Windstar Cruises luxury itinerary
Star Pride October 28-November 8 2026 Cruise & Offers
SAN JUAN to SAN JUAN
Review the complete published itinerary, source-status notes, suite guidance, and current offer assistance with Deluxe Cruises.
October 28-November 8 2026 · 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 · 51 verified voyage-specific shore experiences · 1 panel 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
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
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, Lind Point Trail Eco Hike — Moderate activity
- St. John, Trunk Bay Snorkeling Experience — Moderate activity
- St. John, Cinnamon Beach Getaway — 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
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: Independent Explorer by Car (Easy-Moderate) — Easy-Moderate activity
- St. Barts: Intimate Island Tour (Easy) — Easy activity
- Gustavia, Concierge Collection: Scuba Dive 2 Tank — Strenuous activity
- St Barts, Concierge Collection: St. Barthelemy Beach Day (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
- Gustavia, Concierge Collection: Savor St Barts — Moderate 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
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: Sky Safari Zipline Adventure (Strenuous) — Strenuous activity
- Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts (Easy) — Easy activity
- Basseterre: St Kitts Quad ATV Adventure — Strenuous activity
- Basseterre, Brimstone Hill Fortress & Fairview Great House — Easy-Moderate activity
- Basseterre: Snorkel Safari (Moderate) — Moderate 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
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 & 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
- Falmouth Harbour, Swim with the Stingrays (Moderate) — Moderate 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
- Falmouth Harbour, Make Your Own Rum (Easy-Moderate) — Easy-Moderate activity
- Falmouth Harbour, Antigua Beach Escape (Easy) — Easy activity
Published call times
- November 1, 2026 · Arrival 08:00 · Departure 18:00 · Watersports platform scheduled
November 2, 2026 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 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, Concierge Collection, Sailing the Bay (Moderate) — Moderate-Strenuous activity
- Les Saintes, Terre de Haut Panoramic Tour (Easy) — Easy 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
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 experiences currently listed
- Rodney Bay, Sweet Honey Bee Tour — Moderate activity
- Rodney Bay, Catamaran Cruise to the Pitons — Easy activity
- Rodney Bay, St. Lucian Walking Food Tour — Easy-Moderate activity
- Rodney Bay, Discover Sailing — Moderate-Strenuous activity
- Rodney Bay, Rainforest Canopy Zip Line Adventure — Moderate-Strenuous activity
- Rodney Bay: Let's Make Chocolate — Easy-Moderate activity
- Rodney Bay, Aerial Tram Park — Moderate activity
- Rodney Bay, Panoramic St. Lucia — Easy activity
Published call times
- November 3, 2026 · Arrival 08:00 · Departure 21:30
November 4, 2026 ST. GEORGE'S, GRENADA
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. George's, Great Tower Estate with Tea (Easy-Moderate) — Easy-Moderate activity
- St. George's, Discover Scuba — Moderate activity
- St. George's, Powerboat & Snorkeling at the Statues Park (Moderate-Strenuous) — 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, Spice of Our Lives (Easy-Moderate) — Easy-Moderate activity
- St. George's, Certified One-Tank Dive — Moderate-Strenuous activity
- St. George's, Certified Two-Tank Dive — Moderate-Strenuous activity
Published call times
- November 4, 2026 · Arrival 10:00 · Departure 18:00
November 5, 2026 Sea Days
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
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
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
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.
Personalized cruise planning with Windstar Cruises
Ask Deluxe Cruises about Star Pride Voyage PR20261028-11D
Considering the October 28-November 8, 2026 Star Pride sailing, Voyage PR20261028-11D? A Deluxe Cruises specialist can verify this itinerary's current status and availability and assist with stateroom or suite selection and deck location, fare and inclusion comparisons, eligible offers, available amenities, and personalized planning.
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