Windstar Cruises luxury itinerary
Star Pride October 11-November 1 2027 Cruise & Offers
MONTREAL, QC to SAN JUAN
Review the complete published itinerary, source-status notes, suite guidance, and current offer assistance with Deluxe Cruises.
October 11-November 1 2027 ยท Voyage PR20271011-21D
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.
15 destination panels · 42 verified voyage-specific shore experiences · 5 panels with planning notices
Official voyage overview
Embark in Montreal, City of a Hundred Steeples, and overnight in Quebec City, with its UNESCO World Heritage Old Town, to find 400-year-old ramparts filled with history. Enjoy the breathtaking seascapes of Gaspé, waves crashing against limestone cliffs, and watch sugar maples and birch trees flout their fall colors. Retrace the battles for North America in the Fortress of Louisbourg, the UNESCO town of Lunenburg, the Citadel in Halifax, and Boston — where the Freedom Trail leads you to Paul Revere’s house. Then, trade in your autumn palette for Bermuda’s spring colors — blushing pink beaches and turquoise waters. Wander historic forts and UNESCO sites in Bermuda, St. Kitts and San Juan before sailing on to chic St. Bart. Granite boulders form The Baths on Virgin Gorda, perfect for a soak or snorkel. Colorful Old San Juan will keep you busy as you await your flight home.
October 11, 2027 MONTREAL, QC
About MONTREAL, QC
MONTREAL, QC gives this stage of the itinerary its individual destination focus. Embark in Montreal, City of a Hundred Steeples, and overnight in Quebec City, with its UNESCO World Heritage Old Town, to find 400-year-old ramparts filled with history.
Shore experiences currently listed
- Montreal, Highlights with Basilica with Transfer to Windstar Hotel (Easy) — Easy activity
Published call times
- October 11, 2027 · Embarkation · Departure 17:00
October 12, 2027 CRUISING ST. LAWRENCE RIVER
About CRUISING ST. LAWRENCE RIVER
CRUISING ST. LAWRENCE RIVER is a published scenic navigation or transit call rather than a conventional shore visit. The passage forms part of this Canada & New England route, with the surrounding waterway or coastline providing the principal view from aboard Star Pride. Exact dates and times are retained below; no unlisted stop or activity has been inferred.
Shore planning
No voyage-specific shore experience is published for this scenic navigation or transit call. Deluxe Cruises can help review the final voyage program closer to departure.
Published call times
- October 12, 2027 · Arrival 05:00 · Departure 07:30
October 12, 2027 QUEBEC CITY, QC
About QUEBEC CITY, QC
QUEBEC CITY, QC gives this stage of the itinerary its individual destination focus. Embark in Montreal, City of a Hundred Steeples, and overnight in Quebec City, with its UNESCO World Heritage Old Town, to find 400-year-old ramparts filled with history.
Shore experiences currently listed
- Quebec, Ste Anne Canyon and Basilica (Easy-Moderate) — Easy-Moderate activity
- Quebec,,Walk, Fortification and Maple Toffee Tasting — Moderate activity
- Quebec, Ile of Orleans Food Tour — Easy-Moderate activity
- Quebec City, Historic Quebec with Montmorency Falls (Easy) — Easy activity
- Quebec, Helicopter Tour- 30 Minute Flight — Moderate activity
- Quebec, Concierge Collection. Walking and Reidel Wine Tasting at Chatteau Frontenac — Moderate activity
- Quebec City, Rendez-vous with Wendat First Nation (Easy-Moderate) — Easy-Moderate activity
Published call times
- October 12, 2027 · Arrival 08:00 · Departure 18:00
6 sea days · October 13-October 29, 2027 Sea Days
Published sea days aboard Star Pride
The official Windstar timetable names no port call on 6 sea days · October 13-October 29, 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
- October 13, 2027 · No separately published port call
- October 17, 2027 · No separately published port call
- October 23, 2027 · No separately published port call
- October 24, 2027 · No separately published port call
- October 28, 2027 · No separately published port call
- October 29, 2027 · No separately published port call
October 14, 2027 GASPE, QC
About GASPE, QC
GASPE, QC is a Windstar destination in Canada within the Canada & New England sailing region. Across the current published program, locally focused experience themes include E-Bike Tour, Zodiac Marine Adventure & Whale Watching. 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
- Gaspe, Percé & Cruise around Bonaventure Island & Percé Sectors (Easy) — Easy activity
- Gaspe, Gin and Beer Heritage Tasting — Moderate activity
- Gaspe, Panoramic Tour of Gaspe (Easy) — Easy activity
- Gaspe, Walking in Forillon National Park (Moderate) — Moderate activity
- Gaspe, E-Bike Tour — Easy activity
- Gaspe, Whale Watching (Moderate) — Moderate activity
- Gaspe, Zodiac Marine Adventure — Moderate-Strenuous activity
Published call times
- October 14, 2027 · Arrival 07:00 · Departure 14:00
October 15-16, 2027 SYDNEY, NS
About SYDNEY, NS
SYDNEY, NS is a Windstar destination in Canada within the Canada & New England sailing region. Across the current published program, locally focused experience themes include Fortress or Louisbourg, Historical Sydney Walking Tour & Heart of the 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
- Sydney, Pub Tour (Moderate)
- Sydney, Historical Sydney Walking Tour — Moderate activity
- Sydney, Fortress or Louisbourg — Moderate activity
- Sydney, Heart of the Island (Moderate-Strenuous)
Published call times
- October 15, 2027 · Arrival 15:00 · Departure 23:59 · Overnight stay
- October 16, 2027 · Departure 23:59 · Overnight stay
October 18-19, 2027 HALIFAX, NS
About HALIFAX, NS
HALIFAX, NS gives this stage of the itinerary its individual destination focus. Retrace the battles for North America in the Fortress of Louisbourg, the UNESCO town of Lunenburg, the Citadel in Halifax, and Boston — where the Freedom Trail leads you to Paul Revere’s house.
Shore experiences currently listed
- Halifax, Annapolis Valley Food and Wine — Moderate activity
- Halifax, Taste of Halifax on Foot (Moderate) — Moderate activity
- Halifax Harmony & Heritage Tour — Moderate-Strenuous activity
- Halifax, Scenic Peggy's Cove (Easy-Moderate) — Easy-Moderate activity
- Halifax, Harbor Hopper (Moderate) — Moderate activity
- Halifax, Halifax & The Titanic Connection (Easy-Moderate) — Easy-Moderate activity
Published call times
- October 18, 2027 · Arrival 08:00 · Departure 23:59 · Overnight stay
- October 19, 2027 · Departure 11:00 · Overnight stay
October 20, 2027 BAR HARBOR, ME
About BAR HARBOR, ME
BAR HARBOR, ME is a Windstar destination in United States within the Canada & New England sailing region. Across the current published program, locally focused experience themes include Cranberry Islands, DiscoverAcadia National Park & Haunted Walking Tour Of Bar Harbor. 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
- Bar Harbor, Grand Tour Of Acadia National Park & Lobsterbake (Easy-Moderate) — Easy-Moderate activity
- Bar Harbor, Cranberry Islands (Easy-Moderate) — Easy-Moderate activity
- Bar Harbor, Haunted Walking Tour Of Bar Harbor (Strenuous) — Strenuous activity
- Bar Harbor, DiscoverAcadia National Park (Easy) — Easy activity
Published call times
- October 20, 2027 · Arrival 08:00 · Departure 18:00
October 21, 2027 PORTLAND, ME
About PORTLAND, ME
PORTLAND, ME is a Windstar destination in United States within the Canada & New England sailing region. Across the current published program, locally focused experience themes include Schooner Sail, Kennebunkport and Scenic Cruise & Lighthouses Of Maine. 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
- Portland, A Day in Maine with Kennebunkport — Easy-Moderate activity
- Portland, Bike and Hike Portland (Moderate-Strenuous) — Moderate-Strenuous activity
- Portland, Lighthouses Of Maine (Moderate) — Moderate activity
- Portland, Culinary Walking Tour of Portland (Moderate) — Moderate activity
- Portland, Schooner Sail — Moderate activity
- Portland, Beyond the Old Port Walking Tour w/ Wadsworth Longfellow House — Moderate activity
- Portland, Kennebunkport and Scenic Cruise — Moderate activity
Published call times
- October 21, 2027 · Arrival 08:00 · Departure 18:00
October 22, 2027 BOSTON, MA
About BOSTON, MA
BOSTON, MA gives this stage of the itinerary its individual destination focus. Retrace the battles for North America in the Fortress of Louisbourg, the UNESCO town of Lunenburg, the Citadel in Halifax, and Boston — where the Freedom Trail leads you to Paul Revere’s house.
Shore experiences currently listed
- Boston, City Tour With Transfer To Windstar Hotel (Easy) — Easy activity
- Boston, City Tour With Transfer To Airport (Easy) — Easy activity
Published call times
- October 22, 2027 · Arrival 08:00 · Departure 17:00
October 25-26, 2027 HAMILTON
About HAMILTON
HAMILTON is a Windstar destination in Bermuda within the Canada & New England sailing region. Across the current published program, locally focused experience themes include Crystal Cave Discovery, Harrington Sound ECO Cruise & VIP Sunset Sail. 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
- October 25, 2027 · Arrival 08:45 · Departure 23:59 · Overnight stay
- October 26, 2027 · Departure 07:00 · Overnight stay
October 26-27, 2027 ST GEORGE'S BERMUDA
About ST GEORGE'S BERMUDA
ST GEORGE'S BERMUDA gives this stage of the itinerary its individual destination focus. Then, trade in your autumn palette for Bermuda’s spring colors — blushing pink beaches and turquoise waters. Wander historic forts and UNESCO sites in Bermuda, St.
Shore experiences currently listed
- St. George's, St George's Heritage Walking Tour (Moderate) — Moderate activity
- St. George's, Crystal Caves Discovery Tour (Moderate) — Moderate activity
Published call times
- October 26, 2027 · Arrival 10:00 · Departure 23:59 · Overnight stay
- October 27, 2027 · Departure 12:00 · Overnight stay
October 30, 2027 GUSTAVIA, ST. BARTHELEMY
About GUSTAVIA, ST. BARTHELEMY
GUSTAVIA, ST. BARTHELEMY is a Windstar destination in Saint Barthelemy within the Canada & New England 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 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
- October 30, 2027 · Arrival 10:00 · Departure 22:00 · Watersports platform scheduled
October 31, 2027 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. Granite boulders form The Baths on Virgin Gorda, perfect for a soak or snorkel. This context places the destination within the Canada & New England 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
- October 31, 2027 · Arrival 08:00 · Departure 18:00
November 1, 2027 SAN JUAN
About SAN JUAN
SAN JUAN gives this stage of the itinerary its individual destination focus. Kitts and San Juan before sailing on to chic St. Colorful Old San Juan will keep you busy as you await your flight home. This context places the destination within the Canada & New England route; exact call times and any experiences published for this sailing are listed 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
- November 1, 2027 · Arrival 07:00 · Disembarkation
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
MONTREAL, QC to SAN JUAN aboard Star Pride
On October 11-November 1 2027, Star Pride sails 21 nights from MONTREAL, QC to SAN JUAN. The published route brings together CRUISING ST. LAWRENCE RIVER, QUEBEC CITY, QC, GASPE, QC, SYDNEY, NS, 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 18 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.
For PR20271011-21D, 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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