Windstar Cruises
STAR COLLECTOR: FALL LEAVES & CARIBBEAN BREEZES
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.
Day 1 |
Canada's second-largest city and the most populous city in Québec, Montréal is a cultural capital and replete with magnificent architecture, immersive museums, and lush botanical gardens and parks. Highlights include the cobblestoned Vieux Montréal neighborhood, Notre-Dame Basilica, Montréal Botanical Garden, the Montréal Museum of Archaeology and History, and the Musée des Beaux-Arts. |
Day 2 |
Visit picturesque Quebec City, situated on the mighty St. Lawrence River, and become instantly mesmerized by this historic jewel in Canada’s French province. Replete with striking landmarks and stunning architecture, Quebec City is perfect for sight-seeing and deserves ample time for exploration. The Vieux-Québec quarter, located in the heart of the Quebec City, boasts the city’s most iconic attractions and has been recognized as a UNESCO World Heritage Site. Here, you’ll find la Citadelle de Québec, la Place Royale, Musée de la civilisation, and most notably, the famous Château Frontenac, whose impressive structure towers over the St. Lawrence. Stroll Terrasse Dufferin for a spectacular waterfront view of this massive castle, or head just north of Frontenac to Notre-Dame de Québec Basilica and marvel at the cathedral’s gold-laden Baroque style. The lush beauty of Quebec City’s nature parks, from the verdant Plains of Abraham park (once witness to the Battle of Québec) to the cascading waterfall of Parc de la Chute-Montmorency, complements the city’s man-made wonders. Adventurous travelers will love nearby Jacques-Cartier National Park, where hiking, skiing, canoeing, and kayaking are among the most popular day-time excursions. Venture across the St. Lawrence River to the Île d’Orléans, where local vendors offer the city’s best wines, cheeses, and culinary bites to savor. With so much to see and do, Quebec City is guaranteed to astound you! |
Day 3 |
Visit picturesque Quebec City, situated on the mighty St. Lawrence River, and become instantly mesmerized by this historic jewel in Canada’s French province. Replete with striking landmarks and stunning architecture, Quebec City is perfect for sight-seeing and deserves ample time for exploration. The Vieux-Québec quarter, located in the heart of the Quebec City, boasts the city’s most iconic attractions and has been recognized as a UNESCO World Heritage Site. Here, you’ll find la Citadelle de Québec, la Place Royale, Musée de la civilisation, and most notably, the famous Château Frontenac, whose impressive structure towers over the St. Lawrence. Stroll Terrasse Dufferin for a spectacular waterfront view of this massive castle, or head just north of Frontenac to Notre-Dame de Québec Basilica and marvel at the cathedral’s gold-laden Baroque style. The lush beauty of Quebec City’s nature parks, from the verdant Plains of Abraham park (once witness to the Battle of Québec) to the cascading waterfall of Parc de la Chute-Montmorency, complements the city’s man-made wonders. Adventurous travelers will love nearby Jacques-Cartier National Park, where hiking, skiing, canoeing, and kayaking are among the most popular day-time excursions. Venture across the St. Lawrence River to the Île d’Orléans, where local vendors offer the city’s best wines, cheeses, and culinary bites to savor. With so much to see and do, Quebec City is guaranteed to astound you! |
Day 4 |
Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great. |
Day 5 |
Arrive Time: 7:00 AM – Depart Time: 2:00 PM
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Day 6 |
Arrive Time: 11:00 AM – Depart Time: 6:00 PM
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Day 7 |
On Cape Breton Island's east coast lies Sydney, established by the British in 1785. Once a steel mill town, this urban area is now known for a cosmpolitan atmosphere offset by friendly locals. Be sure to see the Big Fiddle statue, and the Membertou Heritage Park. Arrive Time: 7:00 AM – Depart Time: 2:00 PM
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Day 8 |
The capital of Nova Scotia, Halifax is a charming seaside destination in Eastern Canada. Rich in maritime history and once a major trading hub, this city boasts fresh air, lovely sunsets, and a laid-back vibe. Must-see attractions include the hilltop fort Halifax Citadel, the Victorian-era Halifax Public Gardens, and the Maritime Museum of the Atlantic. Arrive Time: 11:00 AM – Depart Time: 11:00 PM
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Day 9 |
Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great. |
Day 10 |
Dotted with lighthouses along its shoreline, Portland, Maine is a coastal gem in the northeastern United States and a veritable paradise for lovers of fresh seafood, craft breweries, and small-town charm. At the center of downtown Portland, the Old Port neighborhood boasts a number of unique and historical buildings, trendy restaurants and bars, and picturesque views of the Portland Harbor. Take time to relish in Portland’s culinary scene and sample everything from lobster rolls, to clam bakes and chowder, to ceviche, to paella. Unwind in one of a variety of microbreweries and brew pubs throughout downtown, which give you access to the state’s best ales and lagers. Head to the Eastern Promenade or Bug Light Park for spectacular views of the ocean and passing boaters. Better yet, venture south of Portland proper to see the iconic Portland Head Lighthouse, whose warm glow beckons over the glittering waters of the Atlantic Ocean. Portland, Maine awaits you! |
Day 11 |
Dotted with lighthouses along its shoreline, Portland, Maine is a coastal gem in the northeastern United States and a veritable paradise for lovers of fresh seafood, craft breweries, and small-town charm. At the center of downtown Portland, the Old Port neighborhood boasts a number of unique and historical buildings, trendy restaurants and bars, and picturesque views of the Portland Harbor. Take time to relish in Portland’s culinary scene and sample everything from lobster rolls, to clam bakes and chowder, to ceviche, to paella. Unwind in one of a variety of microbreweries and brew pubs throughout downtown, which give you access to the state’s best ales and lagers. Head to the Eastern Promenade or Bug Light Park for spectacular views of the ocean and passing boaters. Better yet, venture south of Portland proper to see the iconic Portland Head Lighthouse, whose warm glow beckons over the glittering waters of the Atlantic Ocean. Portland, Maine awaits you! |
Day 12 |
Cape Cod, Massachusetts, is a captivating destination known for its scenic beauty and charming coastal villages. Stretching out into the Atlantic Ocean, Cape Cod offers a quintessential New England experience with its pristine beaches, historic lighthouses, and quaint towns. A visit to the Cape Cod National Seashore is a must, where visitors can explore miles of sandy shores, salt marshes, and tidal flats. The seashore also features iconic landmarks like the Nauset Light and the Highland Light, perfect for those who enjoy coastal history. For a taste of local culture, the town of Provincetown at the tip of the Cape is renowned for its vibrant arts scene and welcoming atmosphere. Provincetown’s Commercial Street is lined with galleries, shops, and restaurants where you can savor fresh seafood and enjoy eclectic art. The town is also known for its rich history as a safe haven for LGBTQ+ individuals and artists. Don’t miss the opportunity to take a whale-watching tour from Provincetown Harbor, where you might spot humpback and minke whales. Cape Cod's natural beauty extends beyond the beaches to its scenic bike paths and nature trails. The Cape Cod Rail Trail offers a picturesque route for cyclists and walkers, winding through forests, wetlands, and small towns. The trail provides access to charming spots like Chatham and Harwich, where you can explore local shops and enjoy the serene landscape. A fun fact about Cape Cod is that it was the site of the first successful transplant of a human heart in 1984 at Cape Cod Hospital. This historic medical achievement underscores the Cape’s unique place in American history. With its combination of natural beauty, rich history, and charming towns, Cape Cod offers a memorable getaway for visitors seeking relaxation and adventure alike. |
Day 13 |
Architecture, fine art, theater, dining, shopping... what can't you experience in New York City? Cloud-breaching skyscrapers dot its skyline, while Lady Liberty stands proudly in New York Harbor. Visitors taking a bite of the Big Apple will find endless options in this metropolis' five distinct boroughs (Brooklyn, Queens, Manhattan, the Bronx, Staten Island). Central Park, the Brooklyn Bridge, Times Square, Rockefeller Center, and the High Line, a park situated on a former elevated railroad, are just a few of the major NYC attractions.
This behemoth at the nexus of the Hudson River and the Atlantic Ocean is the most populated city in the United States. The character, landscapes, culture and peaks of human achievement that New York City displays make it an indisputably essential travel destination. Alicia Keys may have said it best in her song "Empire State of Mind": "There's nothing you can't do." |
Day 14 |
Architecture, fine art, theater, dining, shopping... what can't you experience in New York City? Cloud-breaching skyscrapers dot its skyline, while Lady Liberty stands proudly in New York Harbor. Visitors taking a bite of the Big Apple will find endless options in this metropolis' five distinct boroughs (Brooklyn, Queens, Manhattan, the Bronx, Staten Island). Central Park, the Brooklyn Bridge, Times Square, Rockefeller Center, and the High Line, a park situated on a former elevated railroad, are just a few of the major NYC attractions.
This behemoth at the nexus of the Hudson River and the Atlantic Ocean is the most populated city in the United States. The character, landscapes, culture and peaks of human achievement that New York City displays make it an indisputably essential travel destination. Alicia Keys may have said it best in her song "Empire State of Mind": "There's nothing you can't do." |
Day 15 |
Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great. |
Day 16 |
Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great. |
Day 17 |
Grenada's capital is set amid an old volcano and a spectacular harbor. Fort George, an 18th-century defensive structure, provides amazing views of St. George's Bay. |
Day 18 |
Grenada's capital is set amid an old volcano and a spectacular harbor. Fort George, an 18th-century defensive structure, provides amazing views of St. George's Bay. |
Day 19 |
Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great. |
Day 20 |
Enjoy this day at sea as you travel to your next port of call. This is an opportunity to swim, catch some sun on deck or take advantage of the many activities that are onboard your ship. Eat heartily, take a nap and get ready for the next port of call ! This is what makes cruising so great. |
Day 21 |
From spectacular beaches, to impressive monuments, to electrifying nightlife, San Juan, Puerto Rico is bursting with historical and cultural attractions that are sure to inspire and exhilarate. A former Spanish colony established by explorer Ponce de León, San Juan is replete with monuments dating back to the sixteenth century. Originally built to fortify the Spanish military against attacks from native Taíno peoples and rival European colonial powers, both the Castillo San Cristóbal and Castillo San Felipe del Morro fortresses are popular sites for educational tours detailing the island’s extensive colonial history. These expansive bastions sit on San Juan’s rocky seaside cliffs and offer spectacular views of the Atlantic Ocean. San Juan’s many beaches beckon you! Relax with warm sands, snorkel in glittering turquoise waters, and marvel at vast lines of palm trees on Condado Beach, Ocean Park Beach, Carolina Beach, and a host of other coastal havens. Better yet, go for a nighttime boat ride in one of Puerto Rico’s three bio-luminescent bays, Laguna Grande, where dinoflagellates illuminate the water in hues of neon aqua. The city’s nearby natural parks and ecological wonders are equally worth a visit, including the limestone caves of Cueva Ventana and the lush tropical ecosystem of El Yunque National Rainforest. Your stay in San Juan won’t be complete without experiencing the city’s thrilling nightlife scene. San Juan boasts a number of bars, breweries, and dance clubs with delicious cocktails and mouthwatering (and authentically Puerto Rican!) culinary creations. Sip on the sweet coconut flavor of a classic piña colada, a Puerto Rico original, or sample some mofongo, a staple dish made of chicharrón and fried plantain. Unwind in this vibrant Caribbean capital and let San Juan regale you with its many charms! |
Travel Dates | Price | ||
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10/07/25 - 10/26/25 |
Starting At $10,249 |
Get A Quote |