Windstar Cruises luxury itinerary
Star Pride November 8-22 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.
November 8-22 2026 ยท Voyage PR20261108-14D
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 · 57 verified voyage-specific shore experiences · 1 panel with planning notices
Official voyage overview
Whether you’re passionate about swimming among undersea wildlife or the intricate cultures and intertwined European histories of the Leeward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands. Stare in wonder at the glow from miniscule bioluminescent organisms stirred by your kayak paddle during a tour of the Fajardo Bio Bay nature reserve near San Juan. Master the art of cooking with distinct spices like nutmeg, cloves and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.
November 8, November 15 & November 22, 2026 SAN JUAN
About SAN JUAN
SAN JUAN gives this stage of the itinerary its individual destination focus. Stare in wonder at the glow from miniscule bioluminescent organisms stirred by your kayak paddle during a tour of the Fajardo Bio Bay nature reserve near San Juan.
Shore experiences currently listed
- San Juan: Old San Juan Fortress & City Walking Tour with Transfer to Airport (Moderate-Strenuous) — Moderate-Strenuous activity
- San Juan, Concierge Collection: Half Day Private SUV with Guide (Easy) — Easy activity
- San Juan, Bacardi Rum Tour & Tasting- With Transfer to Windstar Hotel — Easy-Moderate activity
- San Juan, Bacardi Rum Tour & Tasting- With Transfer to Airport — Easy-Moderate activity
- San Juan: Old San Juan Fortress & City Walking Tour with Transfer to Windstar Hotel (Moderate-Strenu — Moderate-Strenuous activity
Published call times
- November 8, 2026 · Embarkation · Departure 19:00
- November 15, 2026 · Arrival 07:00 · Departure 19:00
- November 22, 2026 · Arrival 07:00 · Disembarkation
November 9, 2026 Sea Days
Published sea days aboard Star Pride
The official Windstar timetable names no port call on November 9, 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 9, 2026 · No separately published port call
November 10, 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. Georges, Fort Frederick Rainforest & Waterfall — Moderate activity
- St. George's, Powerboat & Snorkeling at the Statues Park (Moderate-Strenuous) — Moderate-Strenuous activity
- St. George's, Discover Scuba — Moderate activity
- St. George's, Clear Bottom Kayaking — Moderate-Strenuous activity
- St George's, Spice of Our Lives (Easy-Moderate) — Easy-Moderate activity
- St. George's, Great Tower Estate with Tea (Easy-Moderate) — Easy-Moderate activity
- St. George's, The Best of Grenada (Easy) — Easy activity
- St. George's, Certified One-Tank Dive — Moderate-Strenuous activity
- St. George's, Sailing Cruise to the Statue Park (Moderate-Strenuous) — Moderate-Strenuous activity
- St. George's, Certified Two-Tank Dive — Moderate-Strenuous activity
Published call times
- November 10, 2026 · Arrival 09:00 · Departure 22:00
November 11, 2026 BEQUIA
About BEQUIA
BEQUIA 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 Bequia Snorkel Adventure, Taste of Bequia & Bequia Highlights. 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
- Bequia, Mustique Magic with Lunch (Moderate) — Moderate activity
- Bequia, Bequia Snorkel Adventure — Strenuous activity
- Bequia, Bequia Highlights (Easy-Moderate) — Easy-Moderate activity
- Bequia, Taste of Bequia (Easy-Moderate) — Easy-Moderate activity
- Bequia, Concierge Collection: Rum Tasting at Firefly Plantation — Moderate activity
- Bequia, Bequia Fort & Lower Beach Getaway (Easy-Moderate) — Easy-Moderate activity
Published call times
- November 11, 2026 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
November 12, 2026 MAYREAU
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
- November 12, 2026 · Arrival 08:00 · Departure 17:00
November 13, 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 13, 2026 · Arrival 10:00 · Departure 17:00 · Watersports platform scheduled
November 14, 2026 MARIGOT BAY
About MARIGOT BAY
MARIGOT BAY is a Windstar destination in Saint Martin within the Caribbean sailing region. Across the current published program, locally focused experience themes include Beach Day at KKO With Lunch, French Creole Cooking Class & French and Dutch Island Discovery. 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
- Marigot, French Creole Cooking Class — Easy-Moderate activity
- Marigot, Beach Day at KKO With Lunch — Easy activity
- Marigot, French and Dutch Island Discovery — Easy-Moderate activity
- Marigot, America's Cup Sailboat Racing (Moderate-Strenuous) — Moderate-Strenuous activity
Published call times
- November 14, 2026 · Arrival 08:00 · Departure 15:00
November 16, 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, 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
- November 16, 2026 · Arrival 08:00 · Departure 18:00
November 17, 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, Brimstone Hill Fortress & Fairview Great House — Easy-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
- Basseterre: Sky Safari Zipline Adventure (Strenuous) — Strenuous activity
- Basseterre, Island History & Rum Tasting — Moderate activity
- Basseterre: St Kitts Quad ATV Adventure — Strenuous activity
- Basseterre: Snorkel Safari (Moderate) — Moderate activity
Published call times
- November 17, 2026 · Arrival 08:00 · Departure 17:00
November 18, 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: Savor St Barts — Moderate activity
- Sailing Catamaran to St Barth Nature Reserve — Moderate activity
- St Barts, Concierge Collection: St. Barthelemy Beach Day (Easy-Moderate) — Easy-Moderate activity
- Gustavia, Concierge Collection: Scuba Dive 1 Tank — Strenuous activity
- Gustavia, Concierge Collection: Scuba Dive 2 Tank — Strenuous activity
- St. Barts, Concierge Collection: Sunset Cruise (Easy-Moderate) — Easy-Moderate activity
- Gustavia, Concierge Collection: Jet Ski — Strenuous activity
Published call times
- November 18, 2026 · Arrival 07:00 · Departure 22:00 · Watersports platform scheduled
November 19, 2026 PHILIPSBURG, ST. MAARTEN
About PHILIPSBURG, ST. MAARTEN
PHILIPSBURG, ST. MAARTEN gives this stage of the itinerary its individual destination focus. Master the art of cooking with distinct spices like nutmeg, cloves and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg.
Shore experiences currently listed
- St. Maarten: Under Two Flags Island Tour (Easy) — Easy activity
- St. Maarten, Concierge Collection: Half Day Private Island Tour in SUV or Deluxe Mini Van (Easy) — Easy activity
- Philipsburg, Savor St. Maarten Foodie Tour — Easy-Moderate activity
- St. Maarten: America's Cup Sailboat Racing — Moderate-Strenuous activity
Published call times
- November 19, 2026 · Arrival 08:00 · Departure 22:00
November 20, 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 20, 2026 · Arrival 09:00 · Departure 22:00 · Watersports platform scheduled
November 21, 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: Snorkel Adventure (Moderate-Strenuous) — Moderate-Strenuous activity
- Virgin Gorda: Highlights & Bath Tour (Moderate) — Strenuous activity
Published call times
- November 21, 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 November 8-22 2026, Star Pride sails 14 nights from SAN JUAN to SAN JUAN. The published route brings together ST. GEORGE'S, GRENADA, BEQUIA, MAYREAU, LES SAINTES, GUADELOUPE, 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 14 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.
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