All cruises › Windstar Caribbean cruises from Philipsburg
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Windstar · Wind Surf
- 3 ports
- One way
- Sails Mar 27, 2027
- From $2,805 pp
- Luxury
- Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
- Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk
- Lisbon Sintra: Pena Palace, Cabo da Roca & Cascais (small-group day trip)
Windstar · Wind Surf
- 7 ports
- Round trip
- Sails Jan 2, 2027
- From $2,798 pp
- Luxury
- Falmouth Harbour Antigua Stingray City: Private Shallow-Water Encounter
- Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran
- Sopers Hole The Baths of Virgin Gorda: Private Yacht Day Charter
Windstar · Wind Surf
- 7 ports
- Round trip
- Sails Jan 16, 2027
- From $3,638 pp
- Luxury
- Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran
- Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
- Sopers Hole The Baths of Virgin Gorda: Private Yacht Day Charter
Windstar · Wind Surf
- 7 ports
- Round trip
- Sails Feb 27, 2027
- From $3,008 pp
- Luxury
- Sopers Hole The Baths of Virgin Gorda: Private Yacht Day Charter
- Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
- Virgin Gorda The Baths National Park: Private Guided Boulders & Devil's Bay
Windstar · Wind Surf
- 7 ports
- Round trip
- Sails Mar 13, 2027
- From $2,868 pp
- Luxury
- Falmouth Harbour Antigua Stingray City: Private Shallow-Water Encounter
- Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran
- Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail