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Wind Surf June 2025 Itinerary

For more information, prices, and detailed day-by-day Wind Surf itineraries in June 2025, please click one of the scheduled Wind Surf sailing dates below.

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Sail Date

Itinerary Name and Ports

Duration

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Priced From(per person)

Dec 21, 2025

(Sunday)

7 Night Classic Caribbean Cruise

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

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

7 Nights

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$4,351

Oceanview Stateroom (double occupancy)

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Dec 21, 2025

(Sunday)

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, Mayreau, 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)

Special Promotions
14 Nights

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Suite (double occupancy)

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Dec 28, 2025

(Sunday)

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

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$4,267

Oceanview Stateroom (double occupancy)

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Jan 4, 2026

(Sunday)

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

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$4,210

Oceanview Stateroom (double occupancy)

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Jan 4, 2026

(Sunday)

14 Night Star Collector Leeward and Windward Caribbean Havens Cruise

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

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown

14 Nights

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$7,647

Oceanview Stateroom (double occupancy)

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Jan 4, 2026

(Sunday)

21 Night Star Collector A Lesser Antilles Odyssey Cruise

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

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Beq

21 Nights

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$11,570

Oceanview Stateroom (double occupancy)

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Jan 4, 2026

(Sunday)

28 Night Star Collector The Best of the Windward and Leeward Isles Cruise

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

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Beq

28 Nights

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Oceanview Stateroom (double occupancy)

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Jan 4, 2026

(Sunday)

55 Night Star Collector Grand Caribbean Adventure 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), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Beq

55 Nights

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Oceanview Stateroom (double occupancy)

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Jan 11, 2026

(Sunday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

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

Ports: Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown

7 Nights

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$6,436

Oceanview Stateroom (double occupancy)

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Jan 11, 2026

(Sunday)

14 Night Star Collector Antilles Adventures Cruise

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

Ports: Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St George's, Bridgetown

14 Nights

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$14,759

Oceanview Stateroom (double occupancy)

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