The Caribbean, a tropical paradise comprised of over 7,000 islands and islets, is celebrated for its rich cultural heritage, where a harmonious blend of African, European, and Indigenous influences has given rise to a unique tapestry of traditions, languages, and cuisines. From the reggae beats of Jamaica to the carnival extravaganzas of Trinidad and Tobago, each island carries its distinct character, yet all share a common thread of warm hospitality and laid-back charm. The crystalline waters that lap against pristine beaches host abundant marine life, making the Caribbean a haven for snorkelers and divers alike. Beyond the sun-soaked shores, the lush tropical rainforests, cascading waterfalls, and historic colonial architecture add depth to the region's allure, inviting travellers to explore a world where nature, history, and the rhythm of life converge in a symphony of sensory delights.
Caribbean Itineraries (Page 3)
7 Nights
Windward Island Delights
Windward Island Delights
Departure Date
28 Dec 25
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Basseterre, Saint Kitts, Terre-de-Haut, Roseau, Mayreau Island, Fort-de-France and Bridgetown
|
From £2,231pp
Plus substantial savings from Deluxe Cruises
7 Nights
Windward Island Delights
Windward Island Delights
Departure Date
28 Dec 25
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
From £2,531pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
28 Dec 25
| 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), Marigot, Falmouth, Sandy Ground, Sandy Ground, Road Town, Tortola, Saint John Island and San Juan (Puerto Rico)
|
From £7,100pp
Plus substantial savings from Deluxe Cruises
7 Nights
Bridgetown Roundtrip
Bridgetown Roundtrip
Departure Date
28 Dec 25
| Cruise Line | The Ritz-Carlton Yacht Collection |
| Cruise Type | Ocean |
| Ship | Evrima |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Saint George's, Canouan Island, Port Elizabeth, Bequia, Portsmouth, Soufrière and Bridgetown
|
From £7,300pp
Plus substantial savings from Deluxe Cruises
7 Nights
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
Departure Date
28 Dec 25
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Falmouth, Road Bay, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia and Philipsburg
|
From £3,481pp
Plus substantial savings from Deluxe Cruises
7 Nights
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
Departure Date
28 Dec 25
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
From £2,411pp
Plus substantial savings from Deluxe Cruises
7 Nights
Bridgetown to Philipsburg
Bridgetown to Philipsburg
Departure Date
28 Dec 25
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Shadow |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Philipsburg |
| Itinerary |
Bridgetown, Kingstown, Saint George's, Trois-Ilets, Saint Thomas, Saint John's and Philipsburg
|
From £4,200pp
Plus substantial savings from Deluxe Cruises
8 Nights
A Journey from Miami to San Juan
A Journey from Miami to San Juan
Departure Date
29 Dec 25
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA I |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Miami, Florida, Great Harbour, Jost Van Dyke, Deshaies, Bridgetown, Martinique, Basseterre, Saint Kitts and San Juan (Puerto Rico)
|
From £7,100pp
Plus substantial savings from Deluxe Cruises
10 Nights
Maya & Isle Mementos
Maya & Isle Mementos
Departure Date
29 Dec 25
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Insignia |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Cozumel, Costa Maya, Belize City, Roatán Island, Montego Bay, Georgetown, Grand Cayman and Miami, Florida
|
From Please Call
Plus substantial savings from Deluxe Cruises
15 Nights
An Extended Journey into Shimmering New Dawns and Caribbean Secrets
An Extended Journey into Shimmering New Dawns and Caribbean Secrets
Departure Date
29 Dec 25
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA I |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Great Harbour, Jost Van Dyke, Deshaies, Bridgetown, Martinique, Basseterre, Saint Kitts, San Juan (Puerto Rico), Gustavia, Saint John's, Tortola, Road Bay and Miami, Florida
|
From £11,700pp
Plus substantial savings from Deluxe Cruises
10 Nights
West Indies Explorer
West Indies Explorer
Departure Date
29 Dec 25
| 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), Philipsburg, Castries, Bridgetown, Roseau, Basseterre, Saint Kitts, Saint John's, Charlotte Amalie, Road Town, Tortola, San Juan (Puerto Rico) and San Juan (Puerto Rico)
|
From £4,740pp
Plus substantial savings from Deluxe Cruises
7 Nights
A Journey Savy New Years Celebrations and Caribbean Conviviality
A Journey Savy New Years Celebrations and Caribbean Conviviality
Departure Date
29 Dec 25
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA II |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Miami, Florida |
| Itinerary |
San Juan (Puerto Rico), Road Bay, Cruz Bay, Saint John, Puerto Plata, Key West, Florida and Miami, Florida
|
From Please Call
Plus substantial savings from Deluxe Cruises