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 62)
7 Nights
Windward Islands Surf & Sunsets
Windward Islands Surf & Sunsets
Departure Date
27 Dec 27
| 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), Saint George's, Port Elizabeth, Bequia, Mayreau Island, Terre-de-Haut, Marigot and San Juan (Puerto Rico)
|
From £2,339pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
27 Dec 27
| 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), Saint George's, Port Elizabeth, Bequia, Mayreau Island, Terre-de-Haut, Marigot, San Juan (Puerto Rico), Gustavia, Basseterre, Saint Kitts, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £3,617pp
Plus substantial savings from Deluxe Cruises
13 Nights
Star Collector: Caribbean Explorations
Star Collector: Caribbean Explorations
Departure Date
27 Dec 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, Road Bay, Gustavia, Great Harbour, Jost Van Dyke, Sopers Hole, Tortola and Philipsburg
|
From £3,490pp
Plus substantial savings from Deluxe Cruises
7 Nights
Classic Caribbean
Classic Caribbean
Departure Date
27 Dec 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 £2,355pp
Plus substantial savings from Deluxe Cruises
9 Nights
Tropical Retreat: Roundtrip Bridgetown
Tropical Retreat: Roundtrip Bridgetown
Departure Date
28 Dec 27
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Bridgetown, Speightstown, Soufrière, Martinique, Tobago Cays, Mayreau Island, Union Island, Union Island, Kingstown, Kingstown, Port Elizabeth, Bequia, Port Elizabeth, Bequia and Bridgetown
|
From £6,814pp
Plus substantial savings from Deluxe Cruises
10 Nights
New Year Exuberance
New Year Exuberance
Departure Date
28 Dec 27
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Prestige |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Cozumel, Santo Tomás de Castilla, Harvest Caye, Roatán Island, Falmouth, Georgetown, Grand Cayman and Miami, Florida
|
From £5,449pp
Plus substantial savings from Deluxe Cruises
10 Nights
10-Day Leeward Islands Holiday
10-Day Leeward Islands Holiday
Departure Date
28 Dec 27
| 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), South Friars Bay, Montserrat, Gustavia, Great Harbour, Jost Van Dyke and Miami, Florida
|
From £3,799pp
Plus substantial savings from Deluxe Cruises
17 Nights
Panama Canal & the Pacific Coast
Panama Canal & the Pacific Coast
Departure Date
28 Dec 27
| Cruise Line | Viking Ocean Cruises |
| Cruise Type | Ocean |
| Ship | Viking Vesta |
| Region | Caribbean |
| Departure Port | Fort Lauderdale, Florida |
| Destination Port | Los Angeles, California |
| Itinerary |
Fort Lauderdale, Florida, Cozumel, Cartagena, Colón, Puntarenas, Cabo San Lucas, Ensenada and Los Angeles, California
|
From £5,790pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
28 Dec 27
| Cruise Line | The Ritz-Carlton Yacht Collection |
| Cruise Type | Ocean |
| Ship | Ilma |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Port Elizabeth, Bequia, Canouan Island, Soufrière, Marigot, Norman Island and San Juan (Puerto Rico)
|
From £8,900pp
Plus substantial savings from Deluxe Cruises
14 Nights
Roundtrip Fort Lauderdale
Roundtrip Fort Lauderdale
Departure Date
28 Dec 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, Georgetown, Grand Cayman, Montego Bay, Casa de Campo, San Juan (Puerto Rico), Marigot, Saint John's, Basseterre, Saint Kitts, Road Town, Tortola, Samaná, Grand Turk Island and Fort Lauderdale, Florida
|
From £4,601pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan to San Juan
San Juan to San Juan
Departure Date
28 Dec 27
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Dawn |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Saint John Island, Philipsburg, Roseau, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £3,200pp
Plus substantial savings from Deluxe Cruises
11 Nights
11-Day Yachtsman's Holiday In Aruba, Bonaire & Curacao
11-Day Yachtsman's Holiday In Aruba, Bonaire & Curacao
Departure Date
28 Dec 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, Road Bay, English Harbour, South Friars Bay, Terre-de-Haut, Aruba, Curaçao, Bonaire and Bridgetown
|
From £4,899pp
Plus substantial savings from Deluxe Cruises