequia, Mayreau, Soufriere , Iles des Saintes, Marigot, San Juan, Cruz Bay, Basseterre, Philipsburg (St. Maarten), Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, San Juan
Special Promotions
|
14 Nights
|
Add to Favorites |
Call
For Price Inside (double occupancy) Learn More |
|
Feb 20, 2026
(Friday) |
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, Philipsburg (St. Maarten), Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, San Juan |
7 Nights
|
Add to Favorites |
$10,162
Suite (double occupancy) Includes taxes & feesLearn More |
|
Feb 20, 2026
(Friday) |
14 Night Star Collector Lovely Leewards Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Cruz Bay, Basseterre, Philipsburg (St. Maarten), Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, San Juan, Philipsburg (St. Maarten), Iles des Saintes, Mayreau, Bequia, Soufriere , San Juan
Special Promotions
|
14 Nights
|
Add to Favorites |
Call
For Price Inside (double occupancy) Learn More |
|
Feb 27, 2026
(Friday) |
7 Night Windward Islands Surf and Sunsets Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Philipsburg (St. Maarten), Iles des Saintes, Mayreau, Bequia, Soufriere , San Juan |
7 Nights
|
Add to Favorites |
$5,136
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Feb 27, 2026
(Friday) |
14 Night Star Collector Lovely Leewards Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Philipsburg (St. Maarten), Iles des Saintes, Mayreau, Bequia, Soufriere , 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 |
$9,999
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Mar 6, 2026
(Friday) |
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 |
7 Nights
|
Add to Favorites |
$5,362
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Mar 6, 2026
(Friday) |
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, Marigot, Iles des Saintes, Mayreau, Bequia, Pigeon Island, The Pitons, San Juan
Special Promotions
|
14 Nights
|
Add to Favorites |
$9,796
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Mar 13, 2026
(Friday) |
7 Night Windward Islands Surf and Sunsets Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Marigot, Iles des Saintes, Mayreau, Bequia, Pigeon Island, The Pitons, San Juan |
7 Nights
|
Add to Favorites |
$5,033
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Mar 27, 2026
(Friday) |
10 Night Gems of the Leeward Islands Cruise
From San Juan, Puerto Rico to San Juan, Puerto Rico Ports: San Juan, Cruz Bay, St John's, Iles des Saintes, Pigeon Island, St George's, Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, San Juan |
10 Nights
|
Add to Favorites |
$5,857
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Mar 27, 2026
(Friday) |
17 Night Star Collector Seeking the Antilles Cruise
From San Juan, Puerto Rico to Colon, Panama Ports: San Juan, Cruz Bay, St John's, Iles des Saintes, Pigeon Island, St George's, Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, San Juan, Catalina Island, Santo Domingo, Cartagena, San Blas Islands, Colon
Special Promotions
|
17 Nights
|
Add to Favorites |
$8,584
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
|
Mar 27, 2026
(Friday) |
24 Night Star Collector Historic Caribbean Legendary Islands Colombia and Panama Cruise
From San Juan, Puerto Rico to Puerto Caldera, Costa Rica Ports: San Juan, Cruz Bay, St John's, Iles des Saintes, Pigeon Island, St George's, Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, San Juan, Catalina Island, Santo Domingo, Cartagena, San Blas Islands, Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Puerto Jimenez, |
24 Nights
|
Add to Favorites |
$13,038
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
