At a glance
- Duration:
- 8 Days
- Start/End:
- Boston, MA to New York, NY
- From:
- $5,240
- Time of Year:
- May - October
Embark on the 8-day Yankee Seaports Cruise, sailing between Boston, MA, and New York, NY aboard luxurious small ships featuring the largest staterooms in American waters. This itinerary takes you through the finest seaport towns of the Northeast, exploring New England’s pristine waterways aboard our innovative small ships, perfectly designed to navigate these historic waters.
From the historic districts of Boston to the streets of New York, each stop tells a story of the American Revolution. Visit Plymouth, MA, a charming coastal town rich in history as the site of the Pilgrims’ first settlement. Discover the grandeur of Newport, Rhode Island, a testament to Gilded Age opulence. Explore the maritime heritage of New London, Mystic, and Essex, CT, where knowledgeable local guides lead you through their picturesque streets and vibrant art scenes.
As the day fades, cruise around New York Harbor, witnessing the sparkling city skyline from the ship’s bow—a perfect finale to your unforgettable journey through the heart of the Northeast’s iconic seaports.
Yankee Seaports Cruise Highlights
- Boston, MA
- Plymouth, MA
- Newport, RI
- New London/Mystic, CT
- Sag Harbor, NY
- Old Saybrook, CT
- New York, NY
Yankee Seaports Cruise Details
Day-to-Day Itinerary
Pre-Cruise: Boston Four Seasons Pre-Cruise Package
With our exclusive Pre-Cruise Package in downtown Boston, you can begin your journey a day early. This premier accommodation offers easy access to the entire city, allowing you to arrive at your leisure the day before your cruise.
Start your morning with breakfast, then embark on a guided tour of Boston’s iconic landmarks, including the historic Freedom Trail. Follow the red brick path through cobblestone streets, passing historic sites like the Paul Revere House, Old North Church, and Faneuil Hall, where you can explore the bustling lanes of Quincy Market.
Let American Cruise Lines handle everything, including the seamless transportation of your luggage directly to your stateroom aboard the ship. Finish your exploration at the ship, where you’ll smoothly transition to embarkation and set sail from Boston Harbor for an afternoon of relaxation and scenic cruising along the coast.
Day 1: Boston, MA
Stroll through the charming streets of historic downtown Boston, where red-brick buildings line cobblestone paths, each telling the story of centuries of rich history. Walk along the waterfront, once bustling with ships unloading goods from far-off lands, and enjoy stunning panoramic views of Boston Harbor. Explore Beacon Hill, with its stately brownstone homes and gas-lit streetlamps, evoking the elegance of Boston’s aristocratic past. Visit the lush Boston Public Garden, a peaceful haven filled with vibrant flowers, tranquil ponds, and the iconic swan boats, offering a serene escape from the city hustle. Once aboard, we’ll welcome you with a toast as you meet your dedicated crew and fellow travelers.
Day 2: Plymouth, MA
Experience the coastal charm of Plymouth, Massachusetts, where sandy beaches meet the calm waters of Cape Cod Bay. Wander along the historic shoreline, where weathered fishing boats sway in the harbor, evoking the town’s seafaring heritage. Explore the quaint streets of downtown Plymouth, lined with charming shops and colonial-era buildings that offer a window into the town’s rich history. Visit Pilgrim Memorial State Park, home to the iconic Plymouth Rock, a symbol of the Mayflower Pilgrims’ arrival in the New World, and immerse yourself in the stories of America’s early settlers.
Day 3: Newport, RI
Discover the charm of Newport, Rhode Island, where rugged cliffs meet the shimmering waters of the Atlantic. Take a peaceful walk along the famous Cliff Walk, a scenic path that winds through grand Gilded Age mansions and untamed coastline, offering stunning views of the rocky shore. Explore Newport’s historic downtown, where colonial-era buildings blend with lively shops and waterfront cafes, reflecting the town’s rich maritime heritage. Be sure to visit the iconic Newport Mansions, such as The Breakers and Marble House—once opulent retreats for America’s elite, featuring lavish ballrooms, gilded ceilings, and meticulously manicured gardens, offering a glimpse into a time of unparalleled luxury and indulgence.
Day 4: New London/Mystic, CT
The perfect pairing: New London and Mystic. Mystic is a picturesque maritime village, known for its quintessential New England charm, with a harbor filled with historic tall ships and a lively waterfront. The town boasts a thriving art scene, including the gallery of Russ Kramer, celebrated for his realistic maritime paintings. Famous for inspiring the 1988 film Mystic Pizza, the town also pushes culinary boundaries at local restaurants and bakeries, like the renowned “Sift,” home to melt-in-your-mouth chocolate chip cookies.
Just a short distance away, New London is a historic seaport city where the Thames River meets Long Island Sound. It features a dynamic art scene, with attractions like the Lyman Allyn Art Museum and vibrant cultural festivals. The city blends urban and coastal beauty, with landmarks such as the United States Coast Guard Academy and a lively waterfront district, offering sweeping views and a variety of dining options.
Day 5: Sag Harbor, NY
Set sail for Sag Harbor, a historic port nestled on the shores of Eastern Long Island. Once a bustling whaling hub, this charming village still exudes 19th-century character, with narrow streets and whaler’s cottages that echo its maritime past. Stroll through its streets, lined with art galleries and antique shops, each offering a glimpse into the town’s rich history and artistic spirit. Visit the Whaling Museum to discover the daring journeys of maritime explorers, and stand beside the old windmill, a timeless symbol of the past. Immerse yourself in Sag Harbor’s unique blend of nautical heritage and cultural elegance, where every corner tells a story and each sunset casts the harbor in stunning shades of pink and orange.
Day 6: Old Saybrook, CT
Set off to Old Saybrook, where the Connecticut River meets Long Island Sound. Established in 1635, this charming town holds a rich history and was once the beloved home of silver screen legend Katharine Hepburn. Just a short drive away, explore the picturesque town of Essex, where you can stroll along a waterfront lined with colonial and federal-era architecture, each building a testament to the town’s storied past. Dive into the region’s maritime history at the Connecticut River Museum, a treasure trove of seafaring tales and legends that bring the area’s nautical heritage to life.
Day 7: New York, NY
As we approach the iconic skyline of New York City, get ready for the breathtaking view: the Empire State Building towers above, the Chrysler Building dazzles with its Art Deco elegance, and the One World Trade Center stands tall as a symbol of strength and renewal. Once your ship docks in the vibrant heart of Manhattan, you’ll be in the perfect spot to dive into the city’s dynamic energy. American Cruise Lines offers a carefully curated selection of shore excursions—whether you want to stroll through the lush expanse of Central Park, catch a Broadway show, or wander the historic streets of Greenwich Village. Immerse yourself in the city’s world-class museums, bustling markets, and the electric atmosphere of Times Square. This is more than just a visit—it’s your chance to truly experience the heartbeat of the Big Apple.
Day 8: New York, NY
End your journey in the city that never sleeps. From the vibrant neon lights of Times Square to the serene elms of Central Park, and the stylish boutiques and historic cobblestone streets of SoHo, Manhattan offers an unparalleled urban adventure. Let Lady Liberty greet you as you sail past her and her iconic torch. After enjoying one last breakfast on board, begin your journey home. American Cruise Lines thanks you for choosing to sail with us, and we look forward to welcoming you aboard again soon to explore the beauty of America’s waterways.
