VINCENT VACATIONS
21 NIGHTS | WINDSTAR | STAR PRIDE

21-Night Star Collector: Fall Leaves & Caribbean Breezes Cruise

Aboard Star Pride (Windstar) | Departing Montreal to San Juan | 1 Available Departures from $10,203

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21 NightsDuration
WindstarCruise LineStar PrideCruise ShipMontrealEmbarkation PortCaribbeanRegion$10,203Starting Fare
PORTS OF CALL ON THIS VOYAGEMontreal, Saint Lawrence River, Quebec, Gaspe, Sydney, Halifax, Bar Harbor, Portland
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Upcoming Sailings & Stateroom Fares (1)

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Departure DateReturn DateInsideOceanviewBalconySuiteAdvisor Quote & Perks
Oct 11, 2027
Voyage #PR20271011-21D
Nov 01, 2027Call for Exclusive Rate$10,203$13,878$11,998
PORT-BY-PORT TIMELINE

Day-by-Day Cruise Itinerary

Star Collector: Fall Leaves & Caribbean Breezes Route Map
Day 1

MONTREAL, QC (CAMTR)

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

Day 2

CRUISING ST LAWRENCE RIVER (CA200)

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 2

QUEBEC CITY, QC (CAQUE)

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,

Day 3

At Sea (SEAD)

Day 4

GASPE, QC (CAGPE)

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 cathedr

Day 5

SYDNEY, NS (CASY4)

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 t

Day 6

SYDNEY, NS (CASY4)

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 t

Day 7

At Sea (SEAD)

Day 8

HALIFAX, NS (CAHAL)

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.

Day 9

HALIFAX, NS (CAHAL)

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.

Day 10

BAR HARBOR, ME (USBHB)

One of the best places to appreciate nature is found at Bar Harbor, with its stunning coastal beauty. Surrounded by Acadia National Park, with over 50 square miles of mountains, lakes, forests, soaring granite cliffs and amazing views, Bar Harbor's laid-back atmosphere encourages relaxation and repo

Day 11

PORTLAND, ME (USPWM)

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 cobblesto

Day 12

BOSTON, MA (USBOS)

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 Lib

Day 13

At Sea (SEAD)

Day 14

At Sea (SEAD)

Day 15

HAMILTON (BMHMT)

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 ci

Day 16

HAMILTON (BMHMT)

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 ci

Day 16

ST GEORGES BERMUDA (BMSGB)

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 includin

Day 17

ST GEORGES BERMUDA (BMSGB)

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 includin

Day 18

At Sea (SEAD)

Day 19

At Sea (SEAD)

Day 20

GUSTAVIA, ST BARTHELEMY (BLGUS)

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

Day 21

VIRGIN GORDA/PRICKLY PEAR, BVI (VGVIJ)

The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious a

Day 22

SAN JUAN (PRSJU)

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.

COMPLIMENTARY EXTRAS

Available Promotions & Onboard Credits

Reduced Deposit

One or more fares on this sailing includes a reduced deposit promotion.

THE SIGNATURE TRAVEL NETWORK ADVANTAGE

Why Book 21-Night Star Collector: Fall Leaves & Caribbean Breezes (Star Pride) with Vincent Vacations Instead of Direct?

You pay the exact same promotional cruise line rate with $0 agency booking fees, while unlocking exclusive consortium perks unavailable on retail websites:

✓ $100–$600+ Shipboard Credits✓ Private Car & Driver Shore Excursions✓ Hosted Voyages & VIP Receptions✓ 100% Loyalty Points + Promo Stacking✓ Price-Drop Monitoring Before Final Payment
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EXPERT CRUISE GUIDANCE

Frequently Asked Questions About 21-Night Star Collector: Fall Leaves & Caribbean Breezes (Star Pride)

What is included in the 21-Night Star Collector: Fall Leaves & Caribbean Breezes cruise aboard Star Pride?

This 21-night Windstar voyage aboard Star Pride embarks in Montreal and concludes in San Juan, visiting Montreal, Saint Lawrence River, Quebec, Gaspe, Sydney, Halifax, Bar Harbor, Portland. Fares start at $10,203 per person based on double occupancy, plus eligible Vincent Vacations onboard credits.

How do I claim complimentary onboard credit on Star Pride?

Click any stateroom fare or 'Get Quote & Perks' button in the departure table above, or call 1-888-883-0460. Our certified advisors lock in the lowest promotional rate on Star Pride and attach all eligible Signature Travel Network shipboard credits and VIP amenities.

Signature Travel Network Perks: Up to $600 Shipboard Credit + Price-Match Guarantee + $0 Booking Fees
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