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 4)
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
20 Feb 26
| 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, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Soufrière and San Juan (Puerto Rico)
|
From £4,714pp
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan & the Virgin Islands
San Juan & the Virgin Islands
Departure Date
20 Feb 26
| 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, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £4,796pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Lovely Leewards
Star Collector: Lovely Leewards
Departure Date
20 Feb 26
| 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, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Soufrière and San Juan (Puerto Rico)
|
From Please Call
Plus substantial savings from Deluxe Cruises
7 Nights
San Juan & the Virgin Islands
San Juan & the Virgin Islands
Departure Date
20 Feb 26
| 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, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £2,813pp
Plus substantial savings from Deluxe Cruises
6 Nights
A Journey of Vibrant Landscapes & Island Calm
A Journey of Vibrant Landscapes & Island Calm
Departure Date
20 Feb 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA I |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | Bridgetown |
| Itinerary |
San Juan (Puerto Rico), Oranjestad, Willemstad, Kralendijk and Bridgetown
|
From £2,735pp
Plus substantial savings from Deluxe Cruises
17 Nights
An Extended Journey into Tropical Utopia, Coral Wonders & Blissful Beaches
An Extended Journey into Tropical Utopia, Coral Wonders & Blissful Beaches
Departure Date
20 Feb 26
| 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), Oranjestad, Willemstad, Kralendijk, Bridgetown, Terre-de-Haut, Philipsburg, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Saint John's, Road Bay, Spanish Town, Virgin Gorda, Charlotte Amalie and Miami, Florida
|
From £6,160pp
Plus substantial savings from Deluxe Cruises
10 Nights
A Journey into Historic Charm & Tropical Bliss
A Journey into Historic Charm & Tropical Bliss
Departure Date
20 Feb 26
| Cruise Line | Explora Journeys |
| Cruise Type | Ocean |
| Ship | EXPLORA I |
| Region | Caribbean |
| Departure Port | San Juan (Puerto Rico) |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
San Juan (Puerto Rico), Oranjestad, Willemstad, Kralendijk, Bridgetown, Terre-de-Haut, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)
|
From £4,270pp
Plus substantial savings from Deluxe Cruises
14 Nights
Discover the yachting islands of the Caribbean
Discover the yachting islands of the Caribbean
Departure Date
21 Feb 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Saint John's |
| Destination Port | Saint John's |
| Itinerary |
From Please Call
Plus substantial savings from Deluxe Cruises
7 Nights
Caribbean yachting discovery
Caribbean yachting discovery
Departure Date
21 Feb 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Azzurra |
| Region | Caribbean |
| Departure Port | Antigua |
| Destination Port | San Juan (Puerto Rico) |
| Itinerary |
Antigua, Barbuda, Îles des Saintes, Deshaies, Gustavia, Virgin Gorda, Norman Island and San Juan (Puerto Rico)
|
From Please Call
Plus substantial savings from Deluxe Cruises
21 Nights
Discover the hidden treasures of the Caribbean
Discover the hidden treasures of the Caribbean
Departure Date
21 Feb 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Marigot |
| Destination Port | Bridgetown |
| Itinerary |
Marigot, Anguilla, Virgin Gorda, Norman Island, Great Harbour, Jost Van Dyke, Anegada, Saba, Gustavia, Marigot, Prickly Pear Island, Charlestown, Gustavia, Falmouth, Îles des Saintes, Soufrière, Bridgetown, Speightstown, Kingstown, Port Elizabeth, Bequia, Mayreau Island, Union Island, Tobago Cays and Bridgetown
|
From Please Call
Plus substantial savings from Deluxe Cruises
7 Nights
Cruising the Leeward Islands
Cruising the Leeward Islands
Departure Date
21 Feb 26
| Cruise Line | Emerald Cruises |
| Cruise Type | Ocean |
| Ship | Emerald Sakara |
| Region | Caribbean |
| Departure Port | Marigot |
| Destination Port | Marigot |
| Itinerary |
Marigot, Anguilla, Virgin Gorda, Norman Island, Great Harbour, Jost Van Dyke, Anegada, Saba, Gustavia and Marigot
|
From £12,068pp
Plus substantial savings from Deluxe Cruises
7 Nights
Secret Shores & Cultural Gems
Secret Shores & Cultural Gems
Departure Date
21 Feb 26
| Cruise Line | Regent Seven Seas Cruises |
| Cruise Type | Ocean |
| Ship | Seven Seas Grandeur |
| Region | Caribbean |
| Departure Port | Miami, Florida |
| Destination Port | Miami, Florida |
| Itinerary |
Miami, Florida, Costa Maya, Belize City, Roatán Island, Cozumel and Miami, Florida
|
From Please Call
Plus substantial savings from Deluxe Cruises