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
7 Nights
2026 President’s Mystery Cruise
2026 President’s Mystery Cruise
Departure Date
20 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), Mystery Ports, Mystery Ports, Mystery Ports, Mystery Ports, Mystery Ports, Mystery Ports, Mystery Ports, Mystery Ports, Mystery Ports, Mystery Ports, Mystery Ports, Mystery Ports, San Juan (Puerto Rico) and San Juan (Puerto Rico)
|
From Please Call
Plus substantial savings from Deluxe Cruises
7 Nights
Classic Caribbean
Classic Caribbean
Departure Date
21 Mar 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Philipsburg, Roseau, Roseau, Mayreau Island, Mayreau Island, Terre-de-Haut, Terre-de-Haut, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Gustavia, Gustavia, Philipsburg and Philipsburg
|
From £3,289pp
Plus substantial savings from Deluxe Cruises
9 Nights
Western Caribbean
Western Caribbean
Departure Date
24 Mar 26
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Elizabeth |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Grand Cayman, Montego Bay, Roatán Island, Costa Maya, Cozumel and Miami, Florida
|
From £649pp
Plus substantial savings from Deluxe Cruises
21 Nights
Caribbean
Caribbean
Departure Date
24 Mar 26
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Elizabeth |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Grand Cayman, Montego Bay, Roatán Island, Costa Maya, Cozumel, Miami, Florida, San Juan (Puerto Rico), Saint John's, Castries, Bridgetown, Sint Maarten, Tortola and Miami, Florida
|
From Please Call
Plus substantial savings from Deluxe Cruises
14 Nights
An Extended Journey of Tropical Radiance and Sun-kissed Splendour
An Extended Journey of Tropical Radiance and Sun-kissed Splendour
Departure Date
26 Mar 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA II |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Miami, Florida |
| Itinerary |
San Juan (Puerto Rico), Kralendijk, Willemstad, Oranjestad, Philipsburg, San Juan (Puerto Rico), Saint John's, Gustavia, Gustavia, Puerto Plata, Key West, Florida and Miami, Florida
|
From £48,620pp
Plus substantial savings from Deluxe Cruises
7 Nights
"A Journey from San Juan to San Juan"
"A Journey from San Juan to San Juan"
Departure Date
26 Mar 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA II |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Kralendijk, Willemstad, Oranjestad, Philipsburg and San Juan (Puerto Rico)
|
From £3,150pp
Plus substantial savings from Deluxe Cruises
5 Nights
Fort Lauderdale, Florida Roundtrip
Fort Lauderdale, Florida Roundtrip
Departure Date
26 Mar 26
| Cruise Line | The Ritz-Carlton Yacht Collection |
| Cruise Type | Ocean |
| Ship | Ilma |
| Region | Caribbean |
| Departure Port | Fort Lauderdale, Florida |
| Destination Port | Fort Lauderdale, Florida |
| Itinerary |
Fort Lauderdale, Florida, Cockburn Town, San Salvador Island, Nassau, Bimini Island and Fort Lauderdale, Florida
|
From £4,500pp
Plus substantial savings from Deluxe Cruises
12 Nights
Bermuda Sunset & Southern Charm
Bermuda Sunset & Southern Charm
Departure Date
26 Mar 26
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Grandeur |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Nassau, Kings Wharf, Kings Wharf, Kings Wharf, Norfolk, Virginia, Charleston, South Carolina, Charleston, South Carolina, Port Canaveral, Florida and Miami, Florida
|
From £6,939pp
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 £16,993pp
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), San Juan (Puerto Rico), Terre-de-Haut, Terre-de-Haut, Rodney Bay, Rodney Bay, 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 Please Call
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, Rodney Bay, Rodney Bay, 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 Please Call
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