Star Collector: Fall Leaves & Caribbean Breezes

From $6,222 per person

20 days

Ship: Star Pride

Montreal city hall, showcasing historic architecture and autumn foliage against a clear sky.
Windstar Cruises logo

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.

Journey Summary

  • Day 1 - Montreal
  • Day 2 - Quebec City
  • Day 3 - Quebec City
  • Day 4 -
  • Day 5 - Gaspe
  • Day 6 - Cap aux Meules
  • Day 7 - Sydney, Nova Scotia, Canada
  • Day 8 - Halifax
  • Day 9 -
  • Day 10 - Portland
  • Day 11 - Portland
  • Day 12 - Cape Cod Canal
  • Day 13 - New York City
  • Day 14 - New York City
  • Day 15 -
  • Day 16 -
  • Day 17 - St. George's
  • Day 18 - St. George's
  • Day 19 -
  • Day 20 -

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - October 07, 2025

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.

Day 2 - October 08, 2025

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.

Day 3 - October 09, 2025

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.

Day 4 - October 10, 2025

Day 5 - October 11, 2025

Gaspe

Four hundred miles northeast of Quebec City lies Gaspe, one of <em>National Geographic&rsquo;s</em> Canada&rsquo;s 50 Places of a Lifetime<em>.</em> This wonderful wilderness area is home to four national parks; Perce Rock; North America&rsquo;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.

Day 6 - October 12, 2025

Cap aux Meules

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.

Day 7 - October 13, 2025

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&rsquo;ll find the world&rsquo;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&rsquo; Market or discover the history of the Membertou people at their Heritage Park.

Day 8 - October 14, 2025

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&rsquo;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.

Day 9 - October 15, 2025

Day 10 - October 16, 2025

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 19<sup>th</sup> 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.

Day 11 - October 17, 2025

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 19<sup>th</sup> 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.

Day 12 - October 18, 2025

Cape Cod Canal

Seventeen-mile-long Cape Cod Canal is part of the Atlantic Intracoastal Waterway. Construction began in 1909 and the canal was first used in 1914. At 540 feet wide, it is the widest canal in the world. Cape Cod Canal traverses the neck of land joining Cape Cod to the mainland and occasionally marine life like whales and dolphins can be seen frolicking in the waters. This transit is exclusive to small ships like ours.

Day 13 - October 19, 2025

New York City

The largest city in the United States, New York City sits at the mouth of the Hudson River and is made up of five boroughs &ndash; Brooklyn, Queens, Manhattan, The Bronx and Staten Island. It is the premier gateway for immigrants, with almost 800 languages spoken there. Full of attractions, its iconic sites include the Empire State Building, Times Square, Central Park, The Museum of Modern Art, the Statue of Liberty and The Metropolitan Museum of Art to name just a few.

Day 14 - October 20, 2025

New York City

The largest city in the United States, New York City sits at the mouth of the Hudson River and is made up of five boroughs &ndash; Brooklyn, Queens, Manhattan, The Bronx and Staten Island. It is the premier gateway for immigrants, with almost 800 languages spoken there. Full of attractions, its iconic sites include the Empire State Building, Times Square, Central Park, The Museum of Modern Art, the Statue of Liberty and The Metropolitan Museum of Art to name just a few.

Day 15 - October 21, 2025

Day 16 - October 22, 2025

Day 17 - October 23, 2025

St. George's

In 2000 St. George&rsquo;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&rsquo;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&rsquo;s Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore&rsquo;s Jungle, Cooper&rsquo;s Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

Day 18 - October 24, 2025

St. George's

In 2000 St. George&rsquo;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&rsquo;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&rsquo;s Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore&rsquo;s Jungle, Cooper&rsquo;s Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.

Day 19 - October 25, 2025

Day 20 - October 26, 2025

Dates and Prices

Select year & month:

Unavailable dates are greyed out

JanFebMarAprMayJunJulAugSepOctNovDec

Available dates:

Oct 07, 2025

Ship

Your cruise ship

The Star Pride ship sails serenely on calm waters under a clear blue sky, showcasing its elegant design.
Windstar Cruises logo

consultation

Need information to make a decision?

Reach out to our travel concierges today to create your perfect journey.