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 13)
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
29 Nov 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Pride |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Gustavia, Basseterre, Saint Kitts, Philipsburg, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Saint George's, Port Elizabeth, Bequia, Mayreau Island, Deshaies, Marigot and San Juan (Puerto Rico)
|
From £2,640pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan & the Virgin Islands
San Juan & the Virgin Islands
Departure Date
29 Nov 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Pride |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Gustavia, Basseterre, Saint Kitts, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £1,548pp
Plus substantial savings from Deluxe Cruises
13 Nights
Discover the Vibes of the Caribbean
Discover the Vibes of the Caribbean
Departure Date
30 Nov 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Saint Thomas |
| Itinerary |
Miami, Florida, Nassau, Bahamas, San Salvador Island, Gordon's Beach, Long Island, Grand Turk Island, San Juan (Puerto Rico), Cruz Bay, Saint John, Nevis, Falmouth, Gustavia, Virgin Gorda and Saint Thomas
|
From £9,947pp
Plus substantial savings from Deluxe Cruises
7 Nights
Caribbean escapade
Caribbean escapade
Departure Date
30 Nov 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Miami, Florida, Nassau, Bahamas, San Salvador Island, Gordon's Beach, Long Island, Grand Turk Island and San Juan (Puerto Rico)
|
From £5,775pp
Plus substantial savings from Deluxe Cruises
11 Nights
Waterfalls & Divers
Waterfalls & Divers
Departure Date
30 Nov 26
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Splendor |
| Region | Caribbean |
| Departure Port | Galveston, Texas |
| Destination Port | Galveston, Texas |
| Itinerary |
Galveston, Texas, Georgetown, Grand Cayman, Roatán Island, Belize City, Costa Maya, Cozumel and Galveston, Texas
|
From £4,128pp
Plus substantial savings from Deluxe Cruises
4 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
30 Nov 26
| 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), Marigot, Falmouth, Virgin Gorda and San Juan (Puerto Rico)
|
From £4,100pp
Plus substantial savings from Deluxe Cruises
10 Nights
Miami to Miami
Miami to Miami
Departure Date
30 Nov 26
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Shadow |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Saint John Island, Gustavia, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke and Miami, Florida
|
From £3,500pp
Plus substantial savings from Deluxe Cruises
10 Nights
Sunset Serenity
Sunset Serenity
Departure Date
01 Dec 26
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Mariner |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Tampa, Florida |
| Itinerary |
Miami, Florida, Oranjestad, Willemstad, Kralendijk, Montego Bay, Georgetown, Grand Cayman and Tampa, Florida
|
From £3,535pp
Plus substantial savings from Deluxe Cruises
10 Nights
Cartagena to Puerto Caldera
Cartagena to Puerto Caldera
Departure Date
02 Dec 26
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Serenity |
| Region | Caribbean |
| Departure Port | Cartagena |
| Destination Port | Puerto Caldera |
| Itinerary |
Cartagena, Willemstad, Kralendijk, Oranjestad, Santa Marta, Fuerte Amador, Fuerte Amador and Puerto Caldera
|
From £3,590pp
Plus substantial savings from Deluxe Cruises
10 Nights
Caribbean Island Bliss
Caribbean Island Bliss
Departure Date
02 Dec 26
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Allura |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Charlotte Amalie, Philipsburg, Gustavia, Basseterre, Saint Kitts, Tortola and Miami, Florida
|
From £3,149pp
Plus substantial savings from Deluxe Cruises
17 Nights
Roundtrip Fort Lauderdale
Roundtrip Fort Lauderdale
Departure Date
03 Dec 26
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Symphony |
| Region | Caribbean |
| Departure Port | Fort Lauderdale, Florida |
| Destination Port | Fort Lauderdale, Florida |
| Itinerary |
Fort Lauderdale, Florida, Road Town, Tortola, Gustavia, Pointe-à-Pitre, Kingstown, Castries, Fort-de-France, Basseterre, Saint Kitts, San Juan (Puerto Rico), Great Harbour, Jost Van Dyke, Marigot, Saint John's, Saint Thomas and Fort Lauderdale, Florida
|
From £5,310pp
Plus substantial savings from Deluxe Cruises
3 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
04 Dec 26
| 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), Virgin Gorda, Saint John Island and San Juan (Puerto Rico)
|
From £3,300pp
Plus substantial savings from Deluxe Cruises