Windstar Cruises luxury itinerary

Wind Surf December 19-27 2027 Cruise & Offers

PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN

VoyageSU20271219-8DDatesDecember 19-27 2027Duration8 nightsShipWind 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 19-27 2027 route map from PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN
Wind Surf · Voyage SU20271219-8D · PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN · local schematic map based on the published itinerary sequence

December 19-27 2027 · Voyage SU20271219-8D

Ports & shore experiences

Published journey: Beach Fun & Sun: A Remote Caribbean Getaway

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.

8 destination panels · 10 verified voyage-specific shore experiences · 5 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 27, 2027 PHILIPSBURG, ST. MAARTEN Sint Maarten · 2 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 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 · Disembarkation
December 20, 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, 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 GUSTAVIA, ST. BARTHELEMY Saint Barthelemy · Arrival 08:00 · Departure 22:00

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 & St. Barts: Independent Explorer by Car. 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 21, 2027 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
December 22, 2027 ROAD BAY, ANGUILLA Anguilla · Arrival 08:00 · Departure 18:00

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 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 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. 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 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 British Virgin Islands · 2-day overnight call

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 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 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: 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, 2027 CHARLESTOWN Saint Kitts and Nevis · Arrival 08:00 · Departure 21:00 · 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, Concierge Collection: Deep Sea Fishing (Moderate-Strenuous) — Moderate-Strenuous activity
  • Charlestown, Coastal Boat Cruise Snorkel Adventure (Strenuous) — Strenuous activity
  • Charlestown, Quad Biking Adventure Single — 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

Published call times

  • December 26, 2027 · Arrival 08:00 · Departure 21:00

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 19-27 2027, Wind Surf sails 8 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 10 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.

For SU20271219-8D, 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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Contact Deluxe Cruises before you reserve

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 SU20271219-8D.

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Luxury cruise planning summary

Wind Surf December 19-27 2027: is Voyage SU20271219-8D right for you?

This 8-night voyage aboard Wind Surf sails PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN, with calls including ST. JOHN'S, GUSTAVIA, ROAD BAY, and SOPER'S HOLE. Voyage SU20271219-8D 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 8-night PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN aboard Wind Surf, including ST. JOHN'S, GUSTAVIA, ROAD BAY, and SOPER'S HOLE.
Why Deluxe Cruises
Personal guidance for Voyage SU20271219-8D, 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 SU20271219-8D with Deluxe Cruises?

Deluxe Cruises provides personal planning for Voyage SU20271219-8D, 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 SU20271219-8D?

For the December 19-27 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 SU20271219-8D to request a personalized quote from Deluxe Cruises.

What is included and not included on Wind Surf Voyage SU20271219-8D?

For the December 19-27, 2027 PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN sailing aboard Wind Surf: Cruise-only fares publish accommodation, onboard meals and entertainment, including specialty dining, 24-hour room service, the signature barbecue and welcome champagne. Wi-Fi, selected beer, wine and cocktails and gratuities are included only with an All-Inclusive fare or package or a qualifying promotion, not with every cruise-only booking. Spa, shore excursions and personal services can cost extra. The exact fare and booking confirmation control.

What bed is provided for a child or third guest on Wind Surf Voyage SU20271219-8D?

For the December 19-27, 2027 PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN sailing aboard Wind Surf: Wind Class primary-bed and occupancy arrangements vary by yacht and category. A child or third-guest sleeping surface is not safely verified, so Deluxe Cruises will confirm the exact room and will not assume an extra bed. Deluxe Cruises will confirm the exact room and occupancy before booking.

Are shore excursions included on Wind Surf Voyage SU20271219-8D, and can Deluxe Cruises help with alternatives?

For the December 19-27, 2027 PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN sailing aboard Wind Surf: Windstar shore excursions are optional and charged separately unless the exact booking states otherwise. Watersports-platform access and the Open Bridge are conditional onboard features, not shore-excursion inclusions. Each tour and booking term must be checked. If a preferred shore experience is not included, Deluxe Cruises can compare independent alternatives and check whether a lower price or better value is available than booking through the cruise line. Availability and savings vary and are confirmed before purchase.

How does Internet and Wi-Fi work aboard Wind Surf for Voyage SU20271219-8D?

For the December 19-27, 2027 PHILIPSBURG, ST. MAARTEN to PHILIPSBURG, ST. MAARTEN sailing aboard Wind Surf: Wi-Fi is included only with an All-Inclusive fare or package or a qualifying promotion, not every cruise-only fare. The published package permits up to two connected devices; coverage, speed and uninterrupted performance are not guaranteed. The exact booking confirmation controls.

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 SU20271219-8D 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 SU20271219-8D: 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.

How can I find the best cruise airfare for Wind Surf Voyage SU20271219-8D?

For round-trip flights to and from PHILIPSBURG, ST. MAARTEN around Voyage SU20271219-8D, compare schedules, fare rules, baggage allowances, connection times, and change options—not airfare alone. Visit the Deluxe Cruises Cruise Airfare page to explore flight options designed around your cruise and potential ways to save money. Airfares and savings vary, and Deluxe Cruises will help confirm suitable travel dates and connection time before booking.

Where can I review cruise travel insurance information?

Visit the Deluxe Cruises Cruise Travel Insurance page to prepare for a quote and compare optional protection with Travel Insured.

You can also search the Deluxe Cruises Cruise-Line Travel Insurance Directory for cruise-line-specific plan companies, insurer or administrator contacts, available policy-document links, and published pre-existing-condition purchase guidance. Plan terms and availability can change; the policy or certificate issued for your state controls.

How do I create a MyWindstar account and connect Wind Surf Voyage SU20271219-8D after booking with Deluxe Cruises?

Before you begin: After Deluxe Cruises confirms Wind Surf Voyage SU20271219-8D, use the email address associated with the Windstar reservation and Windstar's cruise-line confirmation details. Do not substitute a Deluxe Cruises invoice, receipt, or payment reference for a Windstar credential.

  1. Step 1 — Open Booked Guests: Choose Booked Guests or My Windstar from Windstar Cruises' official website.
  2. Step 2 — Create or open the account: Sign in with the registered email and password, or choose the account-creation option and use the email associated with the reservation. Existing Yacht Club members can follow Windstar's published profile instructions for their membership number and initial PIN.
  3. Step 3 — Use password recovery when needed: If the email already belongs to an account, use Forgot Password and follow Windstar's reset instructions instead of creating a duplicate.
  4. Step 4 — Find the voyage: Look for Wind Surf Voyage SU20271219-8D after sign-in and complete any matching or guest-information prompts Windstar displays. A current public manual booking-link field sequence has not been verified.
  5. Step 5 — Review available planning: Use My Windstar for the itinerary and released booked-guest services, including applicable shore excursions, transfers, hotels, add-ons, and other planning information.

If Wind Surf Voyage SU20271219-8D does not appear, verify that the My Windstar email matches the reservation, then contact Deluxe Cruises so your advisor can confirm the booking details with Windstar.

Portal functions and advance options vary by voyage and booking stage. Deluxe Cruises remains your travel advisor for reservation changes and assistance. Keep your My Windstar password private.

Ask Deluxe CruisesView Suites & Deck PlansEmail a cruise specialist
Ready to reserve Wind Surf December 19-27 2027?

Contact Deluxe Cruises for current offers, personalized suite guidance, and attentive luxury cruise planning.

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