The 2026 season highlights high-touch personalization, such as "Marina Days" where guests can kayak or paddleboard directly from the ship's stern. Onboard, the Caribbean experience is refined through regional farm-to-table dining, featuring fresh snapper and lobster, while shore excursions lean into private access - think guided hikes to Dominica’s thermal pools or helicopter tours over the turquoise reefs of the Bahamas.
Caribbean Itineraries (Page 31)
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), San Juan (Puerto Rico), Gustavia, Gustavia, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Philipsburg, Philipsburg, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), San Juan (Puerto Rico), Saint George's, Saint George's, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Mayreau Island, Mayreau Island, Terre-de-Haut, Terre-de-Haut, Marigot, Marigot, San Juan (Puerto Rico) and San Juan (Puerto Rico)
|
From £3,611pp
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), San Juan (Puerto Rico), Gustavia, Gustavia, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Philipsburg, Philipsburg, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico) and San Juan (Puerto Rico)
|
From £2,082pp
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 £3,180pp
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 £3,079pp
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, Montego Bay, Roatán Island, Harvest Caye, Cozumel and Miami, Florida
|
From £2,719pp
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 £8,360pp
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 Please Call
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 £6,429pp
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 £5,140pp
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 |
Bridgetown, Oranjestad, Willemstad, Castries, Charlestown, Frederiksted, Saint Croix and San Juan (Puerto Rico)
|
From £1,829pp
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 £3,689pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
28 Dec 26
| 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), Port Elizabeth, Bequia, Canouan Island, Soufrière, Saint John's, Virgin Gorda and San Juan (Puerto Rico)
|
From £7,600pp
Plus substantial savings from Deluxe Cruises