home › Windstar Cruises › All Caribbean Cruises with Windstar Cruises

All Caribbean Cruises with Windstar Cruises

  • 2027
  • 2028
January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026 December 2026
January 2027 February 2027 March 2027 April 2027 May 2027 June 2027 July 2027 August 2027 September 2027 October 2027 November 2027 December 2027
January 2028 February 2028 March 2028
141 cruises
Caribbean: Aruba, Netherlands Antilles, Saint Vincent and the Grenadines, Saint Lucia, Trinidad and Tobago, Barbados
Oranjestad Itinerary Caribbean
Suite from £2,433
price per person Taxes included
See the cruise Book
Star Pride | 15 Mar 2026
Duration: 7 nights
Departure from: Oranjestad Landing: Bridgetown
Itinerary:
1. Oranjestad,
2. Kralendijk,
3. navigation,
4. Kingstown,
5. Pitons,
6. Bequia,
7. Mayreau,
8. Scarborough,
9. Bridgetown
Caribbean: Sint Maarten, British Virgin Islands, Saint Barthelemy, Virgin Islands
Philipsburg Itinerary Caribbean
External from £2,458
price per person Taxes included
See the cruise Book
Wind Surf | 3 Jan 2028
Duration: 6 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Gustavia,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Tortola Island,
7. Philipsburg
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,533
price per person Taxes included
See the cruise Book
Wind Surf | 12 Dec 2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from £2,533
price per person Taxes included
See the cruise Book
Wind Surf | 28 Nov 2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Gustavia,
7. Basseterre,
8. Philipsburg
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from £2,543
price per person Taxes included
See the cruise Book
Star Pride | 15 Nov 2027
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from £2,543
price per person Taxes included
See the cruise Book
Star Pride | 1 Nov 2027
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,547
price per person Taxes included
See the cruise Book
Wind Surf | 5 Dec 2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from £2,603
price per person Taxes included
See the cruise Book
Star Pride | 22 Nov 2027
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from £2,603
price per person Taxes included
See the cruise Book
Star Pride | 8 Nov 2027
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
Caribbean: Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,636
price per person Taxes included
See the cruise Book
Wind Surf | 16 Jan 2028
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
141 cruises