Windstar Cruises luxury itinerary
Star Legend December 20-January 3 2027 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 2027-January 3 2028 · Voyage LE20271220-14D
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 · 33 verified voyage-specific shore experiences · 7 panels 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, 2027, December 27, 2027 & January 3, 2028 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 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
- December 20, 2027 · Embarkation · Departure 19:00
- December 27, 2027 · Arrival 07:00 · Departure 19:00
- January 3, 2028 · Arrival 07:00 · Disembarkation
December 21, 2027 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, Cinnamon Beach Getaway — Moderate activity
- St. John, Trunk Bay Snorkeling Experience — Moderate activity
- St. John, Island tour Featuring Annaberg Ruins — Easy activity
- St. John, Lind Point Trail Eco Hike — Moderate activity
Published call times
- December 21, 2027 · Arrival 08:00 · Departure 18:00
December 22, 2027 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, Island History & Rum Tasting — Moderate activity
- Basseterre, Nevis Panoramic and Beach Tour (Easy-Moderate) — Easy-Moderate activity
- Basseterre: St Kitts Quad ATV Adventure — Strenuous activity
- Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts (Easy) — Easy activity
Published call times
- December 22, 2027 · Arrival 08:00 · Departure 17:00
December 23, 2027 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 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
- December 23, 2027 · Arrival 07:00 · Departure 22:00 · Watersports platform scheduled
December 24, 2027 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 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
- December 24, 2027 · Arrival 08:00 · Departure 22:00
December 25, 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 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
- December 25, 2027 · Arrival 09:00 · Departure 22:00 · Watersports platform scheduled
December 26, 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
- December 26, 2027 · Arrival 08:00 · Departure 17:00
December 28, 2027 Sea Days
Published sea days aboard Star Legend
The official Windstar timetable names no port call on December 28, 2027. 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 28, 2027 · No separately published port call
December 29, 2027 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, Spice of Our Lives (Easy-Moderate) — Easy-Moderate activity
- St. George's, The Best of Grenada (Easy) — Easy 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. George's, Adventure River Tubing (Moderate) — 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, Clear Bottom Kayaking — Moderate-Strenuous activity
- St. George's, Certified One-Tank Dive — Moderate-Strenuous activity
- St. George's, Discover Scuba — Moderate activity
Published call times
- December 29, 2027 · Arrival 09:00 · Departure 22:00
December 30, 2027 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, Taste of Bequia (Easy-Moderate) — Easy-Moderate activity
- Bequia, Bequia Fort & Lower Beach Getaway (Easy-Moderate) — Easy-Moderate activity
- Bequia, Concierge Collection: Rum Tasting at Firefly Plantation — Moderate activity
- Bequia, Bequia Highlights (Easy-Moderate) — Easy-Moderate activity
- Bequia, Bequia Snorkel Adventure — Strenuous activity
Published call times
- December 30, 2027 · Arrival 08:00 · Departure 22:00 · Watersports platform scheduled
December 31, 2027 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 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
- December 31, 2027 · Arrival 08:00 · Departure 17:00
January 1, 2028 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 Historic Tastes & Treasures of Fort Napoleon, Snorkel Experience in Les Saintes & Terre de Haut Panoramic Tour. 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 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
- January 1, 2028 · Arrival 10:00 · Departure 17:00 · Watersports platform scheduled
January 2, 2028 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, Rhum and Rhythm — Easy activity
- Marigot, French and Dutch Island Discovery — Easy-Moderate activity
- Marigot, Beach Day at KKO With Lunch — Easy activity
Published call times
- January 2, 2028 · Arrival 08:00 · Departure 15:00
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 Legend
On December 20 2027-January 3 2028, Star Legend sails 14 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 14 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.
For LE20271220-14D, 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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