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Windstar & Signature Travel Network

Windstar & Signature Travel Network Caribbean Collection

Hidden Harbors. Private Beaches.
Island-Hopping in Windstar Style.

Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht and a yearning to escape to the incomparable Caribbean Islands. Whether you’re cruising through turquoise waters or lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.

The Additional Signature Exclusive Amenities

• Up to $300 SBC per stateroom or suite
• Available on select sailing dates
• Combinable with Windstar Cruises national promotions

MATCHING CRUISES:
28 Results

Listings per page:

17-night Star Collector – Rainforests and Rum Refreshments — Costa Rica to the Bahamas via the Panama Canal Cruise

St. Maarten (Philipsburg)/Puerto Caldera

11/18/2020

Ports: St. Maarten (Philipsburg), Virgin Gorda, At Sea, At Sea, Kralendijk, Willemstad, Curacao, Oranjestad, Aruba, At Sea, Cartagena (Colombia), At Sea, Colon (Panama), Panama Canal, Balboa, Balboa, At Sea, Isla Parida, Golfo Dulce (Puerto Jimenez), Quepos, and Puerto Caldera

Windstar Cruises

Wind Star
#1366569

17-night Star Collector – Rainforests and Rum Refreshments — Costa Rica to the Bahamas via the Panama Canal Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

6-night Yachtsman's Caribbean Cruise

Roundtrip St. Maarten (Philipsburg)

11/29/2020

Ports: St. Maarten (Philipsburg), Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, Virgin Gorda, Gustavia, Falmouth Harbour, Antigua, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1353739

6-night Yachtsman's Caribbean Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Classic Caribbean Cruise

Roundtrip St. Maarten (Philipsburg)

12/05/2020

Ports: St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Basseterre, St. Kitts, Gustavia, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1353740

7-night Classic Caribbean Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – Caribbean Explorations Cruise

Roundtrip St. Maarten (Philipsburg)

12/05/2020

Ports: St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Basseterre, St. Kitts, Gustavia, St. Maarten (Philipsburg), Road Bay, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, Virgin Gorda, Gustavia, Falmouth Harbour, Antigua, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1356580

14-night Star Collector – Caribbean Explorations Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – Caribbean Explorations Cruise

Roundtrip St. Maarten (Philipsburg)

12/19/2020

Ports: St. Maarten (Philipsburg), Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Gustavia, Basseterre, St. Kitts, Charlestown, St. Maarten (Philipsburg), Falmouth Harbour, Antigua, Gustavia, At Sea, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1356582

14-night Star Collector – Caribbean Explorations Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Yachtsman's Caribbean Cruise

Roundtrip St. Maarten (Philipsburg)

12/26/2020

Ports: St. Maarten (Philipsburg), Falmouth Harbour, Antigua, Gustavia, At Sea, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1353746

7-night Yachtsman's Caribbean Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – Leeward and Windward Caribbean Havens Cruise

St. Maarten (Philipsburg)/Bridgetown (Barbados)

12/26/2020

Ports: St. Maarten (Philipsburg), Falmouth Harbour, Antigua, Gustavia, At Sea, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, St. Maarten (Philipsburg), Basseterre, St. Kitts, Gustavia, Little Bay, Iles des Saintes, Roseau, Dominica, Pigeon Island, St. Lucia, and Bridgetown (Barbados)

Windstar Cruises

Wind Surf
#1360602

14-night Star Collector – Leeward and Windward Caribbean Havens Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Windward Islands Surf & Sunsets Cruise

Roundtrip San Juan

01/02/2021

Ports: San Juan, At Sea, St. George's, Grenada, Bequia, Grenadines, Pigeon Island, St. Lucia, Iles des Saintes, St. Maarten (Philipsburg), and San Juan

Windstar Cruises

Star Pride
#1353709

7-night Windward Islands Surf & Sunsets Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – Antilles Adventures Cruise

St. Maarten (Philipsburg)/Bridgetown (Barbados)

01/02/2021

Ports: St. Maarten (Philipsburg), Basseterre, St. Kitts, Gustavia, Little Bay, Iles des Saintes, Roseau, Dominica, Pigeon Island, St. Lucia, Bridgetown (Barbados), Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Castries, The Pitons, Anse Mitan, Mayreau, Grenadines, St. George's, Grenada, Bequia, Grenadines, and Bridgetown (Barbados)

Windstar Cruises

Wind Surf
#1360603

14-night Star Collector – Antilles Adventures Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night San Juan & the Virgin Islands Cruise

Roundtrip San Juan

01/09/2021

Ports: San Juan, Vieques, Gustavia, Little Bay, St. Maarten (Philipsburg), Great Harbour, Jost Van Dyke, Virgin Gorda, and San Juan

Windstar Cruises

Star Pride
#1353714

7-night San Juan & the Virgin Islands Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – The Biggest Little Treasures of the Lesser Antilles Cruise

Roundtrip Bridgetown (Barbados)

01/09/2021

Ports: Bridgetown (Barbados), Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Castries, The Pitons, Anse Mitan, Mayreau, Grenadines, St. George's, Grenada, Bequia, Grenadines, Bridgetown (Barbados), Roseau, Dominica, Little Bay, Gustavia, Falmouth Harbour, Antigua, Iles des Saintes, Pigeon Island, St. Lucia, and Bridgetown (Barbados)

Windstar Cruises

Wind Surf
#1361475

14-night Star Collector – The Biggest Little Treasures of the Lesser Antilles Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Uncovering the Windward Wonders of the Caribbean Cruise

Roundtrip Bridgetown (Barbados)

01/16/2021

Ports: Bridgetown (Barbados), Roseau, Dominica, Little Bay, Gustavia, Falmouth Harbour, Antigua, Iles des Saintes, Pigeon Island, St. Lucia, and Bridgetown (Barbados)

Windstar Cruises

Wind Surf
#1353752

7-night Uncovering the Windward Wonders of the Caribbean Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – The Biggest Little Treasures of the Lesser Antilles Cruise

Roundtrip Bridgetown (Barbados)

01/16/2021

Ports: Bridgetown (Barbados), Roseau, Dominica, Little Bay, Gustavia, Falmouth Harbour, Antigua, Iles des Saintes, Pigeon Island, St. Lucia, Bridgetown (Barbados), Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Castries, The Pitons, Anse Mitan, Mayreau, Grenadines, St. George's, Grenada, Bequia, Grenadines, and Bridgetown (Barbados)

Windstar Cruises

Wind Surf
#1361476

14-night Star Collector – The Biggest Little Treasures of the Lesser Antilles Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Jewels of the Windward Islands Cruise

Roundtrip Bridgetown (Barbados)

01/23/2021

Ports: Bridgetown (Barbados), Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Castries, The Pitons, Anse Mitan, Mayreau, Grenadines, St. George's, Grenada, Bequia, Grenadines, and Bridgetown (Barbados)

Windstar Cruises

Wind Surf
#1353749

7-night Jewels of the Windward Islands Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector: Lovely Leewards Cruise

Roundtrip San Juan

01/23/2021

Ports: San Juan, Vieques, Gustavia, Little Bay, St. Maarten (Philipsburg), Great Harbour, Jost Van Dyke, Virgin Gorda, San Juan, At Sea, St. George's, Grenada, Bequia, Grenadines, Pigeon Island, St. Lucia, Iles des Saintes, St. Maarten (Philipsburg), and San Juan

Windstar Cruises

Star Pride
#1353924

14-night Star Collector: Lovely Leewards Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – Antilles Adventures Cruise

Bridgetown (Barbados)/St. Maarten (Philipsburg)

01/23/2021

Ports: Bridgetown (Barbados), Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Castries, The Pitons, Anse Mitan, Mayreau, Grenadines, St. George's, Grenada, Bequia, Grenadines, Bridgetown (Barbados), Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Little Bay, Gustavia, Basseterre, St. Kitts, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1360604

14-night Star Collector – Antilles Adventures Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Windward Islands Surf & Sunsets Cruise

Roundtrip San Juan

01/30/2021

Ports: San Juan, At Sea, St. George's, Grenada, Bequia, Grenadines, Pigeon Island, St. Lucia, Iles des Saintes, St. Maarten (Philipsburg), and San Juan

Windstar Cruises

Star Pride
#1353711

7-night Windward Islands Surf & Sunsets Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – Caribbean Explorations Cruise

Roundtrip St. Maarten (Philipsburg)

02/06/2021

Ports: St. Maarten (Philipsburg), Road Bay, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, Virgin Gorda, Gustavia, Falmouth Harbour, Antigua, St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Basseterre, St. Kitts, Gustavia, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1356583

14-night Star Collector – Caribbean Explorations Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Classic Caribbean Cruise

Roundtrip St. Maarten (Philipsburg)

02/13/2021

Ports: St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Basseterre, St. Kitts, Gustavia, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1353741

7-night Classic Caribbean Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Windward Islands Surf and Sunsets Cruise

Roundtrip San Juan

02/27/2021

Ports: San Juan, At Sea, St. George's, Grenada, Bequia, Grenadines, Pigeon Island, St. Lucia, Iles des Saintes, St. Maarten (Philipsburg), and San Juan

Windstar Cruises

Star Pride
#1353713

7-night Windward Islands Surf and Sunsets Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – The Biggest Little Treasures of the Lesser Antilles Cruise

Roundtrip Bridgetown (Barbados)

03/06/2021

Ports: Bridgetown (Barbados), Roseau, Dominica, Little Bay, Gustavia, Falmouth Harbour, Antigua, Iles des Saintes, Pigeon Island, St. Lucia, Bridgetown (Barbados), Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Castries, The Pitons, Anse Mitan, Mayreau, Grenadines, St. George's, Grenada, Bequia, Grenadines, and Bridgetown (Barbados)

Windstar Cruises

Wind Surf
#1361478

14-night Star Collector – The Biggest Little Treasures of the Lesser Antilles Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Jewels of the Windward Islands Cruise

Roundtrip Bridgetown (Barbados)

03/13/2021

Ports: Bridgetown (Barbados), Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Castries, The Pitons, Anse Mitan, Mayreau, Grenadines, St. George's, Grenada, Bequia, Grenadines, and Bridgetown (Barbados)

Windstar Cruises

Wind Surf
#1353751

7-night Jewels of the Windward Islands Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – Antilles Adventures Cruise

Bridgetown (Barbados)/St. Maarten (Philipsburg)

03/13/2021

Ports: Bridgetown (Barbados), Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Castries, The Pitons, Anse Mitan, Mayreau, Grenadines, St. George's, Grenada, Bequia, Grenadines, Bridgetown (Barbados), Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Little Bay, Gustavia, Basseterre, St. Kitts, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1360609

14-night Star Collector – Antilles Adventures Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

21-night Star Collector – A Lesser Antilles Odyssey Cruise

Bridgetown (Barbados)/St. Maarten (Philipsburg)

03/13/2021

Ports: Bridgetown (Barbados), Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Castries, The Pitons, Anse Mitan, Mayreau, Grenadines, St. George's, Grenada, Bequia, Grenadines, Bridgetown (Barbados), Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Little Bay, Gustavia, Basseterre, St. Kitts, St. Maarten (Philipsburg), Falmouth Harbour, Antigua, At Sea, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, Virgin Gorda, Gustavia, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1361824

21-night Star Collector – A Lesser Antilles Odyssey Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – Leeward and Windward Caribbean Havens Cruise

Bridgetown (Barbados)/St. Maarten (Philipsburg)

03/20/2021

Ports: Bridgetown (Barbados), Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Little Bay, Gustavia, Basseterre, St. Kitts, St. Maarten (Philipsburg), Falmouth Harbour, Antigua, At Sea, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, Virgin Gorda, Gustavia, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1360611

14-night Star Collector – Leeward and Windward Caribbean Havens Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

10-night Colors of Key West and Central America Cruise

Colon (Panama)/Miami

03/27/2021

Ports: Colon (Panama), Bocas del Toro, Limon, Providencia Island, At Sea, Coxen Hole (Roatan), Belize City, Costa Maya, Cozumel, At Sea, and Miami

Windstar Cruises

Star Legend
#1353105

10-night Colors of Key West and Central America Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

7-night Yachtsman's Caribbean Cruise

Roundtrip St. Maarten (Philipsburg)

03/27/2021

Ports: St. Maarten (Philipsburg), Falmouth Harbour, Antigua, At Sea, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, Virgin Gorda, Gustavia, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1353758

7-night Yachtsman's Caribbean Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET

14-night Star Collector – Caribbean Explorations Cruise

Roundtrip St. Maarten (Philipsburg)

03/27/2021

Ports: St. Maarten (Philipsburg), Falmouth Harbour, Antigua, At Sea, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Virgin Gorda, Virgin Gorda, Gustavia, St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Basseterre, St. Kitts, Gustavia, and St. Maarten (Philipsburg)

Windstar Cruises

Wind Surf
#1356584

14-night Star Collector – Caribbean Explorations Cruise The Signature Collection – Exclusive Amenities
Special Offer: Windstar & Signature Travel Network
Promo Code: WSCARIBSIGNET
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