Windstar 19 Nights Caribbean

Star Collector: Fall Leaves & Caribbean Breezes

Star Pride • Embarkation: Montreal

Voyage Overview

Embark Date 09-Oct-2026
Disembark Date 28-Oct-2026
Duration 19 Nights
Vessel Star Pride

Day-by-Day Itinerary

Day 1: MONTREAL, QC

Montreal is one of North America’s great cultural capitals, where European heritage and contemporary creativity intersect. A UNESCO City of Design, the city is renowned for its architecture, museums, and vibrant arts scene. Explore Old Montreal’s cobblestone streets and historic squares, admire the soaring interior of Basilique Notre-Dame, and discover museums and galleries that reflect the city’s French roots and modern spirit. Then, visit distinct neighborhoods such as Plateau Mont-Royal showcasing Montreal’s trendier and more artistic side.

Day 2: CRUISING ST LAWRENCE RIVER

Sail inland along the St. Lawrence River from the Atlantic, passing the mid-river Phare du Haut-Fond-Prince lighthouse, forested islands, and charming historic river towns as you make your way toward the vibrant city of Montréal.

Day 3: QUEBEC CITY, QC

A focal point of French culture and one of North America's oldest and most beautiful cities, Quebec City sits above the St. Lawrence River on a rocky spur with 328-foot cliffs. This French-speaking city was established in 1608 with the only fortified city walls remaining in America north of Mexico, and declared a UNESCO World Heritage City. The Old Town is packed with museums, cobblestone streets and mansard-roofed houses begging to be explored. Other historic attractions include the Fairmont Chateau Frontenac, Notre Dame Basilica, Battlefields Park and Terrasse Dufferin.

Day 4: QUEBEC CITY, QC

A focal point of French culture and one of North America's oldest and most beautiful cities, Quebec City sits above the St. Lawrence River on a rocky spur with 328-foot cliffs. This French-speaking city was established in 1608 with the only fortified city walls remaining in America north of Mexico, and declared a UNESCO World Heritage City. The Old Town is packed with museums, cobblestone streets and mansard-roofed houses begging to be explored. Other historic attractions include the Fairmont Chateau Frontenac, Notre Dame Basilica, Battlefields Park and Terrasse Dufferin.

Day 5: SEAD

SEAD

Day 6: GASPE, QC

Four hundred miles northeast of Quebec City lies Gaspe, one of National Geographic's Canada's 50 Places of a Lifetime. This wonderful wilderness area is home to four national parks; Perce Rock; North America's largest gannet colony; lighthouses and remarkable historic sites. Visit the modern cathedral built almost entirely of wood and make sure to try some of the local specialties such as French-styled lobsters and game.

Day 7: CAPAUX MEULES, MAGDALEN ISLAND, QC

With its village main street and many restaurants and bars, charming Cap aux Meules is the gateway to the Magdalen Islands Archipelago located in the middle of the Gulf of St. Lawrence. The port bustles with fishing boats, ferries, and a well-equipped marina offering a huge travel lift crane for dry dock. Sites to see include the church of St. Pierre, constructed from the wreckage of ships and the lighthouse which now warns of the offshore shoals.

Day 8: SYDNEY, NS

Sydney is the largest city on Cape Breton Island where the hub of activity can be found at the waterfront where you'll find the world's largest fiddle. A popular tourist destination, grab a Cape Breton Artisan Trail Map and immerse yourself in the lives of local artisans. Hit Casino Nova Scotia or take a mining tour with the help of a local miner. Check out the year-round indoor Cape Breton Farmers' Market or discover the history of the Membertou people at their Heritage Park.

Day 9: HALIFAX, NS

The capital of Nova Scotia was ranked the 4th best place to live in Canada back in 2012. It is a city with more pubs and clubs per capita than any other Canadian city and even one of the mayors was a brewmaster. The boardwalk on the waterfront follows the water's edge and is lined with unique shops. Halifax is home to the longest running saltwater ferry and a 200-year-old restored fishing village. Be sure to find time to try fabled donair (pita, meat and sauce), the official food of Halifax.

Day 10: SEAD

SEAD

Day 11: PORTLAND, ME

The New England charm of Portland is a delightful mix of stylish and sophisticated, modest and folksy, with a reputation for great dining. There is a plethora of local art and music, lovely parks and a pleasing array of 19th century architecture including beautiful Victorian-era homes. The cobblestone lanes of the Old Port district waterfront are alive with working fishing piers and warehouses converted into shops and restaurants.

Day 12: ROCKLAND, ME

Rockland is a classic Maine coastal town and the lobster capital of the world. It has been recognized by National Geographic Travel as the "Top Adventure Town in Maine," and "Coolest Small Town in US" by Budget Travel. Downtown Rockland is full of historic homes, shops and restaurants serving fresh local seafood. An impressive collection of Maine art can be found at the Farnsworth Art Museum and Wyeth Center. Bordering Penobscot Bay, Rockland is also known internationally as one of the best recreational sailing areas of the world.

Day 13: BOSTON, MA

Founded in 1630 by Puritan settlers, Boston is one of the oldest cities in the U.S. It was a pivotal place during the American Revolution for the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill and the Siege of Boston. Tourists to Boston see the Faneuil Hall Marketplace, the JFK Library and Museum, the Museum of Fine Arts, the New England Aquarium, and the USS Constitution.

Day 14: SEAD

SEAD

Day 15: SEAD

SEAD

Day 16: HAMILTON

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

Day 17: HAMILTON

The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.

Day 18: ST GEORGES BERMUDA

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

Day 19: ST GEORGES BERMUDA

In 2000 St. George's was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George's will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter's Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore's Jungle, Cooper's Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

Day 20: SEAD

SEAD

Day 21: SEAD

SEAD

Day 22: SAN JUAN

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

About Star Pride

Star Pride
  • Cruise Line: Windstar
  • Guest Capacity: 3 guests
  • Vessel Type: Ocean Liner / Mega-Cruise Ship
  • IMO Registration: 8707343
Starting From
$6,868
per person / based on double occupancy
Category Estimates
Inside Cabin: Call
Oceanview Cabin: $6,868
Private Balcony: $14,278
Luxury Suite: $6,868
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