itinerary & excursions

Southeast Canadian Explorations

Boston to Montreal

Mon Sep 14, 2026 - Fri Sep 25, 2026,

11 days

on Star Pride

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DATES & FARES

OVERVIEW & ITINERARY

ITINERARY AND SHORE EXCURSIONS

The best on land brought to you by the best at sea. Get to the heart of local cultures with Windstar shore excursions. You don't want to just dip a toe in local culture, you want to dive into the deep end, and that's exactly what Windstar shore excursions are designed to do. All of our excursion are created to provide authentic local experience - the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you're an outdoor enthusiast, a foodie, a history buff, or someone who loves to get to know the faces behind the many places we travel.

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Date

Port

Arrive

Depart

Watersports
Platform

Shore
Excursions

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Mon Sep 14

Boston

Arrive:

Depart:5:00 PM

Watersports Platform:

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.

Tue Sep 15

Rockland

Arrive:8:00 AM

Depart:6:00 PM

Watersports Platform:

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.

Wed Sep 16

Portland

Arrive:8:00 AM

Depart:11:00 PM

Watersports Platform:

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 19^th 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.

Thu Sep 17

AT SEA

Arrive:

Depart:

Watersports Platform:

Fri Sep 18

Halifax

Arrive:8:00 AM

Depart:6:00 PM

Watersports Platform:

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.

Sat Sep 19

Louisbourg

Arrive:12:00 PM

Depart:7:00 PM

Watersports Platform:

First occupied by the Mi’kmaw people, Louisbourg sits on the rocky shoreline of Cape Breton. This modern town has an impressive fortress, interesting walking trails, and fishing wharves bringing in amazing fresh seafood. In this beautiful setting sites to see include the winding Havenside Road, Lighthouse Point, the beaches of Kennington Cove and the Sydney & Louisburg Railway Museum.

Sun Sep 20

Cap aux Meules

Arrive:10:00 AM

Depart:6:00 PM

Watersports Platform:

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.

Mon Sep 21

Gaspe

Arrive:1:00 PM

Depart:7:00 PM

Watersports Platform:

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.

Tue Sep 22

AT SEA

Arrive:

Depart:

Watersports Platform:

Wed Sep 23

Quebec City

Arrive:9:00 AM

Depart:

Watersports Platform:

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.

Thu Sep 24

Quebec City

Arrive:

Depart:4:00 PM

Watersports Platform:

Fri Sep 25

Montreal

Arrive:8:00 AM

Depart:

Watersports Platform:

Montreal is full of interesting architecture and is considered by many to be the creative capital of Canada. Named a UNESCO City of Design, Montreal attractions include Basilique Notre-Dame, Stade Olympique, Canal de Lachine, Old Montreal, and Habitat 67. Enjoy a meal at one of the terraced cafes of Plateau Mont-Royal and make sure you try Kamouraska lamb, Arctic char and poutine.