Southeast Canadian Explorations
 
Boston to Montreal
Fri Sep 26, 2025 - Tue Oct 7, 2025,
 11 days
 on Star Pride
?All-inclusive from
$6,478
?Cruise Only From
$5,499
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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.

Date
Port
Arrive
Depart
Watersports
Platform
Shore
Excursions
Expand
Fri Sep 26
Boston
Arrive:
Depart:5:00 PM
Watersports Platform: 
2 Available
+_
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.
2 Shore Excursions Available
+
_
Boston, City Tour With Transfer To AirportEssentials Collection | Sightseeing
Duration2 Hours
Activity LevelEasy
$149
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Boston, City Tour With Transfer To Windstar HotelEssentials Collection | Sightseeing
Duration2 Hours
Activity LevelEasy
$149
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Sat Sep 27
Portland
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
7 Available
+_
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.
7 Shore Excursions Available
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Portland, Bike and Hike PortlandBiking | Concierge Collection | Hiking | Outdoors | Sightseeing
Duration3 Hours
Activity LevelModerate-Strenuous
$149
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Portland, Kennebunkport and Scenic CruiseBoating | Sightseeing
Duration4.75 Hours
Activity LevelModerate
$179
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Portland, Culinary Walking Tour of PortlandConcierge Collection | Culture | Dining | Sightseeing | Walking
Duration2 Hours
Activity LevelModerate
$189
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Portland, Lighthouses Of Maine Walking | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$119
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Portland, A Day in Maine with KennebunkportCulture | Sightseeing
Duration7 Hours
Activity LevelEasy-Moderate
$229
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Portland, Beyond the Old Port Walking Tour with Wadsworth Longfellow HouseSightseeing | Walking
Duration3.25 Hours
Activity LevelModerate
$79
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Portland, Schooner SailBoating | Outdoors | Sightseeing
Duration4.75 Hours
Activity LevelEasy-Moderate
$149
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Sun Sep 28
AT SEA
Arrive:
Depart:
Watersports Platform: 
Mon Sep 29
Lunenburg
Arrive:8:00 AM
Depart:11:00 PM
Watersports Platform: 
4 Available
+_
This UNESCO site with narrow streets and interesting architecture, Lunenburg has a long and proud seafaring history and a picturesque waterfront. Seventy percent of the original buildings from the 18t and 19th centuries are in use today. This walking town has everything centrally located and has turned into a haven for many artists because of its natural beauty.
4 Shore Excursions Available
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Lunenburg, Bay to Bay Biking TourBiking | Essentials Collection | Sightseeing | UNESCO
Duration4 Hours
Activity LevelStrenuous
$165
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Lunenburg, Mysteries of Oak Island by BoatBoating | Essentials Collection | Sightseeing
Duration2.5 Hours
Activity LevelEasy
$429
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Lunenburg, Gaff Point Hiking Trail & PicnicDining | Essentials Collection | Sightseeing | UNESCO | Walking
Duration4 Hours
Activity LevelModerate-Strenuous
$285
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Lunenburg, Highlights of Lunenburg & Mahone BayEssentials Collection | Sightseeing | UNESCO | Walking
Duration3 Hours
Activity LevelEasy-Moderate
$195
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Tue Sep 30
Halifax
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
6 Available
+_
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.
6 Shore Excursions Available
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Halifax, Harbor Hopper Sightseeing | Boating | Essentials Collection
Duration Hour
Activity LevelModerate
$69
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Halifax, Highlander ExperienceEssentials Collection | Sightseeing | Walking
Duration3 Hours
Activity LevelModerate
$199
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Halifax, Sunset Lobster at Peggys CoveDining | Essentials Collection | Sightseeing
Duration4.5 Hours
Activity LevelEasy-Moderate
$399
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Halifax, Scenic Peggys Cove Outdoors | Walking | Sightseeing | Essentials Collection
Duration3 Hours
Activity LevelEasy-Moderate
$169
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Halifax, Taste of Halifax on Foot *Essentials Collection | Sightseeing | Refreshments | Walking | Wine
Duration3.5 Hours
Activity LevelModerate
$179
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Halifax, Halifax & The Titanic Connection Culture | Essentials Collection
Duration3 Hours
Activity LevelEasy-Moderate
$229
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Wed Oct 1
Louisbourg
Arrive:12:00 PM
Depart:7:00 PM
Watersports Platform: 
3 Available
+_
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.
3 Shore Excursions Available
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Louisbourg, Coastal Drive & Sydney HighlightsEssentials Collection | Sightseeing | Walking | Wildlife
Duration4 Hours
Activity LevelEasy
$219
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Louisburg, Fortress of Louisbourg TourEssentials Collection | Sightseeing | Refreshments
Duration3 Hours
Activity LevelModerate
$249
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Culture | Essentials Collection | Refreshments
Duration3.5 Hours
Activity LevelModerate-Strenuous
$349
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Thu Oct 2
Cap aux Meules
Arrive:10:00 AM
Depart:6:00 PM
Watersports Platform: 
4 Available
+_
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.
4 Shore Excursions Available
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Cap Aux Meules, Magdalen Island, Caves & Cliffs By BoatBoating | Essentials Collection | Sightseeing | Wildlife
Duration1.75 Hours
Activity LevelModerate
$139
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Cap Aux Meules, Magdalen Island, Fisherman & Acadian Culture *Essentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$179
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Cap Aux Meules, Magdalen Island, A Taste of Iles De La MadeleineEssentials Collection | Sightseeing | Refreshments
Duration3.75 Hours
Activity LevelModerate
$189
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Cap Aux Meules, Magdalen Island, Island HighlightsEssentials Collection | Sightseeing | Refreshments
Duration3.25 Hours
Activity LevelModerate
$179
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Fri Oct 3
Gaspe
Arrive:1:00 PM
Depart:7:00 PM
Watersports Platform: 
5 Available
+_
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.
5 Shore Excursions Available
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Gaspe, E-Bike TourBiking | Outdoors | Sightseeing
Duration3 Hours
Activity LevelEasy
$229
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Gaspe, Panoramic Tour of GaspeEssentials Collection | Sightseeing | Refreshments
Duration3 Hours
Activity LevelEasy
$119
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Gaspe, Percé & Cruise around Bonaventure Island & Percé Sectors Outdoors | Wildlife | Boating | Essentials Collection
Duration5 Hours
Activity LevelEasy
$159
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Gaspe, Walking in Forillon National ParkEssentials Collection | Outdoors | Sightseeing | Walking | Wildlife
Duration4.5 Hours
Activity LevelModerate
$149
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Gaspe, Whale WatchingBoating | Essentials Collection | Outdoors | Wildlife
Duration4.5 Hours
Activity LevelModerate
$239
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Sat Oct 4
AT SEA
Arrive:
Depart:
Watersports Platform: 
Sun Oct 5
Quebec City
Arrive:9:00 AM
Depart:
Watersports Platform: 
3 Available
+_
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.
3 Shore Excursions Available
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Quebec, Ste Anne Canyon and BasilicaCulture | Essentials Collection | Sightseeing | Walking
Duration4 Hours
Activity LevelEasy-Moderate
$139
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Quebec City, Historic Quebec with Montmorency FallsEssentials Collection | Sightseeing
Duration3 Hours
Activity LevelEasy
$99
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Quebec City, Rendez-vous with Wendat First NationCulture | Essentials Collection | Sightseeing | Walking
Duration3.5 Hours
Activity LevelEasy-Moderate
$139
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Mon Oct 6
Quebec City
Arrive:
Depart:4:00 PM
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.
Tue Oct 7
Montreal
Arrive:8:00 AM
Depart:
Watersports Platform: 
2 Available
+_
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.
2 Shore Excursions Available
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Montreal, Highlights with Basilica with Transfer to AirportEssentials Collection | Sightseeing
Duration3 Hours
Activity LevelEasy
$179
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Montreal, Highlights with Basilica with Transfer to Windstar HotelEssentials Collection | Sightseeing
Duration2.5 Hours
Activity LevelEasy
$179
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