Windstar Cruises luxury itinerary
Star Pride October 9-28 2026 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 9-28 2026 ยท Voyage PR20261009-19D
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.
14 destination panels · 56 verified voyage-specific shore experiences · 3 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 9, 2026 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 9, 2026 · Embarkation · Departure 18:00
October 10, 2026 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 10, 2026 · Arrival 05:00 · Departure 08:00
October 10-11, 2026 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 City, Historic Quebec with Montmorency Falls (Easy) — Easy activity
- Quebec, Helicopter Tour- 30 Minute Flight — Moderate activity
- Quebec,,Walk, Fortification and Maple Toffee Tasting — Moderate activity
- Quebec, Ile of Orleans Food Tour — Easy-Moderate activity
- Quebec, Ste Anne Canyon and Basilica (Easy-Moderate) — Easy-Moderate activity
- Quebec City, Rendez-vous with Wendat First Nation (Easy-Moderate) — Easy-Moderate activity
- Quebec, Concierge Collection. Walking and Reidel Wine Tasting at Chatteau Frontenac — Moderate activity
Published call times
- October 10, 2026 · Arrival 09:00 · Departure 23:59 · Overnight stay
- October 11, 2026 · Departure 18:00 · Overnight stay
6 sea days · October 12-October 27, 2026 Sea Days
Published sea days aboard Star Pride
The official Windstar timetable names no port call on 6 sea days · October 12-October 27, 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
- October 12, 2026 · No separately published port call
- October 17, 2026 · No separately published port call
- October 21, 2026 · No separately published port call
- October 22, 2026 · No separately published port call
- October 26, 2026 · No separately published port call
- October 27, 2026 · No separately published port call
October 13, 2026 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, Walking in Forillon National Park (Moderate) — Moderate activity
- Gaspe, Gin and Beer Heritage Tasting — Moderate activity
- Gaspe, Percé & Cruise around Bonaventure Island & Percé Sectors (Easy) — Easy activity
- Gaspe, Panoramic Tour of Gaspe (Easy) — Easy activity
- Gaspe, Whale Watching (Moderate) — Moderate activity
- Gaspe, Zodiac Marine Adventure — Moderate-Strenuous activity
- Gaspe, E-Bike Tour — Easy activity
Published call times
- October 13, 2026 · Arrival 07:00 · Departure 14:00
October 14, 2026 CAPAUX MEULES, MAGDALEN ISLAND, QC
About CAPAUX MEULES, MAGDALEN ISLAND, QC
CAPAUX MEULES, MAGDALEN ISLAND, QC is a Windstar destination in Canada within the Canada & New England sailing region. Across the current published program, locally focused experience themes include Cycling around Cap-aux-Meules, Magdalen Island, Island Highlights & Magdalen Island, Lobster Fishing. 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
- Cap aux Meules, Magdalen Island, Lobster Fishing (Easy-Moderate) — Easy-Moderate activity
- Cap aux Meules, Magdalen Island, Havre aux Maison's Highlights and Bagosse Tasting — Easy-Moderate activity
- Cap Aux Meules, Magdalen Island, Fisherman & Acadian Culture (Easy-Moderate) — Easy-Moderate activity
- Cap Aux Meules, Magdalen Island, Caves & Cliffs By Boat (Moderate) — Moderate activity
- Cap Aux Meules, Magdalen Island, Island Highlights (Moderate) — Moderate activity
- Cap-aux-Meules, Cycling around Cap-aux-Meules — Easy-Moderate activity
- Cap Aux Meules, Magdalen Island, A Taste of Iles De La Madeleine (Moderate) — Moderate activity
Published call times
- October 14, 2026 · Arrival 11:00 · Departure 18:00
October 15, 2026 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, Fortress or Louisbourg — Moderate activity
- Sydney, Heart of the Island (Moderate-Strenuous)
- Sydney, Historical Sydney Walking Tour — Moderate activity
Published call times
- October 15, 2026 · Arrival 07:00 · Departure 14:00
October 16, 2026 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 Harmony & Heritage Tour — Moderate-Strenuous activity
- Halifax, Scenic Peggy's Cove (Easy-Moderate) — Easy-Moderate activity
- Halifax, Harbor Hopper (Moderate) — Moderate activity
- Halifax, Taste of Halifax on Foot (Moderate) — Moderate activity
- Halifax, Halifax & The Titanic Connection (Easy-Moderate) — Easy-Moderate activity
- Halifax, Annapolis Valley Food and Wine — Moderate activity
Published call times
- October 16, 2026 · Arrival 11:00 · Departure 23:00
October 18, 2026 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, Lighthouses Of Maine (Moderate) — Moderate activity
- Portland, Kennebunkport and Scenic Cruise — Moderate activity
- Portland, Culinary Walking Tour of Portland (Moderate) — Moderate activity
- Portland, Bike and Hike Portland (Moderate-Strenuous) — Moderate-Strenuous activity
- Portland, A Day in Maine with Kennebunkport — Easy-Moderate activity
- Portland, Schooner Sail — Moderate activity
- Portland, Beyond the Old Port Walking Tour w/ Wadsworth Longfellow House — Moderate activity
Published call times
- October 18, 2026 · Arrival 08:00 · Departure 22:00
October 19, 2026 ROCKLAND, ME
About ROCKLAND, ME
ROCKLAND, 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 The Best Of Mid-Coast Maine, Rockland Wine Experience & Camden & Owls Head Transportation Museum, Lighthouse & Camden. 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
- Rockland, Owls Head Transportation Museum, Lighthouse & Camden (Moderate) — Moderate activity
- Rockland, Rockland Wine Experience & Camden (Easy) — Easy activity
- Rockland, The Best Of Mid-Coast Maine (Moderate) — Moderate activity
- Rockland, Farnsworth Museum, Camden & Mt. Battie (Moderate) — Moderate activity
Published call times
- October 19, 2026 · Arrival 08:00 · Departure 17:00
October 20, 2026 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 Airport (Easy) — Easy activity
- Boston, City Tour With Transfer To Windstar Hotel (Easy) — Easy activity
Published call times
- October 20, 2026 · Arrival 08:00 · Departure 17:00
October 23-24, 2026 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 experiences currently listed
- Hamilton, Mysteries of the Bermuda Triangle and Hamilton Train Tour — Easy activity
- Hamilton, Quintessential Island Drive (Easy) — Easy activity
- Hamilton, Glass Bottom Snorkel & Sightseeing (Easy-Moderate) — Easy-Moderate activity
- Hamilton, Crystal Cave Discovery — Easy-Moderate activity
- Hamilton, VIP Sunset Sail (Easy-Moderate) — Easy-Moderate activity
- Hamilton, Harrington Sound ECO Cruise — Moderate activity
Published call times
- October 23, 2026 · Arrival 08:45 · Departure 23:59 · Overnight stay
- October 24, 2026 · Departure 07:00 · Overnight stay
October 24-25, 2026 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 Georges, Electric E Trike - Explore St. Georges — Moderate-Strenuous activity
- St. George's, Harrington Sound ECO Cruise (Moderate) — Moderate activity
- St. George's, St George's Heritage Walking Tour (Moderate) — Moderate activity
- St George's, Old Town Train — Easy activity
- St. George's, Colonial St. George's Sightseeing Trip (Easy) — Easy activity
- St. George's, Crystal Caves Discovery Tour (Moderate) — Moderate activity
Published call times
- October 24, 2026 · Arrival 10:00 · Departure 23:59 · Overnight stay
- October 25, 2026 · Departure 07:00 · Overnight stay
October 28, 2026 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
- October 28, 2026 · 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 9-28 2026, Star Pride sails 19 nights from MONTREAL, QC to SAN JUAN. The published route brings together CRUISING ST. LAWRENCE RIVER, QUEBEC CITY, QC, GASPE, QC, 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 16 route entries, including embarkation, disembarkation, scenic passages, and any sea days exactly as published.
For PR20261009-19D, 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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