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
16 Nights
Spotlight With Southern Living
Spotlight With Southern Living
Departure Date
13 Jun 26
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Mariner |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | New York, New York |
| Itinerary |
Miami, Florida, Oranjestad, Willemstad, Kralendijk, Saint George's, Castries, Gustavia, San Juan (Puerto Rico), Charleston, South Carolina, Charleston, South Carolina, New York, New York and New York, New York
|
From Please Call
Plus substantial savings from Deluxe Cruises
32 Nights
San Diego to New York City
San Diego to New York City
Departure Date
24 Aug 26
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Symphony |
| Region | Caribbean |
| Departure Port | San Diego, California |
| Destination Port | New York, New York |
| Itinerary |
San Diego, California, Ensenada, Cabo San Lucas, Puerto Vallarta, Acajutla, Playa Flamingo, Puntarenas, Manta, Guayaquil, Fuerte Amador, Fuerte Amador, Fuerte Amador, Cartagena, Santo Domingo, Punta Cana, San Juan (Puerto Rico), Marigot, Roseau, Bridgetown, Castries, Saint John's, Great Harbour, Jost Van Dyke, Samaná, Grand Turk Island and New York, New York
|
From £10,162pp
Plus substantial savings from Deluxe Cruises
9 Nights
Guayaquil to San Juan
Guayaquil to San Juan
Departure Date
05 Sep 26
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Symphony |
| Region | Caribbean |
| Departure Port | Guayaquil |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Guayaquil, Fuerte Amador, Fuerte Amador, Fuerte Amador, Cartagena, Santo Domingo, Punta Cana and San Juan (Puerto Rico)
|
From £3,148pp
Plus substantial savings from Deluxe Cruises
11 Nights
San Juan to New York
San Juan to New York
Departure Date
14 Sep 26
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Symphony |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | New York, New York |
| Itinerary |
San Juan (Puerto Rico), Marigot, Roseau, Bridgetown, Castries, Saint John's, Great Harbour, Jost Van Dyke, Samaná, Grand Turk Island and New York, New York
|
From £3,507pp
Plus substantial savings from Deluxe Cruises
3 Nights
San Juan to Bridgetown
San Juan to Bridgetown
Departure Date
14 Sep 26
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Symphony |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Bridgetown |
| Itinerary |
San Juan (Puerto Rico), Marigot, Roseau and Bridgetown
|
From Please Call
Plus substantial savings from Deluxe Cruises
8 Nights
Bridgetown to New York
Bridgetown to New York
Departure Date
17 Sep 26
| Cruise Line | Crystal |
| Cruise Type | Ocean |
| Ship | Crystal Symphony |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | New York, New York |
| Itinerary |
Bridgetown, Castries, Saint John's, Great Harbour, Jost Van Dyke, Samaná, Grand Turk Island and New York, New York
|
From £3,470pp
Plus substantial savings from Deluxe Cruises
23 Nights
22-Day Wild Labrador Coast & Southern Caribbean
22-Day Wild Labrador Coast & Southern Caribbean
Departure Date
20 Sep 26
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Venture |
| Region | Caribbean |
| Departure Port | Reykjavík |
| Destination Port | Bridgetown |
| Itinerary |
Reykjavík, Kangerlussuaq Havn, Pangnirtung, Nunavut, Lady Franklin Island, Nunavut, Monument Island, Nunavut, Lower Savage Islands, Nunavut, Resolution Island, Qikiqtaaluk, Nachvak Fiord, Newfoundland and Labrador, Saglek Fjord, Newfoundland and Labrador, Hebron, Newfoundland and Labrador, Nain, Newfoundland and Labrador, Indian Harbour, Newfoundland and Labrador, Battle Harbor, Newfoundland and Labrador, L'Anse aux Meadows, Newfoundland and Labrador, Halifax, Nova Scotia, South Friars Bay, Montserrat, Rodney Bay and Bridgetown
|
From £12,833pp
Plus substantial savings from Deluxe Cruises
8 Nights
8-Day Southern Caribbean Yacht Harbors
8-Day Southern Caribbean Yacht Harbors
Departure Date
05 Oct 26
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Venture |
| Region | Caribbean |
| Departure Port | Halifax, Nova Scotia |
| Destination Port | Bridgetown |
| Itinerary |
Halifax, Nova Scotia, South Friars Bay, Montserrat, Rodney Bay and Bridgetown
|
From £3,498pp
Plus substantial savings from Deluxe Cruises
24 Nights
24-Day Southern Caribbean Yacht Harbors & Coast Of Brazil
24-Day Southern Caribbean Yacht Harbors & Coast Of Brazil
Departure Date
05 Oct 26
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Venture |
| Region | Caribbean |
| Departure Port | Halifax, Nova Scotia |
| Destination Port | Rio de Janeiro |
| Itinerary |
Halifax, Nova Scotia, South Friars Bay, Montserrat, Rodney Bay, Bridgetown, Port-of-Spain, Devil's Island, Fortaleza, Natal, Salvador de Bahia, Buzios, Parati and Rio de Janeiro
|
From £9,698pp
Plus substantial savings from Deluxe Cruises
19 Nights
Star Collector: Fall Leaves & Caribbean Breezes
Star Collector: Fall Leaves & Caribbean Breezes
Departure Date
09 Oct 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Pride |
| Region | Caribbean |
| Departure Port | Montréal, Québec |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Montréal, Québec, Isle of Portland, Quebec City, Québec, Quebec City, Québec, Gaspé, Québec, Cap-aux-Meules, Magdalen Islands, Québec, Sydney, Nova Scotia, Halifax, Nova Scotia, Isle of Portland, Rockland, Maine, Boston, Massachusetts, Hamilton, Hamilton, Saint George, Saint George and San Juan (Puerto Rico)
|
From £5,123pp
Plus substantial savings from Deluxe Cruises
12 Nights
Eastern Caribbean
Eastern Caribbean
Departure Date
15 Oct 26
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Elizabeth |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Saint John's, Castries, Bridgetown, Sint Maarten, Tortola and Miami, Florida
|
From £749pp
Plus substantial savings from Deluxe Cruises
21 Nights
Caribbean
Caribbean
Departure Date
15 Oct 26
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Elizabeth |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Saint John's, Castries, Bridgetown, Sint Maarten, Tortola, Miami, Florida, Grand Turk Island, Curaçao, Bonaire, Aruba and Miami, Florida
|
From £1,399pp
Plus substantial savings from Deluxe Cruises