At a glance
- Duration:
- 9 Days
- Start/End:
- Round Trip Baltimore
- From:
- $4,610
- Time of Year:
- April - May; September - October
Set sail from the elegant harbor of Baltimore, MD into the shimmering expanses of Chesapeake Bay, embarking on a 9-day voyage steeped in colonial charm, natural beauty, and curated sophistication.
Explore the storied “Historic Triangle”; Yorktown, VA, Williamsburg, VA, and Jamestown, VA, where well-preserved battlefields, architectural treasures, and cobbled thoroughfares tell the story of America’s earliest chapters. In Williamsburg, stroll under gaslit lamps along streets that remain virtually unchanged since colonial times; let living-history interpreters bring each cobblestone to life.
Drift into the serene town of St. Michaels, MD, a picture-postcard waterfront escape on the bay. Amble along historic streets lined with charming boutiques and art galleries, enjoy leisurely lunches of freshly harvested seafood on the waterfront, and soak in the timeless ambiance.
American Cruise Lines
In Annapolis, MD, the United States’ oldest continuously used state capitol, immerse yourself in 300+ years of maritime heritage. Cobblestones, elegant colonial-era buildings, and bayfront vistas evoke a subtle, bygone grandeur.
Between ports, surrender to unhurried days aboard your intimate river-ship. From the privacy of your balcony, watch herons glide over wetlands, ospreys circle overhead, and lighthouses stand sentinel against the horizon. The gentle rhythm of the bay, soft salt air, and picturesque shorelines create the perfect backdrop for conversation, contemplation, or simply enjoying a quiet moment with a glass in hand.
From the option of a pre-cruise stay at the five-star Four Seasons Hotel Baltimore, where you can enjoy curated concierge luggage service, gourmet breakfast, and a private transfer to the ship, to sumptuous Grand Suites onboard offering sweeping 25-foot balconies, a living room, and spacious ensuite comforts, every detail is curated for your ease and pleasure.
Your Chesapeake Bay voyage isn’t just a cruise, it’s an elegant escape through American history, coastal charm, and quiet luxury.
Chesapeake Bay Cruise Details
Day-to-Day Itinerary
Day 1: Baltimore, MD
Settle into your hotel and enjoy Baltimore often called “Charm City.” This vibrant waterfront destination is known for its bustling Inner Harbor, where historic ships, world-class museums, and lively shops and restaurants create a welcoming atmosphere for visitors. The city played a key role in American history, notably during the War of 1812, when Fort McHenry inspired Francis Scott Key to write “The Star-Spangled Banner.” Today, Baltimore blends its maritime heritage with a thriving arts scene, diverse neighborhoods, and renowned institutions like the National Aquarium and the American Visionary Art Museum, making it a captivating stop on any Chesapeake Bay cruise.
Day 2: Day of Cruising Chesapeake Bay
Step aboard and receive a warm welcome from our crew. It’s the perfect opportunity to meet your fellow travelers as we begin our journey along the legendary Chesapeake Bay. Spend the afternoon cruising past historic shorelines, peaceful coves, and charming waterfront villages. Take in panoramic views of lush wetlands and iconic lighthouses, and keep watch for graceful herons and playful ospreys.
Day 3: Yorktown / Williamsburg, VA
Step back in time in a town that transformed the history of a nation. Yorktown is known for its monumental battlefields, authentic colonial homes, and storied past. Discover museum exhibits, recreated Continental Army camps and restored homes from the 1700’s.
Also visit Colonial Williamsburg, once the political and economic center of the Virginia Colony, today the world’s premier living history site. Under the guidance of expert historians dressed in period attire, stroll through the narrow, time-worn streets that have preserved their colonial character. Engage with blacksmiths, cobblers, and other artisans practicing their crafts just as the first English colonists did. Colonial Williamsburg offers a vivid re-creation of a thriving colonial town, inviting you to step back in time and live the daily life and feel the revolutionary spirit of the era.
Day 4: Cruising Chesapeake Bay
Bask in the beauty of Chesapeake Bay as you cruise along serene and picturesque landscapes and charming waterfront communities. Pass by lush shorelines and small islands that showcase the region’s natural beauty. From the comfort of your private balcony, enjoy the opportunity to spot birds, dolphins, and other marine life.
As we voyage, onboard specialists will enrich your journey with insights into the local culture and heritage. Take a moment to unwind on your personal balcony or join in the fun of kite flying on the upper deck. Come evening, mingle with other guests and revel in the talents of some of the region’s best entertainers
Day 5: St. Michaels, MD
The port of St. Michaels is a picturesque harbor on Chesapeake Bay, well-known as a keystone locale in colonial history, serving as a trading post for farmers in the region.
Docking at the Chesapeake Bay Maritime Museum, once a famed shipbuilding village, get a glimpse of what life was like in the 1800’s. Explore the museums variety of exhibits, including historic boats, artifacts, and interactive displays that highlight the area’s maritime culture, shipbuilding history, and environmental issues.
As you walk through its gorgeous streets, lined with antique shops, galleries, and unique boutiques, you will see a true reflection of America’s historical beginnings.
Day 6: St. Michaels, MD
Spend an additional day exploring St. Michaels, a charming escape with cobblestone streets, historic buildings, and a picturesque waterfront views along the Chesapeake Bay. Peruse the town’s quaint streets, taking in the well-preserved 18th and 19th-century architecture, and browse the local boutiques and art galleries. Enjoy a leisurely lunch at one of the waterfront restaurants, where you can indulge in fresh, locally caught seafood, including crabs, oysters, and fish, while taking in stunning views of the bay.
Day 7: Annapolis, MD
A charming historic city located on the banks of the Chesapeake Bay, Annapolis is known for its rich maritime heritage and picturesque waterfront. As the state capital, the city is home to the Maryland State House, the oldest state capitol in continuous use, where George Washington famously resigned his commission as commander-in-chief.
Delight in the cobblestone streets and colonial-era buildings that provide a glimpse into its storied past. Explore the city’s beautiful waterfront parks, a peaceful retreat offering stunning views of the Bay.
Day 8: Baltimore, MD
Explore the Inner Harbor bustling waterfront area ornamented with historic ships, where you can visit The National Aquarium, home to thousands of marine species, including sharks, dolphins, and sea turtles.
Take a journey through Fort McHenry, the historic site that inspired The Star-Spangled Banner and experience the Baltimore Industry Museum with exhibitions and artifacts that document the contribution of the workers and entrepreneurs who built Baltimore.
A visit to Baltimore wouldn’t be complete without indulging in its famous seafood, especially the famous Maryland crab cakes.
Day 9: Baltimore, MD
Your captivating Chesapeake Bay Cruise through history wraps up in the lively city of Baltimore, where it all started. Have one last breakfast aboard the ship before you disembark to either start your journey home or to extend your stay for further exploration.
If you choose to linger, Baltimore offers an array of attractions, from vibrant cultural districts and historic sites to eclectic dining and shopping opportunities. Take your time to wander through the renowned Inner Harbor, visit world-class museums, and enjoy the local cuisine. You can’t leave without covering something in Old Bay Seasoning which pairs perfectly with fried potatoes or fresh seafood.
