Star Collector: Fall Leaves & Caribbean Breezes
 
Montreal to San Juan
Tue Oct 7, 2025 - Sun Oct 26, 2025,
 19 days
 on Star Pride
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Starting from $10,249 USD
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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
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
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Tue Oct 7
Montreal
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Wed Oct 8
Quebec City
Arrive:  9:00 AM
Depart:  
Watersports Platform: 
Thu Oct 9
Quebec City
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Fri Oct 10
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Oct 11
Gaspe
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sun Oct 12
Cap aux Meules
Arrive:  11:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Oct 13
Sydney, Nova Scotia, Canada
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Tue Oct 14
Halifax
Arrive:  11:00 AM
Depart:  11:00 PM
Watersports Platform: 
Wed Oct 15
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Oct 16
Portland
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Fri Oct 17
Portland
Arrive:  
Depart:  12:00 PM
Watersports Platform: 
Fri Oct 17
Cape Cod Canal
Arrive:  10:00 PM
Depart:  11:59 PM
Watersports Platform: 
Sat Oct 18
New York City
Arrive:  7:30 PM
Depart:  
Watersports Platform: 
Sun Oct 19
New York City
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Mon Oct 20
AT SEA
Arrive:  
Depart:  
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Tue Oct 21
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Oct 22
St. George's
Arrive:  8:00 AM
Depart:  
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Thu Oct 23
St. George's
Arrive:  
Depart:  12:00 PM
Watersports Platform: 
Fri Oct 24
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Oct 25
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Oct 26
San Juan
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
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
ALL DATES &
FARES
Pick Your Perk
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
Tue, Oct 7 - Sun, Oct 26, 2025
STAR PRIDE
$12,130
$10,249
THIS
SAILING
Fri, Oct 9 - Wed, Oct 28, 2026
STAR PRIDE
$7,980
$6,099