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 48)
14 Nights
Star Collector: Caribbean Explorations
Star Collector: Caribbean Explorations
Departure Date
27 Feb 27
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Surf |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Philipsburg, 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, Road Bay, Road Bay, Falmouth, Falmouth, Philipsburg, Philipsburg, Roseau, Roseau, Mayreau Island, Mayreau Island, Terre-de-Haut, Terre-de-Haut, Basseterre, Saint Kitts, Basseterre, Saint Kitts, Gustavia, Gustavia, Philipsburg and Philipsburg
|
From £2,706pp
Plus substantial savings from Deluxe Cruises
7 Nights
7-Day Classic Caribbean Yacht Harbors
7-Day Classic Caribbean Yacht Harbors
Departure Date
27 Feb 27
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Ovation |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Sint Maarten |
| Itinerary |
Bridgetown, Castries, Montserrat, Antigua, South Friars Bay, Great Harbour, Jost Van Dyke and Sint Maarten
|
From £3,059pp
Plus substantial savings from Deluxe Cruises
14 Nights
14-Day Exotic Caribbean In Depth
14-Day Exotic Caribbean In Depth
Departure Date
27 Feb 27
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Ovation |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Castries, Montserrat, Antigua, South Friars Bay, Great Harbour, Jost Van Dyke, Sint Maarten, Frenchman's Cay, South Friars Bay, Trois-Ilets, Port Elizabeth, Bequia, Saint George's and Bridgetown
|
From £5,524pp
Plus substantial savings from Deluxe Cruises
7 Nights
St. Barths & Caribbean Gems
St. Barths & Caribbean Gems
Departure Date
28 Feb 27
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream II |
| Region | Caribbean |
| Departure Port | Charlotte Amalie |
| Destination Port | Charlotte Amalie |
| Itinerary |
Charlotte Amalie, Cruz Bay, Saint John, Sandy Ground, Gustavia, Gustavia, Norman Island, White Bay, Jost Van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda and Charlotte Amalie
|
From £3,145pp
Plus substantial savings from Deluxe Cruises
14 Nights
An Extended Journey through Azure Horizons & Elegant Isles
An Extended Journey through Azure Horizons & Elegant Isles
Departure Date
28 Feb 27
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA III |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Cruz Bay, Saint John, Saint John's, Terre-de-Haut, Charlotte Amalie, San Juan (Puerto Rico), Philipsburg, Gustavia, Gustavia, Basseterre, Saint Kitts, Grand Turk Island and Miami, Florida
|
From £5,550pp
Plus substantial savings from Deluxe Cruises
7 Nights
A Journey from Glorious Shorelines to Nature's Allure
A Journey from Glorious Shorelines to Nature's Allure
Departure Date
28 Feb 27
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA III |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Miami, Florida, Cruz Bay, Saint John, Saint John's, Terre-de-Haut, Charlotte Amalie and San Juan (Puerto Rico)
|
From £3,300pp
Plus substantial savings from Deluxe Cruises
7 Nights
Bridgetown to Bridgetown
Bridgetown to Bridgetown
Departure Date
28 Feb 27
| Cruise Line | Silversea |
| Cruise Type | Ocean |
| Ship | Silver Spirit |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Castries, Gustavia, Saint John Island, Saint John's, Roseau, Port Elizabeth, Bequia and Bridgetown
|
From £3,200pp
Plus substantial savings from Deluxe Cruises
7 Nights
A Journey from Exciting Escapades to Idyllic Tranquillity
A Journey from Exciting Escapades to Idyllic Tranquillity
Departure Date
01 Mar 27
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA I |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Miami, Florida |
| Itinerary |
San Juan (Puerto Rico), Saint John's, Road Bay, Spanish Town, Virgin Gorda, Grand Turk Island and Miami, Florida
|
From £3,075pp
Plus substantial savings from Deluxe Cruises
12 Nights
Prestige Isles
Prestige Isles
Departure Date
05 Mar 27
| 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, Charlotte Amalie, Basseterre, Saint Kitts, Roseau, Castries, Bridgetown, Pointe-à-Pitre, Tortola and Miami, Florida
|
From £7,229pp
Plus substantial savings from Deluxe Cruises
6 Nights
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
Departure Date
05 Mar 27
| 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), Port Elizabeth, Bequia, Fort-de-France, Terre-de-Haut, Gustavia and San Juan (Puerto Rico)
|
From £5,900pp
Plus substantial savings from Deluxe Cruises
14 Nights
Discover the Pearls of the Caribbean
Discover the Pearls of the Caribbean
Departure Date
06 Mar 27
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Marigot |
| Destination Port | Bridgetown |
| Itinerary |
Marigot, Marigot, Anguilla, Virgin Gorda, Norman Island, Norman Island, Great Harbour, Jost Van Dyke, Anegada, Saba, Gustavia, Gustavia, Marigot, Marigot, Prickly Pear Island, Gustavia, Charlestown, Falmouth, Îles des Saintes, Soufrière and Bridgetown
|
From £11,140pp
Plus substantial savings from Deluxe Cruises
7 Nights
Cruising the Leeward Islands
Cruising the Leeward Islands
Departure Date
06 Mar 27
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Marigot |
| Destination Port | Marigot |
| Itinerary |
Marigot, Marigot, Anguilla, Virgin Gorda, Norman Island, Norman Island, Great Harbour, Jost Van Dyke, Anegada, Saba, Gustavia, Gustavia and Marigot
|
From £6,218pp
Plus substantial savings from Deluxe Cruises