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 27)
17 Nights
Idyllic Festive Days In The Caribbean
Idyllic Festive Days In The Caribbean
Departure Date
20 Dec 26
| Cruise Line | Hapag-Lloyd Cruises |
| Cruise Type | Ocean |
| Ship | MS EUROPA |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Gustavia, Saint John's, Fort-de-France, Marigot, Mayreau Island, Port Elizabeth, Bequia, Saint George's, Bridgetown, Bridgetown, Bridgetown, Basse-Terre, Norman Island and Miami, Florida
|
From £8,890pp
Plus substantial savings from Deluxe Cruises
16 Nights
16-Day Leeward Island Holiday
16-Day Leeward Island Holiday
Departure Date
20 Dec 26
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Quest |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Road Bay, South Friars Bay, Marigot, Terre-de-Haut, Fort-de-France, Rodney Bay, Roseau, Montserrat, Antigua, Great Harbour, Jost Van Dyke and Miami, Florida
|
From £6,884pp
Plus substantial savings from Deluxe Cruises
16 Nights
An Extended Journey of Sparkling Skies & Dramatic Natural Beauty
An Extended Journey of Sparkling Skies & Dramatic Natural Beauty
Departure Date
20 Dec 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA III |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Ocho Rios, Isla Catalana, Great Harbour, Jost Van Dyke, Philipsburg, Charlotte Amalie, San Juan (Puerto Rico), Saint John's, Pointe-à-Pitre, Tortola, Samaná, Puerto Plata and Miami, Florida
|
From £9,645pp
Plus substantial savings from Deluxe Cruises
8 Nights
A Journey of Tropical Festivities & Dazzling Island Beauty
A Journey of Tropical Festivities & Dazzling Island Beauty
Departure Date
20 Dec 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA III |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Miami, Florida, Ocho Rios, Isla Catalana, Great Harbour, Jost Van Dyke, Philipsburg, Charlotte Amalie and San Juan (Puerto Rico)
|
From £4,590pp
Plus substantial savings from Deluxe Cruises
7 Nights
A Journey of Caribbean Celebrations & Island Wonders
A Journey of Caribbean Celebrations & Island Wonders
Departure Date
20 Dec 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA I |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Miami, Florida |
| Itinerary |
San Juan (Puerto Rico), Basseterre, Saint Kitts, Tortola, Gustavia, Gustavia, Road Bay and Miami, Florida
|
From £4,250pp
Plus substantial savings from Deluxe Cruises
15 Nights
An Extended Journey into Island Bliss & Lively Celebrations
An Extended Journey into Island Bliss & Lively Celebrations
Departure Date
20 Dec 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA I |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Basseterre, Saint Kitts, Tortola, Gustavia, Gustavia, Road Bay, Miami, Florida, Puerto Plata, Isla Catalana, Cruz Bay, Saint John, Great Harbour, Jost Van Dyke, Basseterre, Saint Kitts, Charlotte Amalie and San Juan (Puerto Rico)
|
From £9,220pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan to San Juan
San Juan to San Juan
Departure Date
20 Dec 26
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Shadow |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Great Harbour, Jost Van Dyke, Little Bay, Castries, Fort-de-France, Sopers Hole, Tortola and San Juan (Puerto Rico)
|
From £2,590pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
20 Dec 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Pride |
| 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), Gustavia, Gustavia, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Philipsburg, Philipsburg, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico) and San Juan (Puerto Rico)
|
From £3,320pp
Plus substantial savings from Deluxe Cruises
7 Nights
Windward Islands Surf & Sunsets
Windward Islands Surf & Sunsets
Departure Date
20 Dec 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Pride |
| 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 £1,623pp
Plus substantial savings from Deluxe Cruises
10 Nights
Roundtrip Fort Lauderdale
Roundtrip Fort Lauderdale
Departure Date
20 Dec 26
| 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, Saint Thomas, Virgin Gorda, Saint John's, San Juan (Puerto Rico), Samaná, Nassau and Fort Lauderdale, Florida
|
From £3,740pp
Plus substantial savings from Deluxe Cruises
19 Nights
Roundtrip Fort Lauderdale
Roundtrip Fort Lauderdale
Departure Date
20 Dec 26
| 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, Saint Thomas, Virgin Gorda, Saint John's, San Juan (Puerto Rico), Samaná, Nassau, Fort Lauderdale, Florida, Cozumel, Belize City, Santo Tomás de Castilla, Roatán Island, Georgetown, Grand Cayman and Fort Lauderdale, Florida
|
From £7,840pp
Plus substantial savings from Deluxe Cruises
20 Nights
Fort Lauderdale to Fort Lauderdale
Fort Lauderdale to Fort Lauderdale
Departure Date
20 Dec 26
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Symphony |
| Region | Caribbean |
| Departure Port | Fort Lauderdale, Florida |
| Destination Port | Fort Lauderdale, Florida |
| Itinerary |
From £8,500pp
Plus substantial savings from Deluxe Cruises