Caribbean cruises Windstar Cruises - 76 deals for 2024, 2025
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2026
Sint Maarten - Antigua and Barbuda - United Kingdom - British Virgin Islands -
Tour Operator: Windstar Cruises
Ship: Wind Surf
Depart from: Sint Maarten
Length: 7 Nights
Date: 22 March 2025
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 -
Tour Operator: Windstar Cruises
Ship: Star Pride
Depart from: Bridgetown
Length: 7 Nights
Date: 29 March 2025
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
Puerto Rico - Virgin Islands - Sint Maarten - Saint Kitts and Nevis - Saint
Tour Operator: Windstar Cruises
Ship: Star Pride
Depart from: San Juan
Length: 7 Nights
Date: 01 November 2025
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
Puerto Rico - Grenada - Saint Vincent and the Grenadines - Sri Lanka - Guadeloupe -
Tour Operator: Windstar Cruises
Ship: Star Pride
Depart from: San Juan
Length: 7 Nights
Date: 08 November 2025
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
Puerto Rico - Virgin Islands - Sint Maarten - Saint Kitts and Nevis - Saint
Tour Operator: Windstar Cruises
Ship: Star Pride
Depart from: San Juan
Length: 7 Nights
Date: 15 November 2025
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
Tour Operator: Windstar Cruises
Ship: Wind Spirit
Depart from: Bridgetown
Length: 11 Nights
Date: 18 November 2025
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
Puerto Rico - Grenada - Saint Vincent and the Grenadines - Sri Lanka - Guadeloupe -
Tour Operator: Windstar Cruises
Ship: Star Pride
Depart from: San Juan
Length: 7 Nights
Date: 22 November 2025
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
Puerto Rico - Virgin Islands - Sint Maarten - Saint Kitts and Nevis - Saint
Tour Operator: Windstar Cruises
Ship: Star Pride
Depart from: San Juan
Length: 7 Nights
Date: 29 November 2025
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
Puerto Rico - Virgin Islands - Sint Maarten - Saint Kitts and Nevis - Saint
Tour Operator: Windstar Cruises
Ship: Star Pride
Depart from: San Juan
Length: 14 Nights
Date: 29 November 2025
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
Tour Operator: Windstar Cruises
Ship: Wind Surf
Depart from: Sint Maarten
Length: 5 Nights
Date: 02 December 2025
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
Tour Operator: Windstar Cruises
Ship: Wind Surf
Depart from: Sint Maarten
Length: 7 Nights
Date: 07 December 2025
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 -
Tour Operator: Windstar Cruises
Ship: Wind Surf
Depart from: Sint Maarten
Length: 7 Nights
Date: 14 December 2025
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
Tour Operator: Windstar Cruises
Ship: Wind Surf
Depart from: Sint Maarten
Length: 7 Nights
Date: 21 December 2025
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
Panama - Spain - Colombia - Aruba - Netherlands Antilles - Grenada - Saint Vincent
Tour Operator: Windstar Cruises
Ship: Wind Spirit
Depart from: Colon
Length: 11 Nights
Date: 27 December 2025
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 -
Tour Operator: Windstar Cruises
Ship: Wind Surf
Depart from: Sint Maarten
Length: 7 Nights
Date: 28 December 2025
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 -
Tour Operator: Windstar Cruises
Ship: Wind Surf
Depart from: Sint Maarten
Length: 7 Nights
Date: 04 January 2026
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
Barbados - Dominica - Sri Lanka - Guadeloupe - Montserrat - Saint Barthelemy - Saint
Tour Operator: Windstar Cruises
Ship: Wind Spirit
Depart from: Bridgetown
Length: 7 Nights
Date: 07 January 2026
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 -
Tour Operator: Windstar Cruises
Ship: Wind Surf
Depart from: Sint Maarten
Length: 7 Nights
Date: 11 January 2026
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
Tour Operator: Windstar Cruises
Ship: Wind Spirit
Depart from: Sint Maarten
Length: 10 Nights
Date: 14 January 2026
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 -
Tour Operator: Windstar Cruises
Ship: Wind Surf
Depart from: Bridgetown
Length: 7 Nights
Date: 18 January 2026
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