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 58)
7 Nights
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
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, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia, Road Bay, Falmouth and Philipsburg
|
From £1,649pp
Plus substantial savings from Deluxe Cruises
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, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia, Road Bay, Falmouth, Philipsburg, Roseau, Mayreau Island, Terre-de-Haut, Basseterre, Saint Kitts, Gustavia and Philipsburg
|
From £2,538pp
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 £5,600pp
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 £3,520pp
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 £3,040pp
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 £7,069pp
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