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 72)
10 Nights
Island Rendezvous
Island Rendezvous
Departure Date
28 Nov 27
| 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, Puerto Plata, San Juan (Puerto Rico), Charlotte Amalie, Philipsburg, Gustavia, Tortola and Miami, Florida
|
From £4,389pp
Plus substantial savings from Deluxe Cruises
12 Nights
Caribbean Carousel
Caribbean Carousel
Departure Date
28 Nov 27
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Sirena |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Oranjestad, Willemstad, Kralendijk, Saint George's, Castries, Pointe-à-Pitre, Philipsburg and Miami, Florida
|
From £2,589pp
Plus substantial savings from Deluxe Cruises
7 Nights
Eastern Caribbean Cruise: Sint Maarten, Saint Kitts & Nevis
Eastern Caribbean Cruise: Sint Maarten, Saint Kitts & Nevis
Departure Date
28 Nov 27
| Cruise Line | Azamara |
| Cruise Type | Ocean |
| Ship | Azamara Quest |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Bridgetown, Castries, Roseau, Basseterre, Saint Kitts, Charlestown, Philipsburg, Charlotte Amalie and San Juan (Puerto Rico)
|
From £1,459pp
Plus substantial savings from Deluxe Cruises
14 Nights
Caribbean Cruise: Dominica, Bequia & Grenada
Caribbean Cruise: Dominica, Bequia & Grenada
Departure Date
28 Nov 27
| Cruise Line | Azamara |
| Cruise Type | Ocean |
| Ship | Azamara Quest |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Castries, Roseau, Basseterre, Saint Kitts, Charlestown, Philipsburg, Charlotte Amalie, San Juan (Puerto Rico), Virgin Gorda, Saint John's, Saint Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough and Bridgetown
|
From £2,749pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Caribbean Explorations
Star Collector: Caribbean Explorations
Departure Date
28 Nov 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, Gustavia, Basseterre, Saint Kitts, Philipsburg, Falmouth, Road Bay, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia and Philipsburg
|
From £3,371pp
Plus substantial savings from Deluxe Cruises
7 Nights
Classic Caribbean
Classic Caribbean
Departure Date
28 Nov 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, Gustavia, Basseterre, Saint Kitts and Philipsburg
|
From £2,126pp
Plus substantial savings from Deluxe Cruises
10 Nights
Classic Panama Canal Passage
Classic Panama Canal Passage
Departure Date
29 Nov 27
| Cruise Line | Viking Ocean Cruises |
| Cruise Type | Ocean |
| Ship | Viking Mars |
| Region | Caribbean |
| Departure Port | Fuerte Amador |
| Destination Port | Fort Lauderdale, Florida |
| Itinerary |
Fuerte Amador, Colón, Limon, Belize City, Cozumel, Progreso, Progreso and Fort Lauderdale, Florida
|
From £3,990pp
Plus substantial savings from Deluxe Cruises
10 Nights
West Indies Explorer
West Indies Explorer
Departure Date
29 Nov 27
| 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 £3,990pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & the Caribbean
Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & the Caribbean
Departure Date
29 Nov 27
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Pride |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Puerto Caldera |
| Itinerary |
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 £3,725pp
Plus substantial savings from Deluxe Cruises
7 Nights
The Spanish Main: Rise of the New World
The Spanish Main: Rise of the New World
Departure Date
29 Nov 27
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Pride |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Colón |
| Itinerary |
San Juan (Puerto Rico), Isla Catalana, Santo Domingo, Cartagena, Cartagena, San Blas Islands and Colón
|
From £2,114pp
Plus substantial savings from Deluxe Cruises
7 Nights
Eastern Caribbean Cruise: Sint Maarten, Martinique & Saint Lucia
Eastern Caribbean Cruise: Sint Maarten, Martinique & Saint Lucia
Departure Date
30 Nov 27
| Cruise Line | Azamara |
| Cruise Type | Ocean |
| Ship | Azamara Onward |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Bridgetown |
| Itinerary |
Miami, Florida, Charlotte Amalie, Philipsburg, Saint Pierre, Castries and Bridgetown
|
From £1,399pp
Plus substantial savings from Deluxe Cruises
14 Nights
Eastern Caribbean Cruise: Sint Maarten, Barbados & Saint Kitts
Eastern Caribbean Cruise: Sint Maarten, Barbados & Saint Kitts
Departure Date
30 Nov 27
| Cruise Line | Azamara |
| Cruise Type | Ocean |
| Ship | Azamara Onward |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Charlotte Amalie, Philipsburg, Saint Pierre, Castries, Bridgetown, Roseau, Basseterre, Saint Kitts, San Juan (Puerto Rico), Key West, Florida and Miami, Florida
|
From £2,709pp
Plus substantial savings from Deluxe Cruises