Windstar Cruises

Windstar Cruises Itineraries (Page 12)

7 Nights

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

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14 Nights

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

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14 Nights

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

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7 Nights

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

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21 Nights

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

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14 Nights

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

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28 Nights

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

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7 Nights

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

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22 Nights

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

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9 Nights

Madrid & Southern Spain Winter Escapes Cruise Tour

Departure Date
23 Feb 26
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Star Legend
Region Mediterranean
Departure Port Madrid
Destination Port Barcelona
Itinerary
Barcelona, Barcelona, Barcelona, Barcelona, Valencia, Cartagena, Gibraltar, Málaga, Málaga, Palma de Mallorca and Barcelona

From £5,142pp

Plus substantial savings from Deluxe Cruises

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10 Nights

Tahiti & the Tuamotu Islands

Departure Date
23 Feb 26
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Star Breeze
Region Pacific
Departure Port Papeete, Tahiti
Destination Port Papeete, Tahiti
Itinerary

From £4,239pp

Plus substantial savings from Deluxe Cruises

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17 Nights

Star Collector: Twice the Tahiti

Departure Date
23 Feb 26
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Star Breeze
Region Pacific
Departure Port Papeete, Tahiti
Destination Port Papeete, Tahiti
Itinerary
Papeete, Tahiti, Fakarava, Rangiroa, Motu Mahaea, Society Islands, Bora-Bora, Bora-Bora, Huahine, Moorea, Papeete, Tahiti, Papeete, Tahiti, Moorea, Raiatea, Raiatea, Motu Mahaea, Society Islands, Bora-Bora, Bora-Bora, Huahine and Papeete, Tahiti

From £7,260pp

Plus substantial savings from Deluxe Cruises

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