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 16)
12 Nights
Tropical Island Rhythms
Tropical Island Rhythms
Departure Date
26 Feb 26
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Nautica |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Oranjestad, Willemstad, Saint George's, Castries, Basseterre, Saint Kitts, San Juan (Puerto Rico), Grand Turk Island and Miami, Florida
|
From £2,329pp
Plus substantial savings from Deluxe Cruises
4 Nights
A Journey through Azure Waters & Island Marvels
A Journey through Azure Waters & Island Marvels
Departure Date
26 Feb 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA I |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Bridgetown, Terre-de-Haut, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £1,835pp
Plus substantial savings from Deluxe Cruises
4 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
26 Feb 26
| Cruise Line | The Ritz-Carlton Yacht Collection |
| Cruise Type | Ocean |
| Ship | Evrima |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Virgin Gorda, Marigot, Saint John Island and San Juan (Puerto Rico)
|
From £3,800pp
Plus substantial savings from Deluxe Cruises
7 Nights
Philipsburg to Bridgetown
Philipsburg to Bridgetown
Departure Date
26 Feb 26
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Shadow |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Saint John Island, Gustavia, Roseau, Saint George's, Trois-Ilets, Kingstown and Bridgetown
|
From £11,600pp
Plus substantial savings from Deluxe Cruises
10 Nights
West Indies Explorer
West Indies Explorer
Departure Date
27 Feb 26
| 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), San Juan (Puerto Rico), Charlotte Amalie, Basseterre, Saint Kitts, Castries, Bridgetown, Roseau, Saint John's, Philipsburg, Frederiksted, Saint Croix and San Juan (Puerto Rico)
|
From £8,990pp
Plus substantial savings from Deluxe Cruises
11 Nights
Fort Lauderdale to Fort Lauderdale
Fort Lauderdale to Fort Lauderdale
Departure Date
27 Feb 26
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Ray |
| Region | Caribbean |
| Departure Port | Fort Lauderdale, Florida |
| Destination Port | Fort Lauderdale, Florida |
| Itinerary |
Fort Lauderdale, Florida, Grand Turk Island, Saint Thomas, Basseterre, Saint Kitts, Saint John's, Philipsburg, San Juan (Puerto Rico) and Fort Lauderdale, Florida
|
From £6,900pp
Plus substantial savings from Deluxe Cruises
7 Nights
Windward Islands Surf & Sunsets
Windward Islands Surf & Sunsets
Departure Date
27 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Mayreau Island and San Juan (Puerto Rico)
|
From £2,792pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
27 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan |
| Destination Port | San Juan |
| Itinerary |
San Juan, Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Mayreau Island, San Juan, Basseterre, Saint Kitts, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke and San Juan
|
From £11,950pp
Plus substantial savings from Deluxe Cruises
7 Nights
Windward Islands Surf & Sunsets
Windward Islands Surf & Sunsets
Departure Date
27 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Soufrière and San Juan (Puerto Rico)
|
From Please Call
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
27 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Soufrière, San Juan (Puerto Rico), Basseterre, Saint Kitts, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From Please Call
Plus substantial savings from Deluxe Cruises
14 Nights
Discover the yachting islands of the Caribbean
Discover the yachting islands of the Caribbean
Departure Date
28 Feb 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Saint Thomas |
| Itinerary |
San Juan (Puerto Rico), Culebra Island, Saint John Island, Great Harbour, Jost Van Dyke, Philipsburg, Gustavia, Little Bay, Saint John's, Gustavia, Îles des Saintes, Deshaies, Barbuda, Virgin Gorda, Norman Island and Saint Thomas
|
From Please Call
Plus substantial savings from Deluxe Cruises
7 Nights
Caribbean Yachting Hideaways
Caribbean Yachting Hideaways
Departure Date
28 Feb 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Antigua |
| Itinerary |
San Juan (Puerto Rico), Culebra Island, Saint John Island, Great Harbour, Jost Van Dyke, Norman Island, Philipsburg, Gustavia, Little Bay and Antigua
|
From Please Call
Plus substantial savings from Deluxe Cruises