21 nights · Quebec Canada · Departs Montreal (Canada) · Visiting Quebec City, Gaspe, Sydney NS, Halifax, Bar Harbor, Portland ME, Boston, Hamilton, St George, Gustavia St Barths, Virgin Gorda Island BVI, San Juan · Aboard Windstar Cruises on the Star Pride
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Star Pride |
| Duration | 21 nights |
| Port calls | 13 |
| Departures | 1 sailings |
| From fare | $8,435 per person |
| Year built | 1988 |
| Guests | 343 |
| Cabins | 156 |
| Crew | 190 |
| Length | 159 m |
| Beam | 19 m |
| Cruising speed | 15.0 kn |
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.
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.
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.
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.
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.
Bar Harbor is the gateway to Acadia National Park, where granite cliffs, spruce forests and coastal trails frame the Atlantic. Closer to town, the Shore Path follows the waterfront past elegant summer cottages and views across Frenchman Bay. Walkable streets lead to independent shops and restaurants serving Maine lobster and other local seafood. Take a boat trip for a different view of the islands, or explore Acadia’s carriage roads and mountain routes.
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.
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.
Hamilton, Bermuda’s compact capital, pairs pastel façades with a sheltered harbor. The island’s daily life unfolds within easy reach of the waterfront. Smaller ships can dock close to Front Street, lined with boutiques, cafés and restaurants. Ferries link Hamilton with Dockyard and other island stops. Allow time for the Bermuda National Gallery or a stroll through leafy side streets before exploring farther afield.
Step ashore in St. George’s, Bermuda’s oldest town and a UNESCO World Heritage site. Its lanes, pastel-fronted houses and historic churches reward an unhurried walk. Once Bermuda’s capital, the town still gathers around King’s Square, where colonial-era buildings frame the waterfront. St. Peter’s Church and nearby Fort St. Catherine deepen a day of walking, with coastal views as your reward.
Gustavia makes a polished first impression, but its appeal is more than designer boutiques and superyachts. Swedish rule left its mark in the town’s name and the ruins of Fort Gustav above the harbor. From the waterfront, cafés, galleries and shops sit within easy walking distance, while Shell Beach lies just beyond the center. Come ashore for French-Caribbean style, with history close at hand.
Virgin Gorda swaps city bustle for clear water, quiet coves and a dramatic coastline. At The Baths, granite boulders form a maze of sea pools and narrow passages beside the beach. Some routes involve ladders and slippery rocks, so wear shoes with grip. Spanish Town is the island’s main settlement; North Sound is known for sheltered anchorages and sailing. Go early to explore The Baths before the busiest hours, then cool off in the Caribbean.
San Juan puts a remarkable piece of Caribbean history within easy reach of your ship. Founded in 1521, Old San Juan is a compact district of blue cobbles, pastel façades and Spanish colonial landmarks. Walk its steep lanes to El Morro, the 16th-century fortress that guards the harbor. From its ramparts, the Atlantic comes into view. Beyond the old walls, cafés, galleries and contemporary restaurants show a city still shaped by its maritime past.
Published September 22, 2026
Last updated October 3, 2026
Author: J. Richard
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