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.

Barbados

Caribbean Itineraries (Page 61)

7 Nights

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

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

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

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

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

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

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

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

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

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

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

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