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 79)
7 Nights
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
Departure Date
30 Jan 28
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Philipsburg, Falmouth, Falmouth, Road Bay, Road Bay, Sopers Hole, Tortola, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia, Gustavia, Philipsburg and Philipsburg
|
From £2,149pp
Plus substantial savings from Deluxe Cruises
11 Nights
Miami to Miami
Miami to Miami
Departure Date
31 Jan 28
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Nova |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Saint John Island, Gustavia, Saint John's, Fort-de-France, Basseterre, Saint Kitts, San Juan (Puerto Rico) and Miami, Florida
|
From £4,800pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
31 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), San Juan (Puerto Rico), Gustavia, Gustavia, Philipsburg, Philipsburg, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), San Juan (Puerto Rico), Saint George's, Saint George's, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Mayreau Island, Mayreau Island, Terre-de-Haut, Terre-de-Haut, Marigot, Marigot, San Juan (Puerto Rico) 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
31 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), San Juan (Puerto Rico), Gustavia, Gustavia, Philipsburg, Philipsburg, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico) and San Juan (Puerto Rico)
|
From £2,218pp
Plus substantial savings from Deluxe Cruises
11 Nights
Leeward & Windward Islands Explorer
Leeward & Windward Islands Explorer
Departure Date
02 Feb 28
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream I |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Charlotte Amalie |
| Itinerary |
Bridgetown, Bridgetown, Port St Charles, Tobago Cays, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Saint Pierre, Terre-de-Haut, Charlestown, South Friars Bay, Marigot, Gustavia, Gustavia, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, White Bay, Jost Van Dyke and Charlotte Amalie
|
From £4,861pp
Plus substantial savings from Deluxe Cruises
10 Nights
Caribbean Splendor
Caribbean Splendor
Departure Date
02 Feb 28
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Sonata |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, San Juan (Puerto Rico), Charlotte Amalie, Basseterre, Saint Kitts, Pointe-à-Pitre, Tortola and Miami, Florida
|
From £3,589pp
Plus substantial savings from Deluxe Cruises
10 Nights
Sweetheart Sojourn
Sweetheart Sojourn
Departure Date
04 Feb 28
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Grandeur |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Saint George's, Oranjestad, Willemstad, Kralendijk, Basseterre, Saint Kitts, Saint John's, Roseau and Bridgetown
|
From £4,539pp
Plus substantial savings from Deluxe Cruises
14 Nights
Discover the Pearls of the Caribbean
Discover the Pearls of the Caribbean
Departure Date
05 Feb 28
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Basseterre, Saint Kitts, Anguilla, Virgin Gorda, Virgin Gorda, Gustavia, Gustavia, Philipsburg, Virgin Gorda, Gustavia, Charlestown, Saint John's, Îles des Saintes, Soufrière and Bridgetown
|
From £10,675pp
Plus substantial savings from Deluxe Cruises
14 Nights
Discover Island Rhythms & Coastal Dreams
Discover Island Rhythms & Coastal Dreams
Departure Date
05 Feb 28
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Kaia |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Miami, Florida |
| Itinerary |
San Juan (Puerto Rico), Vieques, Saint John Island, Great Harbour, Jost Van Dyke, Virgin Gorda, San Juan (Puerto Rico), Saint John Island, Ponce, Grand Turk Island, Gordon's Beach, Long Island, San Salvador Island, Nassau, Nassau and Miami, Florida
|
From £11,457pp
Plus substantial savings from Deluxe Cruises
21 Nights
Epic Voyage: Sint Maarten to Barbados
Epic Voyage: Sint Maarten to Barbados
Departure Date
05 Feb 28
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Basseterre, Saint Kitts, Anguilla, Virgin Gorda, Virgin Gorda, Gustavia, Gustavia, Philipsburg, Virgin Gorda, Gustavia, Charlestown, Saint John's, Îles des Saintes, Soufrière, Bridgetown, Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Mayreau Island, Mayreau Island, Union Island, Union Island, Union Island, Tobago Cays and Bridgetown
|
From £15,964pp
Plus substantial savings from Deluxe Cruises
7 Nights
Cruising the Leeward Islands
Cruising the Leeward Islands
Departure Date
05 Feb 28
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Basseterre, Saint Kitts, Anguilla, Virgin Gorda, Virgin Gorda, Gustavia, Gustavia and Philipsburg
|
From £5,388pp
Plus substantial savings from Deluxe Cruises
5 Nights
Beaches of the Virgin Islands
Beaches of the Virgin Islands
Departure Date
05 Feb 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, Virgin Gorda and San Juan (Puerto Rico)
|
From £4,055pp
Plus substantial savings from Deluxe Cruises