Southeast Canadian Explorations

Sep 26, 2025 — Oct 7, 2025

Starting from $11,990 Displayed pricing is based off of double occupancy per person. Pricing subject to change based on occupancy and cabin selection.

See more routes around Canada & New England

BOSTON, MA → MONTREAL, QC

11 Nights in Star Pride

Quebec’s French-flavored history, the fusion of Acadian and Scottish cultures in Nova Scotia — each province distills its own blend of Old World and New, bucolic and urbane. Overnight in Quebec City and browse the shops and boulangeries along picturesque Petit Champlain, the oldest street in North America. Take in the brilliance of New England’s fall colors and the historic sites of Boston, one of America’s oldest cities.

Additional Information

1
SEP 26, 2025
Boston
EMBARK
1:00 PM
DEPART
5:00 PM
MARINA
NO
SHORE EXCURSIONS
0

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
SEP 27, 2025
Portland
ARRIVE
8:00 AM
DEPART
10:00 PM
MARINA
NO
SHORE EXCURSIONS
7

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.

Portland, Kennebunkport and Scenic Cruise

Time
8:30 AM
Duration
4.75 Hours
Activity Level
Moderate
Price
$179

Portland, Culinary Walking Tour of Portland

Time
8:30 AM
Duration
2 Hours
Activity Level
Moderate
Price
$189

Portland, Lighthouses Of Maine

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$119

Portland, Schooner Sail

Time
8:30 AM
Duration
4.75 Hours
Activity Level
Moderate
Price
$149

Portland, Beyond the Old Port Walking Tour with Wadsworth Longfellow House

Time
8:30 AM
Duration
3.25 Hours
Activity Level
Moderate
Price
$79

Portland, A Day in Maine with Kennebunkport

Time
8:30 AM
Duration
7 Hours
Activity Level
Easy-Moderate
Price
$229

Portland, Bike and Hike Portland

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate-Strenuous
Price
$149
3
SEP 28, 2025
4
SEP 29, 2025
Lunenburg
ARRIVE
8:00 AM
DEPART
11:00 PM
MARINA
NO
SHORE EXCURSIONS
3

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.

Lunenburg, Highlights of Lunenburg & Mahone Bay

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$195

Lunenburg, Mysteries of Oak Island by Boat

Time
8:30 AM
Duration
2.5 Hours
Activity Level
Easy
Price
$429

Lunenburg, Gaff Point Hiking Trail & Picnic

Time
8:30 AM
Duration
4 Hours
Activity Level
Moderate-Strenuous
Price
$285
5
SEP 30, 2025
Halifax
ARRIVE
8:00 AM
DEPART
4:00 PM
MARINA
NO
SHORE EXCURSIONS
6

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.

Halifax, Annapolis Valley Food and Wine

Time
8:30 AM
Duration
5.25 Hours
Activity Level
Moderate
Price
$399

Halifax, Halifax & The Titanic Connection

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$229

Halifax, Harbor Hopper

Time
8:30 AM
Duration
1 Hours
Activity Level
Moderate
Price
$69

Halifax, Taste of Halifax on Foot *

Time
8:30 AM
Duration
3.5 Hours
Activity Level
Moderate
Price
$179

Halifax, Scenic Peggys Cove

Time
8:30 AM
Duration
3 Hours
Activity Level
Easy-Moderate
Price
$169

Halifax, Highlander Experience

Time
8:30 AM
Duration
3 Hours
Activity Level
Moderate
Price
$199
6
OCT 01, 2025
Sydney, Nova Scotia, Canada
ARRIVE
1:00 PM
DEPART
7:00 PM
MARINA
NO
SHORE EXCURSIONS
2

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.

Sydney, Heart of the Island

Time
1:30 PM
Duration
4.5 Hours
Activity Level
N/A
Price
$229

Sydney, Pub Tour

Time
1:30 PM
Duration
3 Hours
Activity Level
N/A
Price
$139
7
OCT 02, 2025
Cap aux Meules
ARRIVE
10:00 AM
DEPART
6:00 PM
MARINA
NO
SHORE EXCURSIONS
6

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.

Cap aux Meules, Magdalen Island, Havre aux Maison's Highlights and Bagosse Tasting

Time
10:30 AM
Duration
2.8333333333333335 Hours
Activity Level
Easy-Moderate
Price
$159

Cap Aux Meules, Magdalen Island, Island Highlights

Time
10:30 AM
Duration
3.25 Hours
Activity Level
Moderate
Price
$179

Cap Aux Meules, Magdalen Island, A Taste of Iles De La Madeleine

Time
10:30 AM
Duration
3.75 Hours
Activity Level
Moderate
Price
$189

Cap Aux Meules, Magdalen Island, Fisherman & Acadian Culture *

Time
10:30 AM
Duration
4 Hours
Activity Level
Easy-Moderate
Price
$179

Cap Aux Meules, Magdalen Island, Caves & Cliffs By Boat

Time
10:30 AM
Duration
1.75 Hours
Activity Level
Moderate
Price
$139

Cap aux Meules, Magdalen Island, Lobster Fishing (Easy-Moderate)

Time
10:30 AM
Duration
2.8333333333333335 Hours
Activity Level
Easy-Moderate
Price
$299

Star Pride

number of decks
6 Decks
yacht length
440 ft (134 meters)
yacht crew size
140 Crew Members
yacht guest capacity
312 Guests

Available Staterooms

Star Balcony Suite

Cabin
11 Cabins
Max. Occupancy
3 Passengers
Room Size
1 Sqft
Amenities

Star Balcony Suite 1

Cabin
11 Cabins
Max. Occupancy
3 Passengers
Room Size
1 Sqft
Amenities

Guaranteed Suite** (chosen by Windstar)

Cabin
10 Cabins
Max. Occupancy
2 Passengers
Room Size
1 Sqft
Amenities

Ocean View Suite 3

Cabin
8 Cabins
Max. Occupancy
3 Passengers
Room Size
277 Sqft
Amenities

Balcony Suite 1

Cabin
16 Cabins
Max. Occupancy
2 Passengers
Room Size
277 Sqft
Amenities

Star Porthole Suite

Cabin
10 Cabins
Max. Occupancy
2 Passengers
Room Size
277 Sqft
Amenities

Star Ocean View Suite 1

Cabin
21 Cabins
Max. Occupancy
3 Passengers
Room Size
1 Sqft
Amenities

Ocean View Suite 1

Cabin
28 Cabins
Availability
Limited
Max. Occupancy
3 Passengers
Room Size
277 Sqft
Amenities

Ocean View Suite 2

Cabin
14 Cabins
Max. Occupancy
3 Passengers
Room Size
277 Sqft
Amenities

Available Dates