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 5)
14 Nights
Star Collector: Leeward & Windward Caribbean Havens
Star Collector: Leeward & Windward Caribbean Havens
Departure Date
21 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Road Bay, Sopers Hole, Tortola, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Gustavia, Philipsburg, Basseterre, Saint Kitts, Gustavia, Falmouth, Terre-de-Haut, Roseau, Mayreau Island and Bridgetown
|
From £5,880pp
Plus substantial savings from Deluxe Cruises
28 Nights
Star Collector: Wind Spirit Grand Caribbean Adventure 2026
Star Collector: Wind Spirit Grand Caribbean Adventure 2026
Departure Date
21 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Road Bay, Sopers Hole, Tortola, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Gustavia, Philipsburg, Basseterre, Saint Kitts, Gustavia, Falmouth, Terre-de-Haut, Roseau, Mayreau Island, 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 £11,652pp
Plus substantial savings from Deluxe Cruises
7 Nights
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
Departure Date
21 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
Philipsburg, Road Bay, Sopers Hole, Tortola, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Gustavia and Philipsburg
|
From £2,294pp
Plus substantial savings from Deluxe Cruises
22 Nights
Star Collector: A Lesser Antilles Odyssey
Star Collector: A Lesser Antilles Odyssey
Departure Date
21 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Road Bay, Sopers Hole, Tortola, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Gustavia, Philipsburg, Basseterre, Saint Kitts, Gustavia, Falmouth, Terre-de-Haut, Roseau, Mayreau Island, Bridgetown, Basseterre, Saint Kitts, Terre-de-Haut, Roseau, Mayreau Island, Trois-Ilets and Bridgetown
|
From £8,802pp
Plus substantial savings from Deluxe Cruises
14 Nights
Star Collector: Leeward & Windward Caribbean Havens
Star Collector: Leeward & Windward Caribbean Havens
Departure Date
21 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Road Bay, Sopers Hole, Tortola, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Gustavia, Philipsburg, Basseterre, Saint Kitts, Gustavia, Terre-de-Haut, Roseau, Mayreau Island and Bridgetown
|
From £3,397pp
Plus substantial savings from Deluxe Cruises
7 Nights
Beach Fun & Sun: A Remote Caribbean Getaway
Beach Fun & Sun: A Remote Caribbean Getaway
Departure Date
21 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Philipsburg |
| Itinerary |
From £2,161pp
Plus substantial savings from Deluxe Cruises
21 Nights
Star Collector: A Lesser Antilles Odyssey
Star Collector: A Lesser Antilles Odyssey
Departure Date
21 Feb 26
| Cruise Line | Windstar Cruises |
| Cruise Type | Ocean |
| Ship | Wind Spirit |
| Region | Caribbean |
| Departure Port | Philipsburg |
| Destination Port | Bridgetown |
| Itinerary |
Philipsburg, Road Bay, Sopers Hole, Tortola, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Gustavia, Philipsburg, Basseterre, Saint Kitts, Gustavia, Terre-de-Haut, Roseau, Mayreau Island, Bridgetown, Basseterre, Saint Kitts, Terre-de-Haut, Roseau, Mayreau Island and Bridgetown
|
From £5,119pp
Plus substantial savings from Deluxe Cruises
7 Nights
7-Day Yachtsman's Caribbean
7-Day Yachtsman's Caribbean
Departure Date
21 Feb 26
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Ovation |
| Region | Caribbean |
| Departure Port | Sint Maarten |
| Destination Port | Bridgetown |
| Itinerary |
Sint Maarten, Frenchman's Cay, South Friars Bay, Saint Pierre, Port Elizabeth, Bequia, Saint George's and Bridgetown
|
From £8,873pp
Plus substantial savings from Deluxe Cruises
14 Nights
14-Day Gems Of The Caribbean
14-Day Gems Of The Caribbean
Departure Date
21 Feb 26
| Cruise Line | Seabourn |
| Cruise Type | Ocean |
| Ship | Seabourn Ovation |
| Region | Caribbean |
| Departure Port | Sint Maarten |
| Destination Port | Sint Maarten |
| Itinerary |
Sint Maarten, Frenchman's Cay, South Friars Bay, Saint Pierre, Port Elizabeth, Bequia, Saint George's, Bridgetown, Castries, Montserrat, Antigua, South Friars Bay, Great Harbour, Jost Van Dyke and Sint Maarten
|
From £6,820pp
Plus substantial savings from Deluxe Cruises
28 Nights
Eastern Caribbean
Eastern Caribbean
Departure Date
22 Feb 26
| Cruise Line | Cunard |
| Cruise Type | Ocean |
| Ship | Queen Victoria |
| Region | Caribbean |
| Departure Port | Southampton |
| Destination Port | Southampton |
| Itinerary |
Southampton, Funchal, Madeira, Tortola, Sint Maarten, Saint Kitts, Dominica, Castries, Bridgetown, Bridgetown, Santa Cruz de Tenerife and Southampton
|
From Please Call
Plus substantial savings from Deluxe Cruises
7 Nights
Windward Islands Explorer
Windward Islands Explorer
Departure Date
22 Feb 26
| Cruise Line | SeaDream Yacht Club |
| Cruise Type | Ocean |
| Ship | SeaDream II |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Philipsburg |
| Itinerary |
Bridgetown, Port Elizabeth, Bequia, Mayreau Island, Rodney Bay, Le Marin, Terre-de-Haut, Falmouth and Philipsburg
|
From Please Call
Plus substantial savings from Deluxe Cruises
9 Nights
Tropical Harmony
Tropical Harmony
Departure Date
22 Feb 26
| Cruise Line | Oceania Cruises |
| Cruise Type | Ocean |
| Ship | Oceania Insignia |
| Region | Caribbean |
| Departure Port | Bridgetown |
| Destination Port | Tampa, Florida |
| Itinerary |
Bridgetown, Oranjestad, Montego Bay, Costa Maya, Cozumel and Tampa, Florida
|
From £1,484pp
Plus substantial savings from Deluxe Cruises