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 36)
7 Nights
Classic Caribbean
Classic Caribbean
Departure Date
20 Feb 27
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Roseau, Mayreau Island, Terre-de-Haut, Basseterre, Saint Kitts, Gustavia and Philipsburg
|
From £2,427pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Caribbean Explorations
Star Collector: Caribbean Explorations
Departure Date
20 Feb 27
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Roseau, Mayreau Island, Terre-de-Haut, Basseterre, Saint Kitts, Gustavia, Philipsburg, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia, Road Bay, Falmouth and Philipsburg
|
From £4,142pp
Plus substantial savings from Deluxe Cruises
7 Nights
7-Day Yachtsman's Caribbean
7-Day Yachtsman's Caribbean
Departure Date
20 Feb 27
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Ovation |
| Region | Caribbean |
| Departure Port | Sint Maarten |
| Destination Port | Bridgetown |
| Itinerary |
Sint Maarten, Frenchman's Cay, South Friars Bay, Trois-Ilets, Port Elizabeth, Bequia, Saint George's and Bridgetown
|
From £4,399pp
Plus substantial savings from Deluxe Cruises
14 Nights
14-Day Caribbean Gems In Depth
14-Day Caribbean Gems In Depth
Departure Date
20 Feb 27
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Ovation |
| Region | Caribbean |
| Departure Port | Sint Maarten |
| Destination Port | Sint Maarten |
| Itinerary |
Sint Maarten, Frenchman's Cay, South Friars Bay, Trois-Ilets, Port Elizabeth, Bequia, Saint George's, Bridgetown, Castries, Montserrat, Antigua, South Friars Bay, Great Harbour, Jost Van Dyke and Sint Maarten
|
From £7,299pp
Plus substantial savings from Deluxe Cruises
7 Nights
St. Barths & Caribbean Gems
St. Barths & Caribbean Gems
Departure Date
21 Feb 27
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream II |
| Region | Caribbean |
| Departure Port | Charlotte Amalie |
| Destination Port | Charlotte Amalie |
| Itinerary |
Charlotte Amalie, Cruz Bay, Saint John, Sandy Ground, Gustavia, Gustavia, Marigot, White Bay, Jost Van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda and Charlotte Amalie
|
From £3,374pp
Plus substantial savings from Deluxe Cruises
8 Nights
Windward Ways & Tobago Cays
Windward Ways & Tobago Cays
Departure Date
22 Feb 27
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Legend |
| Region | Caribbean |
| Departure Port | Oranjestad |
| Destination Port | Bridgetown |
| Itinerary |
Oranjestad, Willemstad, Kralendijk, Saint George's, Rodney Bay, Mayreau Island, Port Elizabeth, Bequia and Bridgetown
|
From £2,911pp
Plus substantial savings from Deluxe Cruises
10 Nights
Golden Caribbean Strands
Golden Caribbean Strands
Departure Date
23 Feb 27
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Marina |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Basseterre, Saint Kitts, Philipsburg, Tortola, Puerto Plata, Great Stirrup Cay and Miami, Florida
|
From £2,419pp
Plus substantial savings from Deluxe Cruises
7 Nights
Windward Ways & Tobago Cays
Windward Ways & Tobago Cays
Departure Date
23 Feb 27
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Legend |
| Region | Caribbean |
| Departure Port | Oranjestad |
| Destination Port | Bridgetown |
| Itinerary |
From £2,400pp
Plus substantial savings from Deluxe Cruises
10 Nights
West Indies Explorer
West Indies Explorer
Departure Date
24 Feb 27
| Cruise Line | Viking Ocean Cruises |
| Cruise Type | Ocean |
| Ship | Viking Sea |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), San Juan (Puerto Rico), Charlotte Amalie, Basseterre, Saint Kitts, Castries, Bridgetown, Roseau, Saint John's, Philipsburg, Frederiksted, Saint Croix and San Juan (Puerto Rico)
|
From £4,895pp
Plus substantial savings from Deluxe Cruises
12 Nights
Eastern Caribbean
Eastern Caribbean
Departure Date
25 Feb 27
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Elizabeth |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Saint John's, Dominica, Bridgetown, Sint Maarten, Tortola and Miami, Florida
|
From Please Call
Plus substantial savings from Deluxe Cruises
21 Nights
Caribbean
Caribbean
Departure Date
25 Feb 27
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Elizabeth |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Saint John's, Dominica, Bridgetown, Sint Maarten, Tortola, Miami, Florida, Grand Cayman, Montego Bay, Roatán Island, Costa Maya, Cozumel and Miami, Florida
|
From Please Call
Plus substantial savings from Deluxe Cruises
10 Nights
Roundtrip Fort Lauderdale
Roundtrip Fort Lauderdale
Departure Date
26 Feb 27
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Symphony |
| Region | Caribbean |
| Departure Port | Fort Lauderdale, Florida |
| Destination Port | Fort Lauderdale, Florida |
| Itinerary |
Fort Lauderdale, Florida, Colón, Puerto Limón, Roatán Island, Belize City, Cozumel and Fort Lauderdale, Florida
|
From £2,894pp
Plus substantial savings from Deluxe Cruises