Windstar Cruises luxury itinerary
Wind Surf December 19-January 3 2027 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 2027-January 3 2028 · Voyage SU20271219-15D
Ports & shore experiences
Published journey: Star Collector: Caribbean Explorations
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 · 17 verified voyage-specific shore experiences · 8 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, 2027, December 27, 2027 & January 3, 2028 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 Half Day Private Island Tour in SUV or Deluxe Mini Van, America's Cup Sailboat Racing with Transfer to Airport & America's Cup Sailboat Racing with Transfer to Windstar 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 planning
No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.
Published call times
- December 19, 2027 · Embarkation · Departure 19:00
- December 27, 2027 · Arrival 06:00 · Departure 19:00
- January 3, 2028 · Arrival 06:00 · Disembarkation
December 20, 2027 ST. JOHN'S, ANTIGUA
About ST. JOHN'S, ANTIGUA
ST. JOHN'S, ANTIGUA is a Windstar destination in Antigua and Barbuda within the Caribbean sailing region. Across the current published program, locally focused experience themes include Beach Escape & Jet Ski 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
- St. John's, Beach Escape (Easy) — Easy activity
- St John's, Concierge Collection, Jet Ski Adventure (Moderate-Strenuous) — Moderate-Strenuous activity
Published call times
- December 20, 2027 · Arrival 08:00 · Departure 22:00
December 21, 2027 & January 2, 2028 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 planning
No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.
Published call times
- December 21, 2027 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
- January 2, 2028 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
December 22, 2027 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 planning
No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.
Published call times
- December 22, 2027 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
December 23, 2027 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 planning
No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.
Published call times
- December 23, 2027 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
December 23-24, 2027 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 planning
No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.
Published call times
- December 23, 2027 · Arrival 19:00 · Departure 23:59 · Overnight stay · Watersports platform scheduled
- December 24, 2027 · Departure 22:00 · Overnight stay · Watersports platform scheduled
December 25, 2027 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, 2027 · Arrival 08:00 · Departure 17:00
December 26 & December 28, 2027 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, Coastal Boat Cruise Snorkel Adventure (Strenuous) — Strenuous activity
- Charlestown, Yachtsmanl Beach Escape — Easy-Moderate activity
- Charlestown, Montravers Hike & Beach Break with Lunch — Moderate-Strenuous activity
- Charlestown, Quad Biking Adventure (Strenuous) — Strenuous activity
- Charlestown, Concierge Collection: Deep Sea Fishing (Moderate-Strenuous) — Moderate-Strenuous activity
- Charlestown, Quad Biking Adventure Single — Strenuous activity
Published call times
- December 26, 2027 · Arrival 08:00 · Departure 21:00
- December 28, 2027 · Arrival 08:00 · Departure 17:00
December 29, 2027 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 River Tubing Adventure, 4X4 Waterfall & Rainforest & Dominica in a Day. 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 planning
No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.
Published call times
- December 29, 2027 · Arrival 08:00 · Departure 16:00
December 30, 2027 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 Tobago Cays 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 planning
No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.
Published call times
- December 30, 2027 · Arrival 08:00 · Departure 17:00
December 31, 2027 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 Historic Tastes & Treasures of Fort Napoleon, Snorkel Experience in Les Saintes & Terre de Haut Panoramic Tour. 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 planning
No voyage-specific shore-experience list is available in the current verified Windstar data for this exact call. Deluxe Cruises can help review the confirmed program closer to departure.
Published call times
- December 31, 2027 · Arrival 12:00 · Departure 18:00 · Watersports platform scheduled
January 1, 2028 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 St Kitts Quad ATV Adventure, Island History & Rum Tasting & Sky Safari Zipline 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
- Basseterre: St Kitts Quad ATV Adventure — Strenuous activity
- Basseterre, Island History & Rum Tasting — Moderate activity
- Basseterre: Snorkel Safari (Moderate) — 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, Nevis Panoramic and Beach Tour (Easy-Moderate) — Easy-Moderate activity
Published call times
- January 1, 2028 · 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 2027-January 3 2028, Wind Surf sails 15 nights from PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN. The published route brings together ST. JOHN'S, ANTIGUA, GUSTAVIA, ST. BARTHELEMY, 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 17 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.
For SU20271219-15D, Deluxe Cruises can compare suite availability, deck location, current fares, eligible promotions, and available amenities. Request a personalized review before reserving so the ship, suite, timing, and complete value fit your plans.
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