STAR COLLECTOR: FALL LEAVES & CARIBBEAN BREEZES on Star Pride

Exterior view of Star Pride sailing near Manhattan, New York
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.
Interests
- Gardens, Foliage, and Nature
About Star Pride
About Windstar Cruises

THE WORLD'S BEST SMALL SHIP CRUISE LINE
All cruise ships let you see the world. Only Windstar’s private yacht style cruises brings you close enough so you can truly experience it. Each of our Windstar Cruises yachts serves between 148 and 342 guests. This intimacy provides you with the luxuries of time, space, and freedom to immerse yourself in both the journey and the destination — in ways you may never have imagined possible.
Oct 07, 2025 through
Oct 26, 2025
Oct 1, 2025
7:00 PM
Category s1
Inside
Outside
Balcony
Suite
8863399
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Itinerary
Day | Port | Arrive | Depart |
---|---|---|---|
1 | Montreal | 6:00 PM | |
2 | Quebec City | 9:00 AM | |
3 | Quebec City | 6:00 PM | |
4 | At Sea | ||
5 | Gaspe | 7:00 AM | 2:00 PM |
6 | Cap aux Meules | 11:00 AM | 6:00 PM |
7 | Sydney, Nova Scotia, Canada | 7:00 AM | 2:00 PM |
8 | Halifax | 11:00 AM | 11:00 PM |
9 | At Sea | ||
10 | Portland | 8:00 AM | |
11 | Portland | ||
11 | Cape Cod Canal | 10:00 PM | |
12 | New York City | 7:30 PM | |
13 | New York City | 6:00 PM | |
14 | At Sea | ||
15 | At Sea | ||
16 | St. George's | 8:00 AM | |
17 | St. George's | ||
18 | At Sea | ||
19 | At Sea | ||
20 | San Juan | 8:00 AM |