Windstar Cruises luxury itinerary

Wind Surf December 19-26 2026 Cruise & Offers

PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN

VoyageSU20261219-7D DatesDecember 19-26 2026 Duration7 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 December 19-26 2026 route map from PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN
Wind Surf · Voyage SU20261219-7D · PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN · local schematic map based on the published itinerary sequence

December 19-26 2026 ยท Voyage SU20261219-7D

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.

7 destination panels · 25 verified voyage-specific shore experiences · 0 panels with planning notices

Official voyage overview

Bask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.

December 19 & December 26, 2026 PHILIPSBURG, ST. MAARTEN Sint Maarten · 2 published calls · 2 listed experiences

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

Published call times

  • December 19, 2026 · Embarkation · Departure 19:00
  • December 26, 2026 · Arrival 06:00 · Disembarkation
December 20, 2026 GUSTAVIA, ST. BARTHELEMY Saint Barthelemy · Arrival 08:00 · Departure 22:00 · 6 listed experiences

About GUSTAVIA, ST. BARTHELEMY

GUSTAVIA, ST. BARTHELEMY is a Windstar destination in Saint Barthelemy within the Caribbean sailing region. Across the current published program, locally focused experience themes include St. Barts: Intimate Island Tour, Jet Ski & Sailing Catamaran to St Barth Nature Reserve. 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

  • 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

Published call times

  • December 20, 2026 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
December 21, 2026 FALMOUTH HARBOUR, ANTIGUA Antigua and Barbuda · Arrival 08:00 · Departure 18:00 · 5 listed experiences

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 Anguilla · Arrival 08:00 · Departure 18:00 · 5 listed experiences

About ROAD BAY, ANGUILLA

ROAD BAY, ANGUILLA gives this stage of the itinerary its individual destination focus. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. This context places the destination within the Caribbean route; exact call times and any experiences published for this sailing are listed 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, Concierge Collection: Relaxing Day at Savi with Lunch — Easy-Moderate activity
  • Road Bay, Snorkel Adventure by Speedboat (Moderate-Strenuous) — Moderate-Strenuous activity
  • Road Bay, Shoal Bay Beach Transfer (Easy) — Easy activity

Published call times

  • December 22, 2026 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
December 23, 2026 SOPER'S HOLE, TORTOLA, BVI British Virgin Islands · Arrival 08:00 · Departure 18:00 · 4 listed experiences

About SOPER'S HOLE, TORTOLA, BVI

SOPER'S HOLE, TORTOLA, BVI gives this stage of the itinerary its individual destination focus. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set.

Shore experiences currently listed

  • Tortola, Tortola Jeep & Beach Tour (Moderate) — Moderate activity
  • Tortola, Island Snorkel and Swim Adventure (Moderate-Strenuous) — Moderate-Strenuous activity
  • Soper's Hole: Cane Garden Bay Beach Break (Moderate) — Moderate activity
  • Tortola, Tortola Scenic Island Tour(Easy) — Easy 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 British Virgin Islands · 2-day overnight call · 1 listed experience

About GREAT HARBOUR, JOST VAN DYKE

GREAT HARBOUR, JOST VAN DYKE gives this stage of the itinerary its individual destination focus. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. This context places the destination within the Caribbean route; exact call times and any experiences published for this sailing are listed 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 British Virgin Islands · Arrival 08:00 · Departure 17:00 · 2 listed experiences

About VIRGIN GORDA/PRICKLY PEAR, BVI

VIRGIN GORDA/PRICKLY PEAR, BVI gives this stage of the itinerary its individual destination focus. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. This context places the destination within the Caribbean route; exact call times and any experiences published for this sailing are listed below.

Shore experiences currently listed

  • Virgin Gorda: Snorkel Adventure (Moderate-Strenuous) — Moderate-Strenuous activity
  • Virgin Gorda: Highlights & Bath Tour (Moderate) — Strenuous activity

Published call times

  • December 25, 2026 · 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 December 19-26 2026, Wind Surf sails 7 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 9 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.

For SU20261219-7D, 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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Luxury cruise planning summary

Wind Surf December 19-26 2026: is Voyage SU20261219-7D right for you?

This 7-night voyage aboard Wind Surf sails PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN, with calls including GUSTAVIA, FALMOUTH HARBOUR, ROAD BAY, and SOPER'S HOLE. Voyage SU20261219-7D 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 7-night PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN aboard Wind Surf, including GUSTAVIA, FALMOUTH HARBOUR, ROAD BAY, and SOPER'S HOLE.
Why Deluxe Cruises
Personal guidance for Voyage SU20261219-7D, 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 SU20261219-7D with Deluxe Cruises?

Deluxe Cruises provides personal planning for Voyage SU20261219-7D, 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 SU20261219-7D?

For the December 19-26 2026 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 SU20261219-7D 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 December itinerary?

Deluxe Cruises packing guidance for this December 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 SU20261219-7D 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 SU20261219-7D: 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.

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Ready to reserve Wind Surf December 19-26 2026?

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