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 11)
San Juan (Puerto Rico) Roundtrip
San Juan (Puerto Rico) Roundtrip
| 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, Saint George's, Soufrière, Portsmouth, Falmouth, Virgin Gorda and San Juan (Puerto Rico)
|
From £6,800pp
Plus substantial savings from Deluxe Cruises
San Juan & the Virgin Islands
San Juan & the Virgin Islands
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Basseterre, Saint Kitts, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £4,277pp
Plus substantial savings from Deluxe Cruises
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Basseterre, Saint Kitts, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Marigot, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Pigeon Island and San Juan (Puerto Rico)
|
From £11,215pp
Plus substantial savings from Deluxe Cruises
San Juan & the Virgin Islands
San Juan & the Virgin Islands
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Basseterre, Saint Kitts, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From Please Call
Plus substantial savings from Deluxe Cruises
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Star Seeker |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Basseterre, Saint Kitts, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Marigot, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Pigeon Island and San Juan (Puerto Rico)
|
From Please Call
Plus substantial savings from Deluxe Cruises
Discover the yachting islands of the Caribbean
Discover the yachting islands of the Caribbean
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Saint John's |
| Destination Port | Saint John's |
| Itinerary |
From £7,314pp
Plus substantial savings from Deluxe Cruises
Caribbean Yachting Discovery
Caribbean Yachting Discovery
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Antigua |
| Destination Port | Saint Thomas |
| Itinerary |
Antigua, Gustavia, Îles des Saintes, Deshaies, Barbuda, Virgin Gorda, Norman Island and Saint Thomas
|
From £12,824pp
Plus substantial savings from Deluxe Cruises
Discover Eastern Caribbean & Grenadines
Discover Eastern Caribbean & Grenadines
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Marigot |
| Itinerary |
Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Mayreau Island, Union Island, Tobago Cays, Bridgetown, Soufrière, Îles des Saintes, Falmouth, Charlestown, Saint Kitts, Gustavia, Prickly Pear Island and Marigot
|
From £24,188pp
Plus substantial savings from Deluxe Cruises
Grenadines & Windwards yachting
Grenadines & Windwards yachting
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Mayreau Island, Union Island, Tobago Cays and Bridgetown
|
From £12,071pp
Plus substantial savings from Deluxe Cruises
British & French Islands Discovery
British & French Islands Discovery
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream I |
| Region | Caribbean |
| Departure Port | Charlotte Amalie |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Charlotte Amalie, Cruz Bay, Saint John, Prickly Pear Island, Gustavia, Sandy Ground, South Friars Bay, Spanish Town, Virgin Gorda, Peter Island and San Juan (Puerto Rico)
|
From Please Call
Plus substantial savings from Deluxe Cruises
Star Collector: Blue Seas of the Windward Islands
Star Collector: Blue Seas of the Windward Islands
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Basseterre, Saint Kitts, Terre-de-Haut, Roseau, Mayreau Island, Trois-Ilets, Bridgetown, Tobago Cays, Pigeon Island, Pigeon Island, Castries, Mayreau Island, Port Elizabeth, Bequia and Bridgetown
|
From £2,624pp
Plus substantial savings from Deluxe Cruises
Windward Island Delights
Windward Island Delights
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Bridgetown |
| Itinerary |
Bridgetown, Basseterre, Saint Kitts, Terre-de-Haut, Roseau, Mayreau Island, Trois-Ilets and Bridgetown
|
From £2,161pp
Plus substantial savings from Deluxe Cruises