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 81)
Classic Caribbean
Classic Caribbean
| 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 £2,209pp
Plus substantial savings from Deluxe Cruises
West Indies Explorer
West Indies Explorer
| Cruise Line | Viking Ocean Cruises |
| Cruise Type | Ocean |
| Ship | Viking Sky |
| 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 £4,490pp
Plus substantial savings from Deluxe Cruises
Paradise At Sea
Paradise At Sea
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Marina |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Nassau, San Juan (Puerto Rico), Basseterre, Saint Kitts, Saint John's, Philipsburg, Charlotte Amalie, Puerto Plata and Miami, Florida
|
From £2,359pp
Plus substantial savings from Deluxe Cruises
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Legend |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), San Juan (Puerto Rico), Saint George's, Saint George's, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Mayreau Island, Mayreau Island, Terre-de-Haut, Terre-de-Haut, Marigot, Marigot, San Juan (Puerto Rico), San Juan (Puerto Rico), Philipsburg, Philipsburg, Gustavia, Gustavia, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico) and San Juan (Puerto Rico)
|
From £3,545pp
Plus substantial savings from Deluxe Cruises
Windward Islands Surf & Sunsets
Windward Islands Surf & Sunsets
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Legend |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), San Juan (Puerto Rico), Saint George's, Saint George's, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Mayreau Island, Mayreau Island, Terre-de-Haut, Terre-de-Haut, Marigot, Marigot, San Juan (Puerto Rico) and San Juan (Puerto Rico)
|
From £2,194pp
Plus substantial savings from Deluxe Cruises
From The Sunshine State To Mundo Maya
From The Sunshine State To Mundo Maya
| Cruise Line | Hapag-Lloyd Cruises |
| Cruise Type | Ocean |
| Ship | MS EUROPA 2 |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Miami, Florida, Key West, Florida, Costa Maya, San Miguel de Cozumel, Progreso, Galveston, Texas, New Orleans, Louisiana, New Orleans, Louisiana, Tampa, Florida and Miami, Florida
|
From £8,818pp
Plus substantial savings from Deluxe Cruises
Panama Canal & Central America
Panama Canal & Central America
| Cruise Line | Viking Ocean Cruises |
| Cruise Type | Ocean |
| Ship | Viking Mars |
| Region | Caribbean |
| Departure Port | Fort Lauderdale, Florida |
| Destination Port | Fort Lauderdale, Florida |
| Itinerary |
Fort Lauderdale, Florida, Montego Bay, Colón, Limon, Roatán Island, Belize City, Cozumel and Fort Lauderdale, Florida
|
From £5,290pp
Plus substantial savings from Deluxe Cruises
Paradise beaches from the U.S. Virgin Islands to The Bahamas
Paradise beaches from the U.S. Virgin Islands to The Bahamas
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Kaia |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Miami, Florida |
| Itinerary |
San Juan (Puerto Rico), Saint John Island, Ponce, Grand Turk Island, Gordon's Beach, Long Island, San Salvador Island, Nassau, Nassau and Miami, Florida
|
From £7,402pp
Plus substantial savings from Deluxe Cruises
Miami to Miami
Miami to Miami
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Nova |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Sopers Hole, Tortola, Basseterre, Saint Kitts, Saint John's, Gustavia, Saint John Island and Miami, Florida
|
From £4,640pp
Plus substantial savings from Deluxe Cruises
Discover Eastern Caribbean & Grenadines
Discover Eastern Caribbean & Grenadines
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Virgin Gorda, Gustavia, Charlestown, Saint John's, Îles des Saintes, Soufrière, Bridgetown, Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Mayreau Island, Mayreau Island, Union Island, Union Island, Union Island, Tobago Cays and Bridgetown
|
From £10,576pp
Plus substantial savings from Deluxe Cruises
Eastern Caribbean with St. Barths
Eastern Caribbean with St. Barths
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Virgin Gorda, Gustavia, Charlestown, Saint John's, Îles des Saintes, Soufrière and Bridgetown
|
From £5,288pp
Plus substantial savings from Deluxe Cruises
Leeward & Windward Islands Explorer
Leeward & Windward Islands Explorer
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream II |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Bridgetown |
| Itinerary |
San Juan (Puerto Rico), Cruz Bay, Saint John, Spanish Town, Virgin Gorda, Norman Island, Gustavia, Gustavia, South Friars Bay, Terre-de-Haut, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Tobago Cays, Mayreau Island and Bridgetown
|
From £4,861pp
Plus substantial savings from Deluxe Cruises