Caribbean: United States, Grenada, Antigua and Barbuda

Suite from $3,338
price per person Taxes included

See the cruise

Book Online

Star Pride | Oct. 19, 2025

Duration: 7 nights

Departure from: New York Landing: Saint Johns

Itinerary:

1. New York,

2. navigation,

3. navigation,

4. Saint George,

5. Saint George,

6. navigation,

7. navigation,

8. Saint Johns

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $3,377
price per person Taxes included

Wind Surf | Dec. 2, 2025

Duration: 5 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Tortola Island,

3. Jost Van Dyke,

4. Jost Van Dyke,

5. Virgin Gorda,

6. Gustavia,

7. Philipsburg

Caribbean: Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Suite from $3,661
price per person Taxes included

See the cruise

Book Online

Star Pride | Oct. 26, 2025

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

Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

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

Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External from $3,873
price per person Taxes included

Wind Surf | Dec. 7, 2025

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: Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Suite from $3,924
price per person Taxes included

See the cruise

Book Online

Star Pride | Nov. 2, 2025

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

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,064
price per person Taxes included

Wind Surf | Dec. 14, 2025

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

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

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

Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

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

Caribbean: Barbados, Saint Vincent and the Grenadines, Sri Lanka, Saint Lucia

External from $4,145
price per person Taxes included

See the cruise Book

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

Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Dominica, Sri Lanka, Barbados

External from $4,152
price per person Taxes included

Wind Spirit | Feb. 28, 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Bridgetown

Itinerary:

1. Philipsburg,

2. Basseterre,

3. Gustavia,

4. St. John ,

5. Les Saintes,

6. Roseau,

7. Pigeon Island,

8. Bridgetown

Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Suite from $4,168
price per person Taxes included

See the cruise

Book Online

Star Pride | Nov. 8, 2026

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

Suite from $4,168
price per person Taxes included

See the cruise

Book Online

Star Pride | Dec. 6, 2026

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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,201
price per person Taxes included

See the cruise Book

Wind Surf | Dec. 2, 2025

Duration: 5 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Tortola Island,

3. Jost Van Dyke,

4. Jost Van Dyke,

5. Virgin Gorda,

6. Gustavia,

7. Philipsburg

Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External from $4,203
price per person Taxes included

See the cruise

Book Online

Wind Surf | Dec. 7, 2025

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, Guadeloupe, Saint Vincent and the Grenadines, Dominica, Saint Kitts and Nevis, Saint Barthelemy

External from $4,203
price per person Taxes included

See the cruise

Book Online

Wind Surf | Jan. 9, 2027

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Les Saintes,

4. Mayreau,

5. Roseau,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Sint Maarten, United States, Dominica, Sri Lanka, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis

External from $4,203
price per person Taxes included

Wind Surf | Feb. 28, 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Roseau,

4. Pigeon Island,

5. Les Saintes,

6. Gustavia,

7. Basseterre,

8. Philipsburg

Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,218
price per person Taxes included

Wind Spirit | Jan. 31, 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

Caribbean: Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands

Suite from $4,221
price per person Taxes included

See the cruise

Book Online

Star Pride | Nov. 29, 2026

Duration: 7 nights

Departure from: Saint Johns Landing: Saint Johns

Itinerary:

1. Saint Johns,

2. St. John ,

3. Gustavia,

4. Basseterre,

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

Suite from $4,221
price per person Taxes included

See the cruise

Book Online

Star Pride | Nov. 15, 2026

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 Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands

Suite from $4,221
price per person Taxes included

See the cruise

Book Online

Star Pride | Dec. 13, 2026

Duration: 7 nights

Departure from: Saint Johns Landing: Saint Johns

Itinerary:

1. Saint Johns,

2. St. John ,

3. Gustavia,

4. Basseterre,

5. Philipsburg,

6. Jost Van Dyke,

7. Virgin Gorda,

8. Saint Johns

Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,229
price per person Taxes included

See the cruise

Book Online

Wind Surf | Jan. 16, 2027

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Tortola Island,

3. Tortola Island,

4. Jost Van Dyke,

5. Jost Van Dyke,

6. Virgin Gorda,

7. Gustavia,

8. navigation,

9. Philipsburg

Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,229
price per person Taxes included

See the cruise

Book Online

Wind Surf | Jan. 2, 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

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,300
price per person Taxes included

Wind Surf | Jan. 4, 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

Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Martinique, Sri Lanka

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

Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada

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

Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada

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

Sint Maarten, United States, Dominica, Sri Lanka, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External from $4,311
price per person Taxes included

Wind Spirit | Feb. 7, 2026

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Roseau,

4. Pigeon Island,

5. Les Saintes,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin

Suite from $4,333
price per person Taxes included

Star Pride | Nov. 9, 2025

Duration: 7 nights

Departure from: San Juan Landing: San Juan

Itinerary:

1. San Juan,

2. navigation,

3. Saint George,

4. Bequia,

5. Pigeon Island,

6. Les Saintes,

7. Marigot,

8. San Juan

Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin

Suite from $4,333
price per person Taxes included

Star Pride | Nov. 23, 2025

Duration: 7 nights

Departure from: San Juan Landing: San Juan

Itinerary:

1. San Juan,

2. navigation,

3. Saint George,

4. Bequia,

5. Pigeon Island,

6. Les Saintes,

7. Marigot,

8. San Juan

All Caribbean Cruises with Windstar Cruises