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 61)
7 Nights
San Juan to San Juan
San Juan to San Juan
Departure Date
27 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), Saint John Island, Basseterre, Saint Kitts, Îles des Saintes, Port Elizabeth, Bequia, Saint Thomas and San Juan (Puerto Rico)
|
From £3,010pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
27 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), Gustavia, Basseterre, Saint Kitts, Philipsburg, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Saint George's, Port Elizabeth, Bequia, Mayreau Island, Terre-de-Haut, Marigot and San Juan (Puerto Rico)
|
From £5,516pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan & the Virgin Islands
San Juan & the Virgin Islands
Departure Date
27 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), Gustavia, Basseterre, Saint Kitts, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £3,179pp
Plus substantial savings from Deluxe Cruises
8 Nights
Bridgetown to Bridgetown
Bridgetown to Bridgetown
Departure Date
27 Dec 26
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Spirit |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Port Elizabeth, Bequia, Fort-de-France, Deshaies, Basseterre, Saint Kitts, Saint George's, Castries and Bridgetown
|
From £3,060pp
Plus substantial savings from Deluxe Cruises
10 Nights
Tropical Island Havens
Tropical Island Havens
Departure Date
28 Dec 26
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Allura |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Charlotte Amalie, Philipsburg, Gustavia, Basseterre, Saint Kitts, Tortola and Miami, Florida
|
From £3,109pp
Plus substantial savings from Deluxe Cruises
9 Nights
Calypso Sunsets
Calypso Sunsets
Departure Date
28 Dec 26
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Vista |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Georgetown, Grand Cayman, Falmouth, Roatán Island, Harvest Caye, Cozumel and Miami, Florida
|
From £2,739pp
Plus substantial savings from Deluxe Cruises
11 Nights
Azure Elegance
Azure Elegance
Departure Date
28 Dec 26
| 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, Progresso, Santo Tomás de Castilla, Harvest Caye, Roatán Island, Falmouth, Georgetown, Grand Cayman and Miami, Florida
|
From £8,999pp
Plus substantial savings from Deluxe Cruises
14 Nights
Blue Seas & Pastel Towns
Blue Seas & Pastel Towns
Departure Date
28 Dec 26
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Splendor |
| Region | Caribbean |
| Departure Port | Galveston, Texas |
| Destination Port | Miami, Florida |
| Itinerary |
Galveston, Texas, Cozumel, Belize City, Santo Tomás de Castilla, Roatán Island, Montego Bay, Willemstad, Oranjestad, Kralendijk and Miami, Florida
|
From £6,389pp
Plus substantial savings from Deluxe Cruises
8 Nights
A Journey of Spectacular Festivities & Caribbean Wonders
A Journey of Spectacular Festivities & Caribbean Wonders
Departure Date
28 Dec 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA III |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Miami, Florida |
| Itinerary |
San Juan (Puerto Rico), Saint John's, Pointe-à-Pitre, Tortola, Samaná, Puerto Plata and Miami, Florida
|
From £4,535pp
Plus substantial savings from Deluxe Cruises
16 Nights
An Extended Journey of Caribbean Celebrations & Tropical Idylls
An Extended Journey of Caribbean Celebrations & Tropical Idylls
Departure Date
28 Dec 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA III |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Saint John's, Pointe-à-Pitre, Tortola, Samaná, Puerto Plata, Miami, Florida, Cruz Bay, Saint John, Gustavia, Saint John's, Tortola, Basseterre, Saint Kitts and San Juan (Puerto Rico)
|
From £7,770pp
Plus substantial savings from Deluxe Cruises
8 Nights
2026 New Year's Eve Cruise: Aruba, Saint Lucia & Saint Croix
2026 New Year's Eve Cruise: Aruba, Saint Lucia & Saint Croix
Departure Date
28 Dec 26
| Cruise Line | Azamara |
| Cruise Type | Ocean |
| Ship | Azamara Journey |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
From £1,649pp
Plus substantial savings from Deluxe Cruises
17 Nights
Caribbean New Year Cruise: Barbados, Aruba & St. Barts
Caribbean New Year Cruise: Barbados, Aruba & St. Barts
Departure Date
28 Dec 26
| Cruise Line | Azamara |
| Cruise Type | Ocean |
| Ship | Azamara Journey |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Miami, Florida |
| Itinerary |
Bridgetown, Oranjestad, Willemstad, Castries, Charlestown, Frederiksted, Saint Croix, San Juan (Puerto Rico), Virgin Gorda, Gustavia, Philipsburg, Saint John's, Basseterre, Saint Kitts, Road Town, Tortola and Miami, Florida
|
From £3,049pp
Plus substantial savings from Deluxe Cruises