Star Collector: Fall Leaves & Caribbean Breezes

 
Montreal to San Juan
Mon Oct 11, 2027 - Mon Nov 1, 2027,
 21 days
 on Star Pride
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Montreal to San Juan
History, natural beauty, culture and cuisine are just a few of the pleasures that await you on the northern part of this voyage, before you make your way south to sparkling Caribbean islands. Start your journey in Montreal, City of a Hundred Steeples, and train your ear to the sound of French – it’s something you’ll hear throughout Quebec. Overnight in Quebec City with its UNESCO World Heritage Old Town and find 400-year-old ramparts filled with compelling history and delicious bistros. Enjoy the breathtaking seascapes of Gaspé, waves crashing against limestone cliffs and sea arches, and watch sugar maples and birch trees flout their fall colors. Retrace the battles for North America in the Fortress of Louisbourg, the UNESCO town of Lunenburg, the Citadel in Halifax, and Boston – where the Freedom Trail leads you to Paul Revere’s house and the Old North Church. Then trade in your autumn palette for a riot of spring colors – blushing pink beaches, hot pink flamingos, pastel colonial towns and turquoise waters. Multi-day stays let you take full measure of Bermuda’s natural beauty, British charms, and 500-year history. Wander the well-preserved lanes of St. George’s, a UNESCO World Heritage Site that captures what a British colonial outpost looked like in the 1600s. Take in a volley of historic forts in Bermuda, St Kitts, and San Juan – many of them UNESCO sites as well. From there, it’s on to chic French St. Bart, which has earned its celebrity endorsements with 20-odd stunning beaches and a multitude of duty-free boutiques. One beach you for-sure won’t want to miss is The Baths on Virgin Gorda, where giant granite boulders form glorious grottos and divine pools perfect for a soak or snorkel. Your voyage ends in Puerto Rico, but colorful Old San Juan and a trio of Spanish forts will keep you busy as you wait for your flight home.
voyage map
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Day 1: Montreal
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.
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Day 2: Quebec City
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.
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Day 4: Gaspe
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.
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Day 5: Sydney, Nova Scotia, Canada
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.
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Day 6: Sydney, Nova Scotia, Canada
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.
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Day 8: Halifax
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.
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Day 9: Halifax
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.
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Day 10: Bar Harbor
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 repose. Bar Harbor was the premier summer resort of the 19th century for some of America’s most powerful families like the Vanderbilts and the Rockefellers until the destructive 1947 fire. Visit the Abbe Museum, which showcases the Wabanaki Indians, the Dorr Museums of Natural History or the Bar Harbor Historical Society Museum.
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Day 11: Portland
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.
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Day 12: Boston
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.
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Day 15: 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.
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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.
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Day 16: St. George's
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.
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Day 17: St. George's
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.
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Day 20: Gustavia
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.
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Day 21: Virgin Gorda / Prickly Pear, British Virgin Islands
  • 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. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns.
 
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.
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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.
Popular Highlights
Basseterre
A favorite tourist stop in Basseterre is Caribelle Batik Store, formerly part of the Windfield Estate sugar plantation’s Romney Manor
Complimentary laundry
Pack light with complimentary daily laundry service
 
Quebec City
Overnight to catch the attractions of Quebec City, a UNESCO site
Hamilton
Overnight in Hamilton with plenty of time for snorkeling amid the abundance of marine life.
Spa
Spend relaxing days at sea with time for making new friends, visiting the spa and attending onboard informational lectures.
Portland
Enjoy the New England charm, lighthouses and lovely Victorian-era architecture in Portland
St. Georges
Overnight in UNESCO site St. George’s with its famous pink-sand beaches and 18th century Town Hall.
Gaspe
See the majesty of Perce Rock near Gaspe
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Mon Oct 11
Montreal
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Tue Oct 12
Quebec City
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Oct 13
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Oct 14
Gaspe
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Fri Oct 15
Sydney, Nova Scotia, Canada
Arrive:  3:00 PM
Depart:  
Watersports Platform: 
Sat Oct 16
Sydney, Nova Scotia, Canada
Arrive:  
Depart:  11:59 PM
Watersports Platform: 
Sun Oct 17
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Oct 18
Halifax
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Tue Oct 19
Halifax
Arrive:  
Depart:  12:00 PM
Watersports Platform: 
Wed Oct 20
Bar Harbor
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Thu Oct 21
Portland
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Oct 22
Boston
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Oct 23
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Oct 24
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Oct 25
Hamilton
Arrive:  8:45 AM
Depart:  
Watersports Platform: 
Tue Oct 26
Hamilton
Arrive:  
Depart:  7:00 AM
Watersports Platform: 
Tue Oct 26
St. George's
Arrive:  10:00 AM
Depart:  
Watersports Platform: 
Wed Oct 27
St. George's
Arrive:  
Depart:  12:00 PM
Watersports Platform: 
Thu Oct 28
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Oct 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Oct 30
Gustavia
Arrive:  10:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Oct 31
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Nov 1
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Marina
*Select voyages
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Beyond Inclusive Package
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Fri, Oct 9 - Wed, Oct 28, 2026
STAR PRIDE
$9,099
$9,099
Mon, Oct 11 - Mon, Nov 1, 2027
STAR PRIDE
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