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 29)
14 Nights
Miami to Miami
Miami to Miami
Departure Date
22 Dec 26
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Ray |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Grand Turk Island, Basseterre, Saint Kitts, Oranjestad, Kralendijk, Willemstad, Saint John Island, San Juan (Puerto Rico) and Miami, Florida
|
From £7,560pp
Plus substantial savings from Deluxe Cruises
12 Nights
San Juan to San Juan
San Juan to San Juan
Departure Date
22 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, Mayreau Island, Saint George's, Oranjestad, Willemstad, Kralendijk, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From Please Call
Plus substantial savings from Deluxe Cruises
12 Nights
Bridgetown to Miami
Bridgetown to Miami
Departure Date
22 Dec 26
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Spirit |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Miami, Florida |
| Itinerary |
Bridgetown, Castries, Saint George's, Kralendijk, Willemstad, Oranjestad, Saint John Island, San Juan (Puerto Rico) and Miami, Florida
|
From Please Call
Plus substantial savings from Deluxe Cruises
7 Nights
Classic Caribbean
Classic Caribbean
Departure Date
26 Dec 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Philipsburg, Gustavia, Gustavia, Roseau, Roseau, Mayreau Island, Mayreau Island, Terre-de-Haut, Terre-de-Haut, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Philipsburg and Philipsburg
|
From £1,735pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Caribbean Explorations
Star Collector: Caribbean Explorations
Departure Date
26 Dec 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Philipsburg, Gustavia, Gustavia, Roseau, Roseau, Mayreau Island, Mayreau Island, Terre-de-Haut, Terre-de-Haut, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Philipsburg, Philipsburg, Falmouth, Falmouth, Road Bay, Road Bay, Sopers Hole, Tortola, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia, Gustavia, Philipsburg and Philipsburg
|
From £2,852pp
Plus substantial savings from Deluxe Cruises
7 Nights
7-Day Yachtsman's Caribbean
7-Day Yachtsman's Caribbean
Departure Date
26 Dec 26
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Ovation |
| Region | Caribbean |
| Departure Port | Sint Maarten |
| Destination Port | Bridgetown |
| Itinerary |
Sint Maarten, Frenchman's Cay, South Friars Bay, Trois-Ilets, Port Elizabeth, Bequia, Saint George's and Bridgetown
|
From £3,824pp
Plus substantial savings from Deluxe Cruises
13 Nights
Discover the Grenadines & Windwards islands
Discover the Grenadines & Windwards islands
Departure Date
27 Dec 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Marigot |
| Itinerary |
Bridgetown, Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Mayreau Island, Mayreau Island, Union Island, Union Island, Union Island, Tobago Cays, Bridgetown, Soufrière, Îles des Saintes, Falmouth, Saint Kitts, Gustavia and Marigot
|
From £10,324pp
Plus substantial savings from Deluxe Cruises
7 Nights
Grenadines & Windwards yachting
Grenadines & Windwards yachting
Departure Date
27 Dec 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Mayreau Island, Mayreau Island, Union Island, Union Island, Union Island, Tobago Cays and Bridgetown
|
From £5,141pp
Plus substantial savings from Deluxe Cruises
7 Nights
Vibes of the Virgin Islands
Vibes of the Virgin Islands
Departure Date
27 Dec 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Saint Thomas |
| Destination Port | Saint Thomas |
| Itinerary |
Saint Thomas, Saint John Island, Virgin Gorda, Norman Island, Norman Island, Sandy Ground, Philipsburg, Philipsburg, Gustavia, Gustavia and Saint Thomas
|
From £4,622pp
Plus substantial savings from Deluxe Cruises
7 Nights
Tropical New Year's I
Tropical New Year's I
Departure Date
27 Dec 26
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream I |
| Region | Caribbean |
| Departure Port | Charlotte Amalie |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Charlotte Amalie, Spanish Town, Virgin Gorda, Norman Island, Marigot, Gustavia, Gustavia, Gustavia, Prickly Pear Island and San Juan (Puerto Rico)
|
From £6,876pp
Plus substantial savings from Deluxe Cruises
7 Nights
Tropical New Year's II
Tropical New Year's II
Departure Date
27 Dec 26
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream II |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Charlotte Amalie |
| Itinerary |
San Juan (Puerto Rico), Cruz Bay, Saint John, Philipsburg, Gustavia, Gustavia, Gustavia, White Bay, Jost Van Dyke and Charlotte Amalie
|
From £8,335pp
Plus substantial savings from Deluxe Cruises
15 Nights
An Extended Journey through Island Joys & Volcanic Majesty
An Extended Journey through Island Joys & Volcanic Majesty
Departure Date
27 Dec 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA I |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Puerto Plata, Isla Catalana, Cruz Bay, Saint John, Great Harbour, Jost Van Dyke, Basseterre, Saint Kitts, Charlotte Amalie, San Juan (Puerto Rico), Philipsburg, Saint John's, Little Bay, Tortola and Miami, Florida
|
From £6,335pp
Plus substantial savings from Deluxe Cruises