The 2026 season highlights high-touch personalization, such as "Marina Days" where guests can kayak or paddleboard directly from the ship's stern. Onboard, the Caribbean experience is refined through regional farm-to-table dining, featuring fresh snapper and lobster, while shore excursions lean into private access - think guided hikes to Dominica’s thermal pools or helicopter tours over the turquoise reefs of the Bahamas.
Caribbean Itineraries (Page 8)
10 Nights
Gems of the Leeward Islands
Gems of the Leeward Islands
Departure Date
27 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), San Juan (Puerto Rico), Terre-de-Haut, Terre-de-Haut, Pigeon Island, Pigeon Island, Saint George's, Saint George's, Gustavia, Gustavia, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico) and San Juan (Puerto Rico)
|
From £4,555pp
Plus substantial savings from Deluxe Cruises
17 Nights
Star Collector: Seeking the Antilles
Star Collector: Seeking the Antilles
Departure Date
27 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Colón |
| Itinerary |
San Juan (Puerto Rico), San Juan (Puerto Rico), Terre-de-Haut, Terre-de-Haut, Pigeon Island, Pigeon Island, Saint George's, Saint George's, Gustavia, Gustavia, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), San Juan (Puerto Rico), Isla Catalana, Isla Catalana, Santo Domingo, Santo Domingo, Cartagena, Cartagena, Cartagena, Cartagena, San Blas Islands, San Blas Islands, Colón and Colón
|
From £8,264pp
Plus substantial savings from Deluxe Cruises
24 Nights
Star Collector: Historic Caribbean: Legendary Islands, Colombia and Panama
Star Collector: Historic Caribbean: Legendary Islands, Colombia and Panama
Departure Date
27 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Puerto Caldera |
| Itinerary |
San Juan (Puerto Rico), Terre-de-Haut, Pigeon Island, Saint George's, Gustavia, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Isla Catalana, Santo Domingo, Cartagena, Cartagena, San Blas Islands, Colón, Fuerte Amador, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos (Puerto Quepos) and Puerto Caldera
|
From Please Call
Plus substantial savings from Deluxe Cruises
49 Nights
Star Collector: Grand Caribbean & Americas Explorer
Star Collector: Grand Caribbean & Americas Explorer
Departure Date
27 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Juneau, Alaska |
| Itinerary |
San Juan (Puerto Rico), Terre-de-Haut, Pigeon Island, Saint George's, Gustavia, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Isla Catalana, Santo Domingo, Cartagena, Cartagena, San Blas Islands, Colón, Fuerte Amador, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos (Puerto Quepos), Puerto Caldera, Curú Wildlife Refuge, Playas del Coco, Puerto Chiapas, Huatulco (Santa María Huatulco), Manzanillo, Puerto Vallarta, Seattle, Washington, Vancouver, British Columbia, Ketchikan, Alaska, Misty Fjords National Monument, Alaska, Wrangell, Alaska, Sitka, Alaska, Haines, Alaska and Juneau, Alaska
|
From Please Call
Plus substantial savings from Deluxe Cruises
10 Nights
Gems of the Leeward Islands
Gems of the Leeward Islands
Departure Date
27 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Terre-de-Haut, Pigeon Island, Saint George's, Gustavia, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £3,379pp
Plus substantial savings from Deluxe Cruises
17 Nights
Star Collector: Seeking the Antilles
Star Collector: Seeking the Antilles
Departure Date
27 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Colón |
| Itinerary |
San Juan (Puerto Rico), Terre-de-Haut, Pigeon Island, Saint George's, Gustavia, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Isla Catalana, Santo Domingo, Cartagena, Cartagena, San Blas Islands and Colón
|
From £4,783pp
Plus substantial savings from Deluxe Cruises
24 Nights
Star Collector: Historic Caribbean: Legendary Islands, Colombia and Panama
Star Collector: Historic Caribbean: Legendary Islands, Colombia and Panama
Departure Date
27 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Puerto Caldera |
| Itinerary |
San Juan (Puerto Rico), Terre-de-Haut, Pigeon Island, Saint George's, Gustavia, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Isla Catalana, Santo Domingo, Cartagena, Cartagena, San Blas Islands, Colón, Fuerte Amador, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos (Puerto Quepos) and Puerto Caldera
|
From £7,590pp
Plus substantial savings from Deluxe Cruises
7 Nights
Eastern Caribbean with St. Barths
Eastern Caribbean with St. Barths
Departure Date
28 Mar 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Marigot |
| Itinerary |
Bridgetown, Soufrière, Îles des Saintes, Falmouth, Charlestown, Saint Kitts, Gustavia, Prickly Pear Island and Marigot
|
From £13,086pp
Plus substantial savings from Deluxe Cruises
7 Nights
Best of British Virgin Islands & St. Barths
Best of British Virgin Islands & St. Barths
Departure Date
28 Mar 26
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream I |
| Region | Caribbean |
| Departure Port | Charlotte Amalie |
| Destination Port | Charlotte Amalie |
| Itinerary |
Charlotte Amalie, Sandy Ground, Gustavia, Gustavia, Philipsburg, Spanish Town, Virgin Gorda, Beef Island, Tortola, White Bay, Jost Van Dyke, Cruz Bay, Saint John and Charlotte Amalie
|
From £4,175pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
28 Mar 26
| Cruise Line | The Ritz-Carlton Yacht Collection |
| Cruise Type | Ocean |
| Ship | Evrima |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Soufrière, Terre-de-Haut, Saint John's, Gustavia, Virgin Gorda and San Juan (Puerto Rico)
|
From £6,600pp
Plus substantial savings from Deluxe Cruises
21 Nights
Star Collector: Spectacular Transatlantic Journey: Caribbean to the Azores
Star Collector: Spectacular Transatlantic Journey: Caribbean to the Azores
Departure Date
28 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Transatlantic and Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Lisbon |
| Itinerary |
Philipsburg, Road Bay, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia, Philipsburg, Ponta Delgada, Azores and Lisbon
|
From £3,327pp
Plus substantial savings from Deluxe Cruises
7 Nights
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
Departure Date
28 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
From £2,004pp
Plus substantial savings from Deluxe Cruises