All Caribbean Cruises with Windstar Cruises in March 2026

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 $2,849
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 $2,990
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 $2,990
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
Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Martinique, Sri Lanka
Bridgetown Itinerary Caribbean
External from $3,171
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 $3,171
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 $3,171
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, Saint Kitts and Nevis, Virgin Islands, Guadeloupe, Dominica, Sri Lanka
Bridgetown Itinerary Caribbean
External from $3,292
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 $3,292
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 $3,295
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 $3,354
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 $3,777
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
Bridgetown Itinerary Caribbean
External from $3,777
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. Mayreau,
8. Bridgetown
Philipsburg Itinerary Caribbean
External from $3,819
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
Aruba, Netherlands Antilles, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, United Kingdom, Barbados
Oranjestad Itinerary Caribbean
Suite from $3,901
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
Philipsburg Itinerary Caribbean
External from $3,960
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
sold out
Barbados, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Martinique
Bridgetown Itinerary Caribbean
External from $4,019
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 $4,081
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
Philipsburg Itinerary Caribbean
External from $4,081
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
18 cruises