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 66)
12 Nights
Miami to Miami
Miami to Miami
Departure Date
03 Jan 28
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Ray |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Saint John Island, Gustavia, Saint John's, Fort-de-France, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke and Miami, Florida
|
From £4,800pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
03 Jan 28
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Legend |
| 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 £3,545pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan & the Virgin Islands
San Juan & the Virgin Islands
Departure Date
03 Jan 28
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Legend |
| 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 £2,218pp
Plus substantial savings from Deluxe Cruises
13 Nights
Star Collector: Caribbean Explorations
Star Collector: Caribbean Explorations
Departure Date
03 Jan 28
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Philipsburg, Road Bay, Road Bay, Gustavia, Gustavia, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Sopers Hole, Tortola, Sopers Hole, Tortola, Philipsburg, Philipsburg, Roseau, Roseau, Mayreau Island, Mayreau Island, Terre-de-Haut, Terre-de-Haut, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Gustavia, Gustavia, Philipsburg and Philipsburg
|
From £3,345pp
Plus substantial savings from Deluxe Cruises
6 Nights
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
Departure Date
03 Jan 28
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Philipsburg, Road Bay, Road Bay, Gustavia, Gustavia, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Sopers Hole, Tortola, Sopers Hole, Tortola, Philipsburg and Philipsburg
|
From £2,004pp
Plus substantial savings from Deluxe Cruises
11 Nights
San Juan to San Juan
San Juan to San Juan
Departure Date
04 Jan 28
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Dawn |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Great Harbour, Jost Van Dyke, Gustavia, Basseterre, Saint Kitts, Fort-de-France, Saint George's, Kralendijk, Willemstad, Oranjestad and San Juan (Puerto Rico)
|
From £3,700pp
Plus substantial savings from Deluxe Cruises
7 Nights
Cruising the Leeward Islands
Cruising the Leeward Islands
Departure Date
05 Jan 28
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Basseterre, Saint Kitts, Anguilla, Virgin Gorda, Virgin Gorda, Gustavia, Gustavia and Philipsburg
|
From £5,388pp
Plus substantial savings from Deluxe Cruises
10 Nights
A Journey In Beauty
A Journey In Beauty
Departure Date
05 Jan 28
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Grandeur |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Bridgetown |
| Itinerary |
Miami, Florida, Tortola, Gustavia, Philipsburg, Pointe-à-Pitre, Roseau, Fort-de-France, Castries and Bridgetown
|
From £4,929pp
Plus substantial savings from Deluxe Cruises
10 Nights
Miami to Cartagena
Miami to Cartagena
Departure Date
05 Jan 28
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Shadow |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Cartagena |
| Itinerary |
Miami, Florida, Great Harbour, Jost Van Dyke, Gustavia, Willemstad, Kralendijk and Cartagena
|
From £6,100pp
Plus substantial savings from Deluxe Cruises
25 Nights
Epic Caribbean Escape: Barbados to Costa Rica
Epic Caribbean Escape: Barbados to Costa Rica
Departure Date
06 Jan 28
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Puerto Caldera |
| Itinerary |
Bridgetown, Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Mayreau Island, Mayreau Island, Union Island, Union Island, Union Island, Tobago Cays, Bridgetown, Port Elizabeth, Bequia, Mayreau Island, Kralendijk, Willemstad, Oranjestad, Santa Marta, Cartagena, San Blas Islands, Panama City, Pearl Islands, Playa del Muerto, Darién National Park, Cébaco Island, Golfito, Quepos (Puerto Quepos), Tortuga Island and Puerto Caldera
|
From £20,795pp
Plus substantial savings from Deluxe Cruises
7 Nights
Grenadines & Windwards yachting
Grenadines & Windwards yachting
Departure Date
06 Jan 28
| 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 £5,288pp
Plus substantial savings from Deluxe Cruises
12 Nights
Miami To Southampton
Miami To Southampton
Departure Date
06 Jan 28
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Elizabeth |
| Region | Northern Europe and Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Southampton |
| Itinerary |
Miami, Florida, Praia da Vitória, Ponta Delgada, Azores and Southampton
|
From £1,449pp
Plus substantial savings from Deluxe Cruises