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 70)
4 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
24 Jan 28
| 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), Saint John Island, Sandy Ground, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £4,400pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
24 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), Saint George's, Port Elizabeth, Bequia, Mayreau Island, Terre-de-Haut, Marigot, San Juan (Puerto Rico), Gustavia, Philipsburg, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £3,545pp
Plus substantial savings from Deluxe Cruises
7 Nights
Windward Islands Surf & Sunsets
Windward Islands Surf & Sunsets
Departure Date
24 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), Saint George's, Port Elizabeth, Bequia, Mayreau Island, Terre-de-Haut, Marigot and San Juan (Puerto Rico)
|
From £2,194pp
Plus substantial savings from Deluxe Cruises
11 Nights
San Juan to San Juan
San Juan to San Juan
Departure Date
25 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, Roseau, Canouan Island, Saint George's, Willemstad, Kralendijk, Saint John Island and San Juan (Puerto Rico)
|
From £3,700pp
Plus substantial savings from Deluxe Cruises
10 Nights
Tropical Heart & Soul
Tropical Heart & Soul
Departure Date
25 Jan 28
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Grandeur |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Kingstown, Castries, Fort-de-France, Pointe-à-Pitre, Gustavia, Basseterre, Saint Kitts, Saint John's, Roseau and Bridgetown
|
From £4,619pp
Plus substantial savings from Deluxe Cruises
12 Nights
Curated Caribbean
Curated Caribbean
Departure Date
26 Jan 28
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Marina |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Oranjestad, Willemstad, Kralendijk, Saint George's, Castries, Gustavia, Tortola and Miami, Florida
|
From £2,899pp
Plus substantial savings from Deluxe Cruises
14 Nights
Panama Canal & Central America
Panama Canal & Central America
Departure Date
26 Jan 28
| 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 £5,290pp
Plus substantial savings from Deluxe Cruises
10 Nights
West Indies Explorer
West Indies Explorer
Departure Date
27 Jan 28
| 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 £4,490pp
Plus substantial savings from Deluxe Cruises
9 Nights
Vibrant Island Culture
Vibrant Island Culture
Departure Date
27 Jan 28
| 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, Gustavia, Basseterre, Saint Kitts, Castries, Philipsburg and Miami, Florida
|
From £5,479pp
Plus substantial savings from Deluxe Cruises
10 Nights
West Indies Explorer
West Indies Explorer
Departure Date
28 Jan 28
| Cruise Line | Viking Ocean Cruises |
| Cruise Type | Ocean |
| Ship | Viking Sky |
| 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 £4,490pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan (Puerto Rico) to Aruba
San Juan (Puerto Rico) to Aruba
Departure Date
28 Jan 28
| Cruise Line | The Ritz-Carlton Yacht Collection |
| Cruise Type | Ocean |
| Ship | Ilma |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Aruba |
| Itinerary |
San Juan (Puerto Rico), Saint John Island, Marigot, Terre-de-Haut, Canouan Island, Willemstad and Aruba
|
From £7,700pp
Plus substantial savings from Deluxe Cruises
7 Nights
Caribbean Yachting Discovery
Caribbean Yachting Discovery
Departure Date
29 Jan 28
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Kaia |
| Region | Caribbean |
| Departure Port | Saint John's |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Saint John's, Basseterre, Saint Kitts, Îles des Saintes, Deshaies, Gustavia, Virgin Gorda, Norman Island and San Juan (Puerto Rico)
|
From £5,627pp
Plus substantial savings from Deluxe Cruises