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 68)
14 Nights
Star Collector: Caribbean Explorations
Star Collector: Caribbean Explorations
Departure Date
16 Jan 28
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Road Bay, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia, Philipsburg, Roseau, Mayreau Island, Terre-de-Haut, Basseterre, Saint Kitts, Gustavia and Philipsburg
|
From £3,490pp
Plus substantial savings from Deluxe Cruises
7 Nights
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
Departure Date
16 Jan 28
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Road Bay, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia and Philipsburg
|
From £2,149pp
Plus substantial savings from Deluxe Cruises
10 Nights
Golden Caribbean Beaches
Golden Caribbean Beaches
Departure Date
17 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, Puerto Plata, San Juan (Puerto Rico), Philipsburg, Gustavia, Saint John's, Tortola and Miami, Florida
|
From £5,929pp
Plus substantial savings from Deluxe Cruises
4 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
17 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), Norman Island, Sandy Ground, Gustavia 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
17 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), Philipsburg, Gustavia, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Saint George's, Port Elizabeth, Bequia, Mayreau Island, Terre-de-Haut, Marigot 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
17 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), Philipsburg, Gustavia, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £2,218pp
Plus substantial savings from Deluxe Cruises
10 Nights
West Indies Explorer
West Indies Explorer
Departure Date
18 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
19 Nights
The Great Diversity Of The Caribbean Sea
The Great Diversity Of The Caribbean Sea
Departure Date
20 Jan 28
| Cruise Line | Hapag-Lloyd Cruises |
| Cruise Type | Ocean |
| Ship | MS EUROPA 2 |
| Region | Caribbean |
| Departure Port | Panama City |
| Destination Port | Miami, Florida |
| Itinerary |
Panama City, Panama City, San Blas Islands, Cartagena, Puerto Limón, Providencia Island, Grand Cayman, Ocho Rios, Port Antonio, La Romana, Puerto Plata, Grand Turk Island, Inagua and Miami, Florida
|
From £12,294pp
Plus substantial savings from Deluxe Cruises
11 Nights
Miami to Miami
Miami to Miami
Departure Date
20 Jan 28
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Nova |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Sopers Hole, Tortola, Basseterre, Saint Kitts, Gustavia, Saint John's, Saint John Island and Miami, Florida
|
From £4,800pp
Plus substantial savings from Deluxe Cruises
3 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
21 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, Virgin Gorda and San Juan (Puerto Rico)
|
From £3,300pp
Plus substantial savings from Deluxe Cruises
14 Nights
Discover the Yachting Islands of the Caribbean
Discover the Yachting Islands of the Caribbean
Departure Date
22 Jan 28
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Kaia |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Vieques, Saint John Island, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Philipsburg, Gustavia, Gustavia, Little Bay, Saint John's, Saint John's, Basseterre, Saint Kitts, Îles des Saintes, Deshaies, Gustavia, Virgin Gorda, Norman Island and San Juan (Puerto Rico)
|
From £11,890pp
Plus substantial savings from Deluxe Cruises
7 Nights
Caribbean Yachting Hideaways
Caribbean Yachting Hideaways
Departure Date
22 Jan 28
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Kaia |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Saint John's |
| Itinerary |
San Juan (Puerto Rico), Vieques, Saint John Island, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Philipsburg, Gustavia, Gustavia, Little Bay, Saint John's and Saint John's
|
From £5,727pp
Plus substantial savings from Deluxe Cruises