Windstar Cruises luxury itinerary
Star Pride December 20-January 3 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.
December 20 2026-January 3 2027 · Voyage PR20261220-14D
Ports & shore experiences
Published journey: Star Collector: Lovely Leewards
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 · 53 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.
December 20, 2026, December 27, 2026 & January 3, 2027 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: Barilito Rum Tour & Tasting with Transfer to Airport (Easy-Moderate) — Easy-Moderate activity
- San Juan: Barilito Rum Tour & Tasting with Transfer to Windstar Hotel (Easy-Moderate) — 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 Airport (Moderate-Strenuous) — Moderate-Strenuous activity
- San Juan: Old San Juan Fortress & City Walking Tour with Transfer to Windstar Hotel (Moderate-Strenu — Moderate-Strenuous activity
Published call times
- December 20, 2026 · Embarkation · Departure 19:00
- December 27, 2026 · Arrival 07:00 · Departure 19:00
- January 3, 2027 · Arrival 07:00 · Disembarkation
December 21, 2026 Sea Days
Published sea days aboard Star Pride
The official Windstar timetable names no port call on December 21, 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
- December 21, 2026 · No separately published port call
December 22, 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, Powerboat & Snorkeling at the Statues Park (Moderate-Strenuous) — Moderate-Strenuous activity
- St. George's, Great Tower Estate with Tea (Easy-Moderate) — Easy-Moderate activity
- St. George's, Certified Two-Tank Dive — Moderate-Strenuous activity
- St. Georges, Fort Frederick Rainforest & Waterfall — Moderate 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, Clear Bottom Kayaking — Moderate-Strenuous activity
- St. George's, Sailing Cruise to the Statue Park (Moderate-Strenuous) — Moderate-Strenuous activity
- St. George's, Discover Scuba — Moderate activity
- St. George's, The Best of Grenada (Easy) — Easy activity
Published call times
- December 22, 2026 · Arrival 09:00 · Departure 22:00
December 23, 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, Concierge Collection: Rum Tasting at Firefly Plantation — Moderate activity
- Bequia, Bequia Highlights (Easy-Moderate) — Easy-Moderate activity
- Bequia, Bequia Snorkel Adventure — Strenuous activity
- Bequia, Bequia Fort & Lower Beach Getaway (Easy-Moderate) — Easy-Moderate activity
- Bequia, Taste of Bequia (Easy-Moderate) — Easy-Moderate activity
- Bequia, Mustique Magic with Lunch (Moderate) — Moderate activity
Published call times
- December 23, 2026 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
December 24, 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 Tobago Cays 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, Tobago Cays Escape — Moderate activity
Published call times
- December 24, 2026 · Arrival 08:00 · Departure 16:30
December 25, 2026 DESHAIES
About DESHAIES
Deshaies is a small fishing village on Guadeloupe’s lush Basse-Terre coast, gathered around a calm bay backed by green hills. Colorful waterfront buildings, nearby beaches, and a celebrated botanical garden give the stop an intimate scale. Rainforest scenery and Creole culture shape the wider island experience.
Shore experiences currently listed
- Deshaies, Botanical Garden Exploration in Guadeloupe Island — Strenuous activity
Published call times
- December 25, 2026 · Arrival 11:00 · Departure 18:00
December 26, 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 and Dutch Island Discovery — Easy-Moderate activity
- Marigot, America's Cup Sailboat Racing (Moderate-Strenuous) — Moderate-Strenuous activity
- Marigot, Half Day Private Island Tour in SUV or Deluxe Mini Van (Easy) — Easy activity
- Marigot, French Creole Cooking Class — Easy-Moderate activity
- Marigot, Beach Day at KKO With Lunch — Easy activity
Published call times
- December 26, 2026 · Arrival 08:00 · Departure 15:00
December 28, 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, Trunk Bay Snorkeling Experience & Island tour Featuring Annaberg Ruins. 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, Island tour Featuring Annaberg Ruins — Easy activity
- St. John, Cinnamon Beach Getaway — Moderate activity
- St. John, Trunk Bay Snorkeling Experience — Moderate activity
Published call times
- December 28, 2026 · Arrival 08:00 · Departure 18:00
December 29, 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 & 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 experiences currently listed
- St Barts, Concierge Collection: St. Barthelemy Beach Day (Easy-Moderate) — Easy-Moderate activity
- Sailing Catamaran to St Barth Nature Reserve — Moderate activity
- St. Barts: Intimate Island Tour (Easy) — Easy activity
- St. Barts, Concierge Collection: Sunset Cruise (Easy-Moderate) — Easy-Moderate activity
- Gustavia, Concierge Collection: Jet Ski — Strenuous activity
- Gustavia, Concierge Collection: Scuba Dive 2 Tank — Strenuous activity
- St. Barts: Independent Explorer by Car (Easy-Moderate) — Easy-Moderate activity
Published call times
- December 29, 2026 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
December 30, 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 St Kitts Quad ATV Adventure, Island History & Rum Tasting & Sky Safari Zipline 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
- Basseterre, Brimstone Hill Fortress & Fairview Great House — Easy-Moderate activity
- Basseterre: Sky Safari Zipline Adventure (Strenuous) — Strenuous activity
- Basseterre, Nevis Panoramic and Beach Tour (Easy-Moderate) — Easy-Moderate activity
- Basseterre: St Kitts Quad ATV Adventure — Strenuous activity
- Basseterre, Irie Rider Speed Boat (Moderate-Strenuous) — Moderate-Strenuous activity
- Basseterre, Island History & Rum Tasting — Moderate activity
- Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts (Easy) — Easy activity
Published call times
- December 30, 2026 · Arrival 08:00 · Departure 17:00
December 31, 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
- Philipsburg: Beach Day at KKO with Lunch — Easy activity
- St. Maarten: Under Two Flags Island Tour (Easy) — Easy activity
- St. Maarten: America's Cup Sailboat Racing — Moderate-Strenuous activity
- Philipsburg, Savor St. Maarten Foodie Tour — Easy-Moderate activity
- St. Maarten, Concierge Collection: Half Day Private Island Tour in SUV or Deluxe Mini Van (Easy) — Easy activity
Published call times
- December 31, 2026 · Arrival 08:00 · Departure 22:00
January 1, 2027 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
- January 1, 2027 · Arrival 09:00 · Departure 22:00 · Watersports platform scheduled
January 2, 2027 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
- January 2, 2027 · 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 December 20 2026-January 3 2027, Star Pride sails 14 nights from SAN JUAN to SAN JUAN. The published route brings together ST. GEORGE'S, GRENADA, BEQUIA, MAYREAU, DESHAIES, 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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