Caribbean cruises Windstar Cruises - 76 deals for 2024, 2025

November
2024
December
2024
January
2025
February
2025
March
2025
April
2025
May
2025
June
2025
July
2025
August
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September
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October
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November
2025
December
2025
January
2026
February
2026
March
2026

Sint Maarten - Antigua and Barbuda - United Kingdom - British Virgin Islands -

$3,932 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Surf
location_on Depart from: Sint Maarten
bedtime Length: 7 Nights
calendar_month Date: 22 March 2025
calendar_month Arrival Date: 29 March 2025
Itinerary:
1 Sint Maarten 2 Falmouth Harbour 3 Anguilla 4 Tortola Island 4 Jost Van Dyke 5 Jost Van Dyke 6 Virgin Gorda 7 Gustavia 8 Sint Maarten

Barbados - Sri Lanka - Saint Lucia - Martinique - Saint Vincent and the Grenadines -

$3,761 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Star Pride
location_on Depart from: Bridgetown
bedtime Length: 7 Nights
calendar_month Date: 29 March 2025
calendar_month Arrival Date: 05 April 2025
Itinerary:
1 Bridgetown 2 Pigeon Island 3 Pigeon Island 3 Castries 3 Pitons 4 Fort de france 5 Mayreau 6 Saint George 7 Bequia 8 Bridgetown
sold out

Puerto Rico - Virgin Islands - Sint Maarten - Saint Kitts and Nevis - Saint

anchor Tour Operator: Windstar Cruises
directions_boat Ship: Star Pride
location_on Depart from: San Juan
bedtime Length: 7 Nights
calendar_month Date: 01 November 2025
calendar_month Arrival Date: 08 November 2025
Itinerary:
1 San Juan 2 St. John 3 Sint Maarten 4 Basseterre 5 Gustavia 6 Jost Van Dyke 7 Virgin Gorda 8 San Juan
sold out

Puerto Rico - Grenada - Saint Vincent and the Grenadines - Sri Lanka - Guadeloupe -

anchor Tour Operator: Windstar Cruises
directions_boat Ship: Star Pride
location_on Depart from: San Juan
bedtime Length: 7 Nights
calendar_month Date: 08 November 2025
calendar_month Arrival Date: 15 November 2025
Itinerary:
1 San Juan 2 Navigation 3 Saint George 4 Bequia 5 Pigeon Island 6 Les Saintes 7 Sint Maarten 8 San Juan
sold out

Puerto Rico - Virgin Islands - Sint Maarten - Saint Kitts and Nevis - Saint

anchor Tour Operator: Windstar Cruises
directions_boat Ship: Star Pride
location_on Depart from: San Juan
bedtime Length: 7 Nights
calendar_month Date: 15 November 2025
calendar_month Arrival Date: 22 November 2025
Itinerary:
1 San Juan 2 St. John 3 Sint Maarten 4 Basseterre 5 Gustavia 6 Jost Van Dyke 7 Virgin Gorda 8 San Juan

Barbados - Saint Vincent and the Grenadines - Grenada - Netherlands Antilles - Aruba

$5,985 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Spirit
location_on Depart from: Bridgetown
bedtime Length: 11 Nights
calendar_month Date: 18 November 2025
calendar_month Arrival Date: 29 November 2025
Itinerary:
1 Bridgetown 2 Bequia 3 Mayreau 4 Saint George 5 Navigation 6 Kralendijk 7 Willemstad 8 Oranjestad 9 Navigation 10 Cartagena 11 Navigation 12 Colon
sold out

Puerto Rico - Grenada - Saint Vincent and the Grenadines - Sri Lanka - Guadeloupe -

anchor Tour Operator: Windstar Cruises
directions_boat Ship: Star Pride
location_on Depart from: San Juan
bedtime Length: 7 Nights
calendar_month Date: 22 November 2025
calendar_month Arrival Date: 29 November 2025
Itinerary:
1 San Juan 2 Navigation 3 Saint George 4 Bequia 5 Pigeon Island 6 Les Saintes 7 Sint Maarten 8 San Juan
sold out

Puerto Rico - Virgin Islands - Sint Maarten - Saint Kitts and Nevis - Saint

anchor Tour Operator: Windstar Cruises
directions_boat Ship: Star Pride
location_on Depart from: San Juan
bedtime Length: 7 Nights
calendar_month Date: 29 November 2025
calendar_month Arrival Date: 06 December 2025
Itinerary:
1 San Juan 2 St. John 3 Sint Maarten 4 Basseterre 5 Gustavia 6 Jost Van Dyke 7 Virgin Gorda 8 San Juan
sold out

Puerto Rico - Virgin Islands - Sint Maarten - Saint Kitts and Nevis - Saint

anchor Tour Operator: Windstar Cruises
directions_boat Ship: Star Pride
location_on Depart from: San Juan
bedtime Length: 14 Nights
calendar_month Date: 29 November 2025
calendar_month Arrival Date: 13 December 2025
Itinerary:
1 San Juan 2 St. John 3 Sint Maarten 4 Basseterre 5 Gustavia 6 Jost Van Dyke 7 Virgin Gorda 8 San Juan 9 Catalina Island 10 Santo Domingo 11 Navigation 12 Cartagena 13 Cartagena 14 San Blas Island 15 Colon

Sint Maarten - British Virgin Islands - Virgin Islands - Saint Barthelemy

$3,248 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Surf
location_on Depart from: Sint Maarten
bedtime Length: 5 Nights
calendar_month Date: 02 December 2025
calendar_month Arrival Date: 07 December 2025
Itinerary:
1 Sint Maarten 2 Tortola Island 2 Jost Van Dyke 3 Jost Van Dyke 4 Virgin Gorda 5 Gustavia 6 Sint Maarten

Sint Maarten - United States - Dominica - Sri Lanka - Guadeloupe - Saint Barthelemy

$3,932 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Surf
location_on Depart from: Sint Maarten
bedtime Length: 7 Nights
calendar_month Date: 07 December 2025
calendar_month Arrival Date: 14 December 2025
Itinerary:
1 Sint Maarten 2 Charlestown 3 Roseau 4 Pigeon Island 5 Les Saintes 6 Gustavia 7 Basseterre 8 Sint Maarten

Sint Maarten - Antigua and Barbuda - United Kingdom - British Virgin Islands -

$4,104 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Surf
location_on Depart from: Sint Maarten
bedtime Length: 7 Nights
calendar_month Date: 14 December 2025
calendar_month Arrival Date: 21 December 2025
Itinerary:
1 Sint Maarten 2 Falmouth Harbour 3 Anguilla 4 Tortola Island 4 Jost Van Dyke 5 Jost Van Dyke 6 Virgin Gorda 7 Gustavia 8 Sint Maarten

Sint Maarten - United States - Dominica - Sri Lanka - Guadeloupe - Saint Barthelemy

$4,617 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Surf
location_on Depart from: Sint Maarten
bedtime Length: 7 Nights
calendar_month Date: 21 December 2025
calendar_month Arrival Date: 28 December 2025
Itinerary:
1 Sint Maarten 2 Charlestown 3 Roseau 4 Pigeon Island 5 Les Saintes 6 Gustavia 7 Basseterre 8 Sint Maarten
sold out

Panama - Spain - Colombia - Aruba - Netherlands Antilles - Grenada - Saint Vincent

anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Spirit
location_on Depart from: Colon
bedtime Length: 11 Nights
calendar_month Date: 27 December 2025
calendar_month Arrival Date: 07 January 2026
Itinerary:
1 Colon 2 Navigation 3 Cartagena 4 Santa Marta 5 Navigation 6 Oranjestad 7 Willemstad 8 Kralendijk 9 Navigation 10 Saint George 11 Mayreau 12 Bridgetown

Sint Maarten - Antigua and Barbuda - United Kingdom - British Virgin Islands -

$4,617 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Surf
location_on Depart from: Sint Maarten
bedtime Length: 7 Nights
calendar_month Date: 28 December 2025
calendar_month Arrival Date: 04 January 2026
Itinerary:
1 Sint Maarten 2 Falmouth Harbour 3 Anguilla 4 Tortola Island 4 Jost Van Dyke 5 Jost Van Dyke 6 Virgin Gorda 7 Gustavia 8 Sint Maarten

Sint Maarten - Antigua and Barbuda - United Kingdom - British Virgin Islands -

$4,275 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Surf
location_on Depart from: Sint Maarten
bedtime Length: 7 Nights
calendar_month Date: 04 January 2026
calendar_month Arrival Date: 11 January 2026
Itinerary:
1 Sint Maarten 2 Falmouth Harbour 3 Anguilla 4 Tortola Island 4 Jost Van Dyke 5 Jost Van Dyke 6 Virgin Gorda 7 Gustavia 8 Sint Maarten
sold out

Barbados - Dominica - Sri Lanka - Guadeloupe - Montserrat - Saint Barthelemy - Saint

anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Spirit
location_on Depart from: Bridgetown
bedtime Length: 7 Nights
calendar_month Date: 07 January 2026
calendar_month Arrival Date: 14 January 2026
Itinerary:
1 Bridgetown 2 Roseau 3 Pigeon Island 4 Les Saintes 5 Little Bay 6 Gustavia 7 Basseterre 8 Sint Maarten

Sint Maarten - Saint Kitts and Nevis - Montserrat - Saint Barthelemy - France -

$4,275 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Surf
location_on Depart from: Sint Maarten
bedtime Length: 7 Nights
calendar_month Date: 11 January 2026
calendar_month Arrival Date: 18 January 2026
Itinerary:
1 Sint Maarten 2 Basseterre 3 Little Bay 4 Gustavia 5 Deshaies 6 Roseau 7 Pigeon Island 8 Bridgetown

Sint Maarten - Saint Kitts and Nevis - Dominica - Saint Lucia - Saint Vincent and

$5,985 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Spirit
location_on Depart from: Sint Maarten
bedtime Length: 10 Nights
calendar_month Date: 14 January 2026
calendar_month Arrival Date: 24 January 2026
Itinerary:
1 Sint Maarten 2 Basseterre 3 Roseau 4 Castries 5 Bequia 6 Saint George 7 Mayreau 8 Fort de france 9 Les Saintes 10 Gustavia 11 Sint Maarten

Barbados - Martinique - Saint Lucia - Sri Lanka - Saint Vincent and the Grenadines -

$4,275 Prices p.p. Incl. taxes
anchor Tour Operator: Windstar Cruises
directions_boat Ship: Wind Surf
location_on Depart from: Bridgetown
bedtime Length: 7 Nights
calendar_month Date: 18 January 2026
calendar_month Arrival Date: 25 January 2026
Itinerary:
1 Bridgetown 2 Fort de france 3 Castries 3 Pigeon Island 4 Pigeon Island 5 Bequia 6 Mayreau 7 Saint George 8 Bridgetown