Windstar Cruises luxury itinerary
Wind Surf December 19-January 2 2026 Cruise & Offers
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN
Review the complete published itinerary, source-status notes, suite guidance, and current offer assistance with Deluxe Cruises.
December 19 2026-January 2 2027 ยท Voyage SU20261219-14D
Ports & shore experiences
Each destination is shown once. Select a destination to reveal every published call date and time, its voyage-specific overview, and exact shore experiences currently listed for this departure.
12 destination panels · 57 verified voyage-specific shore experiences · 0 panels with planning notices
Official voyage overview
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Barbuda, Soper’s Hole in Tortola, Gustavia in St. Barthémy, St. Lucia’s Pigeon Island and much more.
December 19, 2026, December 26, 2026 & January 2, 2027 PHILIPSBURG, ST. MAARTEN
About PHILIPSBURG, ST. MAARTEN
PHILIPSBURG, ST. MAARTEN is a Windstar destination in Sint Maarten within the Caribbean sailing region. Across the current published program, locally focused experience themes include America's Cup Sailboat Racing with Transfer to Airport, America's Cup Sailboat Racing with Transfer to Windstar Hotel & Post Island Tour with Transfer to Hotel. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- St. Maarten: America's Cup Sailboat Racing with Transfer to Windstar Hotel — Moderate-Strenuous activity
- St. Maarten: America's Cup Sailboat Racing with Transfer to Airport — Moderate-Strenuous activity
- St. Maarten, Post Island Tour with Transfer to Airport (Easy) — Easy activity
- St. Maarten, Post Island Tour with Transfer to Hotel (Easy) — Easy-Moderate activity
Published call times
- December 19, 2026 · Embarkation · Departure 19:00
- December 26, 2026 · Arrival 06:00 · Departure 19:00
- January 2, 2027 · Arrival 06:00 · Disembarkation
December 20 & December 27, 2026 GUSTAVIA, ST. BARTHELEMY
About GUSTAVIA, ST. BARTHELEMY
GUSTAVIA, ST. BARTHELEMY gives this stage of the itinerary its individual destination focus. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Barbuda, Soper’s Hole in Tortola, Gustavia in St.
Shore experiences currently listed
- Gustavia, Concierge Collection: Jet Ski — Strenuous activity
- St. Barts: Independent Explorer by Car (Easy-Moderate) — Easy-Moderate activity
- St Barts, Concierge Collection: St. Barthelemy Beach Day (Easy-Moderate) — Easy-Moderate activity
- St. Barts: Intimate Island Tour (Easy) — Easy activity
- Sailing Catamaran to St Barth Nature Reserve — Moderate activity
- St. Barts, Concierge Collection: Sunset Cruise (Easy-Moderate) — Easy-Moderate activity
- Gustavia, Concierge Collection: Scuba Dive 2 Tank — Strenuous activity
- Gustavia, Concierge Collection: Scuba Dive 1 Tank — Strenuous activity
- Gustavia, Concierge Collection: Savor St Barts — Moderate activity
Published call times
- December 20, 2026 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
- December 27, 2026 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
December 21, 2026 FALMOUTH HARBOUR, ANTIGUA
About FALMOUTH HARBOUR, ANTIGUA
FALMOUTH HARBOUR, ANTIGUA is a Windstar destination in Antigua and Barbuda within the Caribbean sailing region. Across the current published program, locally focused experience themes include Antigua Beach Escape, Make Your Own Rum & Open Course Canopy Challenge. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- Falmouth Harbour, Open Course Canopy Challenge (Strenuous) — Strenuous activity
- Falmouth Harbour, Nelson's Dockyard Walking Tour & Boat around English Harbour (Easy-Moderate) — Easy-Moderate activity
- Falmouth Harbour, Make Your Own Rum (Easy-Moderate) — Easy-Moderate activity
- Falmouth Harbour, Concierge Collection, Jet Ski Adventure (Moderate-Strenuous) — Moderate-Strenuous activity
- Falmouth Harbour, Antigua Beach Escape (Easy) — Easy activity
Published call times
- December 21, 2026 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
December 22, 2026 ROAD BAY, ANGUILLA
About ROAD BAY, ANGUILLA
ROAD BAY, ANGUILLA is a Windstar destination in Anguilla within the Caribbean sailing region. Across the current published program, locally focused experience themes include Island Exploration by Moke, Shoal Bay Beach Transfer & Snorkel Adventure by Speedboat. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- Road Bay, Island Exploration by Moke — Strenuous activity
- Road Bay, Iconic Island Highlights with Salt Tasting and Beach Time — Easy activity
- Road Bay, Shoal Bay Beach Transfer (Easy) — Easy activity
- Road Bay, Concierge Collection: Relaxing Day at Savi with Lunch — Easy-Moderate activity
- Road Bay, Snorkel Adventure by Speedboat (Moderate-Strenuous) — Moderate-Strenuous activity
Published call times
- December 22, 2026 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
December 23, 2026 SOPER'S HOLE, TORTOLA, BVI
About SOPER'S HOLE, TORTOLA, BVI
SOPER'S HOLE, TORTOLA, BVI gives this stage of the itinerary its individual destination focus. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Barbuda, Soper’s Hole in Tortola, Gustavia in St.
Shore experiences currently listed
- Tortola, Tortola Jeep & Beach Tour (Moderate) — Moderate activity
- Tortola, Tortola Scenic Island Tour(Easy) — Easy activity
- Tortola, Island Snorkel and Swim Adventure (Moderate-Strenuous) — Moderate-Strenuous activity
- Soper's Hole: Cane Garden Bay Beach Break (Moderate) — Moderate activity
Published call times
- December 23, 2026 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
December 23-24, 2026 GREAT HARBOUR, JOST VAN DYKE
About GREAT HARBOUR, JOST VAN DYKE
GREAT HARBOUR, JOST VAN DYKE is a Windstar destination in British Virgin Islands within the Caribbean sailing region. Across the current published program, locally focused experience themes include Catamaran Cruise & Swim to Norman Island. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- Jost Van Dyke, Catamaran Cruise & Swim to Norman Island (Moderate-Strenuous) — Moderate-Strenuous activity
Published call times
- December 23, 2026 · Arrival 19:00 · Departure 23:59 · Overnight stay · Watersports platform scheduled
- December 24, 2026 · Departure 22:00 · Overnight stay · Watersports platform scheduled
December 25, 2026 VIRGIN GORDA/PRICKLY PEAR, BVI
About VIRGIN GORDA/PRICKLY PEAR, BVI
VIRGIN GORDA/PRICKLY PEAR, BVI is a Windstar destination in British Virgin Islands within the Caribbean sailing region. Across the current published program, locally focused experience themes include Highlights & Bath Tour & Snorkel Adventure. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- Virgin Gorda: Highlights & Bath Tour (Moderate) — Strenuous activity
- Virgin Gorda: Snorkel Adventure (Moderate-Strenuous) — Moderate-Strenuous activity
Published call times
- December 25, 2026 · Arrival 08:00 · Departure 17:00
December 28, 2026 CHARLESTOWN
About CHARLESTOWN
CHARLESTOWN is a Windstar destination in Saint Kitts and Nevis within the Caribbean sailing region. Across the current published program, locally focused experience themes include Yachtsmanl Beach Escape, Quad Biking Adventure Single & Quad Biking Adventure. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- Charlestown, Yachtsmanl Beach Escape — Easy-Moderate activity
- Charlestown, Nevis Half Island & Botanical Garden — Easy-Moderate activity
- Charlestown, Quad Biking Adventure Single — Strenuous activity
- Charlestown, Quad Biking Adventure (Strenuous) — Strenuous activity
- Charlestown, Montravers Hike & Beach Break with Lunch — Moderate-Strenuous activity
- Charlestown, Coastal Boat Cruise Snorkel Adventure (Strenuous) — Strenuous activity
Published call times
- December 28, 2026 · Arrival 08:00 · Departure 17:00
December 29, 2026 ROSEAU, DOMINICA
About ROSEAU, DOMINICA
ROSEAU, DOMINICA is a Windstar destination in Dominica within the Caribbean sailing region. Across the current published program, locally focused experience themes include Dominica in a Day, Indian River Rowboat & River Tubing Adventure. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- Roseau, 4X4 Waterfall & Rainforest — Strenuous activity
- Roseau, Trafalgar Falls & Hot Springs (Moderate) — Moderate activity
- Roseau, River Tubing Adventure — Moderate-Strenuous activity
- Roseau, Concierge Collection: Cooking Caribbean Flavors & Lifestyles (Easy) — Easy activity
- Roseau, Conicerge Collection: Wet & Rugged Dominica (Strenuous) — Strenuous activity
- Roseau, Indian River Rowboat — Easy-Moderate activity
- Roseau, Whale & Dolphin Adventure — Easy activity
- Roseau, Dominica in a Day — Strenuous activity
- Roseau, Champagne Reef Snorkel Adventure (Strenuous) — Strenuous activity
Published call times
- December 29, 2026 · Arrival 08:00 · Departure 16:00
December 30, 2026 MAYREAU
About MAYREAU
MAYREAU is a Windstar destination in Saint Vincent and the Grenadines within the Caribbean sailing region. Across the current published program, locally focused experience themes include Grenadines Island Escape. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- Mayreau, Grenadines Island Escape (Moderate) — Moderate activity
Published call times
- December 30, 2026 · Arrival 08:00 · Departure 17:00
December 31, 2026 LES SAINTES, GUADELOUPE
About LES SAINTES, GUADELOUPE
LES SAINTES, GUADELOUPE is a Windstar destination in Guadeloupe within the Caribbean sailing region. Across the current published program, locally focused experience themes include Blue Escape Kayaking, Terre de Haut Panoramic Tour & Snorkel and Island Tour by Speed Boat. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- Les Saintes, Terre de Haut Panoramic Tour (Easy) — Easy activity
- Les Saintes, Snorkel and Island Tour by Speed Boat — Moderate-Strenuous activity
- Les Saintes, Concierge Collection, Sailing the Bay (Moderate) — Moderate-Strenuous activity
- Les Saintes, Blue Escape Kayaking — Strenuous activity
Published call times
- December 31, 2026 · Arrival 12:00 · Departure 18:00 · Watersports platform scheduled
January 1, 2027 BASSETERRE, ST. KITTS
About BASSETERRE, ST. KITTS
BASSETERRE, ST. KITTS is a Windstar destination in Saint Kitts and Nevis within the Caribbean sailing region. Across the current published program, locally focused experience themes include Snorkel Safari, St Kitts Quad ATV Adventure & Island History & Rum Tasting. Together they give this call an individual sense of place before the exact timetable and voyage-specific options for this sailing are reviewed below.
Shore experiences currently listed
- Basseterre: St Kitts Quad ATV Adventure — Strenuous activity
- Basseterre, Nevis Panoramic and Beach Tour (Easy-Moderate) — Easy-Moderate activity
- Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts (Easy) — Easy activity
- Basseterre, Brimstone Hill Fortress & Fairview Great House — Easy-Moderate activity
- Basseterre: Sky Safari Zipline Adventure (Strenuous) — Strenuous activity
- Basseterre: Snorkel Safari (Moderate) — Moderate activity
- Basseterre, Island History & Rum Tasting — Moderate activity
Published call times
- January 1, 2027 · Arrival 08:00 · Departure 22:00
Published timetable status: Official Windstar itinerary entries and voyage-specific shore experiences are combined without estimating destinations, call times, experience names, or activity levels. Synthetic midnight continuation placeholders from the source are suppressed.
Please note: Shore-experience names, activity levels, availability, and schedules can change before departure. Confirm the final program with Deluxe Cruises closer to sailing. No excursion prices or cruise-line links are included on this page.
A closer look at this sailing
PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN aboard Wind Surf
On December 19 2026-January 2 2027, Wind Surf sails 14 nights from PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN. The published route brings together GUSTAVIA, ST. BARTHELEMY, FALMOUTH HARBOUR, ANTIGUA, ROAD BAY, ANGUILLA, SOPER'S HOLE, TORTOLA, BVI, creating a specific progression of ports for travelers comparing destination variety and voyage pace.
This route includes an official day-by-day schedule and published port times. The source lists 16 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.
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