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Wind Surf
Windstar Cruises
Jan 23, 2027 - Jan 30, 2027 (7 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$3,937pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Les Saintes, F.W.I. • Mayreau Island, Saint Vincent and the Grenadines • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$2,922pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 9, 2027 - Jan 23, 2027 (14 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Les Saintes, F.W.I. • Mayreau Island, Saint Vincent and the Grenadines • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Falmouth (English Harbour), Antigua & Barbuda • Philipsburg, St. Maarten
Average Starting Price
$5,860pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
Philipsburg, St. Maarten • Gustavia, St. Barts • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten
Average Starting Price
$3,552pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Wind Surf
Windstar Cruises
Jan 2, 2027 - Jan 16, 2027 (14 Nights)
Philipsburg, St. Maarten • Falmouth (English Harbour), Antigua & Barbuda • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Philipsburg, St. Maarten • Charlestown, Nevis • Les Saintes, F.W.I. • Mayreau Island, Saint Vincent and the Grenadines • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$5,580pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 26, 2026 - Jan 9, 2027 (14 Nights)
Philipsburg, St. Maarten • Gustavia, St. Barts • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Falmouth (English Harbour), Antigua & Barbuda • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$6,280pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Wind Surf
Windstar Cruises
Dec 19, 2026 - Jan 2, 2027 (14 Nights)
Philipsburg, St. Maarten • Gustavia, St. Barts • Falmouth (English Harbour), Antigua & Barbuda • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Gustavia, St. Barts • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten
Average Starting Price
$6,770pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

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