Windstar Cruises luxury itinerary

Star Pride October 28-November 8 2026 Cruise & Offers

SAN JUAN to SAN JUAN

VoyagePR20261028-11D DatesOctober 28-November 8 2026 Duration11 nights ShipStar Pride

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

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Star Pride October 28-November 8 2026 route map from SAN JUAN to SAN JUAN
Star Pride · Voyage PR20261028-11D · SAN JUAN to SAN JUAN · local schematic map based on the published itinerary sequence

October 28-November 8 2026 ยท Voyage PR20261028-11D

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.

11 destination panels · 45 verified voyage-specific shore experiences · 2 panels with planning notices

Official voyage overview

Everywhere you look is another cover-worthy image on this Caribbean voyage — scenes so striking they’ll inspire your inner artist. Dazzling white sand turns the shallows mesmerizing shades of blue, and fiery sunsets provide a canvas of rich oranges and reds.

October 28 & November 8, 2026 SAN JUAN Puerto Rico · 2 published calls · 3 listed experiences

About SAN JUAN

SAN JUAN is a Windstar destination in Puerto Rico within the Caribbean sailing region. Across the current published program, locally focused experience themes include Half Day Private SUV with Guide, Old San Juan Fortress & City Walking Tour with Transfer to & Bacardi Rum Tour & Tasting- With Transfer to Airport. 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

  • San Juan: Old San Juan Fortress & City Walking Tour with Transfer to Windstar Hotel (Moderate-Strenu — Moderate-Strenuous activity
  • San Juan, Concierge Collection: Half Day Private SUV with Guide (Easy) — Easy activity
  • San Juan: Old San Juan Fortress & City Walking Tour with Transfer to Airport (Moderate-Strenuous) — Moderate-Strenuous activity

Published call times

  • October 28, 2026 · Embarkation · Departure 19:00
  • November 8, 2026 · Arrival 07:00 · Disembarkation
October 29, 2026 CRUZ BAY, ST. JOHN U.S. Virgin Islands · Arrival 08:00 · Departure 18:00 · 4 listed experiences

About CRUZ BAY, ST. JOHN

CRUZ BAY, ST. JOHN is a Windstar destination in U.S. Virgin Islands within the Caribbean sailing region. Across the current published program, locally focused experience themes include Cinnamon Beach Getaway, Lind Point Trail Eco Hike & Trunk Bay Snorkeling Experience. 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, Cinnamon Beach Getaway — Moderate activity
  • St. John, Lind Point Trail Eco Hike — Moderate activity
  • St. John, Trunk Bay Snorkeling Experience — Moderate activity
  • St. John, Island tour Featuring Annaberg Ruins — Easy activity

Published call times

  • October 29, 2026 · Arrival 08:00 · Departure 18:00
October 30, 2026 GUSTAVIA, ST. BARTHELEMY Saint Barthelemy · Arrival 08:00 · Departure 22:00 · 9 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

  • St Barts, Concierge Collection: St. Barthelemy Beach Day (Easy-Moderate) — Easy-Moderate activity
  • St. Barts: Independent Explorer by Car (Easy-Moderate) — Easy-Moderate activity
  • Gustavia, Concierge Collection: Scuba Dive 1 Tank — Strenuous activity
  • Sailing Catamaran to St Barth Nature Reserve — Moderate activity
  • St. Barts, Concierge Collection: Sunset Cruise (Easy-Moderate) — Easy-Moderate activity
  • St. Barts: Intimate Island Tour (Easy) — Easy activity
  • Gustavia, Concierge Collection: Savor St Barts — Moderate activity
  • Gustavia, Concierge Collection: Scuba Dive 2 Tank — Strenuous activity
  • Gustavia, Concierge Collection: Jet Ski — Strenuous activity

Published call times

  • October 30, 2026 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
October 31, 2026 BASSETERRE, ST. KITTS Saint Kitts and Nevis · Arrival 08:00 · Departure 18:00 · 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, Island History & Rum Tasting — Moderate activity
  • Basseterre: St Kitts Quad ATV Adventure — Strenuous activity
  • Basseterre: Sky Safari Zipline Adventure (Strenuous) — Strenuous activity
  • Basseterre, Brimstone Hill Fortress & Fairview Great House — Easy-Moderate activity
  • Basseterre: Snorkel Safari (Moderate) — Moderate activity
  • Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts (Easy) — Easy activity
  • Basseterre, Nevis Panoramic and Beach Tour (Easy-Moderate) — Easy-Moderate activity

Published call times

  • October 31, 2026 · Arrival 08:00 · Departure 18:00
November 1, 2026 FALMOUTH HARBOUR, ANTIGUA Antigua and Barbuda · Arrival 08:00 · Departure 18:00 · 6 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, Make Your Own Rum (Easy-Moderate) — Easy-Moderate activity
  • Falmouth Harbour, Swim with the Stingrays (Moderate) — Moderate activity
  • Falmouth Harbour, Open Course Canopy Challenge (Strenuous) — Strenuous activity
  • Falmouth Harbour, Antigua Beach Escape (Easy) — Easy activity
  • Falmouth Harbour, Concierge Collection, Jet Ski Adventure (Moderate-Strenuous) — Moderate-Strenuous activity
  • Falmouth Harbour, Nelson's Dockyard Walking Tour & Boat around English Harbour (Easy-Moderate) — Easy-Moderate activity

Published call times

  • November 1, 2026 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
November 2, 2026 LES SAINTES, GUADELOUPE Guadeloupe · Arrival 08:00 · Departure 18:00 · 4 listed experiences

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, Blue Escape Kayaking — Strenuous activity
  • Les Saintes, Terre de Haut Panoramic Tour (Easy) — Easy activity
  • Les Saintes, Concierge Collection, Sailing the Bay (Moderate) — Moderate-Strenuous activity
  • Les Saintes, Snorkel and Island Tour by Speed Boat — Moderate-Strenuous activity

Published call times

  • November 2, 2026 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
November 3, 2026 RODNEY BAY Saint Lucia · Arrival 08:00 · Departure 21:30

About RODNEY BAY

Rodney Bay lies on Saint Lucia’s northwestern coast, where a sheltered marina, beach, restaurants, and waterfront paths create a relaxed resort setting. Nearby Pigeon Island adds colonial fortifications and panoramic viewpoints. The bay also provides access to Castries and the island’s greener interior of rainforest and volcanic terrain.

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 3, 2026 · Arrival 08:00 · Departure 21:30
November 4, 2026 ST. GEORGE'S, GRENADA Grenada · Arrival 10:00 · Departure 18:00 · 9 listed experiences

About ST. GEORGE'S, GRENADA

ST. GEORGE'S, GRENADA is a Windstar destination in Grenada within the Caribbean sailing region. Across the current published program, locally focused experience themes include Discover Scuba, Clear Bottom Kayaking & Spice of Our Lives. 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. George's, Clear Bottom Kayaking — Moderate-Strenuous activity
  • St. Georges, Fort Frederick Rainforest & Waterfall — Moderate activity
  • St. George's, Sailing Cruise to the Statue Park (Moderate-Strenuous) — Moderate-Strenuous activity
  • St. George's, Great Tower Estate with Tea (Easy-Moderate) — Easy-Moderate activity
  • St George's, Spice of Our Lives (Easy-Moderate) — Easy-Moderate activity
  • St. George's, Discover Scuba — Moderate activity
  • St. George's, Certified One-Tank Dive — Moderate-Strenuous activity
  • St. George's, Certified Two-Tank Dive — Moderate-Strenuous activity
  • St. George's, Powerboat & Snorkeling at the Statues Park (Moderate-Strenuous) — Moderate-Strenuous activity

Published call times

  • November 4, 2026 · Arrival 10:00 · Departure 18:00
November 5, 2026 Sea Days International waters · No separately published port call

Published sea days aboard Star Pride

The official Windstar timetable names no port call on November 5, 2026. These dates are grouped once as Sea Days; no onboard activity, route detail, or shore program has been inferred.

Shore planning

No shore experience applies to these Sea Days. Windstar's daily onboard program is confirmed aboard and is not estimated on this page.

Published call times

  • November 5, 2026 · No separately published port call
November 6, 2026 GREAT HARBOUR, JOST VAN DYKE British Virgin Islands · Arrival 08:00 · Departure 22:00 · 1 listed experience

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

  • November 6, 2026 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
November 7, 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 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 7, 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

SAN JUAN to SAN JUAN aboard Star Pride

On October 28-November 8 2026, Star Pride sails 11 nights from SAN JUAN to SAN JUAN. The published route brings together CRUZ BAY, ST. JOHN, GUSTAVIA, ST. BARTHELEMY, BASSETERRE, ST. KITTS, FALMOUTH HARBOUR, ANTIGUA, 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 11 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.

For PR20261028-11D, 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

Star Pride October 28-November 8 2026: is Voyage PR20261028-11D right for you?

This 11-night voyage aboard Star Pride sails SAN JUAN to SAN JUAN, with calls including CRUZ BAY, GUSTAVIA, BASSETERRE, and FALMOUTH HARBOUR and 1 published sea day. Voyage PR20261028-11D 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 11-night SAN JUAN to SAN JUAN aboard Star Pride, including CRUZ BAY, GUSTAVIA, BASSETERRE, and FALMOUTH HARBOUR.
Why Deluxe Cruises
Personal guidance for Voyage PR20261028-11D, 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 Star Pride Voyage PR20261028-11D with Deluxe Cruises?

Deluxe Cruises provides personal planning for Voyage PR20261028-11D, 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 PR20261028-11D?

For the October 28-November 8 2026 SAN JUAN to SAN JUAN, 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 PR20261028-11D to request a personalized quote from Deluxe Cruises.

What is included and not included on Star Pride Voyage PR20261028-11D?

For the October 28-November 8, 2026 SAN JUAN to SAN JUAN sailing aboard Star Pride: 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 Star Pride Voyage PR20261028-11D?

For the October 28-November 8, 2026 SAN JUAN to SAN JUAN sailing aboard Star Pride: Selected Star Plus suites publish third-guest capacity, but the current verified guide does not name the sleeping surface. Deluxe Cruises will confirm the exact suite number and will not assume a sofa bed, rollaway, Pullman or berth. Deluxe Cruises will confirm the exact room and occupancy before booking.

Are shore excursions included on Star Pride Voyage PR20261028-11D, and can Deluxe Cruises help with alternatives?

For the October 28-November 8, 2026 SAN JUAN to SAN JUAN sailing aboard Star Pride: 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 Star Pride for Voyage PR20261028-11D?

For the October 28-November 8, 2026 SAN JUAN to SAN JUAN sailing aboard Star Pride: 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 Star Pride's verified headline statistics?
312Guests
200Crew
6Guest decks
522 ftLength
12,995 GRTGross tonnage
What clothes should I bring for this October itinerary?

Deluxe Cruises packing guidance for this October 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 Star Pride?
  • 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 Star Pride 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 Star Pride 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 PR20261028-11D before reserving.

Can children and babies sail aboard Star Pride?
  • 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 PR20261028-11D: do not assume a supervised program, babysitting, crib, or child-specific service unless it is confirmed for this sailing.

How does Star Pride 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 Star Pride?
  • 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.

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.

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Ready to reserve Star Pride October 28-November 8 2026?

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