<

Wind Surf Sailing Dates and Sailing Calendar

For more information, prices, and detailed day-by-day Wind Surf itineraries, please click one of the Wind Surf sailing dates below.

Get FREE Price Alerts

Subscribe to our weekly cruise deals email and enjoy FREE price change alerts and updates for this cruise and others like it.

We promise to protect your privacy and personal data. You can review our privacy policy here.

Sail Date

Itinerary Name and Ports

Duration

Save to Favorites

Priced From(per person)

Dec 7, 2024

(Saturday)

14 Night Ocean Crossing Cruise

From Lisbon, Portugal to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Lisbon, St John's, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
Call
For Price

Inside (double occupancy)

Learn More
Dec 21, 2024

(Saturday)

7 Night Classic Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$2,610

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Dec 21, 2024

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
Call
For Price

Oceanview Stateroom (double occupancy)

Learn More
Dec 28, 2024

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$4,167

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Dec 28, 2024

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
Call
For Price

Suite (double occupancy)

Learn More
Jan 4, 2025

(Saturday)

7 Night Classic Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$3,251

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 4, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Falmouth Harbour, Gustavia St. Barts, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Road Bay, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
$5,519

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 11, 2025

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Gustavia St. Barts, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Road Bay, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$3,267

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 11, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Gustavia St. Barts, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Road Bay, Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
$5,219

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 18, 2025

(Saturday)

7 Night Classic Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$3,251

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 18, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
$5,519

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 25, 2025

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$3,267

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 1, 2025

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$3,567

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 1, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
$5,659

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 8, 2025

(Saturday)

7 Night Classic Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$3,251

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 8, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Falmouth Harbour, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
$5,219

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 15, 2025

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$3,267

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 15, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
$5,219

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 22, 2025

(Saturday)

7 Night Classic Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$3,251

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 22, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
$5,519

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More

Browse Wind Surf Itineraries by Month

Overlay Title