Windstar Cruises luxury itinerary

Wind Surf November 20-December 5 2027 Cruise & Offers

PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN

VoyageSU20271120-15D DatesNovember 20-December 5 2027 Duration15 nights ShipWind Surf

Review the complete published itinerary, source-status notes, suite guidance, and current offer assistance with Deluxe Cruises.

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Wind Surf November 20-December 5 2027 route map from PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN
Wind Surf · Voyage SU20271120-15D · PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN · local schematic map based on the published itinerary sequence

November 20-December 5 2027 ยท Voyage SU20271120-15D

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.

13 destination panels · 18 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.

November 20, November 28 & December 5, 2027 PHILIPSBURG, ST. MAARTEN Sint Maarten · 3 published calls

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 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

  • November 20, 2027 · Embarkation · Departure 19:00
  • November 28, 2027 · Arrival 06:00 · Departure 19:00
  • December 5, 2027 · Arrival 06:00 · Disembarkation
November 21 & December 3, 2027 GUSTAVIA, ST. BARTHELEMY Saint Barthelemy · 2 published calls

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

  • November 21, 2027 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
  • December 3, 2027 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
November 22, 2027 ST. JOHN'S, ANTIGUA Antigua and Barbuda · Arrival 08:00 · Departure 22:00 · 2 listed experiences

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, Concierge Collection, Jet Ski Adventure (Moderate-Strenuous) — Moderate-Strenuous activity
  • St. John's, Beach Escape (Easy) — Easy activity

Published call times

  • November 22, 2027 · Arrival 08:00 · Departure 22:00
November 23, 2027 DESHAIES Guadeloupe · Arrival 07:00 · Departure 17:00

About DESHAIES

Deshaies is a small fishing village on Guadeloupe’s lush Basse-Terre coast, gathered around a calm bay backed by green hills. Colorful waterfront buildings, nearby beaches, and a celebrated botanical garden give the stop an intimate scale. Rainforest scenery and Creole culture shape the wider island experience.

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

  • November 23, 2027 · Arrival 07:00 · Departure 17:00
November 24, 2027 ROAD BAY, ANGUILLA Anguilla · Arrival 08:00 · Departure 18:00

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

  • November 24, 2027 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
November 25, 2027 SOPER'S HOLE, TORTOLA, BVI British Virgin Islands · Arrival 08:00 · Departure 18:00

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

  • November 25, 2027 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
November 25-26, 2027 GREAT HARBOUR, JOST VAN DYKE British Virgin Islands · 2-day overnight call

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

  • November 25, 2027 · Arrival 19:00 · Departure 23:59 · Overnight stay · Watersports platform scheduled
  • November 26, 2027 · Departure 22:00 · Overnight stay · Watersports platform scheduled
November 27, 2027 VIRGIN GORDA/PRICKLY PEAR, BVI British Virgin Islands · Arrival 08:00 · Departure 17:00 · 2 listed experiences

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

  • November 27, 2027 · Arrival 08:00 · Departure 17:00
November 29, 2027 CHARLESTOWN Saint Kitts and Nevis · Arrival 08:00 · Departure 17:00 · 6 listed experiences

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, Quad Biking 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 Single — Strenuous activity
  • Charlestown, Nevis Half Island & Botanical Garden — Easy-Moderate activity

Published call times

  • November 29, 2027 · Arrival 08:00 · Departure 17:00
November 30, 2027 ROSEAU, DOMINICA Dominica · Arrival 08:00 · Departure 16:00

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 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

  • November 30, 2027 · Arrival 08:00 · Departure 16:00
December 1, 2027 MAYREAU Saint Vincent and the Grenadines · Arrival 08:00 · Departure 17:00 · 1 listed experience

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 1, 2027 · Arrival 08:00 · Departure 17:00
December 2, 2027 LES SAINTES, GUADELOUPE Guadeloupe · Arrival 12:00 · Departure 18:00

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 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 2, 2027 · Arrival 12:00 · Departure 18:00 · Watersports platform scheduled
December 4, 2027 BASSETERRE, ST. KITTS Saint Kitts and Nevis · Arrival 08:00 · Departure 17:00 · 7 listed experiences

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, Nevis Panoramic and Beach Tour (Easy-Moderate) — Easy-Moderate activity
  • Basseterre: Sky Safari Zipline Adventure (Strenuous) — Strenuous activity
  • Basseterre: St Kitts Quad ATV Adventure — Strenuous activity
  • Basseterre, Island History & Rum Tasting — Moderate activity
  • Basseterre, Brimstone Hill Fortress & Fairview Great House — Easy-Moderate activity
  • Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts (Easy) — Easy activity
  • Basseterre: Snorkel Safari (Moderate) — Moderate activity

Published call times

  • December 4, 2027 · Arrival 08:00 · Departure 17:00

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 November 20-December 5 2027, Wind Surf sails 15 nights from PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN. The published route brings together GUSTAVIA, ST. BARTHELEMY, ST. JOHN'S, ANTIGUA, DESHAIES, ROAD BAY, ANGUILLA, 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 SU20271120-15D, 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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Ask a specialist to compare the itinerary, suite category, current fare, inclusions, eligible promotions, and available amenities.

Why not check the complete value at the outset? Personal guidance can make important differences in suite location and voyage fit.

Request detailed information for Wind Surf SU20271120-15D.

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Luxury cruise planning summary

Wind Surf November 20-December 5 2027: is Voyage SU20271120-15D right for you?

This 15-night voyage aboard Wind Surf sails PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN, with calls including GUSTAVIA, ST. JOHN'S, DESHAIES, and ROAD BAY. Voyage SU20271120-15D matches the latest verified voyage-search dataset used by this website. Before reserving, ask Deluxe Cruises to compare accommodations, deck location, inclusions, current availability, and any family, medical, dietary, or accessibility arrangements for this exact departure.

Best for
Travelers considering a 15-night PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN aboard Wind Surf, including GUSTAVIA, ST. JOHN'S, DESHAIES, and ROAD BAY.
Why Deluxe Cruises
Personal guidance for Voyage SU20271120-15D, including accommodation, deck location, itinerary, inclusion, and special-request comparisons.
Before you book
Confirm current availability, exact itinerary details, accommodation benefits, applicable preferred-rate opportunities, and documented guest requirements.

Questions travelers ask

Why book Wind Surf Voyage SU20271120-15D with Deluxe Cruises?

Deluxe Cruises provides personal planning for Voyage SU20271120-15D, including accommodation and deck-location comparisons, current availability and preferred-rate guidance, and help documenting family, medical, dietary, or accessibility requests before departure.

What should travelers compare for Voyage SU20271120-15D?

For the November 20-December 5 2027 PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN, compare the published schedule, accommodation category and location, included services, current availability, and any special requirements before you reserve.

How do I request a personalized luxury cruise quote?

Email info@deluxecruises.com, call +1-702-501-7105, or use WhatsApp +1-702-900-9975 and mention Voyage SU20271120-15D to request a personalized quote from Deluxe Cruises.

What are Wind Surf's verified headline statistics?
342Guests
213Crew
6Guest decks
535 ft at the waterline; 615 ft including bowspritLength
14,745 GRTGross tonnage
What clothes should I bring for this November itinerary?

Deluxe Cruises packing guidance for this November warm-weather itinerary

  • Pack lightweight breathable clothing, swimwear, strong sun protection, and a light rain layer for tropical showers.
  • Bring secure non-slip walking shoes plus suitable beach or water footwear where the published activities and local conditions call for it.
  • Add a light wrap or sweater for air-conditioned interiors and breezy evenings, and review local customs before visits to religious or community sites.

Windstar Cruises dress guidance

  • Windstar has no formal nights. Daytime dress is relaxed resort wear, while dinner in the main evening restaurants calls for casually elegant clothing.
  • Published evening examples include slacks or non-distressed jeans with a collared, button-down or polo shirt, or a blouse, skirt, casual dress or sundress. Reserve shorts, T-shirts, hats and flip-flops for daytime.

Packing suggestions are Deluxe Cruises editorial guidance; the cruise line's final documents and the weather forecast control the last check.

What services and amenities are available aboard Wind Surf?
  • Published fleet experiences include open-seating dining, lounges, 24-hour room service from a limited menu, World Spa by Windstar, pools or whirlpools and an Open Bridge when operational.
  • Dining venues, watersports platforms, pools, spa spaces, entertainment and included services differ between Wind Class sailing yachts, Star Plus all-suite yachts and the newer Star Class yachts.

Venues, hours, inclusions, equipment, and operating conditions can vary by ship and sailing. Deluxe Cruises will reconfirm the details for this departure.

What fitness, sports, or wellness facilities does Wind Surf have?
  • Watersports-platform access, swimming and paddle activities depend on sea state, weather, anchorage, local rules and the captain's approval.

Class schedules, age rules, treatment access, operating hours, and equipment availability are confirmed for the exact ship and voyage.

What accommodation features and services can Wind Surf guests expect?
  • Wind Class sailing yachts publish ocean-view staterooms and suites without a fleetwide private-veranda promise. Star Plus yachts are all-suite, while Star Seeker and Star Explorer publish suites with private verandas or infinity windows among their categories.
  • Room size, window or veranda, bed arrangement, bath, accessibility and amenities differ by yacht, category and room number; use the exact deck plan before reserving.

Review the exact room or suite number, category, deck position, layout, and benefits for Voyage SU20271120-15D before reserving.

Can children and babies sail aboard Wind Surf?
  • Windstar cannot accommodate children under eight years old. A guest under 21 must be accompanied in the room by a parent, guardian or chaperone who is at least 21.
  • Windstar does not publish a fleetwide supervised children's program or babysitting service. Shore operators can impose separate age and participation limits, and minors require direct adult supervision.
  • A guest may not board if she will have entered the 24th week of pregnancy when travel with Windstar begins. Notify Windstar early and confirm current documentation requirements.

For Voyage SU20271120-15D: do not assume a supervised program, babysitting, crib, or child-specific service unless it is confirmed for this sailing.

How does Wind Surf handle special needs, medical arrangements, and accessibility?
  • Notify Windstar at booking and complete its Guest Accommodation Request Form. Current guidance requests advance notice for interpreters, equipment, oxygen, dialysis supplies and other services, with timing depending on the request.
  • Guests normally bring an approved wheelchair or scooter; size, weight and storage can prevent acceptance, and crew cannot lift guests or heavy devices. Standard rooms are not barrier-free.
  • Modified suites are published on Star Pride, Star Breeze and Star Legend, but features are limited. Gangways, tenders, stairs, ports and shore transport can restrict access, and personal daily care is not provided.
  • Windstar states that its yachts do not have full medical services. Serious emergencies are referred ashore, and evacuation at sea or from a tender or remote port may be delayed or infeasible.
  • Carry a medical summary and adequate medication, and arrange oxygen, dialysis supplies, sharps or refrigerated medication in advance through the accessibility process. Not every request can be accommodated.

Important: access varies by accommodation, gangway, pier, tender, shore transport, and operating conditions. Document needs when requesting the booking and reconfirm them before travel.

What is the smoking policy aboard Wind Surf?
  • Smoking and vaping are prohibited in every stateroom, suite and indoor public space, including restaurants and corridors. They are permitted only in designated outside-deck smoking areas.

Designated locations and onboard rules can change. Follow the policy, posted signs, and crew instructions in force for the voyage.

Ask Deluxe CruisesView Suites & Deck PlansEmail a cruise specialist
Ready to reserve Wind Surf November 20-December 5 2027?

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