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 8)
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 £3,360pp
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 £4,590pp
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
14 Nights
Discover Eastern Caribbean & Grenadines
Discover Eastern Caribbean & Grenadines
Departure Date
28 Feb 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Marigot |
| Destination Port | Bridgetown |
| Itinerary |
Marigot, Prickly Pear Island, Charlestown, Gustavia, Falmouth, Îles des Saintes, Soufrière, Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Mayreau Island, Union Island, Tobago Cays and Bridgetown
|
From £24,188pp
Plus substantial savings from Deluxe Cruises
7 Nights
Eastern Caribbean with St. Barths
Eastern Caribbean with St. Barths
Departure Date
28 Feb 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Marigot |
| Destination Port | Bridgetown |
| Itinerary |
Marigot, Prickly Pear Island, Charlestown, Gustavia, Falmouth, Îles des Saintes, Soufrière and Bridgetown
|
From £12,118pp
Plus substantial savings from Deluxe Cruises
7 Nights
British Islands Discovery
British Islands Discovery
Departure Date
28 Feb 26
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream I |
| Region | Caribbean |
| Departure Port | Charlotte Amalie |
| Destination Port | Charlotte Amalie |
| Itinerary |
Charlotte Amalie, Cruz Bay, Saint John, Prickly Pear Island, Spanish Town, Virgin Gorda, Beef Island, Tortola, Sandy Ground, Gustavia, Gustavia, Philipsburg and Charlotte Amalie
|
From Please Call
Plus substantial savings from Deluxe Cruises