35 Day Victory Cruise Lines River Cruise from Chicago to Jacksonville 2026

Day 1 CHICAGO (NAVY PIER), ILLINOIS | HOTEL STAY

The journey begins in Chicago, a city that hums with creativity and ambition. Wander the Riverwalk at sunset, marvel at the skyline from the Willis Tower, or lose yourself in the treasures of the Art Institute. As the evening sets in, indulge in Chicago’s renowned culinary scene before settling in for a restful stay along the lakefront.

Day 2 CHICAGO (NAVY PIER), ILLINOIS | EMBARK

Step aboard and bid farewell to the Windy City as the iconic skyline fades into the distance. The bustling Navy Pier sends you off in grand fashion, the perfect launching point for an adventure across these legendary lakes.

Day 3 MILWAUKEE, WISCONSIN

Milwaukee welcomes you with its distinctive blend of old-world charm and modern flair. Sip your way through local craft breweries, take in the striking architecture of the Milwaukee Art Museum, or cruise down the RiverWalk, lined with lively cafés and waterfront parks.

Day 4 ESCANABA, MICHIGAN

Discover the peaceful charm of Escanaba, Michigan, nestled on the tranquil shores of Lake Michigan’s northern reaches. Embrace the serene ambiance as you explore its scenic landscapes and friendly community, where the beauty of the Great Lakes region unfolds in every direction, offering moments of quiet reflection and relaxation.

Day 5 MACKINAC ISLAND, MICHIGAN

Arriving at Mackinac Island feels like stepping into a vintage postcard. Horse-drawn carriages clip along the cobblestone streets, Victorian homes line the hills, and the scent of homemade fudge drifts through the air. Bike around the island’s perimeter for sweeping views of Lake Huron, or explore Fort Mackinac’s storied ramparts.

Day 6 SAULT STE. MARIE (SOO LOCKS), MICHIGAN

Sault Ste. Marie offers a front-row seat to one of engineering’s great spectacles. Watch as massive freighters glide through the Soo Locks, connecting the wild waters of Lake Superior to the gentler tides of Lake Huron. The town’s maritime history and relaxed waterfront make it a captivating stop.

Day 7 SCENIC SAILING ON LAKE HURON

Sailing across Lake Huron feels like venturing into the wild. Its tranquil beauty and diverse coastline offer a glimpse into a quieter, more remote stretch of the region.

Day 8 DETROIT, MICHIGAN

Detroit’s spirit is electric—past and future colliding in a city that never stands still. Dive into the city’s vibrant art scene, explore the historic roots of Motown, or wander the revitalized Eastern Market, where urban energy pulses at every turn.

Day 9 CLEVELAND, OHIO

In Cleveland, the Rock and Roll Hall of Fame beckons music lovers, while the Cleveland Museum of Art and West Side Market offer a taste of the city’s creative spirit. Enjoy the lakefront parks and vibrant neighborhoods that make this city a standout destination.

Day 10 NIAGARA FALLS (PORT COLBORNE), ONTARIO

The roar of Niagara Falls draws you in long before you see it. Feel the spray on your skin as you edge closer to this natural wonder and then retreat to the calm streets of Port Colborne, a quaint town brimming with local artisans and waterfront cafés.

Day 11 TORONTO, ONTARIO

Arrive in Toronto, where urban energy meets cultural diversity. Scale the CN Tower, explore the Royal Ontario Museum, or wander through Kensington Market’s eclectic mix of shops and eateries. The city’s dynamic atmosphere provides the perfect blend of excitement and relaxation.

Day 12 SCENIC SAILING ON LAKE ONTARIO

Let the gentle waves of Lake Ontario guide you as you gaze upon its vast horizon, where moments of peaceful reflection and rejuvenation unfold amidst the serene beauty of one of North America’s Great Lakes.

Day 13 MONTRÉAL, QUÉBEC

Arrive in Montréal, where historic streets and riverfront views welcome you ashore. This storied city opens the St. Lawrence, blending Old World charm with culture before your journey continues onward toward the seaway.

Day 14 QUÉBEC CITY, QUÉBEC

Step into the heart of French Canada as you explore the enchanting streets of Québec City. Marvel at the iconic Château Frontenac, visit the historic Plains of Abraham, or stroll through the artisanal shops and cafés of Petit-Champlain.

Day 15 CRUISING THE SAGUENAY FJORDS

Experience the awe-inspiring beauty of the Saguenay Fjords, where towering cliffs meet deep blue waters. Keep your eyes peeled for whales as you sail through this remarkable region, renowned for its marine wildlife and dramatic landscapes.

Day 16 SCENIC SAILING ON THE GULF OF ST. LAWRENCE

Enjoy a tranquil day at sea on the sparkling waters of the Gulf of Saint Lawrence, where the rhythm of the water and the expansive views offer a chance to relax and recharge. Take in the serene beauty of the open water as you sail toward Prince Edward Island.

Day 17 CHARLOTTETOWN, PRINCE EDWARD ISLAND

Arrive in Charlottetown, the charming capital of Prince Edward Island. Explore the historic sites tied to Canada’s founding, stroll along Victoria Row, and enjoy the island’s famed red-sand beaches. Don’t miss a taste of the region’s fresh lobster and mussels.

Day 18 SCENIC SAILING THROUGH THE STRAIT OF CANSO

Sail through the Strait of Canso, a narrow channel that separates mainland Nova Scotia from Cape Breton Island. Admire the scenic coastline and take in the peaceful ambiance of this picturesque passage.

Day 19 HALIFAX, NOVA SCOTIA

Halifax combines a rich maritime heritage with a modern cultural scene. Walk along the bustling waterfront, visit the Maritime Museum of the Atlantic, or take in panoramic views from the historic Citadel Hill. Halifax’s friendly atmosphere makes it a memorable stop.

Day 20 SCENIC SAILING ON THE ATLANTIC OCEAN

As you sail toward New England, enjoy a leisurely day at sea on the vibrant Atlantic Ocean. Reflect on your journey, partake in onboard activities, or simply relax and watch the horizon stretch endlessly ahead.

Day 21 PORTLAND, MAINE

Board your ship and set sail from Portland’s scenic harbor. The lighthouse-dotted coastline slips into the distance as you cruise toward the open Atlantic, leaving behind the historic port for the adventure ahead.

Day 22 SCENIC SAILING ON THE ATLANTIC OCEAN

As the Atlantic unfolds around you, spend the day embracing the rhythm of the open sea. Take time to unwind onboard, enjoy thoughtful programming, or simply watch shifting horizons accompany your voyage northward.

Day 23 HALIFAX, NOVA SCOTIA

Halifax combines a rich maritime heritage with a modern cultural scene. Walk along the bustling waterfront, visit the Maritime Museum of the Atlantic, or take in panoramic views from the historic Citadel Hill. Halifax’s friendly atmosphere makes it a memorable stop.

Day 24 SCENIC SAILING ON THE ATLANTIC OCEAN

Halifax combines a rich maritime heritage with a modern cultural scene. Walk along the bustling waterfront, visit the Maritime Museum of the Atlantic, or take in panoramic views from the historic Citadel Hill. Halifax’s friendly atmosphere makes it a memorable stop.

Day 25 PORTLAND, MAINE

Portland welcomes you with a working waterfront, cobblestone streets, and celebrated culinary scene. Discover lighthouses, local flavors, and the maritime character of this classic New England port.

Day 26 PROVINCETOWN, MASSACHUSETTS

Arrive by water to Provincetown, a vibrant seaside enclave known for its artistic spirit, historic charm, and sweeping ocean views. Enjoy galleries, beaches, and a lively harborfront.

Day 27 NEWPORT, RHODE ISLAND

Newport offers refined coastal elegance and a storied maritime past. Discover grand waterfront estates, historic streets, and harbors that reflect the city’s seafaring legacy.

Day 28 NEW LONDON, CONNECTICUT

New London offers a rich maritime past and coastal New England charm. Visit historic forts, waterfront parks, and museums that highlight the region’s seafaring legacy.

Day 29 SCENIC SAILING ON THE ATLANTIC OCEAN

Embrace a full day at sea as the Atlantic carries you forward. From quiet moments on deck to engaging onboard experiences, the ever-changing horizon becomes part of the journey.

Day 30 NEWPORT NEWS, VIRGINIA

Newport News offers a proud maritime legacy and riverside Virginia character. Explore historic shipyards, waterfront parks, and museums that reflect the region’s naval heritage.

Day 31 SCENIC SAILING ON THE ATLANTIC OCEAN

Savor a relaxed day on the Atlantic, where open horizons and gentle rhythms invite reflection, onboard enjoyment, and a deeper connection to the journey ahead.

Day 32 WILMINGTON, NORTH CAROLINA

Wilmington offers historic riverfront charm and coastal Carolina character. Explore a scenic riverwalk, preserved districts, and cultural sites that reflect the city’s rich heritage.

Day 33 CHARLESTON, SOUTH CAROLINA

Charleston offers timeless Southern elegance and a deep coastal heritage. Discover historic streets, gracious architecture, and cultural traditions that define this iconic Lowcountry city.

Day 34 SAVANNAH, GEORGIA

Savannah blends elegant Southern traditions with a rich maritime past. Explore historic squares, riverside walks, and cultural landmarks that reveal the city’s enduring character.

Day 36 JACKSONVILLE, FLORIDA | DISEMBARK

Disembark in Jacksonville, where riverfront views and coastal energy define this Florida city. Depart with lasting memories of a remarkable coastal and inland voyage.