All Caribbean Cruises with Windstar Cruises in March 2026

  • 2025
  • 2027
18 cruises
sold out
Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,873
price per person Taxes included
Wind Surf | Mar. 21, 2026
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
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $4,064
price per person Taxes included
Wind Surf | Mar. 28, 2026
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
sold out
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $4,064
price per person Taxes included
Wind Surf | Mar. 14, 2026
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
Bridgetown Itinerary Caribbean
External from $4,145
price per person Taxes included
Wind Spirit | Mar. 15, 2026
Duration: 6 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Tobago Cays,
3. Pigeon Island,
4. Pigeon Island,
5. Castries,
6. Pitons,
7. Mayreau,
8. Bequia,
9. Bridgetown
sold out
Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Martinique, Sri Lanka
Bridgetown Itinerary Caribbean
External from $4,310
price per person Taxes included
Wind Spirit | Mar. 21, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Fort de france,
7. Pigeon Island,
8. Bridgetown
sold out
Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada
Bridgetown Itinerary Caribbean
External from $4,310
price per person Taxes included
Wind Spirit | Mar. 14, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Kingstown,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown
sold out
Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada
Bridgetown Itinerary Caribbean
External from $4,310
price per person Taxes included
Wind Spirit | Mar. 14, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Kingstown,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown
Philipsburg Itinerary Caribbean
External from $4,367
price per person Taxes included
Wind Surf | Mar. 21, 2026
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
Philipsburg Itinerary Caribbean
External from $4,394
price per person Taxes included
Wind Surf | Mar. 28, 2026
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
Bridgetown Itinerary Caribbean
External from $4,475
price per person Taxes included
Wind Spirit | Mar. 21, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Mayreau,
7. Bridgetown
sold out
Barbados, Saint Kitts and Nevis, Virgin Islands, Guadeloupe, Dominica, Sri Lanka
Bridgetown Itinerary Caribbean
External from $4,475
price per person Taxes included
Wind Spirit | Mar. 7, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. St. John ,
5. Les Saintes,
6. Roseau,
7. Pigeon Island,
8. Bridgetown
sold out
Barbados, Saint Kitts and Nevis, Virgin Islands, Guadeloupe, Dominica, Saint Vincent and the Grenadines
Bridgetown Itinerary Caribbean
External from $4,475
price per person Taxes included
Wind Spirit | Mar. 7, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. St. John ,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
Oranjestad Itinerary Caribbean
Suite from $4,480
price per person Taxes included
Star Pride | Mar. 15, 2026
Duration: 7 nights
Departure from: Oranjestad Landing: Bridgetown
Itinerary:
1. Oranjestad,
2. Kralendijk,
3. navigation,
4. Pigeon Island,
5. Pitons,
6. Bequia,
7. Mayreau,
8. Scarborough,
9. Bridgetown
sold out
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $4,559
price per person Taxes included
Wind Surf | Mar. 7, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg
Bridgetown Itinerary Caribbean
External from $4,639
price per person Taxes included
Wind Spirit | Mar. 7, 2026
Duration: 8 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Saint Johns,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Fort de france,
9. Bridgetown
Philipsburg Itinerary Caribbean
External from $4,723
price per person Taxes included
Wind Surf | Mar. 7, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg
Philipsburg Itinerary Caribbean
External from $5,218
price per person Taxes included
Wind Surf | Mar. 14, 2026
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
sold out
Aruba, Netherlands Antilles, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, United Kingdom, Barbados
Oranjestad Itinerary Caribbean
Suite from $5,303
price per person Taxes included
Star Pride | Mar. 15, 2026
Duration: 7 nights
Departure from: Oranjestad Landing: Bridgetown
Itinerary:
1. Oranjestad,
2. Kralendijk,
3. navigation,
4. Pigeon Island,
5. Pitons,
6. Bequia,
7. Mayreau,
8. Man of War Bay,
9. Bridgetown
18 cruises