Windstar Cruises luxury itinerary
Star Pride November 15-22 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 15-22 2026 ยท Voyage PR20261115-7D
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 · 32 verified voyage-specific shore experiences · 0 panels with planning notices
Official voyage overview
Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen — like you. Skip more common and commercial ports like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
November 15 & November 22, 2026 SAN JUAN
About SAN JUAN
SAN JUAN gives this stage of the itinerary its individual destination focus. Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. 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
- San Juan, Bacardi Rum Tour & Tasting- With Transfer to Windstar Hotel — Easy-Moderate 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 Windstar Hotel (Moderate-Strenu — Moderate-Strenuous 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 Airport (Moderate-Strenuous) — Moderate-Strenuous activity
Published call times
- November 15, 2026 · Embarkation · Departure 19:00
- November 22, 2026 · Arrival 07:00 · Disembarkation
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, Trunk Bay Snorkeling Experience — Moderate activity
- St. John, Lind Point Trail Eco Hike — 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, Island History & Rum Tasting — 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: 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
- Gustavia, Concierge Collection: Scuba Dive 1 Tank — Strenuous activity
- St. Barts: Intimate Island Tour (Easy) — Easy activity
- Gustavia, Concierge Collection: Scuba Dive 2 Tank — Strenuous activity
- Gustavia, Concierge Collection: Savor St Barts — Moderate activity
- St. Barts, Concierge Collection: Sunset Cruise (Easy-Moderate) — Easy-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: 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 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, 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: Under Two Flags Island Tour (Easy) — Easy 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 gives this stage of the itinerary its individual destination focus. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.
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 gives this stage of the itinerary its individual destination focus. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. 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
- 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 15-22 2026, Star Pride sails 7 nights from SAN JUAN to SAN JUAN. The published route brings together CRUZ BAY, ST. JOHN, BASSETERRE, ST. KITTS, GUSTAVIA, ST. BARTHELEMY, PHILIPSBURG, ST. MAARTEN, 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 8 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.
For PR20261115-7D, 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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