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 3)

7 Nights

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

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

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

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

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

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

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

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

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

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

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

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