| Cruise line | Windstar Cruises |
|---|---|
| Ship | Star Pride |
| Duration | 11 nights |
| Port calls | 9 |
| Departures | 1 sailings |
| From fare | $5,871 per person |
| Year built | 1988 |
| Guests | 343 |
| Cabins | 156 |
| Crew | 190 |
| Length | 159 m |
| Beam | 19 m |
| Cruising speed | 15.0 kn |
Quebec Canada Cruise from Montréal to Boston — 12 Days
11 nights · Quebec Canada · Departs Montreal (Canada) · Visiting Quebec City, Gaspe, Madeleine-Magdalen Islands, Sydney NS, Halifax, Portland ME, Rockland ME, Boston · Aboard Windstar Cruises on the Star Pride

Image courtesy of Windstar Cruises ©
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Day 1
Montreal, Canada
Montréal is a city of French character and North American energy, best explored on foot. From the Old Port, cobbled streets lead to Old Montréal’s grand squares, cafés and Notre-Dame Basilica. Climb or drive up Mount Royal for a broad view of the skyline and the St. Lawrence River. Then follow the city’s appetite, from market produce and bagels to inventive French-Canadian cooking. Allow time for the museums and lively terraces; Montréal’s pleasures are close together, but never feel hurried.
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Day 2
Quebec City, Canada
Québec City is best explored on foot, where French-speaking Canada feels unmistakably distinct. Within the UNESCO-listed Historic District, stone walls, steep lanes and 17th-century façades tell the story of New France. Ride the funicular between Upper and Lower Town, then browse Petit-Champlain’s boutiques beside the St. Lawrence River. Allow time for the Plains of Abraham, where a pivotal 1759 battle changed the course of Canadian history. Come ashore ready to climb; the finest views reward a little effort.
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Day 5
Gaspe, Canada
Gaspé sits at the eastern end of Quebec’s Gaspé Peninsula. It faces the Gulf of St. Lawrence, with fishing harbours and rugged shoreline close at hand. In 1534, Jacques Cartier met St. Lawrence Iroquoians here and raised a cross for France. Beyond town, Forillon National Park protects cliffs, forests and coastal trails, while whale-watching excursions explore the surrounding waters. At nearby Cap-des-Rosiers, Canada’s tallest lighthouse marks the peninsula’s northern shore.
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Day 6
Madeleine-Magdalen Islands, Canada
The Magdalen Islands rise from the Gulf of St. Lawrence, closer to Prince Edward Island than mainland Quebec. Red cliffs, long beaches and fishing villages keep the sea in view. Explore historic La Grave on Île du Havre-Aubert, where fishers’ cottages and galleries line the waterfront. Follow the coast for smoked herring, fresh lobster and views worth a slower day ashore.
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Day 7
Sydney NS, Canada
Sydney is the working harbour at the heart of Cape Breton Island, where Gaelic, Acadian and Mi’kmaq histories meet. Walk the waterfront to see the Big Fiddle, then browse downtown shops and cafés along Charlotte Street. Beyond town, the reconstructed Fortress of Louisbourg brings 18th-century French colonial life into striking focus. Use Sydney as a base for Cape Breton’s coastal roads, where ocean views and small communities invite an unhurried day.
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Day 8
Halifax, Canada
Halifax rewards visitors who begin on foot, where the harbourfront’s historic warehouses, boardwalk and seafood restaurants meet. Climb to the star-shaped Halifax Citadel for broad harbour views. At the Maritime Museum of the Atlantic, exhibits trace Nova Scotia’s seafaring past and Halifax’s connection to the Titanic. Beyond downtown, Peggy’s Cove pairs a working fishing village with a lighthouse set on wave-worn granite.
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Day 10
Portland ME, USA
Portland follows the Willamette River, with the Columbia to its north and Mount Hood on the eastern horizon. Begin downtown at Powell’s City of Books, a landmark independent bookstore spanning an entire city block. Visit the Japanese American Historical Plaza beside the waterfront, or head to Washington Park’s International Rose Test Garden. Food carts, craft breweries and seasonal produce give the city its distinctive taste. Allow time for the Columbia River Gorge, whose waterfalls and trails lie east of town.
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Day 11
Rockland ME, USA
Rockland puts Maine’s working coast within easy reach, with lobster boats, granite piers and Penobscot Bay on its doorstep. At the Farnsworth Art Museum, paintings by Andrew Wyeth and other American artists offer a compelling counterpoint to the harbor. Walk the nearly mile-long Rockland Breakwater to its lighthouse, then return for fresh seafood along Main Street. Here, art and sea air give the day an unmistakably Maine character.
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Day 12
Boston, USA
Boston rewards visitors who like their history close at hand and their cities easy to explore. From the waterfront, follow the Freedom Trail to landmarks of the American Revolution, including Faneuil Hall. Beacon Hill’s brick streets, the Public Garden and North End cafés reveal distinct sides of the city. Make time for harbor views and New England seafood; Boston’s pleasures are as tangible as its past. Its museums and universities give the compact city a lively, modern edge.
Star Pride Cruises
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- 15 Days One-Way from Oranjestad Aruba to San Juan
- 14 Days One-Way from Panama City to San Juan
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- 15 Days One-Way from Reykjavik to Boston
- 15 Days One-Way from San Juan to Colon
- 15 Days One-Way from San Juan to Puntarenas
- 15 Days Montreal, Canada Round Trip
- 15 Days San Juan, Puerto Rico Round Trip
- 17 Days One-Way from San Juan to Amsterdam
- 17 Days One-Way from San Juan to London-Tilbury
- 18 Days One-Way from Boston to San Juan
- 18 Days One-Way from Copenhagen to Reykjavik
- 19 Days One-Way from Helsinki to Copenhagen
- 20 Days One-Way from London-Tilbury to Helsinki
- 20 Days One-Way from Montreal to San Juan
- 21 Days One-Way from Copenhagen to Reykjavik
- 22 Days One-Way from Montreal to San Juan
- 22 Days One-Way from Oranjestad Aruba to San Juan
- 21 Days One-Way from Puntarenas to San Juan
- 22 Days One-Way from Reykjavik to Boston
- 22 Days One-Way from San Juan to Puntarenas
- 24 Days One-Way from San Juan to Amsterdam
- 26 Days One-Way from Boston to Montreal
- 26 Days One-Way from Montreal to Boston
- 26 Days One-Way from Reykjavik to Montreal
- 4 Days One-Way from London-Tilbury to Amsterdam
- 4 Days London-Tilbury, United Kingdom Round Trip
- 5 Days One-Way from Amsterdam to London-Tilbury
- 7 Days One-Way from Amsterdam to London-Tilbury
- 7 Days Amsterdam, Netherlands Round Trip
- 8 Days One-Way from Colon to Puntarenas
- 8 Days One-Way from Oranjestad Aruba to San Juan
- 7 Days One-Way from Panama City to Oranjestad Aruba
- 8 Days One-Way from Puntarenas to Colon
- 8 Days One-Way from Puntarenas to Panama City
- 8 Days One-Way from San Juan to Colon
- 8 Days London-Tilbury, United Kingdom Round Trip
- 8 Days Reykjavik, Iceland Round Trip
- 8 Days San Juan, Puerto Rico Round Trip
- 9 Days One-Way from Boston to San Juan
- 9 Days One-Way from Copenhagen to Helsinki
- 9 Days One-Way from Helsinki to Copenhagen
Published September 4, 2026
Last updated October 11, 2026
Author: J. Richard
Cruise Disclosure
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