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 39)
8 Nights
Mind, Body and Spirit Collection: Bermuda Bliss
Mind, Body and Spirit Collection: Bermuda Bliss
Departure Date
20 Oct 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Pride |
| Region | Caribbean |
| Departure Port | Boston, Massachusetts |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Boston, Massachusetts, Hamilton, Hamilton, Saint George, Saint George and San Juan (Puerto Rico)
|
From £1,469pp
Plus substantial savings from Deluxe Cruises
14 Nights
Panama Canal & Central America
Panama Canal & Central America
Departure Date
20 Oct 26
| Cruise Line | Viking Ocean Cruises |
| Cruise Type | Ocean |
| Ship | Viking Mars |
| Region | Caribbean |
| Departure Port | Fort Lauderdale, Florida |
| Destination Port | Fort Lauderdale, Florida |
| Itinerary |
Fort Lauderdale, Florida, Montego Bay, Colón, Limon, Roatán Island, Belize City, Cozumel and Fort Lauderdale, Florida
|
From £5,195pp
Plus substantial savings from Deluxe Cruises
14 Nights
An Extended Journey of Maritime Soul & Island Zest
An Extended Journey of Maritime Soul & Island Zest
Departure Date
25 Oct 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA III |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Cruz Bay, Saint John, Saint John's, Terre-de-Haut, Philipsburg, San Juan (Puerto Rico), Tortola, Basseterre, Saint Kitts, Gustavia, Gustavia, Road Bay and Miami, Florida
|
From £5,590pp
Plus substantial savings from Deluxe Cruises
7 Nights
A Journey of Caribbean Adventure & Shimmering Tropical Harmony
A Journey of Caribbean Adventure & Shimmering Tropical Harmony
Departure Date
25 Oct 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA III |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Miami, Florida, Cruz Bay, Saint John, Saint John's, Terre-de-Haut, Philipsburg and San Juan (Puerto Rico)
|
From £2,665pp
Plus substantial savings from Deluxe Cruises
19 Nights
Panama Canal & the Americas
Panama Canal & the Americas
Departure Date
25 Oct 26
| Cruise Line | Viking Ocean Cruises |
| Cruise Type | |
| Ship | Viking Polaris |
| Region | Caribbean |
| Departure Port | New York, New York |
| Destination Port | Valparaiso |
| Itinerary |
New York, New York, San Salvador Island, Inagua, Port Antonio, Fuerte Amador, Callao, Iquique and Valparaiso
|
From £9,990pp
Plus substantial savings from Deluxe Cruises
9 Nights
New York to San Juan
New York to San Juan
Departure Date
26 Oct 26
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Symphony |
| Region | Caribbean |
| Departure Port | New York, New York |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
New York, New York, New York, New York, Kings Wharf, Kings Wharf, Santo Domingo, Samaná and San Juan (Puerto Rico)
|
From £3,290pp
Plus substantial savings from Deluxe Cruises
9 Nights
Western Caribbean
Western Caribbean
Departure Date
27 Oct 26
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Elizabeth |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Grand Turk Island, Curaçao, Bonaire, Aruba and Miami, Florida
|
From £699pp
Plus substantial savings from Deluxe Cruises
21 Nights
Caribbean
Caribbean
Departure Date
27 Oct 26
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Elizabeth |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Grand Turk Island, Curaçao, Bonaire, Aruba, Miami, Florida, San Juan (Puerto Rico), Saint John's, Castries, Bridgetown, Sint Maarten, Tortola and Miami, Florida
|
From £1,699pp
Plus substantial savings from Deluxe Cruises
14 Nights
Caribbean Enchantment
Caribbean Enchantment
Departure Date
28 Oct 26
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Vista |
| Region | Caribbean |
| Departure Port | New York, New York |
| Destination Port | Miami, Florida |
| Itinerary |
New York, New York, Charlotte Amalie, Tortola, Saint John's, Basseterre, Saint Kitts, Castries, Saint George's, Willemstad, Oranjestad and Miami, Florida
|
From £3,809pp
Plus substantial savings from Deluxe Cruises
11 Nights
Masterpieces at Sea: Gems of the Leeward Islands
Masterpieces at Sea: Gems of the Leeward Islands
Departure Date
28 Oct 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, Falmouth, Terre-de-Haut, Pigeon Island, Saint George's, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £2,142pp
Plus substantial savings from Deluxe Cruises
9 Nights
Bermuda, Sint Maarten & British Virgin Islands Cruise: Hamilton, Philipsburg & Road Town
Bermuda, Sint Maarten & British Virgin Islands Cruise: Hamilton, Philipsburg & Road Town
Departure Date
29 Oct 26
| Cruise Line | Azamara |
| Cruise Type | Ocean |
| Ship | Azamara Journey |
| Region | Caribbean |
| Departure Port | New York, New York |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
New York, New York, Hamilton, Hamilton, Hamilton, Philipsburg, Road Town, Tortola and San Juan (Puerto Rico)
|
From £1,269pp
Plus substantial savings from Deluxe Cruises
16 Nights
Caribbean Cruise: New York, Bermuda & Barbados
Caribbean Cruise: New York, Bermuda & Barbados
Departure Date
29 Oct 26
| Cruise Line | Azamara |
| Cruise Type | Ocean |
| Ship | Azamara Journey |
| Region | Caribbean |
| Departure Port | New York, New York |
| Destination Port | Bridgetown |
| Itinerary |
New York, New York, Hamilton, Hamilton, Hamilton, Philipsburg, Road Town, Tortola, San Juan (Puerto Rico), Virgin Gorda, Saint John's, Saint Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough and Bridgetown
|
From £2,279pp
Plus substantial savings from Deluxe Cruises